Synthesis and in vitro leishmanicidal activity of 2-(1-methyl-5-nitro-1H-imidazol-2-yl)-5-substituted-1,3,4-thiadiazole derivatives

被引：62
|
作者：
Foroumadi, A [1 ]
Emami, S
Pournourmohammadi, S
Kharazmi, A
Shafiee, A
机构：
[1] Univ Tehran Med Sci, Dept Med Chem, Tehran 14174, Iran
[2] Univ Tehran Med Sci, Pharmaceut Sci Res Ctr, Tehran 14174, Iran
[3] Kerman Univ Med Sci, Dept Med Chem, Fac Pharm, Kreman 76351, Iran
[4] Mazandaran Univ Med Sci, Fac Pharm, Dept Med Chem, Sari, Iran
[5] LICA Pharmaceut, DK-2100 Copenhagen, Denmark
来源：
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2005年 / 40卷 / 12期
关键词：
5-nitro-1H-imidazole; 1,3,4-thiadiazole; Leishmania major; anti-promastigote activity;
D O I：
10.1016/j.ejmech.2005.07.002
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A series of 2-(1-methyl-5-nitroimidazol-2-yl)-5-(1-piperazinyl, 1-piperidinyl and 1-morpholinyl)-1,3,4-thiadiazoles (3a-g) were synthesized and evaluated for in vitro leishmanicidal activity against Leishmania major promastigotes. The leishmanicidal data revealed that compounds 3a-g had strong and much better leishmanicidal activity than the reference drug pentostam. Compound 3c (piperazine analog) was the most active compound (IC(50) = 0. 19 mu M). (c) 2005 Elsevier SAS. All rights reserved.
引用
收藏
页码：1346 / 1350
页数：5
相关论文
共 50 条
  • [21] 1,3,4-thiadiazole derivatives .5. Heteropolynuclear complexes of 2-amino-5-mercapto-1,3,4-thiadiazole
    Brezeanu, M
    Olar, R
    Meghea, A
    Stanica, N
    Supuran, CT
    REVUE ROUMAINE DE CHIMIE, 1996, 41 (1-2) : 103 - 107
  • [22] Synthesis of Novel 2-(2-Methylsulfonyl-1-methyl-1H-imidazol-5-yl)-5-(alkylsulfonyl)-1,3,4-thiadiazoles
    Javidnia, Azita
    Akbarzadeh, Tahmineh
    Firoozpour, Loghman
    Khoobi, Mehdi
    Shafiee, Abbas
    Foroumadi, Alireza
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 48 (02) : 454 - 457
  • [23] Molluscicidal and Schistosomicidal Activities of 2-(1H-Pyrazol-1-yl)-1,3,4-thiadiazole Derivatives
    Rangel, Leonardo da Silva
    Gonzaga, Daniel Tadeu Gomes
    da Silva, Ana Claudia Rodrigues
    von Ranke, Natalia Lindmar
    Rodrigues, Carlos Rangel
    dos Santos, Jose Augusto Albuquerque
    Boechat, Nubia
    Gomes, Keyla Nunes Farias
    Teixeira, Guilherme Pegas
    Faria, Robson Xavier
    PHARMACEUTICALS, 2025, 18 (03)
  • [24] 5-[(2-Methyl-4-nitro-1H-imidazol-1-yl)-methyl]-1,3,4-thiadiazol-2-amine
    Usha, M. K.
    Kumar, S. Madan
    Jois, H. S. Vidyashree
    Kalluraya, B.
    Lokanath, N. K.
    Reyannasiddaiah, D.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O1825 - +
  • [25] SYNTHESES OF 2-(METHYL-4-NITRO-2-PYRROLYL)-5-SUBSTITUTED-1,3,4-THIADIAZOLES AND 1,3,4-OXADIAZOLES
    SHAFIEE, A
    FIROOZI, F
    JAVIDNIA, K
    KAMALI, M
    FOOLADI, A
    FROOMADI, A
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1994, 95-6 (1-4) : 471 - 472
  • [26] 2-(2-Methyl-5-nitro-1H-imidazol-1-yl)-ethyl 2-nitrobenzoate
    Khan, Sher Bahadar
    Anis, Itrat
    Singh, Kuldip
    Shah, Muhammad Raza
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O548 - U4413
  • [27] 2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-bromobenzoate
    Zeb, Aurang
    Yousuf, Sammer
    Basha, Fatima Z.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O1218 - +
  • [28] Synthesis and antinociceptive activity of 2-[(2-oxobenzothiazolin-3-yl) methyl]-5-aminoalkyl/aryl-1,3,4-thiadiazole
    Önkol, T
    Çakir, B
    Sahin, MF
    Yildirim, E
    Erol, K
    TURKISH JOURNAL OF CHEMISTRY, 2004, 28 (04) : 461 - 468
  • [29] Novel immunomodulatory function of 1,3,4-thiadiazole derivatives with leishmanicidal activity
    Pourrajab, Fatemeh
    Forouzannia, Seyed Khalil
    Tabatabaee, Seyed Ahmad
    JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2012, 67 (08) : 1968 - 1978
  • [30] Synthesis and in vitro antifungal activity of 2-aryl-5-phenylsulfonyl-1,3,4-thiadiazole derivatives
    Foroumadi, A
    Daneshtalab, M
    Shafiee, A
    ARZNEIMITTEL-FORSCHUNG-DRUG RESEARCH, 1999, 49 (12): : 1035 - 1038
12345