Synthesis of piperazinyl benzothiazole/benzoxazole derivatives coupled with 1,3,4-oxadiazole-2-thiol: Novel hybrid heterocycles as anticancer agents

Medicinal Chemistry Research

Volumn 22, Issue 10, 2013, Pages 4980-4991

  Murty, M S R ^a   Ramalingeswara Rao, B ^a   Katiki, Mohana Rao ^a   Nath, Lekshmi R ^b   Anto, Ruby John ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b RAJIV GANDHI CENTRE FOR BIOTECHNOLOGY   (India)

Author keywords

1,3,4 Oxadiazole; Anticancer; Benzothiazole; Benzoxazole; MTT assay; Piperazine

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; 2 [3 [4 (BENZO[D]THIAZOL 2 YL)PIPERAZIN 1 YL]PROPYLTHIO] 5 (4 CHLOROPHENYL) 1,3,4 OXADIAZOLE; 2 [3 [4 (BENZO[D]THIAZOL 2 YL)PIPERAZIN 1 YL]PROPYLTHIO] 5 (4 FLUOROPHENYL) 1,3,4 OXADIAZOLE; 2 [3 [4 (BENZO[D]THIAZOL 2 YL)PIPERAZIN 1 YL]PROPYLTHIO] 5 (4 METHOXYPHENYL) 1,3,4 OXADIAZOLE; 2 [3 [4 (BENZO[D]THIAZOL 2 YL)PIPERAZIN 1 YL]PROPYLTHIO] 5 (4 NITROPHENYL) 1,3,4 OXADIAZOLE; 2 [3 [4 (BENZO[D]THIAZOL 2 YL)PIPERAZIN 1 YL]PROPYLTHIO] 5 (4 TERT BUTOXYPHENYL) 1,3,4 OXADIAZOLE; 2 [3 [4 (BENZO[D]THIAZOL 2 YL)PIPERAZIN 1 YL]PROPYLTHIO] 5 4 TOLYL 1,3,4 OXADIAZOLE; 2 [3 [4 (BENZO[D]THIAZOL 2 YL)PIPERAZIN 1 YL]PROPYLTHIO] 5 PHENYL 1,3,4 OXADIAZOLE; 2 [4 [3 (5 4 TOLYL 1,3,4 OXADIAZOL 2 YLTHIO)PROPYL]PIPERAZIN 1 YL]BENZO[D]OXAZOLE; 2 [4 [3 [(5 PHENYL 1,3,4 OXADIAZOL 2 YLTHIO)THIO]PROPYL]PIPERAZIN 1 YL]BENZO[D]OXAZOLE; 2 [4 [3 [5 (4 BROMOPHENYL) 1,3,4 OXADIAZOL 2 YLTHIO] PROPYL]PIPERAZIN 1 YL]BENZO[D]OXAZOLE; 2 [4 [3 [5 (4 CHLOROPHENYL) 1,3,4 OXADIAZOL 2 YLTHIO] PROPYL]PIPERAZIN 1 YL]BENZO[D]OXAZOLE; 2 [4 [3 [5 (4 FLUOROPHENYL) 1,3,4 OXADIAZOL 2 YLTHIO] PROPYL]PIPERAZIN 1 YL]BENZO[D]OXAZOLE; 2 [4 [3 [5 (4 METHOXYPHENYL) 1,3,4 OXADIAZOL 2 YLTHIO] PROPYL]PIPERAZIN 1 YL]BENZO[D]OXAZOLE; 2 [4 [3 [5 (4 NITROPHENYL) 1,3,4 OXADIAZOL 2 YLTHIO] PROPYL]PIPERAZIN 1 YL]BENZO[D]OXAZOLE; 2 [4 [3 [[5 [4 (TERT BUTOXY)PHENYL] 1,3,4 OXADIAZOL 2 YL]THIO]PROPYL]PIPERAZIN 1 YL]BENZO[D]OXAZOLE; 2 [5 [3 [4 (BENZO[D]OXAZOL 2 YL)PIPERAZIN 1 YL]PROPYLTHIO] 1,3,4 OXADIAZOL 2 YL] N PHENYLACETAMIDE; 2 [[3 [4 (BENZO[D]THIAZOL 2 YL)PIPERAZIN 1 YL]PROPYL]THIO] 5 (4 BROMOPHENYL) 1,3,4 OXADIAZOLE; 4 [5 [3 [4 (BENZO[D]OXAZOL 2 YL)PIPERAZIN 1 YL]PROPYLTHIO] 1,3,4 OXADIAZOL 2 YL]PHENOL; 4 [5 [3 [4 (BENZO[D]THIAZOL 2 YL)PIPERAZIN 1 YL]PROPYLTHIO] 1,3,4 OXADIAZOL 2 YL]PHENOL; ANTINEOPLASTIC AGENT; BENZOTHIAZOLE DERIVATIVE; BENZOXAZOLE DERIVATIVE; CURCUMIN; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN HEPG2; CELL STRAIN MCF 7; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HELA CELL; HUMAN; HUMAN CELL; IN VITRO STUDY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84883449658     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0510-y     Document Type: Article

References (38)

1. Burger A, Sawhney SN (1968) Antimalarials. III. Benzothiazole amino alcohols. J Med Chem 11:270-273
2. Chakole RD, Amnerkar ND, Khedekar PB, Bhusari KP (2005) Synthesis and substituted benzothiazole derivatives of thioquinazoline as anticonvulsant agents. Indian J Heterocycl Chem 15:27-30
3. Cottrell DM, Capers J, Salem MM, DeLuca-Fradley K, Croft SL, Werbovetz KA (2004) Antikinetoplastid activity of 3-aryl-5-thiocyanatomethyl-1,2,4- oxadiazoles. Bioorg Med Chem 12:2815-2824
4. Diaz HM, Molina RV, Andrade RO, Coutino DD, Franco LM, Webster SP, Binnie M, Soto SE, Barajas MI, Rivera IL, Vazquez GN (2008) Antidiabetic activity of N-(6-substituted -1,3-benzothiazol-2-yl)benzenesulfonamides. Bioorg Med Chem Lett 18:2871-2877
5. Guimaraes CRW, Boger DL, Jorgensen WL (2005) Elucidation of fatty acid amide hydrolase inhibition by potent α-ketoheterocycle derivatives from Monte Carlo simulations. J Am Chem Soc 127:17377-17384
6. Ibrahim DA (2009) Synthesis and biological evolution of 3,6-disubstituted[1,2,4]triazole[3,4-b][1,3,4]thiadiazole derivatives as a novel class of potential anti-tumor agents. Eur J Med Chem 44:2776-2781
7. A receptor antagonist, oncolytic. Drugs Future 34:624-633
8. Jayachandran E, BhatiaK Naragud LVG, Roy A (2003) Antihelmentic activity of 2-(3-amino, 5-S-methyl-6-carboxamidepyrazole-1-yl) 6-fluro-7- substituted -1,3-benzothiazoles on Pheretima posthuma. Indian Drugs 40:408-411
9. Jones AM, Helm JM (2009) Emerging treatments in cystic fibrosis. Drugs 69:1903-1910
10. Jones RM, Leonard JN, Buzard DJ, Lehmann J (2009) GPR-119 agonists for the treatment of type 2 diabetes. Expert Opin Ther Pat 19:1339-1359
11. Kamal A, Khanl MNA, Reddy KSR, Srikanth YVV, Sridhar B (2008) Synthesis, structural characterization and biological evaluation of novel [1,2,4]triazolo [1,5-b][1,2,4]benzothiadiazine-benzothiazole conjugates as potential anticancer agents. Chem Biol Drug Des 71:78-86
12. Karegoudar P, Prasad JD, Ashok M, Mahalinga M, Poojary B, Holla SB (2008) Synthesis, antimicrobial and anti-inflammatory activities of some 1,2,4-triazolo[3,4-b][3,4-b] thiadiazoles and 1,2,4 triazolo[3,4-b][1,3,4] thiadiazines bearing trichlorophenyl moiety. Eur J Med Chem 43:808-815
13. Klimesova V, Koci J, Waisser K, Kaustova J, Mollmann U (2009) Preparation and in vitro evaluation of benzylsulfanyl benzoxazole derivatives as potential antituberculosis agents. Eur J Med Chem 44:2286-2293
14. Lee SH, Seo HJ, Lee SH, Jung ME, Park JH, Park HJ, Yoo J, Yun H, Na J, Kang SY, Song KS, Kim MA (2008) Biarylpyrazolyl oxadiazole as potent, selective, orally bioavailable cannabinoid-1 receptor antagonists for the treatment of obesity. J Med Chem 51:7216-7233
15. Leong CO, Gaskell M, Martin EA, Heydon RT, Farmer PB, Bibby MC, Cooper PA, Double JA, Bradshaw TD, Stevens MF (2003) Antitumour 2-(4-aminophenyl) benzothiazoles generate DNA adducts in sensitive tumour cells in vitro and in vivo. Br J Can 88:470-477
16. 1A affinity/selectivity. J Med Chem 40:2653-2656
17. Lopez-Rodríguez ML, Morcillo MJ, Rovat TK, Fernandez E, Vicente B, SanzAM Hernandez M, Orensanz L (1999) Synthesis and structure-activity relationships of a new model of arylpiperazines. 4. 1-[ω-(4-arylpiperazin- 1-yl)alkyl]-3-(diphenylmethylene)-2,5-pyrrolidines and -3-(9H-fluoren-9-ylidene) -2, 5-pyrrolidinones: study of the steric requirements of the terminal amide fragment on 5-HT1A affinity/selectivity. J Med Chem 42:36-49
18. 1A serotonin receptor ligands. J Med Chem 51:4529-4538
19. Mathew V, Keshavayya J, Vaidya PV, Giles D (2007) Studies on synthesis and pharmacological activities of 3,6-disubstituted-1,2,4-triazolo[3,4-b]-1,3,4- thiadiazoles and their dihydro analogues. Eur J Med Chem 42:823-840
20. Mazaahir K, Roona P, Saurav B, Singh S, Luthra PM (2010) Aqua mediated synthesis of 2-amino-6-benzothiazol-2ylsulfanayl-chromones and its in vitro study, explanation of the structure-activity relationships (SARs) as antibacterial agents. Eur J Med Chem 45:5031-5038
21. McBriar MD, Clader JW, Chu I, Del Vecchio RA, Favreau L, Greenlee WJ, Hyde LA, Nomeir AA, Parker EM, Pissarnitski DA, Song L, Zhang L, Zhao Z (2008) Discovery of amide and heteroaryl isosteres as carbamate replacements in a series of orally active γ-secretase inhibitors. Bioorg Med Chem Lett 18:215-219
22. Mizutani H (2007) Mechanism of DNA damage and apoptosis induced by anticancer drugs through generation of reactive oxygen species. Yakugaku Zasshi 127:1837-1842
23. 1A receptor. Synthesis and structure-affinity relationships. Eur J Med Chem 35:677-689
24. 1A receptor. Bioorg Med Chem Lett 10:1089-1092
25. Murty MSR, Ramalingeswara Rao B, Ram KR, Yadav JS, Antony J, John Anto R (2012) Synthesis and preliminary evaluation activity studies of novel 4-(aryl/heteroaryl-2-ylmethyl)-6-phenyl-2-[3-(4-substituted piperazine-1-yl) propyl]pyridazin-3(2H)-one derivatives as anticancer agents. Med Chem Res 21:3161-3169
26. Patani GA, LaVoie EJ (1996) Bioisosterism: a rational approach in drug design. Chem Rev 96:3147-3176
27. Rahman VPM, Mukhtar S, Ansari WH, Lemiere G (2005) Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide. Eur J Med Chem 40:173-184
28. Shafi S, Alam MM, Naveen M, Chaitanya M, Vanaja G, Arunasree MK, Reddanna P, Alam MS (2012) Synthesis of novel 2-mercapto benzothiazole and 1,2,3-triazole based bis-heterocycles: their anti-inflammatory and anti-nociceptive activities. Eur J Med Chem 49:324-333
29. Shi DF, Bradshaw TD, Wrigley S, McCall CJ, Lelieveld P, Fichtner I, Stevens MFG (1996) Antitumor benzothiazoles: synthesis of 2-(4-aminophenyl) benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo. J Med Chem 39:3375-3384
30. Siddiqui N, Alam M, Siddiqui AA (2004) Synthesis and analgesic activity of some 2-[{4-(alkyl thioureido)phenyl sulphonamido]-6-substituted benzothiazoles. Asian J Chem 16:1005-1008
31. Smitha VB, Vineshkumar TP, Deepti A, Nair A, Karunagaran D, Anto RJ (2005) Sensitization of taxol induced apoptosis by curcumin involves down-regulation of nuclear factor-rB and the serine/threonine kinase akt and is independent of tubulin polymerization. J Biol Chem 280:6301-6308
32. Song EY, Kaur N, Park MY, Jin Y, Lee K, Kim G, Lee KY, Yang JS, Shin JH, Nam KY, No KT, Han G (2008) Synthesis of amide and urea derivatives of benzothiazole as Raf-1 inhibitor. Eur J Med Chem 43:1519-1524
33. Summa V, Petrocchi A, Bonelli F, Crescenzi B, Donghi M, Ferrara M, Fiore F, Gardelli C, Gonzalez Paz O, Hazuda DJ, Jones P, Kinzel O, Laufer R, Monteagudo E, Muraglia E, Nizi E, Orvieto F, Pace P, Pescatore G, Scarpelli R, Stillmock K, Witmer MV, Rowley M (2008) Discovery of raltegravir, a potent, selective orally bioavailable HIV-integrase inhibitor for the treatment of HIVAIDS infection. J Med Chem 51:5843-5855
34. Trapani G, Franco M, Latrofa A, Reho A, Liso G (2001) Synthesis, in vitro and in vivo cytotoxicity, and prediction of the intestinal absorption of substituted 2-ethoxycarbonyl-imidazo[2,1-b]benzothiazoles. Eur J Pharm Sci 14:209-216
35. Unangst PC, Shrum GP, Connor DT, Dyer RD, Schrier DJ (1992) Novel 1,2,4-oxadiazoles and 1,2,4-thiadiazoles as dual 5-lipoxygenase and cyclooxygenase inhibitors. J Med Chem 35:3691-3698
36. Varmus H (2006) The new era in cancer research. Science 312:1162-1165
37. Warmus JS, Flamme C, Zhang LY, Barrrett S, Bridges A, Kaufman M, Tecle H, Gowan R, Sebolt-Leopold J, Leopold W, Merriman R, Przybranowski S, Valik H, Chen J, Ohren J, Pavlovsky A, Whithead C, Ahang E (2008) 2-Alkylamino- and alkoxy substituted 2-amino-1,3,4-oxadiazoles O-alkyl benzohydroxamate esters replacements retain the desired inhibition and selectivity against MEK (MAP ERK kinase). Bioorg Med Chem Lett 18:6171-6174
38. Zhang HZ, Kasibhatla S, Kuemmerle J, Kemnitzer W, Ollis-Mason K, Qiu L, Crogan Grundy C, Tseng B, Drewe J, Cai SX (2005) Discovery and structure activity relationship of 3-aryl-5-aryl-1,2,4-oxadiazoles as a new series of apoptosis inducers and potential anticancer agents. J Med Chem 48:5215-5223