232
Views
55
CrossRef citations to date
0
Altmetric
Review

Thiadiazole inhibitors: a patent review

&
Pages 477-505 | Received 01 Sep 2016, Accepted 07 Dec 2016, Published online: 04 Jan 2017

References

  • Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. preparation of potent sulfonamides inhibitors incorporating bile acid tails. Bioorg Med Chem Lett. 2002;12:1551–1557.
  • Franco-Bernardes MF, Maschio LR, De Azeredo-Oliveira MTV, et al. Biochemical and genotoxic effects of a commercial formulation of the herbicide tebuthiuron in Oreochromis niloticus of different sizes. Ecotoxicol Environ Contam. 2014;9:59–67.
  • Enanga B, Ariyanayagam MR, Stewart ML, et al. Activity of megazol, atrypanocidal nitroimidazole, is associated with DNA damage. Antimicrob Agents Chemother. 2003;47:3368–3370.
  • Peddie BA, Little PJ. Sulphamethizole in urinary tract infections. J Antimicrob Chemother. 1979;5:195–200.
  • Schmidt M, Bastians H. Mitotic drug targets and the development of novel anti-mitotic anticancer drugs. Drug Resist Updat. 2007;10:162–181.
  • Owens B. Kinesin inhibitor marches toward first-in-class pivotal trial. Nat Med. 2013;19:1550–1550.
  • Iizawa Y, Okonogi K, Hayashi R, et al. Therapeutic effect of cefozopran (SCE-2787), a new parenteral cephalosporin, against experimental infections in mice. Antimicrob Agents Chemother. 1993;37:100–105.
  • Pham CD, Weber H, Hartmann R, et al. New Cytotoxic 1,2,4-Thiadiazole Alkaloids from the Ascidian Polycarpa aurata. Org Lett. 2013;15:2230–2233.
  • Heitz S, Durgeat M, Guyot M, et al. Nouveau derive indolique du thiadiazole-1,2,4, isole d’un tunicier (Dendrodoa grossularia). Tetrahedron Lett. 1980;21:1457–1458.
  • Yang Z, Huang N, Xu B, et al. Cytotoxic 1,3-thiazole and 1,2,4-thiadiazole alkaloids from penicillium oxalicum: structural elucidation and total synthesis. Molecules. 2016;21:232–244.
  • Elson PJ, Kvols LK, Vogl SE, et al. Phase II trials of 5-day vinblastine infusion (NSC 49842), L-alanosine (NSC 153353), acivicin (NSC 163501), and aminothiadiazole (NSC 4728) in patients with recurrent or metastatic renal cell carcinoma. Invest New Drugs. 1988;6:97–103.
  • Engstrom PF, Ryan LM, Falkson G, et al. Phase II study of aminothiadiazole in advanced squamous cell carcinoma of the esophagus. Am J Clin Oncol. 1991;14:33–35.
  • Asbury R, Blessing JA, Moore D. A phase ii trial of aminothiadiazole in patients with mixed mesodermal tumors of the uterine corpus: a gynecologic oncology group study. Am J Clin Oncol. 1996;19:400–402.
  • Kadi AA, Al-Abdullah ES, Shehata IA, et al. Synthesis antimicrobial and anti-inflammatory activities of novel 5-(1-adamantyl)-1,3,4-thiadiazole derivatives. Eur J Med Chem. 2010;45:5006–5011.
  • Begum T, Molvi KI, Khan SA. Synthesis, characterization and biological evaluation of new 1,3,4-thiadiazole derivatives of coumarins. World J Pharm Pharm Sci. 2014;3:42–56.
  • Alegaon SG, Hirpara MB, Alagawadi KR, et al. Synthesis of novel pyrazole–thiadiazole hybrid as potential potent and selective cyclooxygenase-2 (COX-2) inhibitors. Bioorg Med Chem Lett. 2014;24:5324–5329.
  • Ozadal K, Ozkanl F, Jain S, et al. Synthesis and biological evaluation of isoxazolo[4,5-d]pyridazin-4-(5H)-one analogues as potent anti-inflammatory agents. Bioorg Med Chem. 2012;20:2912–2922.
  • Tiperciuc B, Parvu A, Tamaian R, et al. New anti-inflammatory thiazolyl-carbonyl-thiosemicarbazides and thiazolyl-azoles with antioxidant properties as potential iNOS inhibitors. Arch Pharmacal Res. 2013;36:702–714.
  • Al Mekhlafi S, Alkadi H, El-Sayed MK. Synthesis and anti-inflammatory activity of novel ketoprofen and ibuprofen derivatives. J Chem Pharm Res. 2015;7:503–510.
  • Alam MJ, Alam O, Ali MR, et al. Synthesis and anti-inflammatory activity of some new thiadiazole linked pyrazole benzene sulphonamides as cyclooxygenase inhibitors. Oriental J Chem. 2015;31:1873–1885.
  • Li P, Shi L, Gao M, et al. In this study, antibacterial activities against rice bacterial leaf blight and tomato bacterial wilt of 2-mercapto-5-substituted-1,3,4-oxadiazole/thiadiazole derivatives. Bioorg Med Chem Lett. 2015;25:481–484.
  • Alwan WS, Karpoormath R, Palkar MB, et al. Novel imidazo[2,1-b]-1,3,4-thiadiazoles as promising antifungal agents against clinical isolate of cryptococcus neoformans. Eur J Med Chem. 2015;95:514–525.
  • Chandrakantha B, Isloor AM, Shetty P, et al. Synthesis and biological evaluation of novel substituted 1,3,4-thiadiazole and 2,6-diaryl substituted imidazo[2,1-b][1,3,4]thiadiazole derivatives. Eur J Med Chem. 2014;71:316–323.
  • Fan Z, Zuo X, Wu Q, et al. Preparation of 4-methyl-1,2,3-thiadiazole derivatives as fungicides. From Faming Zhuanli Shenqing CN 101250167 A 20080827; 2008.
  • Bhat AR, Tazeem AA, Choi I, et al. 3-(1,3,4-thiadiazole-2-yl)quinoline derivatives: synthesis, characterization and anti-microbial activity. Eur J Med Chem. 2011;46:3158–3166.
  • Padmavathi V, Reddy GD, Reddy SN, et al. Synthesis and biological activity of 2-(bis((1,3,4-oxadiazolyl/1,3,4-thiadiazolyl)methylthio)methylene) malononitriles. Eur J Med Chem. 2011;46:1367–1373.
  • Bansode S, Kamble R. Synthesis of novel 2-(3′-aryl-sydnon-4′-ylidene)-5′-substituted-[1,3,4]thiadiazolylamines and [1,3,4]-thiadiazol-2′-yl-3-oxo-[1,2,4]-triazoles as antimicrobial agents. Med Chem Res. 2012;21:867–873.
  • Padmavathi V, Reddy GS, Padmaja A, et al. Synthesis, antimicrobial and cytotoxic activities of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles. Eur J Med Chem. 2009;44:2106–2112.
  • Padmavathi V, Reddy SN, Reddy GD, et al. Synthesis and bioassay of aminosulfonyl-1,3,4-oxadiazoles and their interconversion to 1,3,4-thiadiazoles. Eur J Med Chem. 2010;45:4246–4251.
  • Shelke S, Mhaske G, Gadakh S, et al. Green synthesis and biological evaluation of some novel azoles as antimicrobial agents. Bioorg Med Chem Lett. 2010;20:7200–7204.
  • Guzeldemirci NU, Kucukbasmaci O. Synthesis and antimicrobial activity evaluation of new 1,2,4-triazoles and 1,3,4-thiadiazoles bearing imidazo[2,1-b] thiazole moiety. Eur J Med Chem. 2010;45:63–68.
  • Farshori NN, Banday MR, Ahmad A, et al. Synthesis, characterization, and in vitro antimicrobial activities of 5-alkenyl/hydroxyalkenyl-2-phenylamine-1,3,4-oxadiazoles and thiadiazoles. Bioorg Med Chem Lett. 2010;20:1933–1938.
  • Fan Z, Zuo X, Mi N, et al. 4-Methyl-1,2,3-thiadiazole-5-carboxamide derivatives and their preparation, agricultural and horticultural compositions and use in the control of fungal, bacterial and viral infections of plants. Faming Zhuanli Shenqing CN 101875644 A 20101103. 2010.
  • Salomao K, Souza EM, Carvalho SA, et al. In vitro and in vivo activity of 1,3,4-thiadiazole-2-arylhydrazone derivatives of megazol on trypanosoma cruzi. Antimicrob Agents Chemother. 2010;54:2023–2031.
  • Farghaly TA, Abdallah MA, Masaret GS, et al. New and efficient approach for synthesis of novel bioactive [1,3,4]thiadiazoles incorporated with 1,3-thiazole moiety. Eur J Med Chem. 2015;97:320–333.
  • Hu G, Xie S, Hou L, et al. Preparation of 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole linked fluoroquinolone dimers for treating tumor and antimicrobial infection. Faming Zhuanli Shenqing CN 101648962 A 20100217; 2010
  • Khan I, Zaib S, Ibrar A, et al. Synthesis, crystal structure and biological evaluation of some novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines. Eur J Med Chem. 2014;78:167–177.
  • Busch B, Johnson AT, Martin R, et al. Preparation of 3-phenyl-N-(1,3,4-thiadiazol-2-yl)acrylamide derivatives and related compounds as modulators of estrogen-related receptors for the treatment of diseases such as cancer, rheumatoid arthritis or neurological disorders. PCT Int. Appl. WO 2005072731 A1 20050811. 2005.
  • Supuran C, Benedini F, Biondi S, et al. Preparation of nitrate esters of (hetero)arylsulfonamide carbonic anhydrase inhibitors as agents for treating eye disorders and cancer. PCT Int. Appl. WO 2008071421 A1 20080619. 2008.
  • Cui H, Peng S, Gu X, et al. Synthesis and biological evaluation of D-ring fused 1,2,3-thiadiazole dehydroepiandrosterone derivatives as antitumor agents. Eur J Med Chem. 2016;111:126–137.
  • Dawood KM, Gomha SM. synthesis and anti-cancer activity of 1,3,4-thiadiazole and 1,3-thiazole derivatives having 1,3,4-oxadiazole moiety. J Heterocycl Chem. 2015;52:1400–1405.
  • Aurelio L, Scullino CV, Pitman MR, et al. Sphingosine kinase to dihydroceramide desaturase: a structure-activity relationship (sar) study of the enzyme inhibitory and anticancer activity of 4-((4-(4-chlorophenyl)thiazol-2-yl)amino)phenol (SKI-II). J Med Chem. 2016;59:965–984.
  • Al-Rashood ST, Hassan GS, El-Messery SM, et al. Synthesis, biological evaluation and molecular modeling study of 2-(1,3,4-thiadiazolyl-thio and 4-methylthiazolyl-thio)-quinazolin-4-ones as a new class of DHFR inhibitors. Bioorg Med Chem Lett. 2014;24:4557–4567.
  • Juszczak M, Walczak K, Langner E, et al. Neuroprotective activity of 2-amino-1,3,4-thiadiazole derivative 4BrABT - an in vitro study. Ann Agric Environ Med. 2013;20:575–579.
  • Mayhoub AS, Marler L, Kondratyuk TP, et al. Optimizing thiadiazole analogues of resveratrol versus three chemopreventive targets. Bioorg Med Chem. 2012;20:510–520.
  • Naskar A, Singha T, Guria T, et al. Synthesis, characterization and evaluation of anticancer activity of some new schiff bases of 1,3,4-thiadiazole derivatives. Int J Pharm Pharm Sci. 2015;7:397–402.
  • Li Y, Yu Y, Jin K, et al. Synthesis and biological activities of novel 2,5-disubstituted-1,3,4-thiadiazole derivatives. Youji Huaxue. 2015;35:129–136.
  • Romagnoli R, Baraldi PG, Prencipe F, et al. Design, synthesis and antiproliferative activity of novel heterobivalent hybrids based on imidazo[2,1-b][1,3,4]thiadiazole and imidazo[2,1-b][1,3]thiazole scaffolds. Eur J Med Chem. 2015;101:205–217.
  • Jing F, Fu X, Li S, et al. Synthesis and in vitro antiproliferative evaluation of novel hybrids from 1,3,4-thiadiazole and benzisoselenazolone. Chem Pharm Bull. 2015;63:431–437.
  • Gomha SM, Ahmed SA, Abdelhamid AO. Synthesis and cytotoxicity evaluation of some novel thiazoles, thiadiazoles, and pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5(1h)-ones incorporating triazole moiety. Molecules. 2015;20:1357–1376.
  • Muthuppalaniappan P, Viswanadha S, Merikapudi GS, et al. Preparation of pyrazole derivatives as modulators of calcium release-activated calcium channel for treating non-small cell lung cancer. PCT Int. Appl. WO 2011042797 A1 20110414. 2011.
  • Kirkpatrick LD, Johnson JLH Pharmaceutical compositions comprising inhibitors of the pleckstrin homology domain of AKT protein kinase for treating or preventing cancer. PCT Int. Appl. WO 2011032169 A2 20110317. 2011.
  • Yang X, Wen Q, Zhao T, et al. Synthesis, biological evaluation, and molecular docking studies of cinnamic acyl 1,3,4-thiadiazole amide derivatives as novel antitubulin agents. Bioorg Med Chem. 2012;20:1181–1187.
  • Zhang K, Wang P, Xuan L, et al. Synthesis and antitumor activities of novel hybrid molecules containing 1,3,4-oxadiazole and 1,3,4-thiadiazole bearing schiff base moiety. Bioorg Med Chem Lett. 2014;24:5154–5156.
  • Sun J, Yang Y, Li W, et al. Synthesis, biological evaluation and molecular docking studies of 1,3,4-thiadiazole derivatives containing 1,4-benzodioxane as potential antitumor agents. Bioorg Med Chem Lett.2011;21:6116–6121.
  • Kumar D, Kumar NM, Chang KH, et al. Synthesis and anticancer activity of 5-(3-indolyl)-1,3,4-thiadiazoles. Eur J Med Chem. 2010;45:4664–4668.
  • Noolvi MN, Patel HM, Singh N, et al. Synthesis and anticancer evaluation of novel 2-cyclopropylimidazo[2,1-b][1,3,4]-thiadiazole derivatives. Eur J Med Chem. 2011;46:4411–4418.
  • Noolvi MN, Patel HM, Kamboj S, et al. 2,6-disubstituted imidazo[2,1-b][1,3,4]thiadiazoles: search for anticancer agents. Eur J Med Chem. 2012;56:56–69.
  • Gireesh TM, Kamble RR, Taj T. Synthesis and antimicrobial and anticancer activity of new of imidazo[2,1-b][1,3,4]thiadiazoles. Pharm Chem J. 2011;45:313–316.
  • Gireesh TM, Kamble RR, Taj T, et al. Synthesis of novel imidazo[2,1-b][1,3,4]thiadiazoles appended to sydnone as anticancer agents. Med Chem Res. 2013;22:4367–4375.
  • Aliabadi A, Eghbalian E, Kiani A. Synthesis and evaluation of the cytotoxicity of a series of 1, 3,4 thiadiazole based compounds as anticancer agents. Iran J Basic Med Sci. 2013;16:1133–1138.
  • Liu T, Wan Y, Fang H. Synthesis and antiproliferative activity of novel 1,3,4-thiadiazole derivatives. Youji Huaxue. 2016;36:417–424.
  • Zhang Y, Wang X, Liu W, et al. Design, synthesis and biological evaluation of heterocyclic azoles derivatives containing pyrazine moiety as potential telomerase inhibitors. Bioorg Med Chem. 2012;20(21):6356–6365.
  • Dawood KM, Eldebss TMA, El-Zahabi HAS, et al. Synthesis of some new pyrazole-based 1,3-thiazoles and 1,3,4-thiadiazoles as anticancer agents. Eur J Med Chem. 2013;70:740–749.
  • Almasirad A, Firoozpour L, Nejati M, et al. Design, synthesis and biological evaluation of new series of 2-amido-1,3,4-thiadiazole derivatives as cytotoxic agents. Zeit Naturforsch B Chem Sci. 2016;71(3):205–210.
  • Polkam N, Rayam P, Anireddy JS, et al. Synthesis, in vitro anticancer and antimycobacterial evaluation of new 5-(2,5-dimethoxyphenyl)-1,3,4-thiadiazole-2-amino derivatives. Bioorg Med Chem Lett. 2015;25:1398–1402.
  • Zhao H, Shi Y, Liu Y, et al. Synthesis and antitumor-evaluation of 1,3-selenazole-containing 1,3,4-thiadiazole derivatives. Bioorg Med Chem Lett. 2013;23:6577–6579.
  • Kumar BR, Vaddula K, Chang KS. One-pot synthesis and anticancer studies of 2-arylamino-5-aryl-1,3,4- thiadiazoles. Bioorg Med Chem Lett. 2011;21:2320–2323.
  • Yadagiri B, Gurrala S, Bantu R, et al. Synthesis and evaluation of benzosuberone embedded with 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole moieties as new potential anti proliferative agents. Bioorg Med Chem Lett. 2015;25:2220–2224.
  • Kumar D, Kumar NM, Noel B, et al. A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles as potent cytotoxic agents. Eur J Med Chem. 2012;55:432–438.
  • Mavrova AT, Wesselinova D, Tsenov JA, et al. Synthesis and antiproliferative activity of some new thieno[2,3-d]pyrimidin-4(3H)-ones containing 1,2,4-triazole and 1,3,4-thiadiazole moiety. Eur J Med Chem. 2014;86:676–683.
  • Li W, Wang X, Zheng R, et al. Discovery of the novel potent and selective flt3 inhibitor 1-{5-[7-(3-morpholino-propoxy)quinazolin-4-ylthio]-[1,3,4]thiadiazol-2-yl}-3-ptolylurea and its anti-acute myeloid leukemia (aml) activities in vitro and in Vivo. J Med Chem. 2012;55:3852−3866.
  • Skrzypek A, Matysiak J, Niewiadomy A, et al. Synthesis and biological evaluation of 1,3,4-thiadiazole analogues as novel AChE and BuChE inhibitors. Eur J Med Chem. 2013;62:311–319.
  • Palmer T, Niclas H, Schuster C, et al. Preparation of 1,2,4-thiadiazole-5-thiones and related compounds as urease and nitrification inhibitors. PCT Int. Appl. WO 2005007636 A1 20050127; 2005.
  • Cheruvallath ZS, Loweth CJ, Nutt RF, et al. Thiazole and thiadiazole derivatives as inhibitors of tyrosine phosphatases, their preparation, pharmaceutical compositions, and use in therapy. PCT Int. Appl. WO 2006028970 A1 20060316; 2006.
  • Barnes D, Coppola GM, Stams T, et al. Preparation of thiadiazole derivatives as antidiabetic agents. PCT Int. Appl. WO 2008148744 A1 20081211. 2008.
  • Martinez GA, Gil AC, Palomo RV, et al. Preparation of substituted 5-imino-1,2,4-thiadiazoles as PDE7 inhibitors for treating neuro-degenerative diseases. PCT Int. Appl. WO 2011039403 A1 20110407. 2011.
  • Li Y, Yu Y, Jin K, et al. Synthesis and biological evaluation of novel thiadiazole amides as potent Cdc25B and PTP1B inhibitors. Bioorg Med Chem Lett. 2014;24:4125–4128.
  • Barnes D, Bebernitz GR, Coppola GM, et al. 1,2,5-Thiadiazolidine derivatives useful for treating conditions mediated by protein tyrosine phosphatases (PTPASE) and their preparation and pharmaceutical compositions. PCT Int. Appl. WO 2007067613 A1 20070614; 2007.
  • Ciufolini M, Benjahad A, Giethlen B, et al. Arylamino-substituted five-membered heterocycles as tyrosine kinase modulators, their preparation, pharmaceutical compositions, and use in therapy. PCT Int. Appl. WO 2006064375 A2 20060622; 2006.
  • Pevarello P, Garcia Collazo AM, Garcia G, et al. Preparation of imidazolothiadiazole derivatives as protein kinase inhibitors. PCT Int. Appl. WO 2009040552 A2 20090402; 2009.
  • Westman J Preparation of thiadiazole-based compounds as medicaments for treating conditions improved by AMPK activation. PCT Int. Appl. WO 2010073011 A2 20100701. 2010.
  • Patel HM, Sing B, Bhardwaj V, et al. Design, synthesis and evaluation of small molecule imidazo[2,1-b][1,3,4]thiadiazoles as inhibitors of transforming growth factor-β type-I receptor kinase (ALK5). Eur J Med Chem. 2015;93:599–613.
  • Gallagher JL, Gahman TC Topical pharmaceutical formulation comprising an iNOS inhibitor. PCT Int. Appl. WO 2008086176 A2 20080717. 2008.
  • Lopez-Cara LC, Carrion MD, Entrena A, et al. 1,3,4-Thiadiazole derivatives as selective inhibitors of iNOS versus nNOS: synthesis and structure-activity dependence. Eur J Med Chem. 2012;50:129–139.
  • Bouillot AMJ, Boyer T, Daugan AC, et al. Preparation of thiadiazole derivatives as inhibitors of stearoyl-CoA desaturase. PCT Int. Appl. WO 2008104524 A1 20080904. 2008.
  • Kamboj R, Zhang Z, Fu J, et al. Preparation of piperazinylthiadiazole carboxamides as inhibitors of stearoyl-CoA desaturase. PCT Int. Appl. WO 2006034315 A2 20060330. 2006.
  • Bhavar PK, Vakkalanka SKVS, Viswanadha S, et al. Preparation of thiadiazole derivatives as glutaminase inhibitors for treatment and prevention of glutaminerelated disorders. PCT Int. Appl. WO 2015101957 A2. 2015.
  • Bhavar PK, Vakkalanka SKVS, Viswanadha S, et al. Preparation of thiadiazole derivatives as glutaminase inhibitors for treatment and prevention of glutaminerelated disorders. PCT Int. Appl. WO 2015101958 A2 20150709. 2015.
  • Bennett MK, Gross MI, Bromley SD, et al. Preparation of heterocyclic inhibitors of glutaminase. PCT Int. Appl. WO 2014089048 A1 20140612. 2014.
  • Bolea C Preparation of 4-amino-thiazoles and 3-amino-1,2,4-thiadiazoles and their use as allosteric modulators of metabotropic glutamate receptors. PCT Int. Appl. WO 2011086163 A1 20110721. 2011.
  • Bolea C Novel pyrazole derivatives as positive allosteric modulators of metabotropic glutamate receptors and their preparation. PCT Int. Appl. WO 2011010222 A1 20110127. 2011.
  • Kashtoh H, Hussain S, Khan A, et al. Oxadiazoles and thiadiazoles: novel α-glucosidase inhibitors. Bioorg Med Chem. 2014;22:5454–5465.
  • Biden TJ, Pearson GL. Method of treating glucose metabolism disorders comprising an antagonist of lysosomal acid lipase either alone or in combination. PCT Int. Appl. WO 2014000058 A1 20140103. 2014.
  • Pradaux-Caggiano F, Su X, Vicker N, et al. Synthesis and evaluation of thiadiazole derivatives as inhibitors of 11β-hydroxysteroid dehydrogenase type 1. Med Chem Comm. 2012;3:1117–1124.
  • De Monte C, Carradori S, Secci D, et al. Synthesis and pharmacological screening of a large library of 1,3,4-thiadiazolines as innovative therapeutic tools for the treatment of prostate cancer and melanoma. Eur J Med Chem. 2015;105:245–262.
  • De Iuliis F, Taglieri L, Salerno G, et al. The kinesin Eg5 inhibitor K858 induces apoptosis but also survivin-related chemoresistance in breast cancer cells. Invest New Drugs. 2016;34:399–406.
  • Yehye WA, Abdul Rahman N, Alhadi AA, et al. Butylated hydroxytoluene analogs: synthesis and evaluation of their multipotent antioxidant activities. Molecules. 2012;17:7645–7665.
  • Ariffin A, Rahman NA, Yehye WA, et al. PASS-assisted design, synthesis and antioxidant evaluation of new butylated hydroxytoluene derivatives. Eur J Med Chem. 2014;87:564–577.
  • Chitra S, Paul N, Muthusubramanian S, et al. Synthesis of 3-heteroarylthioquinoline derivatives and their in vitro antituberculosis and cytotoxicity studies. Eur J Med Chem. 2011;46:4897–4903.
  • Marganakop SB, Kamble RR, Taj T, et al. An efficient one-pot cyclization of quinoline thiosemicarbazones to quinolines derivatized with 1,3,4-thiadiazole as anticancer and anti-tubercular agents. Med Chem Res. 2012;21:185–191.
  • Alegaon SG, Alagawadi KR, Sonkusare PV, et al. Novel imidazo[2,1-b][1,3,4]thiadiazole carrying rhodanine-3-acetic acid as potential antitubercular agents. Bioorg Med Chem Lett. 2012;22:1917–1921.
  • Ramprasad J, Nayak N, Dalimba U. Design of new phenothiazine-thiadiazole hybrids via molecular hybridization approach for the development of potent antitubercular agents. Eur J Med Chem. 2015;106:75–84.
  • Dawood KM, Eldebss TMA, El-Zahabi HAS, et al. Synthesis and antiviral activity of some new bis-1,3-thiazole derivatives. Eur J Med Chem. 2015;102:266–276.
  • Chen Z, Xu W, Liu K, et al. Synthesis and antiviral activity of 5-(4-chlorophenyl)-1,3,4-thiadiazole sulfonamides. Molecules. 2010;15:9046–9056.
  • Cui T, Chum MP, Lam Y, et al. Compounds for use as anti-viral agents. Singapore Pat. Appl. SG 162629 A1 20100729; 2010.
  • Xu W, Li S, He M, et al. Synthesis and bioactivities of novel thioether/sulfone derivatives containing 1,2,3-thiadiazole and 1,3,4-oxadiazole/thiadiazole moiety. Bioorg Med Chem Lett. 2013;23:5821–5824.
  • Hajimahdi Z, Zarghi A, Zabihollahi R, et al. Synthesis, biological evaluation, and molecular modeling studies of new 1,3,4-oxadiazole- and 1,3,4-thiadiazole-substituted 4-oxo-4H-pyrido[1,2-a]pyrimidines as anti-HIV-1 agents. Med Chem Res. 2013;22:2467–2475.
  • Zhana P, Liu X, Lia Z, et al. 1,2,3-thiadiazole thioacetanilides part 21. Synthesis and biological evaluation of a new series of 2-{[4-(3,4-dichlorophenyl)-1,2,3-thiadiazol-5-yl]sulfanyl}acetanilides as HIV-1 inhibitors. Chem Biodivers. 2010;7:1717–1727.
  • Rai D, Chen W, Zhan P, et al. Synthesis and anti-HIV activity of 4-(naphthalen-1-yl)-1,2,5-thiadiazol-3-hydroxyl derivatives. Chem Biol Drug Des. 2014;84:420–430.
  • Hamad NS, Al-Haidery NH, Al-Masoudi IA, et al. Amino acid derivatives, part 4: synthesis and anti-HIV activity of new naphthalene derivatives. Arch Pharm Chem Life Sci. 2010;343:397–403.
  • Bromley SD, Bennett MK, Gross MI, et al. Treatment of viral infections with inhibitors of glutaminase. PCT Int. Appl. WO 2015061432 A1 20150430. 2015.
  • Kornacker MG, Mapelli C, Riexinger DJ Preparation of protease activated receptor 4 (PAR4) agonist peptides and their use as PAR4 receptor activation for measuring the activity of PAR4 antagonist imidazothiadiazole and imidazopyridazine derivatives and analogs. PCT Int. Appl. WO 2013163248 A1 20131031. 2013.
  • Tehrani KHME, Sardari S, Mashayekhi V, et al. One pot synthesis and biological activity evaluation of novel schiff bases derived from 2-hydrazinyl-1,3,4-thiadiazole. Chem Pharm Bull. 2013;61:160–166.
  • Mashayekhi V, Tehrani KHME, Amidi S, et al. Synthesis of novel indole hydrazone derivatives and evaluation of their antiplatelet aggregation activity. Chem Pharm Bull. 2013;61(2):144–150.
  • Coller BS, Thomas C, Filizola M Preparation of piperazinyl substituted thiadiazolopyrimidinones for inhibiting or reducing platelet aggregation and adhesion. PCT Int. Appl. WO 2012009688 A1 20120119. 2012.
  • Proshin AN, Serkov IV, Bachurin SO Preparation of 5-amino-1,2,4-thiadiazole derivatives as neuroprotectants. PCT Int. Appl. WO 2012050484 A2 20120419. 2012.
  • Serkov IV, Proshin AN, Petrova LN, et al. Novel 1,2,4-thiadiazoles with an NO-producing fragment. Doklady Chem. 2010;435:311–313.
  • Yusuf M, Khan RA, Khan M, et al. An interactive human carbonic anhydrase-II (hCA-II) receptor-pharmacophore molecular model & anticonvulsant activity of the designed and synthesized 5-amino-1,3,4-thiadiazole-2-thiol conjugated imine derivatives. Chem Biol Drug Design. 2013;81(5):666–673.
  • Fett E, Mougenot P, Namane C, et al. Preparation of thiadiazole and oxadiazole derivatives as inhibitors of biosynthesis of triglycerides. Fr. Demande FR 2941457 A1 20100730. 2010.
  • Fett E, Mougenot P, Namane C, et al. Preparation of thiadiazole and oxadiazole derivatives as inhibitors of biosynthesis of triglycerides. PCT Int. Appl. WO 2010086551 A1 20100805. 2010.
  • Li Z, Wang W, Lu W, et al. Synthesis and biological evaluation of nonsymmetrical aromatic disulfides as novel inhibitors of acetohydroxyacid synthase. Bioorg Med Chem Lett. 2013;23(13):3723–3727.
  • Duan W, Li X, Ma X, et al. Synthesis and herbicidal activity of 5-dehydroabietyl-1,3,4-thiadiazole derivatives. Linchan Huaxue Yu Gongye. 2011;31:1–8.
  • Feng L, Qin Y, Wan J, et al. Application of thiadiazole compound in inhibiting algae growth and enzyme activity, and as algicide for inhibiting algae growth. Faming Zhuanli Shenqing CN 104920387 A 20150923. 2015.
  • Babich O, Garyantes T, Luo RZ, et al. Preparation of thiadiazolyl sulfonamide derivatives as sodium channel modulators for the treatment of pain and diabetes. PCT Int. Appl. WO 2015038533 A2 20150319. 2015.
  • Joshi P, Krenitsky P, Termin A, et al. Preparation of heteroaryl amides useful as inhibitors of voltage-gated sodium channels. PCT Int. Appl. WO 2009049180 A2 20090416. 2009.
  • Tahghighi A, Marznaki FR, Kobarfard F, et al. Synthesis and antileishmanial activity of novel 5-(5-nitrofuran-2-y1)- 1,3,4-thiadiazoles with piperazinyl-linked benzamidine substituents. Eur J Med Chem. 2011;46:2602–2608.
  • Alipour E, Emami S, Meymand YA, et al. Synthesis and antileishmanial activity of 5-(5-nitroaryl)-2-substituted-thio-1,3,4-thiadiazoles. J Enz Inhib Med Chem. 2010;26:123–128.
  • Griffioen G, Wera S, Duhamel HR, et al. Thiadiazole derivatives for the treatment of neuro-degenerative diseases and their preparation. PCT Int. Appl. WO 2008061781 A1 20080529. 2008.
  • Kuo G, Shen L, Wang A, et al. Preparation of 4-[(thiadiazolylalkyl)thio]-phenoxyacetic acids and analogs for treating PPAR mediated conditions. U.S. Pat. Appl. Publ. US 20050096362 A1 20050505. 2005.
  • Hoveyda H, Dutheuil G, Fraser G Preparation of N-acyl-(3-substituted)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazines as selective NK-3 receptor antagonists. PCT Int. Appl. WO 2014154895 A1 20141002. 2014.
  • Madden J, Hallett DJ, Parkes A, et al. Preparation of sulfonylaminomethyl five-membered heterocyclic carboxamide derivatives as bradykinin B1 antagonists and their preparation, pharmaceutical compositions and use in the treatment of inflammatory related disorders. PCT Int. Appl. WO 2010020556 A1 20100225. 2010.
  • Patel HM, Noolvi MN, Goyal A, et al. 2,5,6-trisubstituted imidazo[2,1-b]-[1,3,4]thiadiazoles: search for antihyperlipidemic agents. Eur J Med Chem. 2013;65:119–133.
  • Biju PJ, Taveras AG, Yu Y, et al. Preparation of diaminothiadiazoles as CXC- and CC-chemokine receptor ligands. PCT Int. Appl. WO 2005066147 A1 20050721. 2005.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.