Synthesis and screening of 2-(2-(4-substituted piperazine-1-yl)-5- phenylthiazol-4-yl)-3-aryl quinazolinone derivatives as anticancer agents

Medicinal Chemistry Research

Volumn 22, Issue 6, 2013, Pages 2788-2794

  Sharma, Ritesh N ^a   Ravani, Rasik ^a  

^a GANPAT UNIVERSITY   (India)

Author keywords

Anticancer; MTT assay; Piperazine; Quinazolinone; Thiazole

Indexed keywords

2 [2 (4 BENZOYLPIPERAZIN 1 YL) 5 PHENYL THIAZOL 4 YL] 3 (PHENYLAMINO)QUINAZOLIN 4(3H) ONE; 2 [2 (4 BENZOYLPIPERAZIN 1 YL) 5 PHENYLTHIAZOL 4 YL] 3 (2 METHOXYPHENYL)QUINAZOLIN 4(3H) ONE; 2 [2 (4 BENZOYLPIPERAZIN 1 YL) 5 PHENYLTHIAZOL 4 YL] 3 (2 NITROPHENYL)QUINAZOLIN 4(3H) ONE; 2 [2 (4 BENZOYLPIPERAZIN 1 YL) 5 PHENYLTHIAZOL 4 YL] 3 (4 CHLOROPHENYL)QUINAZOLIN 4(3H) ONE; 2 [2 (4 BENZOYLPIPERAZIN 1 YL) 5 PHENYLTHIAZOL 4 YL] 3 PHENYLQUINAZOLIN 4(3H) ONE; 2 [2 (4 METHYLPIPERAZIN 1 YL) 5 PHENYLTHIAZOL 4 YL] 3 (2 NITROPHENYL)QUINAZOLIN 4(3H) ONE; 2 [2 (4 METHYLPIPERAZIN 1 YL) 5 PHENYLTHIAZOL 4 YL] 3 PHENYLQUINAZOLIN 4(3H) ONE; 3 (2 METHOXYPHENYL) 2 (5 PHENYL 2 (PIPERAZIN 1 YL)THIAZOL 4 YL]QUINAZOLIN 4(3H) ONE; 3 (2 METHOXYPHENYL) 2 [2 (4 METHYLPIPERAZIN 1 YL) 5 PHENYLTHIAZOL 4 YL]QUINAZOLIN 4(3H) ONE; 3 (2 NITROPHENYL) 2 (5 PHENYL 2 (PIPERAZIN 1 YL)THIAZOL 4 YL]QUINAZOLIN 4(3H) ONE; 3 (4 CHLOROPHENYL) 2 [2 (4 METHYLPIPERAZIN 1 YL) 5 PHENYLTHIAZOL 4 YL]QUINAZOLIN 4(3H) ONE; 3 (4 CHLOROPHENYL) 2 [5 PHENYL 2 (PIPERAZIN 1 YL)THIAZOL 4 YL]QUINAZOLIN 4(3H) ONE; 3 (4 METHOXY PHENYLAMINO) 2 [5 PHENYL 2 (PIPERAZIN1 YL) THIAZOL 4 YL]QUINAZOLINONE; 3 (4 METHOXYPHENYLAMINO) 2 [5 PHENYL 2 (PIPERAZIN 1 YL)THIAZOL 4 YL]QUINAZOLIN 4(3H) ONE; 3 PHENYL 2 [5 PHENYL 2 (PIPERAZIN 1 YL)THIAZOL 4 YL]QUINAZOLIN 4(3H) ONE; ANTINEOPLASTIC AGENT; FLUOROURACIL; METHOTREXATE; QUINAZOLINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL PROLIFERATION; CELL STRAIN HEK293; CELL STRAIN MCF 7; COMPETITIVE INHIBITION; CONTROLLED STUDY; CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME LINKED IMMUNOSORBENT ASSAY; HUMAN; HUMAN CELL; IN VITRO STUDY; LUNG CANCER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; THIN LAYER CHROMATOGRAPHY;

EID: 84879696557     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0260-2     Document Type: Article

References (17)

1. Ahmed K, Vijaya BE, Surekha Z, Aarti J (2010) Quinazolinone linked pyrrolo [2,1-c][1,4] benzodiazepine (PBD) conjugates: design, synthesis and biological evaluation as potential anticancer agents. Bioorg Med Chem 18:526-542
2. Al-Obaid AM, Abdel-Hamide SG, El-kashef HA, Abdel-Aziz AA, El-Azab AS, Al-Khamees HA, El-Subbagh HI (2009) Substituted quinazolines, part 3. Synthesis, in vitro antitumor activity and molecular modeling study of certain 2-thieno-4(3H)-quinazolinone analogs. Eur J Med Chem 44:2379-2391
3. Ashok K, Chatrasal SR (2009) Synthesis and anti-inflammatory activity of newer quinazolin-4-one derivatives. Eur J Med Chem 44(1):83-90
4. Buyuktimkin S, Ekinici AC (1992) Pharmacological studies on quarternized-4-(3H)-quinazolinones. J Pharm Sci 81(11):1092-1094
5. Fawzia MR, Amry E (2005) The antihyperlipidemic activities of 4-(3H)-quinazolinone and two halogenated derivatives in rats. Lipid Health Dis 4:22-24
6. Freshney IR (2005) Culture of animal cells: a manual of basic technique, 5th edn. Wiley, New York, pp 359-370
7. Hui H, Jian FG, Ling HC, Duo ZW, Zhin BZ (2009) Synthesis of novel thioglycoside derivatives containing quinazolinone. J Chinese Chem Soc 56:419-424
8. Kunes J, Bazant J, Pour M, Waisser K, Slosárek M, Janota J (2000) Quinazoline derivatives with antitubercular activity. Farmaco 55(11-12):725-729
9. Prakash S, Poonam S, Sarav AD, Maulik PS (2011) In vitro cytotoxicity evaluation of novel N-substituted bis-benzimidazole derivatives for anti-lung and anti-breast cancer activity. Ann Biol Res 2:51-59
10. Rajan G, Hardik T, Tony G, Williams J, Rogers D, Kamala V, Vasudevan S (2010a) Design, synthesis and evaluation of novel 2-thiophen-5-yl-3H-quinazolin- 4-one analogues as inhibitors of transcription factors NF-rB and AP-1 mediated transcriptional activation: Their possible utilization as anti-inflammatory and anti-cancer agents. Bioorg Med Chem 18:2796-2808
11. Rajan G, Hardik T, Tony G, Bing C, Sam N, Kamala V, Vasudevan S (2010b) Synthesis and evaluation of quinazolinone derivatives as inhibitors of NF-kB, AP-1 mediated transcription and eIF-4E mediated translational activation: inhibitors of multi-pathways involve in cancer. Eur J Med Chem 45:3558-3563
12. Rajiv D, Anil K (2008) Synthesis and biological activity of peptide derivatives of Iodoquinazolinones. Molecules 13(4):958-976
13. Rathi SG, Suthar M, Patel P, Bhaskar VH, Rajgor NB (2009) J Young Pharm 1:239-243
14. Shang LC, Yu PF, Run TL, Guo YD, Yu YZ (2005) Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains. Bioorg Med Chem Lett 15:1915-1917
15. Shashikant RP, VV KrishnaR, Manvi FV, Desai BG, Bhatt AR (2006) Synthesis of N-3(4-(4-chlorphenyl thiazole-2-yl)-(2-aminomethyl)-quinazolinone and their derivatives as anti tubercular activity. Indian J Chem 45b:1778-1781
16. Shuren Z, Joe W, Gudise C, Erika S, Xianjun L, Yongshen Z (2010) Synthesis and evaluation of 4-quinazolinone compounds as potential antimalarial agents. Eur J Med Chem 45(9):3864-3869
17. Wasfy AAF (2003) Synthesis and antimicrobial evaluation of some 2,2-disubstituted-3,3-biquinazolin-4-(3H)-ones. Indian J Chem B 42B:3102-3107