Synthesis and in vitro Anti-Bacterial Activity of 2-(5-Nitro-2-heteroaryl)-1,3,4-Thiadiazole Derivatives

A new series of 2-(5-nitro-2-heteroaryl)-1,3,4-thiadiazole derivatives, including nitro furan, nitro thiophene and nitro imidazole, were synthesized and screened in vitro for their inhibitory activity against eight bacterial strains. The results showed that most of the synthesized compounds were active against Gram-positive bacteria, determined by MIC method. Among them, compounds 6a, 6b and 6d exhibited strong anti-bacterial effects against the Gram-positive bacteria. The oxidation of synthesized compounds to sulfinyl and sulfonyl bearing analogues did not improve the activity.

[1]  Sameh Eid,et al.  Design, synthesis, antimicrobial evaluation and molecular docking studies of some new thiophene, pyrazole and pyridone derivatives bearing sulfisoxazole moiety. , 2014, European journal of medicinal chemistry.

[2]  Fuhao Chu,et al.  Oleanolic acid synthetic oligoglycosides: a review on recent progress in biological activities. , 2014, Die Pharmazie.

[3]  Kerly F. M. Pasqualoto,et al.  Exploring 5-nitrofuran derivatives against nosocomial pathogens: synthesis, antimicrobial activity and chemometric analysis. , 2014, Bioorganic & medicinal chemistry.

[4]  Zhong-Chang Wang,et al.  Design and synthesis of 2-styryl of 5-Nitroimidazole derivatives and antimicrobial activities as FabH inhibitors. , 2014, European journal of medicinal chemistry.

[5]  A. Shafiee,et al.  Synthesis and biological evaluation of novel benzyl piperazine derivatives of 5-(5-nitroaryl)-1,3,4-thiadiazoles as Anti-Helicobacter pylori agents , 2013, DARU Journal of Pharmaceutical Sciences.

[6]  Zhong-Chang Wang,et al.  Potentiating 1-(2-hydroxypropyl)-2-styryl-5-nitroimidazole derivatives against antibacterial agents: design, synthesis and biology analysis. , 2013, European journal of medicinal chemistry.

[7]  A. Jain,et al.  1,3,4‐Thiadiazole and its Derivatives: A Review on Recent Progress in Biological Activities , 2013, Chemical biology & drug design.

[8]  N. S. El-Gohary,et al.  Synthesis, antimicrobial, antiquorum-sensing, antitumor and cytotoxic activities of new series of fused [1,3,4]thiadiazoles. , 2013, European journal of medicinal chemistry.

[9]  M. Faramarzi,et al.  7-Piperazinylquinolones with methylene-bridged nitrofuran scaffold as new antibacterial agents , 2013, Medicinal Chemistry Research.

[10]  F. Manvi,et al.  Synthesis, characterization and molecular docking studies of novel S-substituted phenacyl-1,3,4-thiadiazole-thiol derivatives as antimicrobial agents , 2012 .

[11]  B. Çetinkaya,et al.  Synthesis and antimicrobial activities of hexahydroimidazo[1,5-a]pyridinium bromides with varying benzyl substituents. , 2011, European journal of medicinal chemistry.

[12]  A. Foroumadi.  Discovery of a Novel Nitroimidazolyl—Oxazolidinone Hybrid with Potent anti Gram‐Positive Activity: Synthesis and Antibacterial Evaluation. , 2011 .

[13]  A. Shafiee,et al.  Synthesis and antileishmanial activity of 5-(5-nitroaryl)-2-substituted-thio-1,3,4-thiadiazoles , 2011, Journal of enzyme inhibition and medicinal chemistry.

[14]  F. Safari,et al.  Synthesis and anti-Helicobacter pylori activity of 5-(nitroaryl)-1,3,4-thiadiazoles with certain sulfur containing alkyl side chain. , 2008, Bioorganic & medicinal chemistry letters.

[15]  Y. Uehara,et al.  Design of antiangiogenic hypoxic cell radiosensitizers: 2-nitroimidazoles containing a 2-aminomethylene-4-cyclopentene-1,3-dione moiety. , 2008, Bioorganic & medicinal chemistry.

[16]  E. Šturdı́k,et al.  Antimicrobial effects of esters and amides of 3-(5-nitro-2-furyl)acrylic acid , 2008, Folia Microbiologica.

[17]  L. C. Tavares,et al.  A new class of nifuroxazide analogues: synthesis of 5-nitrothiophene derivatives with antimicrobial activity against multidrug-resistant Staphylococcus aureus. , 2007, Bioorganic & medicinal chemistry.

[18]  A. Foroumadi,et al.  Antituberculosis agents VIII. Synthesis and in vitro antimycobacterial activity of alkyl alpha-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-ylthio]acetates. , 2003, Farmaco.

[19]  J. Chern,et al.  Investigation of anticancer mechanism of thiadiazole-based compound in human non-small cell lung cancer A549 cells. , 2003, Biochemical pharmacology.

[20]  M. Mirzaei,et al.  Antituberculosis agents, I: Synthesis and antituberculosis activity of 2-aryl-1,3,4-thiadiazole derivatives. , 2001, Die Pharmazie.

[21]  M. Mirzaei,et al.  Antituberculosis agents II. Evaluation of in vitro antituberculosis activity and cytotoxicity of some 2-(1-methyl-5-nitro-2-imidazolyl)-1,3,4-thiadiazole derivatives. , 2001, Farmaco.

[22]  A. Shafiee,et al.  Synthesis and in vitro antifungal activity of 2-aryl-5-phenylsulfonyl-1,3,4-thiadiazole derivatives. , 2011, Arzneimittel-Forschung.