Antimycobacterial activity of new 3-substituted 5-(pyridin-4-yl)-3H-1,3,4-oxadiazol-2-one and 2-thione derivatives.: Preliminary molecular modeling investigations

被引：117
|
作者：
Mamolo, MG
Zampieri, D
Vio, L
Fermeglia, M
Ferrone, M
Pricl, S
Scialino, G
Banfi, E
机构：
[1] Univ Trieste, Dept Pharmaceut Sci, I-34127 Trieste, Italy
[2] Univ Trieste, Dept Chem Environm & Raw Mat Engn, I-34127 Trieste, Italy
[3] Univ Trieste, Dept Biomed Sci, Microbiol Sect, I-34127 Trieste, Italy
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2005年 / 13卷 / 11期
关键词：
antimycobacterial; synthesis; biological activity; molecular modeling;
D O I：
10.1016/j.bmc.2005.03.013
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
3H-1,3,4-Oxadiazole-2-thione and 3H-1,3,4-oxadiazol-2-one derivatives were synthesized and tested for their in vitro antimycobacterial activity. Oxadiazolone derivatives showed an interesting antimycobacterial activity against the tested strain of Myeobacterium tuberculosis H(37)Rv, whereas the corresponding thione derivatives were devoid of activity. Molecular modeling investigations showed that the active compounds may interact at the active site of the mycobacterial cytochrome P450-dependent sterol 14 alpha-demethylase in the sterol biosynthesis pathway and that their binding free energy values are in agreement with their MIC values. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3797 / 3809
页数：13
相关论文
共 50 条
  • [41] Synthesis and antitumoral activity of novel 3-(2-substituted-1,3,4-oxadiazol-5-yl) and 3-(5-substituted-1,2,4-triazol-3-yl) β-carboline derivatives
    Nazari Formagio, Anelise S.
    Duesman Tonin, Lilian T.
    Foglio, Mary Ann
    Madjarof, Christiana
    de Carvalho, Joao Ernesto
    da Costa, Willian Ferreira
    Cardoso, Flavia P.
    Sarragiotto, Maria Helena
    BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (22) : 9660 - 9667
  • [42] CoII-catalysed synthesis of N-(4-methoxyphenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine hemihydrochloride monohydrate
    Gautam, Ram N.
    Sonkar, Sankatha P.
    Yadav, Shailendra
    Nath, Paras
    Bharty, Manoj K.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2024, 80 : 351 - +
  • [43] Synthesis, Biological Activity, and Computational Study of 1-[5-(4-Methylthiazol-5-yl)-2-phenyl-1,3,4-oxadiazol-3(2H)-yl]ethanone Derivatives
    Darekar, Nirmala R.
    Takate, Sushama J.
    Akolkar, Hemant N.
    Shaikh, Mubarak H.
    Khedkar, Vijay M.
    Karale, Bhausaheb K.
    Mhaske, Sadhana D.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2022, 92 (08) : 1511 - 1518
  • [44] Synthesis of 5-substituted-3H-[1,3,4]-oxadiazol-2-one derivatives: a carbon dioxide route (CDR)
    Brahmayya, M.
    Dai, Shenghong A.
    Suen, S. -Y.
    RSC ADVANCES, 2015, 5 (80): : 65351 - 65357
  • [45] Synthesis and antimycobacterial activity of [5-(pyridin-2-yl)-1,3,4-thiadiazol-2-ylthio]acetic acid arylidene-hydrazide derivatives
    Mamolo, MG
    Falagiani, V
    Zampieri, D
    Vio, L
    Banfi, E
    FARMACO, 2001, 56 (08): : 587 - 592
  • [46] Synthesis and SAR studies of 5-(pyridin-4-yl)-1,3,4-thiadiazol-2-amine derivatives as potent inhibitors of Bloom helicase
    Rosenthal, Andrew S.
    Dexheimer, Thomas S.
    Gileadi, Opher
    Nguyen, Giang H.
    Chu, Wai Kit
    Hickson, Ian D.
    Jadhav, Ajit
    Simeonov, Anton
    Maloney, David J.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (20) : 5660 - 5666
  • [47] Synthesis, Crystal Structure and Antifungal Activity of 2-((2-Fluorobenzyl)thio)-5-(pyridin-4-yl)-1,3,4-oxadiazole
    Sun Guo-Xiang
    Shi Yan-Xia
    Zhai Zhi-Wen
    Sun Zhao-Hui
    Weng Jian-Quan
    Tan Cheng-Xia
    Liu Xing-Hai
    Li Bao-Ju
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2016, 35 (12) : 1855 - 1859
  • [48] Synthesis,Crystal Structure and Antifungal Activity of 2-((2-Fluorobenzyl)thio)-5-(pyridin-4-yl)-1,3,4-oxadiazole
    孙国香
    石延霞
    翟志文
    孙召慧
    翁建全
    谭成侠
    刘幸海
    李宝聚
    结构化学, 2016, 35 (12) : 1855 - 1859
  • [49] THE SYNTHESIS OF HETEROCYCLES .9. REACTIONS OF 3-SUBSTITUTED 5-TRIFLUOROMETHYL-1,3,4-OXADIAZOL-2(3H)-ONE WITH NUCLEOPHILES
    KRISTINSSON, H
    WINKLER, T
    MOLLENKOPF, M
    HELVETICA CHIMICA ACTA, 1986, 69 (02) : 333 - 339
  • [50] SYNTHESIS OF 2-(SUBSTITUTED PHENYL)-3-[5-(2-OXO-2H-CHROMEN-3-YL)-1,3,4-OXADIAZOL-2-YL]-1,3-THIAZOLIDIN-4-ONES WITH ANTIMICROBIAL ACTIVITY
    Bhat, Mashooq A.
    Al-Omar, Mohammed A.
    Siddiqui, Nadeem
    ACTA POLONIAE PHARMACEUTICA, 2011, 68 (02): : 295 - 299
12345