Imidazothiazole and related heterocyclic systems. Synthesis, chemical and biological properties

European Journal of Medicinal Chemistry

Volumn 90, Issue , 2015, Pages 666-683

  Fascio, Mirta L ^a   Errea, Mariá Inés ^b   D'Accorso, Norma Beatriz ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^b INSTITUTO TECNOLÓGICO DE BUENOS AIRES   (Argentina)

Author keywords

Biological activities; Imidazo 2 1 b thiazoles; Imidazo 2 1 b 1 3 4 thiadiazoles; Imidazo 2 1 c 1 2 4 triazoles; Pyrrolo 2 1 b thiazoles

Indexed keywords

ALPRAZOLAM; AMPICILLIN; ANASTROZOLE; ANTINEOPLASTIC AGENT; BLEOMYCIN; ESTAZOLAM; ETOPERIDONE; FLUCONAZOLE; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; ITRACONAZOLE; LETROZOLE; NEFAZODONE; NEW DRUG; PYRROLE DERIVATIVE; RIBAVIRIN; RILMAZAFONE; TERCONAZOLE; THIAZOLE DERIVATIVE; TRAPIDIL; TRAZODONE; VOROZOLE; ANTIINFECTIVE AGENT; ANTIVIRUS AGENT;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CANCER CELL LINE; CATALYST; CHRONOTROPISM; CYCLIZATION; DEACETYLATION; DRUG BINDING SITE; DRUG SYNTHESIS; ENZYME ACTIVITY; HEATING; HUMAN; HYDROGEN BOND; HYDROLYSIS; INOTROPISM; ISOMERIZATION; MICROWAVE RADIATION; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; NONHUMAN; OXIDATION; REACTION TIME; THERAPY EFFECT; ANIMAL; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECTS; SYNTHESIS;

ANIMALS; ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CELL PROLIFERATION; HETEROCYCLIC COMPOUNDS; HUMANS; IMIDAZOLES; THIAZOLES;

EID: 84949120432     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.12.012     Document Type: Review

References (90)

1. A.E. Rashad A.E. Mahmoud M.M. Ali Synthesis and anticancer effects of some novel pyrazolo[3,4-d[pyrimidine derivatives by generating reactive oxygen species in human breast adenocarcinoma cells Eur. J. Med. Chem. 46 2011 1019 1026
2. A.H. Shamroukh M.E. Zaki E.M. Morsy F.M. Abdel-Motti F.M. Abdel-Megeid Synthesis of pyrazolo[4g'2,3g'2:5,6] pyrano[2,3-d[pyrimidine derivatives for antiviral evaluation Arch. Pharm. Chem. Life Sci. 340 2007 236 243
3. B. Singh A. Maheshwari G. Dak K. Sharma G. Talesara Studies of antimicrobial activities of some 4-thiazolidinone fused pyrimidines, [1,5]-benzodiazepines and their oxygen substituted hydroxylamine derivatives Indian J. Pharm. Sci. 72 2010 607 612
4. D. Kim L. Wang J.J. Hale C.L. Lynch R.J. Budhu M. MacCoss S.G. Mills L. Malkowitz S.L. Gould J.A. DeMartino M.S. Springer D. Hazuda M. Miller J. Kessler R.C. Hrin G. Carver A. Carella K. Henry J. Lineberger W.A. Schleif E.A. Emini Potent 1,3,4-trisubstituted pyrrolidine CCR5 receptor antagonists: effects of fused heterocycles on antiviral activity and pharmacokinetic properties Bioorg. Med. Chem. Lett. 15 2005 2129 2134
5. A. Kamal G.B. Ramesh Khanna T. Krishnaji R. Ramu A new facile chemoenzymatic synthesis of levamisole Bioorg. Med. Chem. Lett. 15 2005 613 615
6. H. Amarouch P.R. Loiseau C. Bacha R. Caujolle M. Payard P.M. Loiseau C. Bories P. Gayral Imidazo[2,1-b[thiazoles: analogues du lévamisole Eur. J. Med. Chem. 22 1987 463 466
7. D.C. Cole J.R. Stock W.J. Lennox R.C. Bernotas J.W. Ellingboe S. Boikess J. Coupet D.L. Smith L. Leung G. Zhang X. Feng M.F. Kelly R. Galante P. Huang A.D. Lee K. Marquis S.R. Lipson C.E. Beyer L.E. Schechter Discovery of N1-(6-chloroimidazo[2,1-b[[1,3]thiazole-5-sulfonyl)tryptamine as a potent, selective, and orally active 5-HT6 receptor agonist J. Med. Chem. 50 2007 5535 5538
8. N.U. Güzeldemirci Ö. Küçükbasmac± 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. 45 2010 63 68
9. J.K. Malik H. Soni A.K. Singhai Synthesis, characterization and evaluation for antifungal activity of substituted diaryl imidazo [2, 1, b[-benzothiazole J. Pharm. Res. 7 2013 39 46
10. E. Gürsoy N.U. Güzeldemirci Synthesis and primary cytotoxicity evaluation of new imidazo[2,1-b[thiazole derivatives Eur. J. Med. Chem. 42 2007 320 326
11. A. Andreani M. Granaiola A. Leoni A. Locatelli R. Morigi M. Rambaldi L. Varoli D. Lannigan J. Smith D. Scudiero S. Kondapaka R.H. Shoemaker Imidazo[2,1-b[thiazole guanylhydrazones as RSK2 inhibitors Eur. J. Med. Chem. 46 2011 4311 4323
12. J.-H. Park M.I. El-Gamal Y.S. Lee C.-H. Oh New imidazo[2,1-b[thiazole derivatives: synthesis, in vitro anticancer evaluation, and in silico studies Eur. J. Med. Chem. 46 2011 5769 5777
13. S.D. Fidanze S.A. Erickson G.T. Wang R. Mantei R.F. Clark B.K. Sorensen N.Y. Bamaung P. Kovar E.F. Johnson K.K. Swinger K.D. Stewart Q. Zhang L.A. Tucker W.N. Pappano J.L. Wilsbacher J. Wang G.S. Sheppard R.L. Bell S.K. Davidsen R.D. Hubbard Imidazo[2,1-b[thiazoles: multitargeted inhibitors of both the insulin-like growth factor receptor and members of the epidermal growth factor family of receptor tyrosine kinases Bioorg. Med. Chem. Lett. 20 2010 2452 2455
14. M. Hasegawa A. Nakayama S. Yokohama T. Hosokami Y. Kurebayashi T. Ikeda Y. Shimoto S. Ide Y. Honda N. Suzuki Synthesis and pharmacological activities of novel bicyclic thiazoline derivatives as hepatoprotective agents. II. (7-alkoxycarbonyl-2, 3, 5, 6-tetrahydropyrrolo[2, 1-b[thiazol-3-ylidene)acetamide derivatives Chem. Pharm. Bull. 43 1995 1125 1131
15. G. Trapani M. Franco A. Latrofa A. Carotti S. Cellamare M. Serra C.A. Ghiani G. Tuligi G. Biggio G. Liso Synthesis and anticonvulsant activity of some 1,2,3,3 a-tetrahydropyrrolo[2,1-b[-benzothiazol-,-thiazol-or-oxazolg'''1g'''ones in Rodents J. Pharm. Pharmacol. 48 1996 834 840
16. T.D. Aicher B. Balkan P.A. Bell L.J. Brand S.H. Cheon R.O. Deems J.B. Fell W.S. Fillers J.D. Fraser J. Gao D.C. Knorr G.G. Kahle C.L. Leone J. Nadelson R. Simpson H.C. Smith Substituted tetrahydropyrrolo[2,1-b[oxazol-5(6 H)-ones and tetrahydropyrrolo[2,1-b[thiazol-5(6 H)-ones as hypoglycemic agents J. Med. Chem. 41 1998 4556 4566
17. A.V. Tverdokhlebov Pyrrolo[2,1-b[thiazoles Heterocycles 71 2007 761 798
18. K. Sztanke K. Pasternak A. Sidor-Wojtowicz J. TruchliÅ.,ska K. Jozwiak Synthesis of imidazoline and imidazo[2,1-c[[1,2,4]triazole aryl derivatives containing the methylthio group as possible antibacterial agents Bioorg. Med. Chem. 14 2006 3635 3642
19. B.A. Bhongade S. Talath R.A. Gadad A.K. Gadad Biological activities of imidazo[2,1-b[[1,3,4]thiadiazole derivatives: a review J. Saudi Chem. Soc. 2013
20. I.A.M. Khazi A.K. Gadad R.S. Lamani B.A. Bhongade Chemistry of imidazo[2,1-b[[1,3,4]thiadiazoles Tetrahedron 67 2011 3289 3316
21. Y. Li M. Giulianotti R.A. Houghten High throughput synthesis of 2,3,6-trisubstituted-5,6-dihydroimidazo[2,1-b[thiazole derivatives Tetrahedron Lett. 52 2011 696 698
22. A.T. Taher H.H. Georgey H.I. El-Sabbagh Novel 1,3,4-heterodiazole analogues: synthesis and in-vitro antitumor activity Eur. J. Med. Chem. 47 2012 445 451
23. N. Swathi T. Kumar K. Haribabu C. Subrahmanyam Synthesis and biological evaluation of substituted thiazolamines, imidazo[2,1-b[thiazol-6(5 H)-ones, thiazolo[3,2-a[pyrimidin-5-ones and thiazolylthioureas Indian J. Heterocycl. Chem. 21 2012 263 268
24. A.R. Ali E.R. El-Bendary M.A. Ghaly I.A. Shehata Novel acetamidothiazole derivatives: synthesis and in vitro anticancer evaluation Eur. J. Med. Chem. 69 2013 908 919
25. A. Andreani A. Leoni A. Locatelli R. Morigi M. Rambaldi R. Cervellati E. Greco T.P. Kondratyuk E.-J. Park K. Huang R.B. van Breemen J.M. Pezzuto Chemopreventive and antioxidant activity of 6-substituted imidazo[2,1-b[thiazoles Eur. J. Med. Chem. 68 2013 412 421
26. M. Cuendet C.P. Oteham R.C. Moon J.M. Pezzuto Quinone reductase induction as a biomarker for cancer chemoprevention J. Nat. Prod. 69 2006 460 463
27. A. Jemal F. Bray M.M. Center J. Ferlay E. Ward D. Forman Global cancer statistics CA Cancer J. Clin. 61 2011 69 90
28. W.A. Remers Antineoplastic agents J.H. Block J.M. Beale Text Book of Organic, Medicinal and Pharmaceutical Chemistry eleventh ed. 2004 Lippincott Company Philadelphia 793 806
29. H.I. El-Subbagh I.E. Al-Khawad R.R. El-Bendary A.M. Al-Obaid Substituted thiazoles IV: synthesis and antitumor activity of new substituted imidazo[2,1-b[thiazole analogs Saudi Pharm. J. 9 2001 14 20
30. K. Srimanth V.R. Rao D.R. Krishna Synthesis of 3-(1-aryl-2-mercaptoimidazolyl)-2 H-1-benzopyran-2-one Arzneim. Forsch. 52 2002 388 392
31. A. Andreani M. Granaiola A. Leoni A. Locatelli R. Morigi M. Rambaldi G. Lenaz R. Fato C. Bergamini G. Farruggia Potential antitumor agents synthesis and antitumor activity of guanylhydrazones from imidazo[2,1-b[thiazoles and from the new heterocyclic system thiazolo[2g'2,3,2:2,3]imidazo[4,5-c[quinolone J. Med. Chem. 48 2005 3085 3089
32. J.-H. Park C.-H. Oh Synthesis of new 6-(4-fluorophenyl)-5-(2-substituted pyrimidin-4-yl)imidazo[2,1-b[ thiazole derivatives and their antiproliferative activity against melanoma cell line Bull. Korean Chem. Soc. 31 2010 2854 2860
33. 1: synthesis and potential coanthracyclinic activity of imidazo[2,1-b[thiazole guanylhydrazones Bioorg. Med. Chem. 8 2000 2359 2366
34. Y. Xia Z.W. Dong B.X. Zhao X. Ge N. Meng D.S. Shin Synthesis and structure-activity relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide derivatives as potential agents against A549 lung cancer cells Bioorg. Med. Chem. 15 2007 6893 6899
35. G. Daidone B. Maggio D. Raffa S. Plescia D. Schillaci Maria V. Raimondi Synthesis and in vitro antileukemic activity of new 4-triazenopyrazole derivatives Farmaco 59 2004 413 417
36. A.R. Farghaly Synthesis of some new indole derivatives containing pyrazoles with potential antitumor activity ARKIVOC 11 2010 177 187
37. E.A. Soliman M.I. El-Zahar A.H. El-Masry M. Kamel R.S. Gohar Synthesis and anticancer evaluation of novel tetrahydronaphthalen-6-ylthiazole heterocycles against human HePG2 and MCF7 cell lines Der Pharma Chem. 2 2010 507 521
38. M.I. El-Zahar S.A. EL-Karim M.E. Haiba M.A. Khedr Synthesis, antitumor activity and molecular docking study of novel benzofuran-2-yl pyrazole pyrimidine derivatives Acta Pol. Pharm. Drug. Res. 68 2011 357 373
39. R. Kalirajan L. Rathore S. Jubie B. Gowramma S. Gomathy S. Sankar Microwave assisted synthesis of some novel pyrazole substituted benzimidazoles and evaluation of their biological activities Indian J. Chem. 50B 2011 1794 1799
40. A.R. Ali E.R. El-Bendary M.A. Ghaly I.A. Shehata Synthesis, in vitro anticancer evaluation and in silico studies of novel imidazo[2,1-b[thiazole derivatives bearing pyrazole moieties Eur. J. Med. Chem. 75 2014 492 500
41. J.-H. Park M.I. El-Gamal Y.S. Lee C.-H. Oh New imidazo[2,1-b[thiazole derivatives: synthesis, in vitro anticancer evaluation and in silico studies Eur. J. Med. Chem. 46 2011 5769 5777
42. J.C. Milne P.D. Lambert S. Schenk D.P. Carney J.J. Smith D.J. Gagne L.J. Olivier Boss R.B. Perni C.B. Vu J.E. Bemis R. Xie J.S. Disch P.Yee Ng J.J. Nunes A.V. Lynch H. Yang H. Galonek K. Israelian W. Choy A. Iffland S. Lavu O. Medvedik D.A. Sinclair J.M. Olefsky M.R. Jirousek P.J. Elliott C.H. Westphal Small molecule activators of SIRT1 as therapeutics for the treatment of type 2 diabetes Nature 450 2007 712 716
43. B.J. Morris Seven sirtuins for seven deadly diseases of aging Free Radic. Biol. Med. 56 2013 133 171
44. B.P. Hubbard A.P. Gomes H. Dai J. Li A.W. Case T. Considine T.V. Riera J.E. Lee S. Yen E D.W. Lamming B.L. Pentelute E.R. Schuman L.A. Stevens A.J.Y. Ling S.M. Armour S. Michan H. Zhao Y. Jiang S.M. Sweitzer C.A. Blum J.S. Disch P. Yee Ng K.T. Howitz A.P. Rolo Y. Hamuro J. Moss R.B. Perni J.L. Ellis G.P. Vlasuk D.A. Sinclair Evidence for a common mechanism of SIRT1 regulation by allosteric activators Science 339 2013 1216 1219
45. P. Hubbard D.A. Sinclair Small molecule SIRT1 activators for the treatment of aging and age-related diseases Trends Pharmacol. Sci. 35 2014 146 154
46. B. Vu J.E. Bemis J.S. Disch P. Yee Ng J.J. Nunes J.C. Milne D.P. Carney A.V. Lynch J.J. Smith S. Lavu P.D. Lambert D.J. Gagne M.R. Jirousek S. Schenk J.M. Olefsky R.B. Perni Discovery of imidazo[1,2-b[thiazole derivatives as novel SIRT1 activators J. Med. Chem. 52 2009 1275 1283
47. R.J. Sundberg D.J. Dahlhausen G. Manikumar B. Mavunkel A. Biswa V. Srinivasan F. King P. Waid Preparation of 2-aryl and 2-aryloxymethyl imidazo[1,2-a[pyridines and related compounds J. Heterocycl. Chem. 25 1988 129 137
48. D.J. Triggle Calcium-channel drugs: structure-function relationships and selectivity of action J. Cardiovasc. Pharmacol. 18 1991 S1 S6
49. R. Budriesi P. Ioan A. Locatelli S. Cosconati A. Leoni M.P. Ugenti A. Andreani R. Di Toro A. Bedini S. Spampinato L. Marinelli E. Novellino A. Chiarini Imidazo[2,1-b[thiazole system: a scaffold endowing dihydropyridines with selective cardiodepressant activity J. Med. Chem. 51 2008 1592 1600
50. A. Locatelli S. Cosconati M. Micucci A. Leoni L. Marinelli A. Bedini P. Ioan S.M. Spampinato E. Novellino A. Chiarini R. Budriesi Ligand based approach to L-type calcium channel by imidazo[2,1-b[thiazole-1,4-dihydropyridines: from heart activity to brain affinity J. Med. Chem. 56 2013 3866 3877
51. T.A. Kamali M. Bakherad M. Nasrollahzadeh S. Farhangi D. Habibi Synthesis of 6-substituted imidazo[2,1-b[thiazoles via Pd/Cu-mediated Sonogashira coupling in water Tetrahedron Lett. 50 2009 5459 5462
52. J.S. Barradas M.I. Errea C.S. Sepúlveda L.B. Talarico E.B. Damonte N.B. DÁccorso Synthesis and antiviral activity of azoles obtained from carbohydrates Carbohydr. Res. 343 2008 2468 2474
53. J.S. Barradas M.I. Errea C.S. Sepúlveda L.B. Talarico E.B. Damonte N.B. DÁccorso Imidazo[2,1-b[thiazole carbohydrate derivatives: synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever Eur. J. Med. Chem. 46 2011 259 264
54. B. Madhu Babu G. Santosh Kumar P.B. Thakur V.M. Bangade H.M. Meshram A mild and novel synthesis of functionalized fused imidazole analogues under environmentally benign reaction media, Tetrahedron Lett. 55 2014 3473 3477
55. R. Chaniyara S. Tala C.-W. Chen P.-C. Lee R. Kakadiya H. Dong B. Marvania C.-H. Chen T.-C. Chou T.-C. Lee A. Shah T.-L. Su Synthesis and antitumor evaluation of novel Benzo[d]pyrrolo[2,1-b[thiazole derivatives Eur. J. Med. Chem. 53 2012 28 40
56. M.I.L. Soares A.F. Brito M. Laranjo A.M. Abrantes M.F. Botelho J.A. Paixaõ A. Matos Beja M. Ramos Silva T.M.V.D. Pinho e Melo Chiral 6-hydroxymethyl-1H,3H-pyrrolo[1,2-c[thiazoles: novel antitumor DNA monoalkylating agents Eur. J. Med. Chem. 45 2010 4676 4681
57. M.I.L. Soares A.F. Brito M. Laranjo J.A. Paixaõ M.F. Botelho T.M.V.D. Pinho e Melo Chiral 6,7-bis(hydroxymethyl)-1 H,3 H-pyrrolo[1,2-c[thiazoles with anti-breast cancer properties Eur. J. Med. Chem. 60 2013 254 262
58. J.S. Barradas M.I. Errea C.S. Sepúlveda E.B. Damonte N.B. DÁccorso Microwave-assisted synthesis of pyrrolo[2,1-b[thiazoles linked to a carbohydrate moiety J. Heterocycl. Chem. 51 2014 96 100
59. P.F. VonVoigtlander R.N. Straw Alprazolam: review of pharmacological, pharmacokinetic and clinical data Drug Dev. Res. 6 1985 1 12
60. K. Sztanke T. Tuzimski J. Rzymowska K. Pasternak M. Kandefer-Szerszen Synthesis, determination of the lipophilicity, anticancer and antimicrobial properties of some fused 1,2,4-triazole derivatives Eur. J. Med. Chem. 43 2008 404 419
61. P. Koppulal N. Purohit Synthesis of new biologically active triazolo, tetrazolo and coumarinoyl derivatives of isocoumarins Org. Commun. 6 2013 148 161
62. H. Singh K.N. Shukla R. Dwivedi L.D.S. Yadav Synthesis of some new heterocycles compounds containing bridgehead nitrogen atom as antifungal drugs Indian J. Pharm. Sci. 52 1990 9 12
63. P. Molina E. Aller A. Lorenzo Bis(iminophosphorane)-mediated 1,2,4-triazoloannulation on imidazole amd benzoimidazole rings. Preparation of imidazo[1,2-b[[1,2,4]-triazoles and 1,2,4-triazolo[1,5-a[benzimidazoles Heterocycles 1994 997 1018
64. P. Molina A. Lorenzo E. Aller Fused imidazoles: an novel synthesis of imidazo[1,2-b[[1,2,4]-triazoles and imidazo[5,1-f[triazine derivatives Synthesis 1989 843 847
65. Y. Huang X.-Q. Hu D.-P. Shen Y.-F. Chen P.-F. Xu Synthesis of 1 H-imidazo[1,2-b[-1,2,4-triazol-6-amines Mol. Divers. 2007 73 80
66. G. Kolavi V. Hegde I.A. Khazi Intramolecular amidation: synthesis of novel imidazo[2,1-b[[1,3,4]thiadiazole and imidazo[2,1-b[[1,3]thiazole fused diazepinones Tetrahedron Lett. 47 2006 2811 2814
67. M. Kidwai S. Rastogi Use of ionic liquids as neoteric solvents in the synthesis of fused heterocycles Lett. Org. Chem. 3 2006 149 152
68. X. Wang M. Wang Z. Quan Z. Li A neat and rapid synthesis of 2-aryloxymethylene-6-arylimidazo[2,1-b[-1,3,4-thiadiazole under microwave irradiation Synth. Commun. 35 2005 2881 2888
69. V.J. Ram M. Nath Synthesis of azoles, azines and azoloazines: a versatile approach Phosphorus, Sulfur, Silicon Relat. Elem. 105 1995 11 15
70. G. deStevens M. Eager C. Tarby Steric and electronic effects controlling the synthesis of bridgehead nitrogen heterocycles Heterocycles 35 1993 763 773
71. I.T. Barnish P.E. Cross R.P. Dickinson B. Gadsby M.J. Parry M.J. Randall I.W. Sinclair Cerebrovasodilatation through selective inhibition of the enzyme carbonic anhydrase. 2. Imidazo[2,1-b[thiadiazole and imidazo[2,1-b[thiazolesulfonamides J. Med. Chem. 23 1980 117 121
72. P. Vachal L.M. Toth General facile synthesis of 2,5-diarylheteropentalenes Tetrahedron Lett. 45 2004 7157 7161
73. S. Ferrari F. Morandi D. Motiejunas E. Nerini S. Henrich R. Luciani A. Venturelli S. Lazzari S. Calo S. Gupta V. Hannaert P.A.M. Michels R.C. Wade M.P. Costi Virtual screening identification of nonfolate compounds, including a CNS drug, as antiparasitic agents inhibiting pteridine reductase J. Med. Chem. 54 2011 211 221
74. M.A. Hilfiker N. Wang X. Hou Z. Du M.A. Pullen M. Nord R. Nagilla H.E. Fries C.W. Wu A.C. Sulpizio J.-P. Jaworski D. Morrow R.M. Edwards J. Jin Discovery of novel aminothiadiazole amides as selective EP3 receptor antagonists Bioorg. Med. Chem. Lett. 19 2009 4292 4295
75. Q. Zeng M.P. Bourbeau G.E. Wohlhieter G. Yao H. Monenschein J.T. Rider M.R. Lee S. Zhang J. Lofgren D. Freeman C. Li E. Tominey X. Huang D. Hoffman H. Yamane A.S. Tasker C. Dominguez V.N. Viswanadhan R. Hungate X. Zhang 2-Aminothiadiazole inhibitors of AKT1 as potential cancer therapeutics Bioorg. Med. Chem. Lett. 20 2010 1652 1656
76. A. Foroumadi A. Rineh S. Emami F. Siavoshi S. Massarrat F. Safari S. Rajabalian M. Falahati E. Lotfali A. Shafiee 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 2008 3315 3320
77. V. Jatav S. Kashaw P. Mishra Synthesis, antibacterial and antifungal activity of some novel 3-[5-(4-substituted phenyl) 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones Med. Chem. Res. 17 2008 169 181
78. K.-Y. Jung S.-K. Kim Z.-G. Gao A.S. Gross N. Melman K.A. Jacobson Y.-C. Kim Structure-activity relationships of thiazole and thiadiazole derivatives as potent and selective human adenosine A3 receptor antagonists Bioorg. Med. Chem. 12 2004 613 623
79. C. Copin N. Henry F. Buron S. Routier Synthesis of 2,6-disubstituted imidazo[2,1-b[[1,3,4]thiadiazoles through cyclization and Suzuki-Miyaura cross-coupling reactions Eur. J. Org. Chem. 34 2012 6804 6806
80. T. Zarganes-Tzitzikas C.G. Neochoritis J. Stephanidou-Stephanatou C.A. Tsoleridis G. Buth G.E. Kostakis Azodicarboxylates: valuable reagents for the multicomponent synthesis of novel 1,3,4-thiadiazoles and imidazo[2,1-b[[1,3,4]thiadiazoles Tetrahedron 69 2013 5008 5015
81. S.G. Alegaon K.R. Alagawadi P.V. Sonkusare S.M. Chaudhary D.H. Dadwe A.S. Shah Novel imidazo[2,1-b[[1,3,4]thiadiazole carrying rhodanine-3-acetic acid as potential antitubercular agents Bioorg. Med. Chem. Lett. 22 2012 1917 1921
82. S.D. Joshi K. Manish A. Badiger Synthesis and evaluation of antibacterial and antitubercular activities of some novel imidazo[2,1-b[[1,3,4]thiadiazole derivatives Med. Chem. Res. 22 2013 869 878
83. R. Yadav A. Kaur D. Yadav S. Paliwal Synthesis and antimicrobial activity of some newer biphenyl imidazo[2,1-b[[1,3,4]thiadiazoles derivatives Int. J. Res. Dev. Pharm. Life Sci. 1 2012 57 62
84. S. Dhepe S. Kumar R. Vinayakumar S.A. Ramareddy S.S. Karki Microwave-assisted synthesis and antimicrobial activity of some imidazo[2,1-b[[1,3,4]thiadiazole derivatives Med. Chem. Res. 21 2012 1550 1556
85. M.N. Noolvi H.M. Patel S. Kamboj A. Kaur V. Mann 2,6-disubstituted imidazo[2,1-b[[1,3,4]thiadiazoles: search for anticancer agents Eur. J. Med. Chem. 56 2012 56 69
86. A. Kamal M.P.N. Rao P. Das P. Swapna S. Polepalli V.D. Nimbarte K. Mullagiri J. Kovvuri N. Jain Synthesis and biological evaluation of imidazo[2,1-b[[1,3,4] thiadiazole-linked oxindoles as potent tubulin polymerization inhibitors ChemMedChem 9 2014 1463 1475
87. H.M. Patel M.N. Noolvi A. Goyal B.S. Thippeswamy 2,5,6-trisubstituted imidazo[2,1-b[[1,3,4]thiadiazoles: search for antihyperlipidemic agents Eur. J. Med. Chem. 65 2013 119 133
88. K.M. Honorio R.C. Garratt I. Polikarpova A.D. Andricopulo Hologram quantitative structure-activity relationships for a series of farnesoid X receptor activatos Bioorg. Med. Chem. Lett. 15 2005 3119 3125
89. G. Tu S. Li H. Huang G. Li F. Xiong X. Mai H. Zhu B. Kuang W.F. Xu Novel aminopeptidase N inhibitors derived from 1,3,4-thiadiazole scaffold Bioorg. Med. Chem. 16 2008 6663 6668
90. G. Kolavi V. Hegde I.A. Kazi P. Gadad Synthesis and evaluation of antitubercular activity of imidazo[2,1-b[[1,3,4]thiadiazole derivatives Bioorg. Med. Chem. 14 2006 3069 3080