Design and synthesis of 1H-1,2,3-triazoles derived from econazole as antitubercular agents

Suhyun Kim, Sang Nae Cho, Taegwon Oh, Pilho Kim

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Econazole has been known to be active against Mycobacterium tuberculosis. We have designed and synthesized 1H-1,2,3-triazoles derived from econazole as antitubercular agents. The majority of triazole derivatives have been prepared by microwave-assisted click chemistry. It turned out that all of the prepared triazoles had no antifungal activities. However, most of the hydroxy-triazoles (6a and 10) apparently turned out to have antitubercular activities. Overall, hydroxy-triazoles 10 were more active than their corresponding ether-triazoles 11. While the MIC value of hydroxy-triazole 10d was as good as econazole (16 μg/mL), the MIC value of 10a was two-fold more active than econazole, suggesting that this 1H-1,2,3-triazole scaffold (3) could be further optimized to develop Mtb specific agents.

Original languageEnglish
Pages (from-to)6844-6847
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number22
DOIs
Publication statusPublished - 2012 Nov 15

Fingerprint

Econazole
Antitubercular Agents
Triazoles
Click Chemistry
Microwaves
Mycobacterium tuberculosis
Scaffolds
Ether
Derivatives

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

@article{60bbeb0b1ccf41998a5a3e8000927f59,
title = "Design and synthesis of 1H-1,2,3-triazoles derived from econazole as antitubercular agents",
abstract = "Econazole has been known to be active against Mycobacterium tuberculosis. We have designed and synthesized 1H-1,2,3-triazoles derived from econazole as antitubercular agents. The majority of triazole derivatives have been prepared by microwave-assisted click chemistry. It turned out that all of the prepared triazoles had no antifungal activities. However, most of the hydroxy-triazoles (6a and 10) apparently turned out to have antitubercular activities. Overall, hydroxy-triazoles 10 were more active than their corresponding ether-triazoles 11. While the MIC value of hydroxy-triazole 10d was as good as econazole (16 μg/mL), the MIC value of 10a was two-fold more active than econazole, suggesting that this 1H-1,2,3-triazole scaffold (3) could be further optimized to develop Mtb specific agents.",
author = "Suhyun Kim and Cho, {Sang Nae} and Taegwon Oh and Pilho Kim",
year = "2012",
month = "11",
day = "15",
doi = "10.1016/j.bmcl.2012.09.041",
language = "English",
volume = "22",
pages = "6844--6847",
journal = "Bioorganic and Medicinal Chemistry Letters",
issn = "0960-894X",
publisher = "Elsevier Limited",
number = "22",

}

Design and synthesis of 1H-1,2,3-triazoles derived from econazole as antitubercular agents. / Kim, Suhyun; Cho, Sang Nae; Oh, Taegwon; Kim, Pilho.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 22, No. 22, 15.11.2012, p. 6844-6847.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Design and synthesis of 1H-1,2,3-triazoles derived from econazole as antitubercular agents

AU - Kim, Suhyun

AU - Cho, Sang Nae

AU - Oh, Taegwon

AU - Kim, Pilho

PY - 2012/11/15

Y1 - 2012/11/15

N2 - Econazole has been known to be active against Mycobacterium tuberculosis. We have designed and synthesized 1H-1,2,3-triazoles derived from econazole as antitubercular agents. The majority of triazole derivatives have been prepared by microwave-assisted click chemistry. It turned out that all of the prepared triazoles had no antifungal activities. However, most of the hydroxy-triazoles (6a and 10) apparently turned out to have antitubercular activities. Overall, hydroxy-triazoles 10 were more active than their corresponding ether-triazoles 11. While the MIC value of hydroxy-triazole 10d was as good as econazole (16 μg/mL), the MIC value of 10a was two-fold more active than econazole, suggesting that this 1H-1,2,3-triazole scaffold (3) could be further optimized to develop Mtb specific agents.

AB - Econazole has been known to be active against Mycobacterium tuberculosis. We have designed and synthesized 1H-1,2,3-triazoles derived from econazole as antitubercular agents. The majority of triazole derivatives have been prepared by microwave-assisted click chemistry. It turned out that all of the prepared triazoles had no antifungal activities. However, most of the hydroxy-triazoles (6a and 10) apparently turned out to have antitubercular activities. Overall, hydroxy-triazoles 10 were more active than their corresponding ether-triazoles 11. While the MIC value of hydroxy-triazole 10d was as good as econazole (16 μg/mL), the MIC value of 10a was two-fold more active than econazole, suggesting that this 1H-1,2,3-triazole scaffold (3) could be further optimized to develop Mtb specific agents.

UR - http://www.scopus.com/inward/record.url?scp=84867868400&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84867868400&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2012.09.041

DO - 10.1016/j.bmcl.2012.09.041

M3 - Article

C2 - 23058885

AN - SCOPUS:84867868400

VL - 22

SP - 6844

EP - 6847

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 22

ER -