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image of Imidazo[2,1-b] [1,3,4]thiadiazole: A Versatile Scaffold in Anticancer Drug Discovery - Impact of C-2, C-5, and C-6 Substitutions

Abstract

Imidazo[2,1-b][1,3,4]thiadiazoles, a class of fused bicyclic heterocycles, have garnered significant interest in medicinal chemistry due to their diverse biological activities, particularly their anticancer properties. Over recent decades, extensive research has been conducted to explore and enhance their therapeutic potential. This comprehensive review spans six decades of research on the imidazo[2,1-b][1,3,4]thiadiazole scaffold, focusing on structural variations at C-2, C-5, and C-6 position on this scaffold and their implications for anticancer activity. Modifications at these positions have been shown to significantly impact the compound’s efficacy against various cancer cell lines. Continuous exploration and optimization of these substitutions hold promise for the development of novel anticancer therapeutics.

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2025-10-22
2025-11-01

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References

  1. Ahmad M. Aslam S. Rizvi S. U. F. Muddassar M. Ashfaq U. A.; Montero,C. Ollinger, O.. Detorio, M,. Rizvi S. Siddiqui H.L. Gardiner J.M. Schinazi R. F. Molecular docking and antiviral activity of n substituted Benzyl/Phenyl 2 (3,4 Dimethyl 5,5 dioxidopyrazolo[4,3 c][1,2] benzothiazin 2(4H) yl)acetamides Bioorg Med. Chem. Res. Lett 2013 25 6 1348 1351 10.1016/j.bmcl.2015.01.007
    [Google Scholar]
  2. Ahmad M. Siddiqui H.L. Gardiner J.M. Parvez M. Aslam S. Synthesis and antioxidant studies of novel N-substituted benzyl/phenyl-2-(3,4-dimethyl-5,5-dioxidopyrazolo[4,3-c][1,2]ben-zothiazin-2(4H)-yl)acetamides. Med. Chem. Res. 2013 22 2 794 805 10.1007/s00044‑012‑0062‑6
    [Google Scholar]
  3. Aslam S. Zaib S. Ahmad M. Gardiner J.M. Ahmad A. Hameed A. Furtmann N. Gütschow M. Bajorath J. Iqbal J. Novel struc-tural hybrids of pyrazolobenzothiazines with benzimidazoles as cholinesterase inhibitors. Eur. J. Med. Chem. 2014 78 106 117 10.1016/j.ejmech.2014.03.035 24681070
    [Google Scholar]
  4. Ahmad M. Siddiqui H.L. Zia-ur-Rehman M. Parvez M. Anti-oxidantand anti-bacterial activities of novel N′-arylmethylidene-2-(3,4-Dimethyl-5,5-dioxidopyrazolo[4,3-c][1,2] benzothiazin-2(4H)-yl)acetohydrazides. Eur. J. Med. Chem. 2010 45 2 698 704 10.1016/j.ejmech.2009.11.016 19962218
    [Google Scholar]
  5. Kanwal A. Saddique F.A. Aslam S. Ahmad M. Zahoor A.F. Mohsin N.A. Benzimidazole ring system as a privileged template for anticancer agents. Pharm. Chem. J. 2018 51 12 1068 1077 10.1007/s11094‑018‑1742‑4
    [Google Scholar]
  6. Khalid Z. Shafqat S.S. Ahmad H.A. Rehman H.M. Munawar M.A. Ahmad M. Asiri A.M. Ashraf M. Synthesis of 1,2,3-benzotriazin-4(3H)-one derivatives as α-glucosidase inhibitor and their in-silico study. Med. Chem. Res. 2022 31 5 819 831 10.1007/s00044‑022‑02883‑1
    [Google Scholar]
  7. Kanwal A. Ullah S. Ahmad M. Pelletier J. Aslam S. Sultan S. Sévigny J. Iqbal M. Iqbal J. Synthesis and nucleotide pyrophosp-hatase/phosphodiesterase inhibition studies of carbohydrazides based on benzimidazole‐benzothiazine skeleton. ChemistrySelect 2020 5 45 14399 14407 10.1002/slct.202003479
    [Google Scholar]
  8. Bukhari M.H. Ahmad M. Hussain T. Umar S. Ahmad N. Synthesis and biological studies of a novel series of 4-(4-(1H-imidazol-1-yl)phenyl)-6-arylpyrimidin-2-amines. Med. Chem. Res. 2013 22 11 5248 5254 10.1007/s00044‑013‑0523‑6
    [Google Scholar]
  9. Chalkappa P.K.B. Aralihalli S. Sudileti M. Aithal S.J. Praveen B.M. Birjadar K. The medicinal panorama of benzimidazoles and their scaffolds as anticancer and antithrombotic agents: A review. Arch. Pharm. 2023 356 10 2300206 10.1002/ardp.202300206 37440107
    [Google Scholar]
  10. Shetty P. Praveen B.M. Raghavendra M. Manjunath K. Cheruku S. Synthesis and antimicrobial evaluation of novel 4-amino-6-(1,3,4-oxadiazolo/1,3,4-thiadiazolo)-pyrimidine derivatives. Mol. Divers. 2016 20 2 391 398 10.1007/s11030‑015‑9640‑0 26498121
    [Google Scholar]
  11. G, S.; Majid, F.A.A.; Pradeep, S.; Hudiyanti, D.; Nik, W.M.N.W.; Naha, S.; Praveen, B.M. Synthesis, In silico studies and antitumor activi-ty of new 4-bromo-2-(1H-1,2,4-triazol-3-yl)aniline derived schiff bases. J. Mol. Struct. 2025 1345 142987 10.1016/j.molstruc.2025.142987
    [Google Scholar]
  12. Govindaiah S. Naha S. Madhuchakrapani Rao T. Revanasiddappa B.C. Srinivasa S.M. Parashuram L. Velmathi S. Sreenivasa S. Sulfated magnesium zirconate catalyzed synthesis, antimicrobial, antioxidant, anti-inflammatory, and anticancer activity of ben-zo[d]thiazole-hydrazone analogues and its molecular docking. Results Chem. 2021 3 100197 10.1016/j.rechem.2021.100197
    [Google Scholar]
  13. Atmaram U.A. Roopan S.M. Biological activity of oxadiazole and thiadiazole derivatives. Appl. Microbiol. Biotechnol. 2022 106 9-10 3489 3505 10.1007/s00253‑022‑11969‑0 35562490
    [Google Scholar]
  14. Castaño T. Encinas A. Pérez C. Castro A. Campillo N.E. Gil C. Design, synthesis, and evaluation of potential inhibitors of nitric oxide synthase. Bioorg. Med. Chem. 2008 16 11 6193 6206 10.1016/j.bmc.2008.04.036 18477512
    [Google Scholar]
  15. Bogle R.G. Whitley G.S.J. Soo S.C. Johnstone A.P. Vallance P. Effect of anti‐fungal imidazoles on mRNA levels and enzyme activity of inducible nitric oxide synthase. Br. J. Pharmacol. 1994 111 4 1257 1261 10.1111/j.1476‑5381.1994.tb14881.x 7518297
    [Google Scholar]
  16. Fascio M.L. Errea M.I. D’Accorso N.B. Imidazo-thiazoles: Synthesis, chemical and biological properties. Eur. J. Med. Chem. 2015 95 347 358 10.1016/j.ejmech.2014.12.012 25499987
    [Google Scholar]
  17. Park J-H. El-Gamal M.I. Lee Y.S. Oh C-H. Novel Imidazo[2,1-b][1,3,4]thiadiazole derivatives: Synthesis, in vitro anticancer evalua-tion and in silico studies. Eur. J. Med. Chem. 2011 46 1235 1244 10.1016/j.ejmech.2011.08.024 22033063
    [Google Scholar]
  18. Serban G. Stanasel O. Serban E. Bota S. 2-Amino-1,3,4-thiadiazole as a potential scaffold for promising antimicrobial agents. Drug Des. Devel. Ther. 2018 12 1545 1566 10.2147/DDDT.S155958 29910602
    [Google Scholar]
  19. Barboiu M. Cimpoesu M. Guran C. Supuran C.T. 1,3,4-thiadiazole derivatives. Part 9. Synthesis and biological activity of metal com-plexes of 5-(2-aminoethyl)-2-amino-1,3,4-thiadiazole. Met. Based Drugs 1996 3 5 227 232 10.1155/MBD.1996.227 18472898
    [Google Scholar]
  20. Li X. He L. Chen H. Wu W. Jiang H. Copper-catalyzed aerobic C(sp2)-H functionalization for C-N bond formation: Synthesis of pyrazoles and indazoles. J. Org. Chem. 2013 78 8 3636 3646 10.1021/jo400162d 23547954
    [Google Scholar]
  21. Matsukawa T. Ban S. Reaction of α-bromoacetophenones with 2-Amino-1,3,4-thiadiazoles (Studies on Chemotherapeutics XXVII). Yakugaku Zasshi 1952 72 5 610 614 10.1248/yakushi1947.72.5_610
    [Google Scholar]
  22. Taflan E. Bayrak H. Er M. Alpay Karaoğlu Ş. Bozdeveci A. Novel imidazo[2,1-b][1,3,4]thiadiazole (ITD) hybrid compounds: De-sign, synthesis, efficient antibacterial activity and antioxidant effects. Bioorg. Chem. 2019 89 102998 10.1016/j.bioorg.2019.102998 31128819
    [Google Scholar]
  23. Ramprasad J. Nayak N. Dalimba U. Yogeeswari P. Sriram D. One-pot synthesis of new triazole—Imidazo[2,1-b][1,3,4]thiadiazole hybrids via click chemistry and evaluation of their antitubercular activity. Bioorg. Med. Chem. Lett. 2015 25 19 4169 4173 10.1016/j.bmcl.2015.08.009 26298500
    [Google Scholar]
  24. Ramprasad J. Nayak N. Dalimba U. Yogeeswari P. Sriram D. Peethambar S.K. Achur R. Kumar H.S.S. Synthesis and biological evaluation of new imidazo[2,1-b][1,3,4]thiadiazole-benzimidazole derivatives. Eur. J. Med. Chem. 2015 95 49 63 10.1016/j.ejmech.2015.03.024 25794789
    [Google Scholar]
  25. Alegaon S.G. Alagawadi K.R. Sonkusare P.V. Chaudhary S.M. Dadwe D.H. Shah A.S. Novel imidazo[2,1-b][1,3,4]thiadiazole ca-rrying rhodanine-3-acetic acid as potential antitubercular agents. Bioorg. Med. Chem. Lett. 2012 22 5 1917 1921 10.1016/j.bmcl.2012.01.052 22325950
    [Google Scholar]
  26. Patel H.M. Noolvi M.N. Sethi N.S. Gadad A.K. Cameotra S.S. Synthesis and antitubercular evaluation of imidazo[2,1- b][1,3,4]thiadiazole derivatives. Arab. J. Chem. 2017 10 S996 S1002 10.1016/j.arabjc.2013.01.001
    [Google Scholar]
  27. Hakan Tahtaci H. Karacık H. Askin S. Design, synthesis, SAR, and molecular modeling studies of novel imidazo[2,1-b][1,3,4]thiadiazole derivatives as highly potent antimicrobial agents. Mol. Inform. 2017 36 1700147 10.1002/minf.201700083
    [Google Scholar]
  28. Ibrahim Ozcan I. Akkoc S. Tunel H. Mustafa Er M. Novel thioether-bridged 2,6-disubstituted and 2,5,6-trisubstituted imidazo[2,1-b][1,3,4]thiadiazole analogues: Synthesis, antiproliferative activity, ADME, and molecular docking studies. Chem. Biodivers. 2022 19 12 202200884 10.1002/cbdv.202200884
    [Google Scholar]
  29. Askin S. Tahtaci H. Türkeş C. Demir Y. Ece A. Akalın Çiftçi G. Beydemir Ş. Design, synthesis, characterization, in vitro and in silico evaluation of novel imidazo[2,1-b][1,3,4]thiadiazoles as highly potent acetylcholinesterase and non-classical carbonic anhydrase in-hibitors. Bioorg. Chem. 2021 113 105009 10.1016/j.bioorg.2021.105009 34052739
    [Google Scholar]
  30. Noolvi M.N. Patel H.M. Ghatole M. Narqund L.G. Synthesis, spectral studies and biological evaluation of a novel series of 2-substituted-5,6-diarylsubstituted imidazo[2,1-b][1,3,4]thiadiazole derivatives as possible antitubercular agents. Med. Chem. Res. 2012 21 1313 1321 10.1007/s00044‑011‑9646‑9
    [Google Scholar]
  31. Haider S. Alam M.S. Hamid H. 1,3,4-Thiadiazoles: A potent multi targeted pharmacological scaffold. Eur. J. Med. Chem. 2015 92 156 177 10.1016/j.ejmech.2014.12.035 25553540
    [Google Scholar]
  32. Talath S. Gadad A.K. Synthesis, antibacterial and antitubercular activities of some 7-[4-(5-amino-[1,3,4]thiadiazole-2-sulfonyl)-piperazin-1-yl] fluoroquinolonic derivatives. Eur. J. Med. Chem. 2006 41 8 918 924 10.1016/j.ejmech.2006.03.027 16781799
    [Google Scholar]
  33. Kamal A. Khan F. Farahat O.O.M. Ahmed-Farag I.S. El-Gazzar A.B. A facile regioselective synthesis of novel spiro-thioxanthene and spiro-xanthene-9′,2′-[1,3,4]-thiadiazole derivatives as potential analgesic and anti-inflammatory agents. Bioorg. Med. Chem. Lett. 2008 18 4538 4543 10.1016/j.bmcl.2008.07.042 18667305
    [Google Scholar]
  34. Kamal A. Farahat O.O.M. Atta K.F.M. Marei M.G.S. Synthesis and antibacterial activities of novel imidazo[2,1-b][1,3,4]-thiadiazoles. Molecules 2011 16 7 5496 5506 10.3390/molecules16075496 21712761
    [Google Scholar]
  35. Kadi A.A. Al-Abdullah E.S. Shehata I.A. Habib E.E. Ibrahim T.M. El-Emam A.A. Synthesis, antimicrobial and anti-inflammatory activities of novel 5-(1-adamantyl)-1,3,4-thiadiazole derivatives. Eur. J. Med. Chem. 2010 45 11 5006 5011 10.1016/j.ejmech.2010.08.007 20801553
    [Google Scholar]
  36. Khazi I.A.M. Gadad A.K. Lamani R.S. Bhongade B.A. Chemistry of imidazo[2,1-b][1,3,4]thiadiazoles. Tetrahedron 2011 67 19 3289 3316 10.1016/j.tet.2011.03.027
    [Google Scholar]
  37. Bhongade B.A. Talath S. Gadad R.A. Gadad A.K. Biological activities of imidazo[2,1-b][1,3,4]thiadiazole derivatives: A review. J. Saudi Chem. Soc. 2016 20 S1 S463 S475 10.1016/j.jscs.2013.01.010
    [Google Scholar]
  38. Cativiela C. García J.I. Marín A. Valls N. Elguero J. Molecular electrostatic potential-anthelmintic activity relationships of 5H-mebendazole and some related heterocyclic carbamates. Farmaco 1989 44 7-8 671 682 10.1016/0014‑827X(89)80033‑0 2590365
    [Google Scholar]
  39. Ivashchenko A.V. Torgova S.I. Karamysheva L.A. Abolin A.G. Imidazo [2, 1-b]-1,3,4-thiadiazoles. A new class of liquid-crystalline compounds. Liq. Cryst. 1990 7 4 475 485 10.1080/02678299008033824
    [Google Scholar]
  40. Jag M. Shikha. Facile synthesis and antimicrobial activity of some thiadiazole derivatives. Indian J. Heterocycl. Chem. 2005 14 365 366
    [Google Scholar]
  41. Fascio M.L. Errea M.I. D’Accorso N.B. Imidazothiazole and related heterocyclic systems. Synthesis, chemical and biological proper-ties. Eur. J. Med. Chem. 2015 90 666 683 10.1016/j.ejmech.2014.12.012 25499987
    [Google Scholar]
  42. Scozzafava A. Supuran C.T. Complexes with biologically active ligands. Part 10 1 inhibition of carbonic anhydrase isozymes I and II with metal complexes of imidazo[2, 1-b]‐1,3,4‐thiadiazole‐2‐sulfonamide. Met. Based Drugs 1997 4 1 19 26 10.1155/MBD.1997.19 18475761
    [Google Scholar]
  43. Taher A.T. Georgey H.H. El-Subbagh H.I. Novel 1,3,4-heterodiazole analogues: Synthesis and in-vitro antitumor activity. Eur. J. Med. Chem. 2012 47 1 445 451 10.1016/j.ejmech.2011.11.013 22119151
    [Google Scholar]
  44. Kaur A. Kumar R. Kalidhar U. Synthesis, spectral studies and biological activity of some novel biphenyl imidazo[2,1-b][1,3,4]thiadiazole derivatives. Res. J. Pharm. Biol. Chem. Sci. 2012 3 1084 1096
    [Google Scholar]
  45. Kumar S. Karki S. Saini V. Maurya I.K. Sindhu J. Kumari M. Kataria R. Khushwah S. Gokulkrishnan S. Nirgude S. Ravin-dran F. Choudhary B. Synthesis, molecular docking, dynamics study, and preliminary cytotoxicity study of some coumarin-linked imi-dazo[2,1-b][1,3,4]thiadiazoles. J. Mol. Struct. 2024 1321 10 139943 10.1016/j.molstruc.2024.139943
    [Google Scholar]
  46. Petri L. Giovanna; Pecoraro, Camilla; Randazzo, Ornella; Zoppi, Silvia; Cascioferro, Stella M.; Parrino, Barbara; Carbone, Daniela; El Hassouni, Btissame; Cavazzoni, Andrea; Zaffaroni, Nadia; Cirrincione, Girolamo; Diana, Patrizia J.; Peters, Godefridus J.; Giovannetti, Elisa. Anticancer Res. 2020 40 4913 4919 10.21873/anticanres.14494
    [Google Scholar]
  47. Cascioferro S.M. Petri L. Giovanna; Parrino, Barbara; Carbone, Daniela; Funel, Niccola; Bergonzini, Cecilia; Mantini, Giulia; Dekker, Henk; Geerke, Daan; Peters, Godefridus J.; Cirrincione, Girolamo; Giovannetti, Elisa; Diana, Patrizia. Eur. J. Med. Chem. 2020 189 112088 10.1016/j.ejmech.2020.112088 32007666
    [Google Scholar]
  48. Romagnoli R. Baraldi P.G. Prencipe F. Balzarini J. Liekens S. Estévez F. 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 10.1016/j.ejmech.2015.06.042 26141911
    [Google Scholar]
  49. Shaik K.S. N, S.; G, N.R. Rational design, synthesis, and anticancer evaluation of amide derivatives of Pyridin3-yl)imidazo[2,1-b][1,3,4]thiadiazole linked 1,3,4-oxadiazoles. Chemical Data Collections 2024 52 101147 10.1016/j.cdc.2024.101147
    [Google Scholar]
  50. Terzioğlu N. Gürsoy 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 7-8 781 786 10.1016/S0223‑5234(03)00138‑7 12932910
    [Google Scholar]
  51. Karki S.S. Panjamurthy K. Kumar S. Nambiar M. Ramareddy S.A. Chiruvella K.K. Raghavan S.C. Synthesis and biological evalua-tion of novel 2-aralkyl-5-substituted-6-(4′-fluorophenyl)-imidazo[2,1-b][1,3,4]thiadiazole derivatives as potent anticancer agents. Eur. J. Med. Chem. 2011 46 6 2109 2116 10.1016/j.ejmech.2011.02.064 21439690
    [Google Scholar]
  52. Noolvi M.N. Patel H.M. Singh N. Gadad A.K. Cameotra S.S. Badiger A. Synthesis and anticancer evaluation of novel 2-cyclopropylimidazo[2,1-b][1,3,4]-thiadiazole derivatives. Eur. J. Med. Chem. 2011 46 9 4411 4418 10.1016/j.ejmech.2011.07.012 21820217
    [Google Scholar]
  53. Gadad A.K. Karki S.S. Rajurkar V.G. Bhongade B.A. Synthesis and biological evaluation of 6-aryl-N-[(dimethylamino) methylene]-5-formylimidazo [2, 1-b]-1, 3, 4-thiadiazole-2-sulfona-mides as antitumor agents. Arzneimittelforschung 1999 49 858 863 10.1055/s‑0031‑1299688 10554665
    [Google Scholar]
  54. Kamiya S. Tanno M. Miyahara M. Synthesis of antitumor heterocyclic compounds. Eisei Shikenjo Hokoku 1983 101 101 71 75 [Synthesis of antitumor heterocyclic compounds 6675776
    [Google Scholar]
  55. Miyahara M. Kamiya S. Nakadate M. Sueyoshi S. Tanno M. Miyahara M. Antitumor effect of compounds synthesized in the Division of Synthetic Chemistry (VI) Eisei Shikenjo Hokoku 1982 100 100 163 165 Antitumor effect of compounds synthesized in the Divi-sion of Synthetic Chemistry (VI) 7183380
    [Google Scholar]
  56. Ibrahim S.A. Salem M.M. Elsalam H.A.A. Noser A.A. Design, synthesis, in-silico and biological evaluation of novel 2-Amino-1,3,4-thiadiazole based hydrides as B-cell lymphoma-2 inhibitors with potential anticancer effects. J. Mol. Struct. 2022 1268 133673 10.1016/j.molstruc.2022.133673
    [Google Scholar]
  57. Singh S. Bhandari D.D. Gupta M. Singh J. Design, synthesis and anticancer potential evaluation of novel naphthoic acid-linked imida-zo[2,1-b][1,3,4]thiadiazoles. Res. J. Pharm. Biol. Chem. Sci. 2022 15 10 2022 10.52711/0974‑360X.2022.00738
    [Google Scholar]
  58. Bhogireddy D.N. Surapureddi S.R. Palle S. Tadiboina B.R. Synthesis and biological evaluation of amide derivatives of benzoxazole linked Imidazo[2,1-b][1,3,4]thiadiazole as antiproliferative agents. Chem. Data Collect 2022 39 100856 10.1016/j.cdc.2022.100856
    [Google Scholar]
  59. Choodomani B. Kumar S. Gupta A.K. Schols D. Tahtaci H. Karakurt T. Kotha S.B.S. Setty R. Karki S.S. Synthesis, molecular docking, and preliminary cytotoxicity study of some novel 2-(naphthalen-1-yl)-methylimidazo[2,1-b][1,3,4]thiadiazoles. J. Mol. Struct. 2021 1234 130174 10.1016/j.molstruc.2021.130174
    [Google Scholar]
  60. Alugubelli G.R. Reddymasu S. Babu V.H. Rao Y.J.P. Susithra E. Basaveswara M.V.P.S. Rao. “Design, synthesis, and anticancer evaluation of quinazolinone-imidazo[2,1-b][1,3,4]thiadiazole hybrid derivatives.”. Chemical Data Collections 2021 31 100614 10.1016/j.cdc.2020.100614
    [Google Scholar]
  61. Sridhar G. Palle S. Vantikommu J. Gangarapu K. Design, synthesis, and biological evaluation of amide derivatives of imidazo[2,1- b][1,3,4]thiadiazole as anticancer agents. Synth. Commun. 2020 50 21 3221 3233 10.1080/00397911.2020.1797814
    [Google Scholar]
  62. Narasimha Rao M.P. Nagaraju B. Kovvuri J. Polepalli S. Alavala S. Vishnuvardhan M.V.P.S. Swapna P. Nimbarte V.D. Laksh-mi J.K. Jain N. Kamal A. Synthesis of imidazo-thiadiazole linked indolinone conjugates and evaluated their microtubule network dis-rupting and apoptosis inducing ability. Bioorg. Chem. 2018 76 420 436 10.1016/j.bioorg.2017.11.021 29275261
    [Google Scholar]
  63. Kumar S. Metikurki B. Bhadauria V.S. De Clercq E. Schols D. Tokuda H. Karki S.S. Synthesis and pharmacological activity of imidazo[2,1-b][1,3,4]thiadiazole derivatives as possible biologically active agents. Acta. Pol. Pharm. Drug Res. 2016 73 4 913 929 10.1080/00397911.2020.1797814 29648717
    [Google Scholar]
  64. Kumar S. Gopalakrishnan V. Hegde M. Rana V. Dhepe S.S. Ramareddy S.A. Leoni A. Locatelli A. Morigi R. Rambaldi M. Srivastava M. Raghavan S.C. Karki S.S. Synthesis and antiproliferative activity of imidazo[2,1- b][1,3,4]thiadiazole derivatives. Bioorg. Med. Chem. Lett. 2014 24 19 4682 4688 10.1016/j.bmcl.2014.08.032 25205189
    [Google Scholar]
  65. Kumar S. Hegde M. Gopalakrishnan V. Renuka V.K. Ramareddy S.A. De Clercq E. Schols D. Gudibabande Narasimhamurthy A.K. Raghavan S.C. Karki S.S. 2-(4-Chlorobenzyl)-6-arylimidazo[2,1-b][1,3,4]thiadiazoles: Synthesis, cytotoxic activity and mecha-nism of action. Eur. J. Med. Chem. 2014 84 687 697 10.1016/j.ejmech.2014.07.054 25064346
    [Google Scholar]
  66. Abdel Rahman D.E. Mohamed K.O. Synthesis of novel 1,3,4-thiadiazole analogues with expected anticancer activity. Pharma. Chem. 2014 6 1 323 335
    [Google Scholar]
  67. Kamal A. Rao M.P.N. Das P. Swapna P. Polepalli S. Nimbarte V.D. Mullagiri K. Kovvuri J. Jain N. Synthesis and biological evaluation of imidazo[2,1-b][1,3,4]thiadiazole-linked oxindoles as potent tubulin polymerization inhibitors. ChemMedChem 2014 9 7 1463 1475 10.1002/cmdc.201400069 24715721
    [Google Scholar]
  68. Tegginamath G. Kamble R.R. Taj T. Kattimani P.P. Meti G.Y. Synthesis of novel imidazo[2,1-b][1,3,4]thiadiazoles appended to sydnone as anticancer agents. Med. Chem. Res. 2013 22 9 4367 4375 10.1007/s00044‑012‑0441‑z
    [Google Scholar]
  69. Gireesh T.M. Kamble R.R. Taj T. Synthesis and antimicrobial and anticancer activity of new of imidazo[2,1-b][1,3,4]thiadiazoles. Pharm. Chem. J. 2011 45 5 313 316 10.1007/s11094‑011‑0624‑9
    [Google Scholar]
  70. Noolvi M.N. Patel H.M. Kamboj S. Kaur A. Mann V. 2,6-Disubstituted imidazo[2,1-b][1,3,4]thiadiazoles: Search for anticancer agents. Eur. J. Med. Chem. 2012 56 56 69 10.1016/j.ejmech.2012.08.012 22960694
    [Google Scholar]
  71. Dwarakanath D. Nayak Y.N. Kulal A. Pandey S. Pai K.S.R. Gaonkar S.L. In vitro and in silico insights into antimicrobial and anti-cancer activities of novel imidazo[2,1-b][1,3,4]thiadiazoles. Sci. Rep. 2024 14 1 31994 10.1038/s41598‑024‑83498‑x 39738776
    [Google Scholar]
  72. Mirghani A.H. Pehlivanoglu S. Alici H. Tahtaci H. Uysal S. Synthesis and characterization of schiff bases and their Ag(I) complexes containing 2,5,6‐trisubstituted imidazothiadiazole derivatives: Molecular docking and in vitro cytotoxic effects against nonsmall lung can-cer cell line. J. Biochem. Mol. Toxicol. 2025 39 2 70142 10.1002/jbt.70142 39829402
    [Google Scholar]
  73. Li Petri G. Pecoraro C. Randazzo O. Zoppi S. Cascioferro S.M. Parrino B. Carbone D. El Hassouni B. Cavazzoni A. Zaffaroni N. Cirrincione G. Diana P. Peters G.J. Giovannetti E. New Imidazo[2,1- b][1,3,4]thiadiazole derivatives inhibit FAK phosphorylation and potentiate the antiproliferative effects of gemcitabine through modulation of the human equilibrative nucleoside transporter-1 in peri-toneal mesothelioma. Anticancer Res. 2020 40 9 4913 4919 10.21873/anticanres.14494 32878779
    [Google Scholar]
  74. Kamal A. Reddy V.S. Santosh K. Bharath Kumar G. Shaik A.B. Mahesh R. Chourasiya S.S. Sayeed I.B. Kotamraju S. Synthesis of imidazo[2,1-b][1,3,4]thiadiazole–chalcones as apoptosis inducing anticancer agents. MedChemComm 2014 5 11 1718 1723 10.1039/C4MD00228H
    [Google Scholar]
  75. Indelicato S. Bongiorno D. Mauro M. Cascioferro S. Recent developments of 1,3,4-thiadiazole compounds as anticancer agents. Pharmaceuticals 2025 18 4 580 10.3390/ph18040580 40284015
    [Google Scholar]
  76. Aliabadi A. 1,3,4-thiadiazole based anticancer agents. Anticancer. Agents Med. Chem. 2016 16 10 1301 1314 10.2174/1871520616666160628100936 27484056
    [Google Scholar]
  77. Szeliga M. Thiadiazole derivatives as anticancer agents. Pharmacol. Rep. 2020 72 5 1079 1100 10.1007/s43440‑020‑00154‑7 32880874
    [Google Scholar]
/content/journals/mrmc/10.2174/0113895575415617251007055129
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Imidazo[2,1-b] [1,3,4]thiadiazole: A Versatile Scaffold in Anticancer Drug Discovery - Impact of C-2, C-5, and C-6 Substitutions
Bentham Science Publishers ; https://doi.org/10.2174/0113895575415617251007055129
/content/journals/mrmc/10.2174/0113895575415617251007055129
/content/journals/mrmc/10.2174/0113895575415617251007055129
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  • Article Type:     Review Article
Keywords: scaffold ; versatile ; Anticancer ; cell line ; herbicidal ; Imidazo[2,1-b] ; [1,3,4]thiadiazole

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