THIADIAZOLE ANALOGS AS POTENTIAL PHARMACOLOGICAL AGENTS: A BRIEF REVIEW
Keywords:
Antimicrobial, Antiinflammatory, Anticonvulsant, AntiviralAbstract
Recently, heterocyclic compounds analogues and their derivatives have attracted strong interest in medicinal chemistry due to their biological and pharmacological properties. The small and simple thiadiazole nucleus possesses numerous biological properties like - antitumor, antimicrobial, anti-inflammatory, anticonvulsant, and antidiabetic activities. These activities are also possessed by its substituted derivatives as well. The present review focuses on pharmacological activities of thiadiazole derivatives
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Sreenivasa GM, Jayachandran E, Jayaraj Kumar K, Srinivas Rao D. Synthesis of Bioactive molecules Fluoro Substituted Benzothiazole comprising potent heterocyclic moieties for biological and pharmacological screening. J Res Rev Biomed Biotech 2010;1(1):24-30.
Sunil D, http://shodhganga.inflibnet.ac.in/bitstream/10603/ 6581/13/13_chapter4.pdf, 2013.
Bak B, Nygard L, Pederson AJ, Andersen RJ. Microwave spectra of isotopic 1,3,4-thiadiazole:Molecular structure of 1,3,4-thiadiazole. J Mol Spectra 1966;19:283-88.
Bhattacharya P, Leonard JT, Roy K. Exploring QSAR of thiazole and thiadiazole derivatives as potent and selective human adenosine A3 receptor antagonists using FA and GFA techniques. J Bioorg Med Chem 2005;13:1159-65.
Jung KY, Soo-Kyung Kim KS, Gao ZG, Gross AS, Melman N, Jacobson KA, Kim YC. Structure–activity relationships of thiazole and thiadiazole derivatives as potent and selective human adenosine A3 receptor antagonists. J Bioorg Med Chem 2004;12:613-23.
Sivasubramanian N, Vikramaditya Reddy M, Aravinda M, Sravanthi R, Sirisha S. Synthesis, Characterization, Anti-Microbial and Anti Cancer Activity of Novel Heterocyclic System Containing Bridgehead Nitrogen Atom. J Chem Sci Trans 2012;1(2):401-9.
Mavrova D, Wesselinova. Examinations on the cytotoxicity of some 2,5-disubstitutes-1,2,4-triazoles and 1,3,4-thiadiazoles and their precursors towards guinea hen cells. J Uni Chem Tech Meta 2012;47(3):251-6.
Mamdouh AZ, Abu-Zaied, Galal AM, Nawwar, Randa HS, Shahinaz H, El-Sayed. Synthesis and screening of new 5-substituted-1,3,4-oxadiazole-2-thioglycosides as potent anticancer agents. J Pharmacology & Pharmacy 2012;3:254-61.
Dhanya S, Arun MI, Prakash S, Pai KSR. Toxicity studies of triazolo-thiadiazoles in ehrlich ascitic carcinoma cells. Res J Pharma Sci 2013;2(6):1-6.
Kaliappan I, Parthiban V. Facile synthesis and cytotoxic activity of 3,6â€disubstituted 1,2,4â€triazoloâ€[3,4â€b]-1,3,4-thiadiazoles. Eur J Chem 2010;1:50-53.
Kamelia MA, Magdi IZ, Manal MA, Mohsen MK, Maaly HM. Synthesis and anticancer activity of novel tetralin-6-yl-pyridine and tetralin-6-yl-pyrimidine derivatives. J Acta Polo Pharma Drug Res 2009;66(3):279-91.
Juan XZ, Zhang SW, Liu Y, Liu ZM, Gao JW, Song QL, Pan Y, Zhang JZ, Li XJ. Anti-tumor Metastasis and Crystal Structure of N1-(1,3,4-Thiadiazole-2-yl)-N3-m-chlorobenzoyl-urea. Chinese J Struct Chem 2011;30:1001-5.
Juszczak M, Matysiak M, Niewiadomy A, Rzeski W. The activity of a new 2-amino-1,3,4-thiadiazole derivative 4CIABT cancer and normal cells. J Folia Histo Et Cytobio 2011;49(3):436-44.
Supuran CT, Scozzafava A. Carbonic anhydrase inhibitors-1,3,4-Thiadiazole-2-sulfonamide derivatives as antitumor agents. Eur J Med Chem 2000;35:867-74.
Ibrahim DA. Synthesis and biological evaluation of 3,6-disubstituted [1,2,4]-triazolo-[3,4-b][1,3,4]-thiadiazole derivatives as a novel class of potential anti-tumor agents. Eur J Med Chem 2009;44:2776-81.
Shen LH, Li HY, Shang HX, Tian ST, Lai SY, Liu LJ. Synthesis and cytotoxic evaluation of new colchicine derivatives bearing 1,3,4-thiadiazole moieties. J Chin Chem Lett 2013;24:299-302.
Zhao HC, Shi YP, Liu YM, Li CW, Xuan LN, Wang P, et al. Synthesis and antitumor-evaluation of 1,3-selenazole-containing 1,3,4-thiadiazole derivatives. J Bioorg Med Chem Lett 2013;23:6577-79.
Terzioglu N, Gursoy A. Synthesis and anticancer evaluation of some new hydrazone derivatives of 2,6-dimethylimidazo-[2,1-b]-[1,3,4]-thiadiazole-5-carbohydrazide. Eur J Med Chem 2003;38:781-6.
Song XJ, Shao Y, Dong XJ. Microwave-assisted synthesis of some novel fluorinated pyrazolo-[3,4-d]-pyrimidine derivatives containing 1,3,4-thiadiazole as potential antitumor agents. Chin Chem Lett 2011;22:1036-8.
Misra U, Hitkari A, Saxena AK, Gurtu S, Shanker K. Biologically active indolylmethyl-1,3,4-oxadiazoles, 1,3,4-thiadiazoles, 1,3,4-triazoles and 1,2,4-triazines. Eur J Med Chem 1996;31:629-34.
Yusuf M, Riaz AK, Ahmed B. Synthesis and anti-depressant activity of 5-amino-1, 3, 4-thiadiazole-2-thiolimines and thiobenzyl derivatives. J Bioorg Med Chem 2008;16:8029-34.
Loscher W. New vision in the pharmacology of anticonvulsion. Eur J Pharma Sci 1998;342:1-13.
Brodie MJ. Monotherapy Trials:prerequisite data. J Epilepsy Res 2001;45(1-3):61-4.
Foroumadi A, Sheibani V, Sakhteman A, Rameshk M, Abbasi M, Farazifard R, et al. Synthesis and anticonvulsant activity of novel 2-amino-5-[4-chloro-2-(2 chlorophenoxy) phenyl]-1,3,4-Thiadiazole derivatives. J DARU 2007;15(2):89-93.
Singh T, Kumar D, Samal HB, Sudhakar P. Synthesis, characterisation and pharmacological activity of novel thiadiazole analogues. IRJP 2012;3(4):390-4.
Bhandari SV, Deshmane BJ, Dangare SC, Gore ST, Raparti VT, Khachane CV, Sarkate AP. Anticovulsant activities of some novel 3-[5-substituted, 3,4-thiadiazole-yl]-2-styryl quinazoline-4(3h)-ones. J Pharmacologyonline 2008;2:604-13.
Mohammad SY, Mohammad WA. Synthesis and anticonvulsant activity of substituted oxadiazole and thiadiazole derivatives. J Acta Polo Pharm Drug Res 2009;66(4):393-7.
Ali A, Nasim V, Sayyed AT, Abbas K, Abbas S. Synthesis, anticonvulsant and muscle relaxant activities of substituted 1, 3, 4-oxadiazole, 1, 3, 4-thiadiazole and 1, 2, 4-triazole. J Acta Chim Slov 2007;54:317-24.
Botros S, Khalil NA, Naguib BH, Dash Y. Synthesis and anticonvulsant activity of new phenytoin derivatives. Eur J Med Chem 2013;60:57-63.
Gosken US, Nesrin GK, Ozgur G, Yavuz K, Ekrem K, Samil I, et al. J Bioorg Med Chem 2007;15:5738-51.
Gilani SJ, Suroor A, Khan SA, Siddiqui N. Synthesis and pharmacological evaluation of condensed heterocyclic 6-substituted 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole and 1,3,4-oxadiazole derivatives of isoniazid. J Bioorg Med Chem Lett 2010;20:4762-65.
Shakya AK, Patnaik GK, Mishra P. Synthesis and biological evaluation of 2-substituted acetyl-l-amino-5-alkyl-1,3,4-thiadiazoles. Eur J Med Chem 1992;27:67-71.
Schenone S, Brullo C, Bruno O, Bondavalli F, Ranise A, Filippelli W, et al. New 1,3,4-thiadiazole derivatives endowed with analgesic and anti-inflammatory activities. J Bioorg Med Chem 2006;14:1698-705.
Amir M, Kumar H, Javed SA. Condensed bridgehead nitrogen heterocyclic system:Synthesis and pharmacological activities of 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole derivatives of ibuprofen and biphenyl-4-yloxy acetic acid. Eur J Med Chem 2008;43:2056-66.
Toma A, Hapau D, Laurian V, Cristina M, Valentin Z. Heterocycles 31. Synthesis and anti-inflammatory activity of 5-(pyridin-4-yl)-1,3,4-oxadiazole-2-thiol, 5-(pyridin-4-yl)-1,3,4-thiadiazole-2-thiol and 5-(pyridin-4-yl)-1,2,4-triazole-3-thiol derivatives. J Clujul Medical 2013;86(1):S34-S39.
Arvind KS, Parthsarthy R, Kshitiz J, Mishra G. Synthesis, characterization and antibacterial activity of 1, 3, 4 thiadiazole derivatives. Int J Sci Inn Dis 2011;1(3):353-61.
Vedavathi M, Rajareddy A, Sreenivasa GM, Jayachandran E. The in vitro anti-denaturation effects induced by synthetic products in bovine serum albumin is proposed as a screening assay for the detection of anti-inflammatory compounds without the use of animals. Int J Pharm Sci 2010;2(1):404-10.
Gangadhar S, Sreenivasa GM, Jayachandran E. Synthesis of fluoro substituted benzothiazoles incorporated with 1,3,4-thiadiazoles for biological and pharmacological screening. Ori J Chem 2008;24(2):475-84.
Mohammad A, Kumar S. Synthesis and evaluation of anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation properties of ibuprofen derivatives. J Acta Pharm 2007;57:31-45.
Salunkhe NG. Green synthesis, characterization and biological evaluation of some triazole and thiadiazole. J Curr Chem Pharm Sci 2012;2(2):100-6.
Jalhan S, Jindal A, Gupta A, Hemraj. Synthesis, biological activities and chemistry of thiadiazole derivatives and schiff bases. Asian J Pharm Clin Res 2012;5(3):199-208.
Swamy SN, Bassapa BS, Priya B, Prabhuswamy BH, Doreswamy J, Prasad S, Rangappa KS. Synthesis of pharmaceutically important condensed heterocyclic 4,6-disubstituted-1,2,4-triazolo-1,3,4-thiadiazole derivatives as antimicrobials. Eur J Med Chem 2006;41:531-8.
Thaker KM, Joshi HS. Synthesis and pharmacological evaluation of 2-(3’,5’-dicholorobenzo[b]thiophen-2’-yl)-5-arylamino-1,3,4-thiadiazoles. Indian J Chem 2005;44B:410-2.
Sah P, Gharu CP. Organic Synthesis and Medicinal Synthesis, Characterization and Antimicrobial Evaluation of Schiff Bases of 4-Thiazolidinone Bearing Thiadiazole Moiety. J Cur Pharm Res 2012;9(1):44-8.
Ionuţ I, Nastasa C, Tiperciuc B, Smarandaoniga, Pirnau A, et al. Synthesis and antimicrobial activity evaluation of some N1 arylidene-thiosemicarbazone and 1,3,4-thiadiazoline derivatives. J Bas Res Clu Med 2013;86:S27-S33.
Nareshvarma S, Satya P, Shrivastava, Somarouthu P. Synthesis and antimicrobial activity of some novel fused heterocyclic moieties. J Org Commun 2013;6(2):78-85.
Abdulrasool MM, Jawad AH, Jawad K. Synthesis, characterization and evaluation of biological activity of new heterocyclic compounds containing 1,2,4-triazole and 1,3,4-thiadiazole rings. Int J App Sci Tech 2012;2(10):155-64.
Raj M, Patel HV, Raj LM, Patel NK. Synthesis and biological evaluation of some new 1,3,4 thiadiazole derivatives for their antimicrobial activities. Int J Pharm Chem Bio Sci 2013;3(3):814-9.
Gilani SJ, Khan SA, Alam O, Siddiqui N. Synthesis and in vitro antimicrobial evaluation of condensed heterocyclic 6-substituted 1,2,4-triazolo-[3,4-b]-1,3,4 thiadiazole and 1,3,4-oxadiazole derivatives of isoniazid. J Acta Polo Pharm Drug Res 2011;68(2):205-11.
Pawankar N, Waikar S, Gurunani G. Synthesis of some novel 1, 3, 4 thiadiazole carrying benzimidazole moiety and their antimicrobial evaluation. Int J Pharmacy Pharm Sci 2012;4(2):4506-13.
Mendhe K, Waikar S, Gurunani G. Synthesis and evaluation of some novel 2-amino 1, 3, 4 thiadiazole derivatives for their antimicrobial activity. Int J Phar Tech 2012;4(2):4569-76.
Parimi U, Pappu L. Synthesis and antimicrobial evaluation of imino substituted 1, 3, 4 oxa and thiadiazoles. Int J Pharmacy Pharm Sci 2012;4(5):523-7.
Hussain S, Sharma J, Mohd A. Synthesis and antimicrobial activities of 1,2,4-triazole and 1,3,4-thiadiazole derivatives of 5-amino-2-hydroxybenzoic acid. Eur J Chem 2008;5:963-8.
Atta K, Farahat O.M, Ahmed ZA, Mohamed G. Synthesis and antibacterial activities of novel imidazo-[2,1-b]-1,3,4-thiadiazoles. J Molecules 2011;16:5496-506.
Vasoya SL, Paghdar DJ, Chovatia PT, Joshi HS. Synthesis of some New Thiosemicarbazide and 1,3,4-Thiadiazole Heterocycles Bearing Benzo-[b]-Thiophene Nucleus as a Potent Antitubercular and Antimicrobial Agents. J Sci 2005;16(1):33-6.
Solak N, Rollas S. Synthesis and antituberculosis activity of 2-(aryl/alkylamino)-5-(4-aminophenyl)-1,3,4-thiadiazoles and their Schiff bases. J ARKIVOC 2006;(xii):173-181.
Shen L, Zhang Y, Wang A, Sieber-McMaster E, Chen X. Synthesis and structure–activity relationships of thiadiazole-derivatives as potent and orally active peroxisome proliferator-activated receptors a/Æ dual agonists. J Bioorg Med Chem 2008;16:3321-41.
Jayakumar Swamy BHM, Pramod N, Patel AH, Rao R, Kumar S, Kumar H. Thiadiazole-quinoline derivatives as potential wound healing activity. Int J Phytopharma 2012;3(2):157-62.
Karagozoglu Y, Turkoglu S, Parlak A, Alayunt N. The effects of hydroxyurea derivative 1, 3, 4-thiadiazoles on serum biochemical parameters and antioxidant status in liver of rats. Dig J Nanomat Biostru 2013;8(1):247-53.
Rahman Farghalya A, Clercq ED, El-Kashefa H. Synthesis and antiviral activity of novel [1,2,4]-triazolo-[3,4-b]-[1,3,4]-thiadiazoles, [1,2,4]-triazolo-[3,4-b] [1,3,4]-thiadiazines and [1,2,4]-triazolo-[3,4-b][1,3,4]-thiadiazepines. J ARKIVOC 2006:137-51.
Modzelewska-Banachiewich B, Jagiello-Wojtowicz E, Tokarzewska-Wielosz E. Synthesis and biological activity of Bis-1,2,4-trizole and Bis-1,3,4-Thiadiazole derivatives. J Acta Polo Pharm Drug Res 2000;57(3):199-204.
Asif M, Asthana. Synthesis of the 2,4-diphenyl-5-imino-δ2-1,3,4-thiadiazole derivatives as potential antinociceptive compounds. Mala J Pharm Sci 2010;8(1):29-43.