SYNTHESIS, CHARACTERIZATION, AND BIOLOGICAL ACTIVITY OF NOVEL N-PHENYLPROPYL-3-SUBSTITUTED INDOLINE-2-ONE DERIVATIVES
DOI:
https://doi.org/10.22159/ijpps.2017v9i10.21083Keywords:
Indole-2, 3-diones, Pyridine, Thiophene, Antimicrobial, AntioxidantAbstract
Objective: The objective of the present work deals with the synthesis, characterization and evaluation of antimicrobial and antioxidant activity of N-phenylpropyl-3-substituted indoline-2-one derivatives.
Methods: A series of new 3-hydroxy-3-(2-oxoethyl)-1-(3-phenylpropyl) indolin-2-one derivatives 3(a-l) and 3-(2-oxoethylidene)-1-(3-phenylpropyl) indolin-2-one derivatives 4(a-l) were synthesized by knoevenagel condensation of N-phenylpropyl–5-substituted indole-2,3-diones with various acetophenones analogues. The chemical structures of synthesized compounds were confirmed by IR, 1HNMR and Mass spectroscopic and elemental data. These compounds were also screened for their in vitro antimicrobial and antioxidant activities.
Results: Novel compounds 3-hydroxy-3-(2-oxoethyl)-1-(3-phenylpropyl) indolin-2-one derivatives 3(a-l) and 3-(2-oxoethylidene)-1-(3-phenylpropyl) indolin-2-one derivatives 4(a-l) were synthesised and characterized using spectral and analytical data. The results of antibacterial and antifungal and antioxidant activities showed that some of the synthesized compounds exhibited promising results.
Conclusion: All the newly synthesized compounds were screened for antimicrobial activity by cup plate method and antioxidant activity by the DPPH method using Ciprofloxacin and Amphotericin B as standards against gram positive and gram negative bacteria and fungi respectively.
Downloads
References
Vendemiale G, Grattagliano I, Altomare E. An update on the role of free radicals and antioxidant defense in human disease. Int J Clin Lab Res 1999;29:49-55.
Valko M, Rhodes CJ, Moncol J, Izakovic M, Mazur M. Free radicals, metals and antioxidants in oxidative stress-induced cancer. Chem Biol Interact 2006;160:1-40.
Archana D, Dixitha M, Santhy Ks. Antioxidant and anti clastogenic potential of piper longum L. Int J Appl Pharm 2015;7:11-4.
Richardson JS. Free radicals in the genesis of Alzheimer’s disease. Ann N Y Acad Sci 2006;695:73-6.
Olanow CW. An introduction to the free radical hypothesis in Parkinson’s disease. Ann Neurol 1992;32:2-9.
Bankson DD, Kestin M, Rifai N. Role of free radicals in cancer and atherosclerosis. Clin Lab Med 1993;13:463-80.
Zelika Mega Ramadhania, Muhamad Insanu, Neni Sri Gunarti, Komar Ruslan Wirasutisna, Sukrasno Sukrasno, Rika Hartati. Antioxidant activity from ten species of myrtaceae. Asian J Pharm Clin Res 2017;Special Issue:1-7.
Mak JC, Chan YMM. Reactive oxidant species in asthma. Curr Opin Pulm Med 2006;12:7-11.
Vineet Mehta, Arun Sharma, Pallavi Kailkhura, Udayabanu Malairaman. Antioxidant, anti-inflammatory, and antidiabetic activity of hydroalcoholic extract of ocimum sanctum: an in vitro and in silico study. Asian J Pharm Clin Res 2016;9:44-9.
Glover V, Halket JM, Watkins PJ, Clow A, Goodwin BL, Sandler M. Isatin: Identity with the purified endogenous monoamine oxidase inhibitor tribulin. J Neurochem 1988;51:656-9.
Joaquim FM da Silva, Simon J Garden, Angelo C. The chemistry of istains: a review from 1975 to 1999. J Braz Chem Soc 2001;12:273-324.
Chiyanzu I, Clarkson C, Smith PJ, Lehman J, Gut J, Rosenthal PJ, et al. Design, synthesis and anti-plasmodial evaluation in vitro of new 4-aminoquinoline isatin derivatives. Bioorg Med Chem 2005;13:3249-61.
Da Silva JFM, Garden SJ, Pinto AC. The chemistry of istains: a review from 1975 to 1999. J Braz Chem Soc 2001;12:273-324.
Batanero B, Barba F. Electrosynthesis of tryptanthrin. Tetrahedron Lett 2006;47:8201-3.
Tarek Aboul Fadl, Fayzah AS Bin Jubair, Omima Aboul Wafa. Schiff bases of indoline-2,3-dione (isatin) derivatives and nalidixic acid carbohydrazide, synthesis, antitubercular activity and pharmacophoric model building. Eur J Med Chem 2010;45:4578-86.
Domenech A, Domenech-Carbo MT, Sanchez del Rio M, Vazquez de Agredos Pascual ML, Lima E. Maya blue as a nanostructured polyfunctional hybrid organic–inorganic material: the need to change paradigms. New J Chem 2009;33:2371-9.
Renu Dixit, AK Halve, CP Shinde, Pradeep K Soni. Synthetic and antimicrobial activity of 4 thiazolidinones. Int J Curr Pharm Res 2015;7:92-4.
Amal Raj A, Raghunathan R, Sridevi Kumari MR, Raman N. Synthesis, antimicrobial and antifungal activity of a new class of spiro pyrrolidines. Bioorg Med Chem 2003;11:407-19.
Quenelle D, Keith K, Kern E. In vitro and in vivo evaluation of isatin-β-thiosemicarbazone and marboran against vaccinia and cowpox virus infections. Antiviral Res 2006;71:24-30.
Bal TR, Anand B, Yogeeswari P, Sriram D. Synthesis and evaluation of anti-HIV activity of isatin β-thiosemicarbazone derivatives. Bioorg Med Chem Lett 2005;15:4451-5.
Karal N, Gürsoy A, Kandemirli F, Shvets N, Kaynak FB, Ozbey S, et al. Synthesis and structure–antituberculosis activity relationship of 1H-indole-2,3-dione derivatives. Bioorg Med Chem 2007;15:5888-904.
Gursoy A, Karal N. Synthesis and primary cytotoxicity evaluation of 3-[[(3-phenyl-4(3H)-quinazolinone-2-yl)mercaptoacetyl]hydrazono]-1H-2-indolinones. Eur J Med Chem 2003;38:633-43.
Sridhar SK, Ramesh A. Synthesis and pharmacological activities of hydrazones, Schiff and Mannich bases of isatin derivatives. Biol Pharm Bull 2001;24:1149-52.
Verma M, Pandeya SN, Singh KN, Stables JP. Anticonvulsant activity of schiff bases of isatin derivatives. Acta Pharm 2004;54:49-56.
Bhattacharya SK. Anticonvulsant activity of intraventricularly administered atrial natriuretic peptide and its inhibition by isatin. Biog Amines 1988;14:131-41.
Gang Chen, Ye Wang, Xiaojiang Hao, Shuzhen Mu, Qianyun Sun. Simple isatin derivatives as free radical scavengers: synthesis, biological evaluation and structure-activity relationship. Chem Cent J 2011;37:1-5.
Basavaraj Shivabasappa Naraboli, Jayaprakash Sharanappa Biradar. Synthesis, characterization and biological evaluation of indole derivatives bearing benzimidazole/benzothiazole moiety. Int J Pharm Pharm Sci 2017;9:128-38.
Published
How to Cite
Issue
Section
