Synthesis of metronidazole based thiazolidinone analogs as promising antiamoebic agents

被引：13

作者：

Ansari, Mohammad Fawad ^{[1
]}

Inam, Afreen ^{[1
]}

Ahmad, Kamal ^{[2
]}

Fatima, Shehnaz ^{[3
]}

Agarwal, Subhash M. ^{[3
]}

Azam, Amir ^{[1
]}

机构：

[1] Jamia Millia Islamia, Dept Chem, New Delhi 110025, India

[2] Jamia Millia Islamia, Ctr Interdisciplinary Res Basic Sci, New Delhi 110025, India

[3] ICMR Natl Inst Canc Prevent & Res, Bioinformat Div, I-7,Sect 39, Noida 201301, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2020年 / 30卷 / 23期

关键词：

Metronidazole; Thiazolidinone; Amoebiasis; Entamoeba histolytica; Molecular docking; BIOLOGICAL EVALUATION; ANTICANCER ACTIVITY; DERIVATIVES; DESIGN; 4-THIAZOLIDINONES; OPTIMIZATION; DOCKING; GROWTH;

D O I：

10.1016/j.bmcl.2020.127549

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Metronidazole and its derivatives are widely used for the treatment of amoebiasis. However, metronidazole is considered as the standard drug but it has many side effects. The present study describes the synthesis of a series of metronidazole based thiazolidinone analogs via Knoevenagel condensation of 4-[2-(2-methyl-5-nitro-1Himidazole-1-yl)ethoxy]benzaldehyde 1 with various thiazolidinone derivatives 2-14 to get the new scaffold (15-27) having better activity and lesser toxicity. Six compounds have shown better efficacy and lesser cytotoxicity than the standard drug metronidazole towards HM1: IMSS strain of Entamoeba histolytica. These compounds may combat the problem of drug resistance and might be effective in identifying potential alternatives for future drug discovery against EhOASS.

引用

页数：5

共 28 条

[1] Synthesis and antiamoebic activity of metronidazole thiosemicarbazone analogues [J].

Abid, Mohammad ;

Agarwal, Subhash M. ;

Azam, Amir .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (09) :2035-2039

[2] Design, synthesis and biological evaluation of novel pyridine-thiazolidinone derivatives as anticancer agents: Targeting human carbonic anhydrase IX [J].

Ansari, Mohammad Fawad ;

Idrees, Danish ;

Hassan, Md. Imtaiyaz ;

Ahmad, Kamal ;

Avecilla, Fernando ;

Azam, Amir .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 144 :544-556

[3] Synthesis, antiamoebic and molecular docking studies of furan-thiazolidinone hybrids [J].

Ansari, Mohammad Fawad ;

Siddiqui, Shadab Miyan ;

Ahmad, Kamal ;

Avecilla, Fernando ;

Dharavath, Sudhaker ;

Gourinath, Samudrala ;

Azam, Amir .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 124 :393-406

[4] Metronidazole hydrazone conjugates: Design, synthesis, antiamoebic and molecular docking studies [J].

Ansari, Mohammad Fawad ;

Siddiqui, Shadab Miyan ;

Agarwal, Subhash M. ;

Vikramdeo, Kunwar Somesh ;

Mondal, Neelima ;

Azam, Amir .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (17) :3545-3549

[5] Synthesis and biological evaluation of novel 2-imino-4-thiazolidinone derivatives as potent anti-cancer agents [J].

Appalanaidu, K. ;

Kotcherlakota, Rajesh ;

Dadmal, T. L. ;

Bollu, Vishnu Sravan ;

Kumbhare, Ravindra M. ;

Patra, Chitta Ranjan .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (21) :5361-5368

[6] QSAR-Based Models for Designing Quinazoline/Imidazothiazoles/Pyrazolopyrimidines Based Inhibitors against Wild and Mutant EGFR [J].

Chauhan, Jagat Singh ;

Dhanda, Sandeep Kumar ;

Singla, Deepak ;

Agarwal, Subhash M. ;

Raghava, Gajendra P. S. .

PLOS ONE, 2014, 9 (07)

[7] NPred: QSAR classification model for identifying plant based naturally occurring anti-cancerous inhibitors [J].

Dhiman, Kanika ;

Agarwal, Subhash Mohan .

RSC ADVANCES, 2016, 6 (55) :49395-49400

[8] Axially chiral 2-arylimino-3-aryl-thiazolidine-4-one derivatives: Enantiomeric separation and determination of racemization barriers by chiral HPLC [J].

Erol, Sule ;

Dogan, Ilknur .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (07) :2494-2500

[9] Synthesis and biological activity evaluation of 5-pyrazoline substituted 4-thiazolidinones [J].

Havrylyuk, Dmytro ;

Zimenkovsky, Borys ;

Vasylenko, Olexandr ;

Day, Craig W. ;

Smee, Donald F. ;

Grellier, Philippe ;

Lesyk, Roman .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 66 :228-237

[10] Synthesis of New 4-Thiazolidinone-, Pyrazoline-, and Isatin-Based Conjugates with Promising Antitumor Activity [J].

Havrylyuk, Dmytro ;

Zimenkovsky, Borys ;

Vasylenko, Olexandr ;

Gzella, Andrzej ;

Lesyk, Roman .

JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (20) :8630-8641

← 1 2 3 →