Document Type : Original Paper
Authors
- M. Yazdanian 1
- B Zihayat 1
- MH Moshafi 1
- A Khodadadi 1
- A Peimani 1
- A Shamsaddini 1
- M Nourhashemi 2
- Alireza Foroumadi 2
1 Kerman University of Medical Sciences
2 Tehran University of Medical Sciences
Abstract
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.
Keywords
- Nasr T., Bondock S., and Eid S. Design, synthesis, antimicrobial evaluation and molecular docking studies of some new thiophene, pyrazole and pyridone derivatives bearing sulfisoxazole moiety. Eur. J. Med. Chem. 84: 491-504 (2014).
- Duan Y.-T., Wang Z.-C., Sang Y.-L., Tao X.-X., Teraiya S.B., Wang P.-F., Wen Q., Zhou X.J., Ding L., Yang Y.H., and Zhu H.L. Design and synthesis of 2-styryl of 5-Nitroimidazole derivatives and antimicrobial activities as FabH inhibitors. Eur. J. Med. Chem. 76: 387-396 (2014).
- Foroumadi A., Rineh A., Emami S., Siavoshi F., Massarrat S., Safari F., Rajabalian S., Falahati M., Lotfali E., and Shafiee A. Synthesis and anti-Helicobacter pylori activity of 5-(nitroaryl)-1,3,4-thiadiazoles with certain sulfur containing alkyl side chain. Bioorg. Med. Chem. Lett. 18: 3315–3320 (2008).
- Noolvi M.N., Patel H.M., Kamboj S., and Cameotra S.S. Synthesis and antimicrobial evaluation of novel 1,3,4-thiadiazole derivatives of 2-(4-formyl-2-methoxyphenoxy) acetic acid. Arab. J. Chem. 9: 1283-1289 (2012).
- Demirbas A., Sahin D., Demirbas N., and Karaoglu S.A. Synthesis of some new 1,3,4-thiadiazol-2-ylmethyl-1,2,4-triazole derivatives and investigation of their antimicrobial activities. Eur. J. Med. Chem. 44: 2896-2903 (2009).
- Chou J.-Y., Lai S.-Y., Pan S.-L., Jow G.-M., Chern J.-W., and Guh J.-H. Investigation of anticancer mechanism of thiadiazole-based compound in human non-small cell lung cancer A549 cells. Biochem. Pharmacol. 66: 115-124 (2003).
- El-Gohary N.S., and Shaaban M.I. Synthesis, antimicrobial, antiquorum-sensing, antitumor and cytotoxic activities of new series of fused [1,3,4] thiadiazoles. Eur. J. Med. Chem. 63: 185-195 (2013).
- Jakhar A., and Makrandi J. Microwave assisted synthesis and antibacterial properties of some new 2-alkyl/aryl-(6-substitutedconmarin-3-yl) imidazo [2,1-b][1,3,4] thiadiazoles. Indian J. Chem. 51: 291-296 (2012) .
- Kerur S., Alagawadi K., Zhu H., and Manvi F. Synthesis, characterization and molecular docking studies of novel S-substituted phenacyl-1,3, 4-thiadiazole-thiol derivatives as antimicrobial agents. Eur. J. Chem. 3: 293-297 (2012).
- Jain A.K., Sharma S., Vaidya A., Ravichandran V., and Agrawal R.K. 1,3,4-Thiadiazole and its Derivatives: A Review on Recent Progress in Biological Activities. Chem. Biol. Drug Des. 81: 557-576 (2013).
- Alipour E., Emami E., Yahya-Meymandi A., Nakhjiri M., Johari M., Ardestani S.K., Poorrajab F., Hosseini M., Shafiee A., Foroumadi A. Synthesis and antileishmanial activity of 5-(5-nitroaryl)-2-substituted-thio-1,3,4-thiadiazoles. J. Enzyme Inhib. Med. Chem. 26: 123-128 (2010).
- Wang Z.-C., Duan Y.-T., Qin Y.-J., Wang P.-F., Luo Y., Wen Q., Yang Y.A., Sun J., Hu Y., Sang Y.L., and Zhu H.L. Potentiating 1-(2-hydroxypropyl)-2-styryl-5-nitroimidazole derivatives against antibacterial agents: Design, synthesis and biology analysis. Eur. J. Med. Chem. 65: 456-463 (2013).
- Uto Y, Nagasawa H, Jin C-Z, Nakayama S, Tanaka A, Kiyoi S, Nakashima H., Shimamura M., Inayama S., Fujiwara T., Takeuchi Y., Uehara Y., Kirk K.L., Nakata E., and Hori H. Design of antiangiogenic hypoxic cell radiosensitizers: 2-Nitroimidazoles containing a 2-aminomethylene-4-cyclopentene-1,3-dione moiety. Bioorg. Med. Chem. 16: 6042-6053 (2008).
- Mohammadhosseini N., Saniee P., Ghamaripour A., Aryapour H., Afshar F., Edraki N., Siavoshi F., Foroumadi A., and Shafiee A. Synthesis and biological evaluation of novel benzyl piperazine derivatives of 5-(5-nitroaryl)-1,3,4-thiadiazoles as Anti-Helicobacter pylori agents. Daru, 21: 66-70 (2013).
- Masunari A., and Tavares L.C. A new class of nifuroxazide analogues: Synthesis of 5-nitrothiophene derivatives with antimicrobial activity against multidrug-resistant Staphylococcus aureus. Bioorg. Med. Chem. 15: 4229-4236 (2007).
- Türkmen H., Ceyhan N., Yavaşoğlu N.Ü.K., Özdemir G., and Çetinkaya B. Synthesis and antimicrobial activities of hexahydroimidazo [1,5-a] pyridinium bromides with varying benzyl substituents. Eur. J. Med. Chem. 46: 2895-2900 (2011).
- Kellová G., Šturdík E., Štibrányi L., Drobnica L., Augustin J. Antimicrobial effects of esters and amides of 3-(5-nitro-2-furyl) acrylic acid. Folia microbiol. 29: 23-34 (1984).
- Zorzi R.R., Jorge S.D., Palace-Berl F., Pasqualoto K.F., Bortolozzo Lde S., de Castro Siqueira A.M., and Tavares L.C. Exploring 5-nitrofuran derivatives against nosocomial pathogens: Synthesis, antimicrobial activity and chemometric analysis. Bioorg. Med. Chem. 22: 2844-2854 (2014).
- Foroumadi A., Daneshtalab M., and Shafiee A.Synthesis and in vitro antifungal activity of 2-aryl-5-phenylsulfonyl-1,3,4-thiadiazole derivatives. Arzneimittelforschung, 49: 1035-1038 (1999).
- Foroumadi A, Kiani Z, and Soltani F. Antituberculosis agents VIII: Synthesis and in vitro antimycobacterial activity of alkyl α-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-ylthio] acetates. Farmaco. 58: 1073-1076 (2003).
- Foroumadi A., Mirzaei M., and Shafiee A. 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. Farmaco. 56: 621-623 (2001).
- Foroumadi A., Mirzaei M., and Shafiee A. Antituberculosis agents, I: Synthesis and antituberculosis activity of 2-aryl-1,3,4-thiadiazole derivatives. Pharmazie. 56: 610-612 (2001).
- Khalaj A., Nakhjiri M., Negahbani A.S., Samadizadeh M., Firoozpour L., Rajabalian S., Samadi, N., Faramarzi, M.A., Adibpour, N., Shafiee, A., Foroumadi, A. Discovery of a novel nitroimidazolyl-oxazolidinone hybrid with potent anti Gram-positive activity: Synthesis and antibacterial evaluation. Eur. J. Med. Chem. 46: 65-70 (2011).
- Emami, S. Shahrokhirad, N, Foroumadi, A., Faramarzi, M.A., Samadi, N., Soltani-Ghofrani, N. 7-Piperazinylquinolones with methylene-bridged nitrofuran scaffold as new antibacterial agents. Med. Chem. Res. 22: 5940-5947 (2013).
)