Synthesis and in vitro biological evaluation of 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivatives as antifungal compounds fluconazole analogues View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2019-04

AUTHORS

Armando Zambrano-Huerta, Damián David Cifuentes-Castañeda, Joanatan Bautista-Renedo, Hugo Mendieta-Zerón, Roberto Carlos Melgar-Fernández, Sergio Pavón-Romero, Macario Morales-Rodríguez, Bernardo A. Frontana-Uribe, Nelly González-Rivas, Erick Cuevas-Yañez

ABSTRACT

A novel series of 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivatives was synthesized from 1-aryl-1,3-diazidopropan-2-ol derivatives and diverse alkynes using copper catalyzed azide-alkyne cycloaddition in the key step. Most of synthesized compounds showed high activity against Candida spp. strains at a 0.04–0.5 μg/mL concentration range compared to Itraconazole and Fluconazole (MIC 2.56 and 1.28 μg/mL, respectively), which were used as reference compounds. A 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivative (R1 = F and R2 = cyclopropyl) displayed an outstanding selectivity against Candida albicans and Candida krusei (MIC = 0.0075 µg/mL). Moreover, Artemia salina bioassay on 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivatives revealed low toxicity in this kind of compounds. In addition, molecular docking studies suggest good binding affinity of halogen atoms in some 1-aryl-1,3-diazidopropan-2-ol derivatives to HEME group present in 14-alpha demethylase (CYP51), which might explain the high antifungal activity found in these compounds. More... »

PAGES

571-579

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s00044-019-02317-5

DOI

http://dx.doi.org/10.1007/s00044-019-02317-5

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1112672564


Indexing Status Check whether this publication has been indexed by Scopus and Web Of Science using the SN Indexing Status Tool
Incoming Citations Browse incoming citations for this publication using opencitations.net

JSON-LD is the canonical representation for SciGraph data.

TIP: You can open this SciGraph record using an external JSON-LD service: JSON-LD Playground Google SDTT

[
  {
    "@context": "https://springernature.github.io/scigraph/jsonld/sgcontext.json", 
    "about": [
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0302", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Inorganic Chemistry", 
        "type": "DefinedTerm"
      }, 
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/03", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Chemical Sciences", 
        "type": "DefinedTerm"
      }
    ], 
    "author": [
      {
        "affiliation": {
          "alternateName": "Universidad Aut\u00f3noma del Estado de M\u00e9xico", 
          "id": "https://www.grid.ac/institutes/grid.412872.a", 
          "name": [
            "Centro Conjunto de Investigaci\u00f3n en Qu\u00edmica Sustentable UAEM-UNAM. Universidad Aut\u00f3noma del Estado de M\u00e9xico, Carretera Toluca-Atlacomulco Km 14.5, 50200, Toluca, Estado de M\u00e9xico, Mexico", 
            "Signa S.A. de C.V., Av. Industria Automotriz No. 301, Zona Industrial Toluca, 50071, Toluca, Estado de M\u00e9xico, Mexico"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Zambrano-Huerta", 
        "givenName": "Armando", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Universidad Aut\u00f3noma del Estado de M\u00e9xico", 
          "id": "https://www.grid.ac/institutes/grid.412872.a", 
          "name": [
            "Centro Conjunto de Investigaci\u00f3n en Qu\u00edmica Sustentable UAEM-UNAM. Universidad Aut\u00f3noma del Estado de M\u00e9xico, Carretera Toluca-Atlacomulco Km 14.5, 50200, Toluca, Estado de M\u00e9xico, Mexico"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Cifuentes-Casta\u00f1eda", 
        "givenName": "Dami\u00e1n David", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Universidad Aut\u00f3noma del Estado de M\u00e9xico", 
          "id": "https://www.grid.ac/institutes/grid.412872.a", 
          "name": [
            "Centro Conjunto de Investigaci\u00f3n en Qu\u00edmica Sustentable UAEM-UNAM. Universidad Aut\u00f3noma del Estado de M\u00e9xico, Carretera Toluca-Atlacomulco Km 14.5, 50200, Toluca, Estado de M\u00e9xico, Mexico"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Bautista-Renedo", 
        "givenName": "Joanatan", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Universidad Aut\u00f3noma del Estado de M\u00e9xico", 
          "id": "https://www.grid.ac/institutes/grid.412872.a", 
          "name": [
            "Facultad de Medicina, Universidad Aut\u00f3noma del Estado de Mexico, Paseo Tollocan/Jes\u00fas Carranza s/n, 50120, Toluca, Estado de M\u00e9xico, Mexico"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Mendieta-Zer\u00f3n", 
        "givenName": "Hugo", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "name": [
            "Signa S.A. de C.V., Av. Industria Automotriz No. 301, Zona Industrial Toluca, 50071, Toluca, Estado de M\u00e9xico, Mexico"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Melgar-Fern\u00e1ndez", 
        "givenName": "Roberto Carlos", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Universidad Aut\u00f3noma del Estado de M\u00e9xico", 
          "id": "https://www.grid.ac/institutes/grid.412872.a", 
          "name": [
            "Departamento de Microbiolog\u00eda, Facultad de Qu\u00edmica, Universidad Aut\u00f3noma del Estado de Mexico, Paseo Colon/Paseo Tollocan s/n, 50120, Toluca, Estado de M\u00e9xico, Mexico"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Pav\u00f3n-Romero", 
        "givenName": "Sergio", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Universidad Aut\u00f3noma del Estado de M\u00e9xico", 
          "id": "https://www.grid.ac/institutes/grid.412872.a", 
          "name": [
            "Departamento de Microbiolog\u00eda, Facultad de Qu\u00edmica, Universidad Aut\u00f3noma del Estado de Mexico, Paseo Colon/Paseo Tollocan s/n, 50120, Toluca, Estado de M\u00e9xico, Mexico"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Morales-Rodr\u00edguez", 
        "givenName": "Macario", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Universidad Aut\u00f3noma del Estado de M\u00e9xico", 
          "id": "https://www.grid.ac/institutes/grid.412872.a", 
          "name": [
            "Centro Conjunto de Investigaci\u00f3n en Qu\u00edmica Sustentable UAEM-UNAM. Universidad Aut\u00f3noma del Estado de M\u00e9xico, Carretera Toluca-Atlacomulco Km 14.5, 50200, Toluca, Estado de M\u00e9xico, Mexico"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Frontana-Uribe", 
        "givenName": "Bernardo A.", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Universidad Aut\u00f3noma del Estado de M\u00e9xico", 
          "id": "https://www.grid.ac/institutes/grid.412872.a", 
          "name": [
            "Centro Conjunto de Investigaci\u00f3n en Qu\u00edmica Sustentable UAEM-UNAM. Universidad Aut\u00f3noma del Estado de M\u00e9xico, Carretera Toluca-Atlacomulco Km 14.5, 50200, Toluca, Estado de M\u00e9xico, Mexico"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Gonz\u00e1lez-Rivas", 
        "givenName": "Nelly", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Universidad Aut\u00f3noma del Estado de M\u00e9xico", 
          "id": "https://www.grid.ac/institutes/grid.412872.a", 
          "name": [
            "Centro Conjunto de Investigaci\u00f3n en Qu\u00edmica Sustentable UAEM-UNAM. Universidad Aut\u00f3noma del Estado de M\u00e9xico, Carretera Toluca-Atlacomulco Km 14.5, 50200, Toluca, Estado de M\u00e9xico, Mexico"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Cuevas-Ya\u00f1ez", 
        "givenName": "Erick", 
        "type": "Person"
      }
    ], 
    "citation": [
      {
        "id": "https://doi.org/10.1016/j.ejmech.2011.07.010", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1002717500"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1080/10426500490485066", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1003306562"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/cr0783479", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1003689578"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/cr0783479", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1003689578"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1186/1472-6750-2-17", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1003744395", 
          "https://doi.org/10.1186/1472-6750-2-17"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.jep.2005.03.030", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1008642800"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.jep.2005.03.030", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1008642800"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1039/c2md00205a", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1019125393"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1128/aac.00925-15", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1019842623"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.tet.2006.09.021", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1020240361"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/s0140-6736(88)92919-4", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1020382911"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/s0140-6736(88)92919-4", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1020382911"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/0960-894x(96)00363-0", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1024101670"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1039/b613014n", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1026248446"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/s0378-8741(02)00186-1", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1026483500"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.bmcl.2007.04.038", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1027038291"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.ejmech.2015.02.007", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1027710754"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1002/ejoc.200500483", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1033326267"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1002/ejoc.200500483", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1033326267"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1248/cpb.48.982", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1035044400"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.bmcl.2008.12.026", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1035120301"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1080/00397910802563420", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1035559644"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1002/asia.201100432", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1036239467"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1128/aac.32.1.1", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1037736786"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/s12154-013-0103-8", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1040420540", 
          "https://doi.org/10.1007/s12154-013-0103-8"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1128/aac.00291-11", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1040700319"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1128/aac.30.3.418", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1042502699"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1128/aac.27.5.832", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1043841590"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.bmcl.2012.02.042", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1044534868"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.2165/11596540-000000000-00000", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1045362272", 
          "https://doi.org/10.2165/11596540-000000000-00000"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.3390/molecules15064129", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1046084440"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.3390/molecules15064129", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1046084440"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.bmcl.2007.11.111", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1048339106"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/cr200409f", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1051585649"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.3390/molecules190811333", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1052762348"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.3390/molecules190811333", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1052762348"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/jm049856v", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055949309"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/jm049856v", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055949309"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.14233/ajchem.2014.15956", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1067222136"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.14800/ics.95", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1067370791"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.7326/0003-4819-109-3-177", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1073693061"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1128/aac.43.9.2116", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1074515051"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1093/oxfordjournals.aje.a118408", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1083592874"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.drudis.2017.05.014", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1090325155"
        ], 
        "type": "CreativeWork"
      }
    ], 
    "datePublished": "2019-04", 
    "datePublishedReg": "2019-04-01", 
    "description": "A novel series of 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivatives was synthesized from 1-aryl-1,3-diazidopropan-2-ol derivatives and diverse alkynes using copper catalyzed azide-alkyne cycloaddition in the key step. Most of synthesized compounds showed high activity against Candida spp. strains at a 0.04\u20130.5 \u03bcg/mL concentration range compared to Itraconazole and Fluconazole (MIC 2.56 and 1.28 \u03bcg/mL, respectively), which were used as reference compounds. A 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivative (R1 = F and R2 = cyclopropyl) displayed an outstanding selectivity against Candida albicans and Candida krusei (MIC = 0.0075 \u00b5g/mL). Moreover, Artemia salina bioassay on 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivatives revealed low toxicity in this kind of compounds. In addition, molecular docking studies suggest good binding affinity of halogen atoms in some 1-aryl-1,3-diazidopropan-2-ol derivatives to HEME group present in 14-alpha demethylase (CYP51), which might explain the high antifungal activity found in these compounds.", 
    "genre": "research_article", 
    "id": "sg:pub.10.1007/s00044-019-02317-5", 
    "inLanguage": [
      "en"
    ], 
    "isAccessibleForFree": false, 
    "isPartOf": [
      {
        "id": "sg:journal.1102690", 
        "issn": [
          "1054-2523", 
          "1554-8120"
        ], 
        "name": "Medicinal Chemistry Research", 
        "type": "Periodical"
      }, 
      {
        "issueNumber": "4", 
        "type": "PublicationIssue"
      }, 
      {
        "type": "PublicationVolume", 
        "volumeNumber": "28"
      }
    ], 
    "name": "Synthesis and in vitro biological evaluation of 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivatives as antifungal compounds fluconazole analogues", 
    "pagination": "571-579", 
    "productId": [
      {
        "name": "readcube_id", 
        "type": "PropertyValue", 
        "value": [
          "3f8749f988638b7ec32fd84910bdd44ad31669fe088c9f1c10a6a2a7f43728e0"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1007/s00044-019-02317-5"
        ]
      }, 
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1112672564"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1007/s00044-019-02317-5", 
      "https://app.dimensions.ai/details/publication/pub.1112672564"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2019-04-11T13:17", 
    "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
    "sdPublisher": {
      "name": "Springer Nature - SN SciGraph project", 
      "type": "Organization"
    }, 
    "sdSource": "s3://com-uberresearch-data-dimensions-target-20181106-alternative/cleanup/v134/2549eaecd7973599484d7c17b260dba0a4ecb94b/merge/v9/a6c9fde33151104705d4d7ff012ea9563521a3ce/jats-lookup/v90/0000000368_0000000368/records_78935_00000001.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "https://link.springer.com/10.1007%2Fs00044-019-02317-5"
  }
]
 

Download the RDF metadata as:  json-ld nt turtle xml License info

HOW TO GET THIS DATA PROGRAMMATICALLY:

JSON-LD is a popular format for linked data which is fully compatible with JSON.

curl -H 'Accept: application/ld+json' 'https://scigraph.springernature.com/pub.10.1007/s00044-019-02317-5'

N-Triples is a line-based linked data format ideal for batch operations.

curl -H 'Accept: application/n-triples' 'https://scigraph.springernature.com/pub.10.1007/s00044-019-02317-5'

Turtle is a human-readable linked data format.

curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1007/s00044-019-02317-5'

RDF/XML is a standard XML format for linked data.

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1007/s00044-019-02317-5'


 

This table displays all metadata directly associated to this object as RDF triples.

233 TRIPLES      21 PREDICATES      64 URIs      19 LITERALS      7 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1007/s00044-019-02317-5 schema:about anzsrc-for:03
2 anzsrc-for:0302
3 schema:author N24e191e2b6684188aab253aee76c6809
4 schema:citation sg:pub.10.1007/s12154-013-0103-8
5 sg:pub.10.1186/1472-6750-2-17
6 sg:pub.10.2165/11596540-000000000-00000
7 https://doi.org/10.1002/asia.201100432
8 https://doi.org/10.1002/ejoc.200500483
9 https://doi.org/10.1016/0960-894x(96)00363-0
10 https://doi.org/10.1016/j.bmcl.2007.04.038
11 https://doi.org/10.1016/j.bmcl.2007.11.111
12 https://doi.org/10.1016/j.bmcl.2008.12.026
13 https://doi.org/10.1016/j.bmcl.2012.02.042
14 https://doi.org/10.1016/j.drudis.2017.05.014
15 https://doi.org/10.1016/j.ejmech.2011.07.010
16 https://doi.org/10.1016/j.ejmech.2015.02.007
17 https://doi.org/10.1016/j.jep.2005.03.030
18 https://doi.org/10.1016/j.tet.2006.09.021
19 https://doi.org/10.1016/s0140-6736(88)92919-4
20 https://doi.org/10.1016/s0378-8741(02)00186-1
21 https://doi.org/10.1021/cr0783479
22 https://doi.org/10.1021/cr200409f
23 https://doi.org/10.1021/jm049856v
24 https://doi.org/10.1039/b613014n
25 https://doi.org/10.1039/c2md00205a
26 https://doi.org/10.1080/00397910802563420
27 https://doi.org/10.1080/10426500490485066
28 https://doi.org/10.1093/oxfordjournals.aje.a118408
29 https://doi.org/10.1128/aac.00291-11
30 https://doi.org/10.1128/aac.00925-15
31 https://doi.org/10.1128/aac.27.5.832
32 https://doi.org/10.1128/aac.30.3.418
33 https://doi.org/10.1128/aac.32.1.1
34 https://doi.org/10.1128/aac.43.9.2116
35 https://doi.org/10.1248/cpb.48.982
36 https://doi.org/10.14233/ajchem.2014.15956
37 https://doi.org/10.14800/ics.95
38 https://doi.org/10.3390/molecules15064129
39 https://doi.org/10.3390/molecules190811333
40 https://doi.org/10.7326/0003-4819-109-3-177
41 schema:datePublished 2019-04
42 schema:datePublishedReg 2019-04-01
43 schema:description A novel series of 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivatives was synthesized from 1-aryl-1,3-diazidopropan-2-ol derivatives and diverse alkynes using copper catalyzed azide-alkyne cycloaddition in the key step. Most of synthesized compounds showed high activity against Candida spp. strains at a 0.04–0.5 μg/mL concentration range compared to Itraconazole and Fluconazole (MIC 2.56 and 1.28 μg/mL, respectively), which were used as reference compounds. A 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivative (R1 = F and R2 = cyclopropyl) displayed an outstanding selectivity against Candida albicans and Candida krusei (MIC = 0.0075 µg/mL). Moreover, Artemia salina bioassay on 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivatives revealed low toxicity in this kind of compounds. In addition, molecular docking studies suggest good binding affinity of halogen atoms in some 1-aryl-1,3-diazidopropan-2-ol derivatives to HEME group present in 14-alpha demethylase (CYP51), which might explain the high antifungal activity found in these compounds.
44 schema:genre research_article
45 schema:inLanguage en
46 schema:isAccessibleForFree false
47 schema:isPartOf N1f5103eb0cc54dc9a10907dcad821559
48 Ne18274eaa6434ab18fa69b7bad04ae20
49 sg:journal.1102690
50 schema:name Synthesis and in vitro biological evaluation of 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivatives as antifungal compounds fluconazole analogues
51 schema:pagination 571-579
52 schema:productId N5e72f3bc769b48139b2308d835e77d35
53 N7ebfa23000204c0e9b04ae97d679323a
54 Nc49bca4cce2b4653b094fd22992f3c7c
55 schema:sameAs https://app.dimensions.ai/details/publication/pub.1112672564
56 https://doi.org/10.1007/s00044-019-02317-5
57 schema:sdDatePublished 2019-04-11T13:17
58 schema:sdLicense https://scigraph.springernature.com/explorer/license/
59 schema:sdPublisher Nc705951eaefc4e35ba89ab0d811b0899
60 schema:url https://link.springer.com/10.1007%2Fs00044-019-02317-5
61 sgo:license sg:explorer/license/
62 sgo:sdDataset articles
63 rdf:type schema:ScholarlyArticle
64 N062647643e54483a80642959b02057ce rdf:first N9a075db18f614f068d362b4ec643f9e8
65 rdf:rest N1688a0b393bd4a8eb49a10f9efc11947
66 N1688a0b393bd4a8eb49a10f9efc11947 rdf:first N7d2cdd0f207e40e0861b6df837a65eef
67 rdf:rest N8172850d1e844abb93ff74827968fd1e
68 N1b1846ec96e64859a355a1dbfea6d4f0 schema:affiliation https://www.grid.ac/institutes/grid.412872.a
69 schema:familyName Cuevas-Yañez
70 schema:givenName Erick
71 rdf:type schema:Person
72 N1f5103eb0cc54dc9a10907dcad821559 schema:issueNumber 4
73 rdf:type schema:PublicationIssue
74 N24e191e2b6684188aab253aee76c6809 rdf:first Nd63da63490c944e0bc1352fbf4defaa6
75 rdf:rest N062647643e54483a80642959b02057ce
76 N4dc8786e34bb404bab6f14dd1e6d8d0d schema:affiliation https://www.grid.ac/institutes/grid.412872.a
77 schema:familyName Frontana-Uribe
78 schema:givenName Bernardo A.
79 rdf:type schema:Person
80 N5835e40887de412dafbf9f271f787de7 rdf:first N1b1846ec96e64859a355a1dbfea6d4f0
81 rdf:rest rdf:nil
82 N5e72f3bc769b48139b2308d835e77d35 schema:name dimensions_id
83 schema:value pub.1112672564
84 rdf:type schema:PropertyValue
85 N62ac6a799f62426196896d6b3d29d39a rdf:first N4dc8786e34bb404bab6f14dd1e6d8d0d
86 rdf:rest Nc497b2643a6147d581ff7b304a1444e6
87 N70e7e809f2064337bab488e8302ad454 schema:affiliation https://www.grid.ac/institutes/grid.412872.a
88 schema:familyName Pavón-Romero
89 schema:givenName Sergio
90 rdf:type schema:Person
91 N75e2d292272b49ddb154e4a8bc88d47b rdf:first N70e7e809f2064337bab488e8302ad454
92 rdf:rest Nec370952ce764709a3a8e70559f78c0e
93 N7d2cdd0f207e40e0861b6df837a65eef schema:affiliation https://www.grid.ac/institutes/grid.412872.a
94 schema:familyName Bautista-Renedo
95 schema:givenName Joanatan
96 rdf:type schema:Person
97 N7ebfa23000204c0e9b04ae97d679323a schema:name readcube_id
98 schema:value 3f8749f988638b7ec32fd84910bdd44ad31669fe088c9f1c10a6a2a7f43728e0
99 rdf:type schema:PropertyValue
100 N8172850d1e844abb93ff74827968fd1e rdf:first N8fb01078e9474674a02aa11523d01c7d
101 rdf:rest Ndcaf0fd2584344f78b45efa082bac6db
102 N8fb01078e9474674a02aa11523d01c7d schema:affiliation https://www.grid.ac/institutes/grid.412872.a
103 schema:familyName Mendieta-Zerón
104 schema:givenName Hugo
105 rdf:type schema:Person
106 N900c50e7cd7f4779a60ed86a123f6676 schema:name Signa S.A. de C.V., Av. Industria Automotriz No. 301, Zona Industrial Toluca, 50071, Toluca, Estado de México, Mexico
107 rdf:type schema:Organization
108 N9a075db18f614f068d362b4ec643f9e8 schema:affiliation https://www.grid.ac/institutes/grid.412872.a
109 schema:familyName Cifuentes-Castañeda
110 schema:givenName Damián David
111 rdf:type schema:Person
112 Nb8c31787779e4bacb2f08e7b7593342a schema:affiliation https://www.grid.ac/institutes/grid.412872.a
113 schema:familyName González-Rivas
114 schema:givenName Nelly
115 rdf:type schema:Person
116 Nc1f7a4938b3d47fe8985fb86c475991c schema:affiliation N900c50e7cd7f4779a60ed86a123f6676
117 schema:familyName Melgar-Fernández
118 schema:givenName Roberto Carlos
119 rdf:type schema:Person
120 Nc497b2643a6147d581ff7b304a1444e6 rdf:first Nb8c31787779e4bacb2f08e7b7593342a
121 rdf:rest N5835e40887de412dafbf9f271f787de7
122 Nc49bca4cce2b4653b094fd22992f3c7c schema:name doi
123 schema:value 10.1007/s00044-019-02317-5
124 rdf:type schema:PropertyValue
125 Nc705951eaefc4e35ba89ab0d811b0899 schema:name Springer Nature - SN SciGraph project
126 rdf:type schema:Organization
127 Nd63da63490c944e0bc1352fbf4defaa6 schema:affiliation https://www.grid.ac/institutes/grid.412872.a
128 schema:familyName Zambrano-Huerta
129 schema:givenName Armando
130 rdf:type schema:Person
131 Ndcaf0fd2584344f78b45efa082bac6db rdf:first Nc1f7a4938b3d47fe8985fb86c475991c
132 rdf:rest N75e2d292272b49ddb154e4a8bc88d47b
133 Ne18274eaa6434ab18fa69b7bad04ae20 schema:volumeNumber 28
134 rdf:type schema:PublicationVolume
135 Ne757f7cc1a6a401ba7377502ed8a928f schema:affiliation https://www.grid.ac/institutes/grid.412872.a
136 schema:familyName Morales-Rodríguez
137 schema:givenName Macario
138 rdf:type schema:Person
139 Nec370952ce764709a3a8e70559f78c0e rdf:first Ne757f7cc1a6a401ba7377502ed8a928f
140 rdf:rest N62ac6a799f62426196896d6b3d29d39a
141 anzsrc-for:03 schema:inDefinedTermSet anzsrc-for:
142 schema:name Chemical Sciences
143 rdf:type schema:DefinedTerm
144 anzsrc-for:0302 schema:inDefinedTermSet anzsrc-for:
145 schema:name Inorganic Chemistry
146 rdf:type schema:DefinedTerm
147 sg:journal.1102690 schema:issn 1054-2523
148 1554-8120
149 schema:name Medicinal Chemistry Research
150 rdf:type schema:Periodical
151 sg:pub.10.1007/s12154-013-0103-8 schema:sameAs https://app.dimensions.ai/details/publication/pub.1040420540
152 https://doi.org/10.1007/s12154-013-0103-8
153 rdf:type schema:CreativeWork
154 sg:pub.10.1186/1472-6750-2-17 schema:sameAs https://app.dimensions.ai/details/publication/pub.1003744395
155 https://doi.org/10.1186/1472-6750-2-17
156 rdf:type schema:CreativeWork
157 sg:pub.10.2165/11596540-000000000-00000 schema:sameAs https://app.dimensions.ai/details/publication/pub.1045362272
158 https://doi.org/10.2165/11596540-000000000-00000
159 rdf:type schema:CreativeWork
160 https://doi.org/10.1002/asia.201100432 schema:sameAs https://app.dimensions.ai/details/publication/pub.1036239467
161 rdf:type schema:CreativeWork
162 https://doi.org/10.1002/ejoc.200500483 schema:sameAs https://app.dimensions.ai/details/publication/pub.1033326267
163 rdf:type schema:CreativeWork
164 https://doi.org/10.1016/0960-894x(96)00363-0 schema:sameAs https://app.dimensions.ai/details/publication/pub.1024101670
165 rdf:type schema:CreativeWork
166 https://doi.org/10.1016/j.bmcl.2007.04.038 schema:sameAs https://app.dimensions.ai/details/publication/pub.1027038291
167 rdf:type schema:CreativeWork
168 https://doi.org/10.1016/j.bmcl.2007.11.111 schema:sameAs https://app.dimensions.ai/details/publication/pub.1048339106
169 rdf:type schema:CreativeWork
170 https://doi.org/10.1016/j.bmcl.2008.12.026 schema:sameAs https://app.dimensions.ai/details/publication/pub.1035120301
171 rdf:type schema:CreativeWork
172 https://doi.org/10.1016/j.bmcl.2012.02.042 schema:sameAs https://app.dimensions.ai/details/publication/pub.1044534868
173 rdf:type schema:CreativeWork
174 https://doi.org/10.1016/j.drudis.2017.05.014 schema:sameAs https://app.dimensions.ai/details/publication/pub.1090325155
175 rdf:type schema:CreativeWork
176 https://doi.org/10.1016/j.ejmech.2011.07.010 schema:sameAs https://app.dimensions.ai/details/publication/pub.1002717500
177 rdf:type schema:CreativeWork
178 https://doi.org/10.1016/j.ejmech.2015.02.007 schema:sameAs https://app.dimensions.ai/details/publication/pub.1027710754
179 rdf:type schema:CreativeWork
180 https://doi.org/10.1016/j.jep.2005.03.030 schema:sameAs https://app.dimensions.ai/details/publication/pub.1008642800
181 rdf:type schema:CreativeWork
182 https://doi.org/10.1016/j.tet.2006.09.021 schema:sameAs https://app.dimensions.ai/details/publication/pub.1020240361
183 rdf:type schema:CreativeWork
184 https://doi.org/10.1016/s0140-6736(88)92919-4 schema:sameAs https://app.dimensions.ai/details/publication/pub.1020382911
185 rdf:type schema:CreativeWork
186 https://doi.org/10.1016/s0378-8741(02)00186-1 schema:sameAs https://app.dimensions.ai/details/publication/pub.1026483500
187 rdf:type schema:CreativeWork
188 https://doi.org/10.1021/cr0783479 schema:sameAs https://app.dimensions.ai/details/publication/pub.1003689578
189 rdf:type schema:CreativeWork
190 https://doi.org/10.1021/cr200409f schema:sameAs https://app.dimensions.ai/details/publication/pub.1051585649
191 rdf:type schema:CreativeWork
192 https://doi.org/10.1021/jm049856v schema:sameAs https://app.dimensions.ai/details/publication/pub.1055949309
193 rdf:type schema:CreativeWork
194 https://doi.org/10.1039/b613014n schema:sameAs https://app.dimensions.ai/details/publication/pub.1026248446
195 rdf:type schema:CreativeWork
196 https://doi.org/10.1039/c2md00205a schema:sameAs https://app.dimensions.ai/details/publication/pub.1019125393
197 rdf:type schema:CreativeWork
198 https://doi.org/10.1080/00397910802563420 schema:sameAs https://app.dimensions.ai/details/publication/pub.1035559644
199 rdf:type schema:CreativeWork
200 https://doi.org/10.1080/10426500490485066 schema:sameAs https://app.dimensions.ai/details/publication/pub.1003306562
201 rdf:type schema:CreativeWork
202 https://doi.org/10.1093/oxfordjournals.aje.a118408 schema:sameAs https://app.dimensions.ai/details/publication/pub.1083592874
203 rdf:type schema:CreativeWork
204 https://doi.org/10.1128/aac.00291-11 schema:sameAs https://app.dimensions.ai/details/publication/pub.1040700319
205 rdf:type schema:CreativeWork
206 https://doi.org/10.1128/aac.00925-15 schema:sameAs https://app.dimensions.ai/details/publication/pub.1019842623
207 rdf:type schema:CreativeWork
208 https://doi.org/10.1128/aac.27.5.832 schema:sameAs https://app.dimensions.ai/details/publication/pub.1043841590
209 rdf:type schema:CreativeWork
210 https://doi.org/10.1128/aac.30.3.418 schema:sameAs https://app.dimensions.ai/details/publication/pub.1042502699
211 rdf:type schema:CreativeWork
212 https://doi.org/10.1128/aac.32.1.1 schema:sameAs https://app.dimensions.ai/details/publication/pub.1037736786
213 rdf:type schema:CreativeWork
214 https://doi.org/10.1128/aac.43.9.2116 schema:sameAs https://app.dimensions.ai/details/publication/pub.1074515051
215 rdf:type schema:CreativeWork
216 https://doi.org/10.1248/cpb.48.982 schema:sameAs https://app.dimensions.ai/details/publication/pub.1035044400
217 rdf:type schema:CreativeWork
218 https://doi.org/10.14233/ajchem.2014.15956 schema:sameAs https://app.dimensions.ai/details/publication/pub.1067222136
219 rdf:type schema:CreativeWork
220 https://doi.org/10.14800/ics.95 schema:sameAs https://app.dimensions.ai/details/publication/pub.1067370791
221 rdf:type schema:CreativeWork
222 https://doi.org/10.3390/molecules15064129 schema:sameAs https://app.dimensions.ai/details/publication/pub.1046084440
223 rdf:type schema:CreativeWork
224 https://doi.org/10.3390/molecules190811333 schema:sameAs https://app.dimensions.ai/details/publication/pub.1052762348
225 rdf:type schema:CreativeWork
226 https://doi.org/10.7326/0003-4819-109-3-177 schema:sameAs https://app.dimensions.ai/details/publication/pub.1073693061
227 rdf:type schema:CreativeWork
228 https://www.grid.ac/institutes/grid.412872.a schema:alternateName Universidad Autónoma del Estado de México
229 schema:name Centro Conjunto de Investigación en Química Sustentable UAEM-UNAM. Universidad Autónoma del Estado de México, Carretera Toluca-Atlacomulco Km 14.5, 50200, Toluca, Estado de México, Mexico
230 Departamento de Microbiología, Facultad de Química, Universidad Autónoma del Estado de Mexico, Paseo Colon/Paseo Tollocan s/n, 50120, Toluca, Estado de México, Mexico
231 Facultad de Medicina, Universidad Autónoma del Estado de Mexico, Paseo Tollocan/Jesús Carranza s/n, 50120, Toluca, Estado de México, Mexico
232 Signa S.A. de C.V., Av. Industria Automotriz No. 301, Zona Industrial Toluca, 50071, Toluca, Estado de México, Mexico
233 rdf:type schema:Organization
 




Preview window. Press ESC to close (or click here)


...