Drug Res (Stuttg) 2014; 64(10): 505-509
DOI: 10.1055/s-0034-1368720
Original Article
© Georg Thieme Verlag KG Stuttgart · New York

Synthesis, Antimicrobial and Anticancer Evaluation of N′-(Substituted Benzylidene)-2-(Benzo[d]oxazol-3(2H)-yl)acetohydrazide Derivatives

P. Rohilla
1   Department of Pharmaceutical Chemistry, Hindu College of Pharmacy, Sonepat, India
,
A. Deep
2   Faculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak, India
,
M. Kamra
1   Department of Pharmaceutical Chemistry, Hindu College of Pharmacy, Sonepat, India
,
B. Narasimhan
2   Faculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak, India
,
K. Ramasamy
3   Faculty of Pharmacy, Universiti Teknologi MARA (UiTM), 42300 Bandar Puncak Alam, Selangor, Malaysia
4   Collaborative Drug Discovery Research (CDDR) Group, Brain and ­Neuroscience Communities of Research, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Selangor Darul Ehsan, Malaysia
,
V. Mani
3   Faculty of Pharmacy, Universiti Teknologi MARA (UiTM), 42300 Bandar Puncak Alam, Selangor, Malaysia
5   Collaborative Drug Discovery Research (CDDR) Group, Brain and ­Neuroscience Communities of Research, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Selangor Darul Ehsan, Malaysia
,
R. K. Mishra
3   Faculty of Pharmacy, Universiti Teknologi MARA (UiTM), 42300 Bandar Puncak Alam, Selangor, Malaysia
5   Collaborative Drug Discovery Research (CDDR) Group, Brain and ­Neuroscience Communities of Research, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Selangor Darul Ehsan, Malaysia
,
S. M. Lim
3   Faculty of Pharmacy, Universiti Teknologi MARA (UiTM), 42300 Bandar Puncak Alam, Selangor, Malaysia
4   Collaborative Drug Discovery Research (CDDR) Group, Brain and ­Neuroscience Communities of Research, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Selangor Darul Ehsan, Malaysia
› Author Affiliations
Further Information

Publication History

received 28 September 2013

accepted 11 November 2013

Publication Date:
03 July 2014 (online)

Abstract

A series of N′-(substituted benzylidene)-2-(benzo[d]oxazol-3(2H)-yl)acetohydrazide derivatives was synthesized and evaluated for its in vitro antimicrobial and anticancer activities. Antimicrobial activity results revealed that compound 12 was found to be the most potent antimicrobial agent. Results of anticancer study indicated that the synthesized compounds exhibited average anticancer potential. Compound 7 (IC 50 =3.12 µM) and compound 16 (IC 50 =2.88 µM) were found to be most potent against breast cancer (MCF7) cell lines. In conclusion, compound 12 and 16 have the potential to be selected as lead compound for the developing of novel antimicrobial and anticancer agents respectively.

 
  • References

  • 1 Gouveia FL, de Oliveira RMB, de Oliveira TB et al. Synthesis, antimicrobial and cytototoxic activities of some 5-arylidene-4-thioxo-thiazolidine-2-ones. Eur J Med Chem 2009; 44: 2038-2043
  • 2 Murty MSR, Ram KR, Rao RV et al. Synthesis and preliminary evaluation of 2-substituted-1,3-benzoxazole and 3-[(3-substituted)propyl]-1,3-benzoxazol-2(3H)-one derivatives as potent anticancer agents. Med Chem Res 2011; 20: 576-586
  • 3 Murty MSR, Ram KR, Rao RV et al. CsF–Celite catalyzed facile N-alkylation of 2(3H)-benzoxazolones and antimicrobial properties of 2-substituted benzoxazole and 3-substituted-2(3H)-benzoxazolone derivatives. Med Chem Res 2011; 20: 626-636
  • 4 Aiello S, Wells G, Stone EL et al. Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648). J Med Chem 2008; 28; 51: 5135-5139
  • 5 Kamal A, Reddy KS, Khan MN et al. Synthesis, DNA-binding ability and anticancer activity of benzothiazole/benzoxazole-pyrrolo[2,1-c][1,4]benzodiazepine conjugates. Bioorg Med Chem 2010; 1; 18: 4747-4761
  • 6 Padalkar VS, Gupta VD, Phatangare KR et al. Synthesis of novel dipodal-benzimidazole, benzoxazole and benzothiazole from cyanuric chloride: Structural, photophysical and antimicrobial studies. Arb J Chem In press 2011;
  • 7 Kozic J, Novotna E, Volkova M et al. Synthesis and in vitro antimycobacterial and isocitrate lyase inhibition properties of novel 2-methoxy-2′-hydroxybenzanilides, their thioxo analogues and benzoxazoles. Eur J Med Chem 2012; 56: 108-119
  • 8 Jeon R, Park S. Synthesis and biological activity of benzoxazole containing thiazolidinedione derivatives. Arch Pharm Res 2004; 27: 1099-1105
  • 9 Srinivas A, Sagar JV, Sarangapani M. Design, Synthesis and biological evaluation of benzoxazole derivatives as cyclooxygensase-2 Inhibitors. Int J Pharm Sci 2010; 2: 7-12
  • 10 Srikanth L, Naik U, Jadhav R et al. Synthesis and evaluation of new phenylaminothiadiazolo-oxadiazolo-1,3benzoxazoles for their antibacterial activity. Int J Pharm Bio Sci 2010; 4: 260-227
  • 11 Cappucino JG, Sherman N. Microbiology – A Laboratory Manual. Addison Wesley; California: 1999: 263
  • 12 Giuseppe SA, Sorbello L, Banerjee D et al. Cytotoxicity and Cell Growth Assays. Cell Biology. ElS Sci USA 2006; 315-322