Synthesis, antiproliferative and apoptosis-inducing activity of thiazolo[5,4-d]pyrimidines

European Journal of Medicinal Chemistry

Volumn 70, Issue , 2013, Pages 864-874

  Singh, Baljinder ^a,b   Guru, Santosh K ^a   Kour, Smit ^a,b   Jain, Shreyans K ^a,b   Sharma, Rajni ^a,b   Sharma, Parduman R ^a   Singh, Shashank K ^a,b   Bhushan, Shashi ^a,b   Bharate, Sandip B ^a,b   Vishwakarma, Ram A ^a,b  

^a CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

^b ACADEMY OF SCIENTIFIC AND INNOVATIVE RESEARCH ACSIR   (India)

Author keywords

A549; Anticancer; Apoptosis; HL 60; KF alumina; Thiazolo 5,4 d pyrimidines

Indexed keywords

1,3 DIBENZYL 1 (7 CHLOROTHIAZOLO[5,4 D]PYRIMIDIN 2 YL)THIOUREA; 2 (4 CHLOROPHENYLAMINO) 7 (4 METHYLPIPERAZIN 1 YL)THIAZOLO[5,4 D]PYRIMIDINE; 2 (4 CHLOROPHENYLAMINO) 7 (MORPHOLIN 4 YL)THIAZOLO[5,4 D]PYRIMIDINE; 2 (4 CHLOROPHENYLAMINO) 7 (PIPERIDIN 1 YL)THIAZOLO[5,4 D]PYRIMIDINE; 2 (4 CHLOROPHENYLAMINO) 7 (PYRROLIDIN 1 YL)THIAZOLO[5,4 D]PYRIMIDINE; 2 (4 CHLOROPHENYLAMINO) 7 CHLOROTHIAZOLO[5,4 D]PYRIMIDINE; 2 (4 CHLOROPHENYLAMINO) 7 DIETHYLAMINO THIAZOLO[5,4 D]PYRIMIDINE; 2 (4 CHLOROPHENYLAMINO) 7 DIMETHYLAMINO THIAZOLO[5,4 D]PYRIMIDINE; 2 (4 METHOXYPHENYLAMINO) 7 CHLOROTHIAZOLO[5,4 D]PYRIMIDINE; 2 (4 NITROPHENYLAMINO) 7 CHLOROTHIAZOLO[5,4 D]PYRIMIDINE; 2 BENZOYLAMINO 7 CHLORO THIAZOLO[5,4 D]PYRIMIDINE; 2 BENZYLAMINO 7 CHLOROTHIAZOLO[5,4 D]PYRIMIDINE; 2 P TOLYL 7 CHLOROTHIAZOLO[5,4 D]PYRIMIDINE; 2 PHENYLAMINO 7 (4 ETHYLPIPERAZIN 1 YL)THIAZOLO[5,4 D]PYRIMIDINE; 2 PHENYLAMINO 7 (4 METHYLPIPERAZIN 1 YL)THIAZOLO[5,4 D]PYRIMIDINE; 2 PHENYLAMINO 7 (MORPHOLIN 4 YL)THIAZOLO[5,4 D]PYRIMIDINE; 2 PHENYLAMINO 7 (PIPERAZIN 1 YL)THIAZOLO[5,4 D]PYRIMIDINE; 2 PHENYLAMINO 7 CHLOROTHIAZOLO[5,4 D]PYRIMIDINE; 2 PHENYLAMINO 7 DIETHYLAMINO THIAZOLO[5,4 D]PYRIMIDINE; 2 PHENYLAMINO 7 DIMETHYLAMINO THIAZOLO[5,4 D]PYRIMIDINE; 2 PHENYLAMINO 7 PIPERIDIN 1 YL THIAZOLO[5,4 D]PYRIMIDINE; 2 PHENYLAMINO 7 [4 (PIPERIDIN 1 YL)PIPERIDIN 1 YL]THIAZOLO[5,4 D]PYRIMIDINE; ALUMINUM OXIDE; ERLOTINIB; ISOTHIOCYANIC ACID DERIVATIVE; MORPHOLINE; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE 1; PROCASPASE 3; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; BREAST CELL; CATALYST; CELL STRAIN HL 60; CELL STRUCTURE; CHEMICAL REACTION; CHROMATOGRAPHY; CONTROLLED STUDY; DRUG PURIFICATION; DRUG SYNTHESIS; ENZYME INHIBITION; EPIDERMIS CELL; FEMALE; GLIOBLASTOMA; HUMAN; HUMAN CELL; IC 50; LUNG ALVEOLUS CELL; MALE; MITOCHONDRION; PANCREAS CELL; PROSTATE; PROTEIN CLEAVAGE; SUBSTITUTION REACTION; TUMOR CELL LINE; WESTERN BLOTTING;

A549; ANTICANCER; APOPTOSIS; HL-60; KF/ALUMINA; THIAZOLO[5,4-D]PYRIMIDINES;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HL-60 CELLS; HUMANS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 84887655232     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.10.039     Document Type: Article

References (43)

1. E.E. Flefel, M.A. Salama, M. El-Shahat, M.A. El-Hashash, and A.F. El-Farargy A novel synthesis of some new pyrimidine and thiazolopyrimidine derivatives for anticancer evaluation Phosphorus Sulfur Silicon Relat. Elem. 182 2007 1739 1756
2. R. Lin, S.G. Johnson, P.J. Connolly, S.K. Wetter, E. Binnun, T.V. Hughes, W.V. Murray, N.B. Pandey, S.J. Moreno-Mazza, M. Adams, A.R. Fuentes-Pesquera, and S.A. Middleton Synthesis and evaluation of 2,7-diamino-thiazolo[4,5-d] pyrimidine analogues as anti-tumor epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors Bioorg. Med. Chem. Lett. 19 2009 2333 2337
3. H.T.Y. Fahmy, S.A.F. Rostom, M.N. Saudi, J.K. Zjawiony, and D.J. Robins Synthesis and in vitro evaluation of the anticancer activity of novel fluorinated thiazolo[4,5-d]pyrimidines Arch. Pharm. Pharm. Med. Chem. 336 2003 216 225 (Pubitemid 36988292)
4. G. Castanedo, D.M. Goldstein, R.K. Kondru, M.C. Lucas, W.S. Palmer, S. Price, B. Safina, P.P.A. Savy, E.M. Seward, D.P. Sutherlin, Z.K. Sweeney, Bicyclic indole-pyrimidine PI3K inhibitor compounds selective for P110 delta, and methods of use, in, US 8158625, Genentech, Inc., 2012.
5. G.M. Castanedo, J.L. Gunzner, K. Malesky, S. Mathieu, A.G. Olivero, D.P. Sutherlin, S. Wang, B.-Y. Zhu, I. Chuckowree, A. Folkes, Thiazolopyrimidine PI3K Inhibitor Compounds and Methods of Use, in, US 8158626, Genentech, Inc., 2012.
6. T.C. Hancox, N.A. Pegg, M.C. Beswick, T.J. Blench, E.A. Dechaux, J.J. Kulagowski, A.J. Nadin, S. Price, Thiazolopyrimidines and their Use as Inhibitors of Phosphatidylinositol-3 kinase, in, US 2011098270, Genentech, Inc., 2011.
7. D.P. Sutherlin, D. Sampath, M. Berry, G. Castanedo, Z. Chang, I. Chuckowree, J. Dotson, A. Folkes, L. Friedman, R. Goldsmith, T. Heffron, L. Lee, J. Lesnick, C. Lewis, S. Mathieu, J. Nonomiya, A. Olivero, J. Pang, W.W. Prior, L. Salphati, S. Sideris, Q. Tian, V. Tsui, N.C. Wan, S. Wang, C. Wiesmann, S. Wong, and B.-Y. Zhu Discovery of (thienopyrimidin-2-yl) aminopyrimidines as potent, selective, and orally available Pan-PI3-kinase and dual Pan-PI3-kinase/mTOR inhibitors for the treatment of cancer J. Med. Chem. 53 2010 1086 1097
8. A.A. Bekhit, H.T.Y. Fahmy, S.A.F. Rostom, and A.M. Baraka Design and synthesis of some substituted 1H-pyrazolyl-thiazolo[4,5-d]pyrimidines as anti-inflammatory-antimicrobial agents Eur. J. Med. Chem. 38 2003 27 36 (Pubitemid 36197852)
9. Y. Yonetoku, K. Negoro, K. Onda, M. Hayakawa, D. Sasuga, T. Nigawara, K. Iikubo, H. Moritomo, S. Yoshida, T. Ohishi, Aromatic-ring-fused Pyrimidine Derivative, in, WO 2006040966, Astellas Pharma Inc., 2006.
10. J.C. Sircar, M.J. Suto, M.E. Scott, M.K. Dong, and R.B. Gilbertsen Inhibitors of human purine nucleoside phosphorylase. Synthesis, purine nucleoside phosphorylase inhibition, and T-cell cytotoxicity of 2,5-diaminothiazolo[5,4-d]pyrimidin-7(6H)-one and 2,5-diaminothiazolo[4,5-d] pyrimidin-7(6H)-one. Two thioisosteres of 8-aminoguanine J. Med. Chem. 29 1986 1804 1806 (Pubitemid 16018220)
11. A.F. Lewis, J.C. Drach, S.M. Fennewal, J.H. Huffman, R.G. Ptak, J.-P. Sommadossi, and G.R. Revankar Inhibition of human cytomegalovirus in culture by alkenyl guanine analogs of the thiazolo[4,5-d]pyrimidine ring system Antimicrob. Agents Chemother. 38 1994 2889 2895 (Pubitemid 24374453)
12. J. Liu, A.E. Fitzgerald, A.D. Lebsack, and N.S. Mani Scale-up synthesis of a TRPV1 antagonist featuring a facile thiazolo[5,4-d]pyrimidine formation Org. Process. Res. Dev. 15 2011 382 388
13. M.Y. Jang, S. De Jonghe, K. Segers, J. Anne, and P. Herdewijn Synthesis of novel 5-amino-thiazolo[4,5-d]pyrimidines as E. coli and S. aureus SecA inhibitors Bioorg. Med. Chem. 19 2011 702 714
14. G. Nordvall, T. Rein, D. Sohn, R. Zemribo, New 2-Substituted, 4-Amino-thiazolo[4,5-d] Pyrimidines, Useful as Chemokine Receptor Antagonists, esp. cx3cr1, in, WO 2005033115, Astrazeneca, 2005.
15. R.W.A. Luke, C.D. Jones, W. McCoull, B.R. Hayter, Condensed pyridines and pyrimidines with tie2 (tek) activity, in, WO 2004013141, Astrazeneca, 2004.
16. S. Kolb, O. Mondésert, M.-L. Goddard, D. Jullien, B.O. Villoutreix, B. Ducommun, C. Garbay, and E. Braud Development of novel thiazolopyrimidines as CDC25B phosphatase inhibitors ChemMedChem 4 2009 633 648
17. J. Liu, R.J. Patch, C. Schubert, and M.R. Player Single-step syntheses of 2-amino-7-chlorothiazolo[5,4-d]pyrimidines: intermediates for bivalent thiazolopyrimidines J. Org. Chem. 70 2005 10194 10197 (Pubitemid 41689202)
18. S.F. Mohamed, E.M. Flefel, A.E.-G.E. Amr, and D.N.A. El-Shafy Anti-HSV-1 activity and mechanism of action of some new synthesized substituted pyrimidine, thiopyrimidine and thiazolopyrimidine derivatives Eur. J. Med. Chem. 45 2010 1494 1501
19. F. Azam, I.A. Alkskas, and M.A. Ahmed Synthesis of some urea and thiourea derivatives of 3-phenyl/ethyl-2-thioxo-2,3-dihydrothiazolo[4,5-d]pyrimidine and their antagonistic effects on haloperidol-induced catalepsy and oxidative stress in mice Eur. J. Med. Chem. 44 2009 3889 3897
20. C. Landreau, D. Deniaud, and J.C. Meslin From thiourea to bicyclic structures: an original route to imidazo[2,1-b]thiazoles, 5H-thiazolo[3,2-a] pyrimidines, 7H-imidazo[2,1-b][1,3] thiazines, and 2H,6H-pyrimido[2,1-b] [1,3]thiazines J. Org. Chem. 68 2003 4912 4917
21. H. Zhi, L.-m. Chen, L.-l. Zhang, S.-j. Liu, D.C.C. Wan, H.-q. Lin, and C. Hua Design, synthesis, and biological evaluation of 5H-thiazolo[3,2-a] pyrimidine derivatives as a new type of acetylcholinesterase inhibitors ARKIVOC xiii 2008 266 277
22. S. Fatima, A. Sharma, R. Saxena, R. Tripathi, S.K. Shukla, S.K. Pandey, R. Tripathi, and R.P. Tripathi One pot efficient diversity oriented synthesis of polyfunctional styryl thiazolopyrimidines and their bio-evaluation as antimalarial and anti-HIV agents Eur. J. Med. Chem. 55 2012 195 204
23. F.A.M. Al-Omary, G.S. Hassan, S.M. El-Messery, and H.I. El-Subbagh Substituted thiazoles V. Synthesis and antitumor activity of novel thiazolo[2,3-b]quinazoline and pyrido[4,3-d]thiazolo[3,2-a]pyrimidine analogues Eur. J. Med. Chem. 47 2012 65 72
24. S. Mohammed, A.K. Padala, B.A. Dar, B. Singh, B. Sreedhar, R.A. Vishwakarma, and S.B. Bharate Recyclable clay supported Cu (II) catalyzed tandem one-pot synthesis of 1-aryl-1,2,3-triazoles Tetrahedron 68 2012 8156 8162
25. S.B. Bharate, R. Mudududdla, J.B. Bharate, N. Battini, S. Battula, R.R. Yadav, B. Singh, and R.A. Vishwakarma Tandem one-pot synthesis of flavans by recyclable silica-HClO4 catalyzed Knoevenagel condensation and [4 + 2]-Diels-Alder cycloaddition Org. Biomol. Chem. 10 2012 5143 5150
26. R. Mudududdla, S.K. Jain, J.B. Bharate, A.P. Gupta, B. Singh, R.A. Vishwakarma, and S.B. Bharate Ortho-amidoalkylation of phenols via tandem one-pot approach involving oxazine intermediate J. Org. Chem. 77 2012
27. S.B. Bharate, J.B. Bharate, S.I. Khan, B.L. Tekwani, M.R. Jacob, R. Mudududdla, R.R. Yadav, B. Singh, P.R. Sharma, S. Maity, B. Singh, I.A. Khan, and R.A. Vishwakarma Discovery of 3,3′-diindolylmethanes as potent antileishmanial agents Eur. J. Med. Chem. 63 2013 435 443
28. S.K. Jain, S. Meena, B. Singh, J.B. Bharate, P. Joshi, V.P. Singh, R.A. Vishwakarma, and S.B. Bharate KF/alumina catalyzed regioselective benzylation and benzoylation using solvent-free grind-stone chemistry RSC Adv. 2 2012 8929 8933
29. T. Ando, S.J. Brown, J.H. Clark, D.G. Cork, T. Hanafusa, J. Ichihara, J.M. Miller, and M.S. Robertson J. Chem. Soc. Perkin Trans. 2 1986 1133 1139
30. W.-x. Lu, C.-g. Yan, and R. Yao Potassium fluoride supported on alumina induced aldol condensation of fluorene Synth. Commun. 26 1996 3719 3723 (Pubitemid 26300379)
31. J. Yamawaki, T. Kawate, T. Ando, and T. Hanafusa Potassium fluoride on alumina. An efficient solid base for elimination, addition, and condensation Bull. Chem. Soc. Jpn. 56 1983 1885 1886
32. I.P. Singh, S. Jain, A. Kaur, S. Singh, R. Kumar, P. Garg, S. Sharma, and S. Arora Synthesis and antileishmanial activity of piperoyl-amino acid conjugates Eur. J. Med. Chem. 45 2010 3439 3445
33. S.W. Lowe, and A.W. Lin Apoptosis in cancer Carcinogenesis 21 2000 485 495 (Pubitemid 30137934)
34. A.L. Bertho, M.A. Santiago, and S.G. Coutinho Flow cytometry in the study of cell death Mem. Inst. Oswaldo Cruz 95 2000 429 433
35. Z. Darzynkiewicz, G. Juan, X. Li, W. Gorczyca, T. Murakami, and F. Traganos Cytometry in cell necrobiology: analysis of apoptosis and accidental cell death (necrosis) Cytometry 27 1997 1 20 (Pubitemid 27059777)
36. D. D'Amours, F.R. Sallmann, V.M. Dixit, and G.G. Poirier Gain-of-function of poly(ADP-ribose) polymerase-1 upon cleavage by apoptotic proteases: implications for apoptosis J. Cell Sci. 114 2001 3771 3778 (Pubitemid 33041059)
37. Q.P. Peterson, D.R. Goode, D.C. West, K.N. Ramsey, J.J.Y. Lee, and P.J. Hergenrother PAC-1 activates procaspase-3 in vitro through relief of zinc-mediated inhibition J. Mol. Biol. 388 2009 144 158
38. J.A. Brinkman, A.W.-h. Cheung, F. Firooznia, K.R. Guertin, N. Marcopulos, L. Qi, J.K. Racha, R. Sarabu, J. Tan, J.W. Tilley, Thiazolo-pyrimidine/pyridine urea derivatives, in, US20070270433, Hoffmann-La Roche Inc., 2007.
39. P. Houghton, R. Fang, I. Techatanawat, G. Steventon, P.J. Hylands, and C.C. Lee The sulphorhodamine (SRB) assay and other approaches to testing plant extracts and derived compounds for activities related to reputed anticancer activity Methods 42 2007 377 387 (Pubitemid 46860387)
40. H. Zhu, and N.J. Gooderham Mechanisms of induction of cell cycle arrest and cell death by cryptolepine in human lung adenocarcinoma a549 cells Toxicol. Sci. 91 2006 132 139
41. H. Zhu, A.R. Boobis, and N.J. Gooderham The food-derived carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine activates S-phase checkpoint and apoptosis, and induces gene mutation in human lymphoblastoid TK6 cells Cancer Res. 60 2000 1283 1289 (Pubitemid 30151996)
42. R.K. Singh, T.S. Lange, K.K. Kim, S.K. Shaw, and L. Brard A novel indole ethyl isothiocyanate (7Me-IEITC) with anti-proliferative and pro-apoptotic effects on platinum-resistant human ovarian cancer cells Gynecol. Oncol. 109 2008 240 249
43. S. Bhushan, A. Kumar, F. Malik, S. Andotra, V. Sethi, I. Kaur, S. Taneja, G. Qazi, and J. Singh A triterpenediol from Boswellia serrata induces apoptosis through both the intrinsic and extrinsic apoptotic pathways in human leukemia HL-60 cells Apoptosis 12 2007 1911 1926 (Pubitemid 47498241)