Synthesis, Antioxidant, and Anti-Inflammatory Evaluation of Novel Thiophene-Fused Quinoline Based β-Diketones and Derivatives
Pravin Mahajan
Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, Maharashtra, 431 004 India
Search for more papers by this authorMukesh Nikam
Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, Maharashtra, 431 004 India
Search for more papers by this authorAshish Asrondkar
Haffkine Institute for Training, Research and Testing, Parel, Mumbai, Maharashtra, 400 012 India
Search for more papers by this authorAnil Bobade
Haffkine Institute for Training, Research and Testing, Parel, Mumbai, Maharashtra, 400 012 India
Search for more papers by this authorCorresponding Author
Charansingh Gill
Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, Maharashtra, 431 004 India
E-mail: [email protected]Search for more papers by this authorPravin Mahajan
Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, Maharashtra, 431 004 India
Search for more papers by this authorMukesh Nikam
Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, Maharashtra, 431 004 India
Search for more papers by this authorAshish Asrondkar
Haffkine Institute for Training, Research and Testing, Parel, Mumbai, Maharashtra, 400 012 India
Search for more papers by this authorAnil Bobade
Haffkine Institute for Training, Research and Testing, Parel, Mumbai, Maharashtra, 400 012 India
Search for more papers by this authorCorresponding Author
Charansingh Gill
Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, Maharashtra, 431 004 India
E-mail: [email protected]Search for more papers by this authorAbstract
Novel thieno[2,3-b]quinoline-2-carboxylic acid derivatives including β-diketone, pyrazole, and flavone were prepared under ultrasonication and evaluated for in vitro antioxidant and anti-inflammatory activities. Antioxidant activity was determined by DPPH radical scavenging method and anti-inflammatory activity by HRBC membrane stabilization method. Some of the Compounds showed good antioxidant activity, whereas, some of the compounds bearing pyrazole core showed good anti-inflammatory activity. Further in silico physicochemical properties were also calculated for good oral drug bioavailability and drug likeness of synthesized compounds.
Supporting Information
| Filename | Description |
|---|---|
| jhet2722-sup-0001-SI.docxWord 2007 document , 570.3 KB | Data S1 Supporting info item |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References and Notes
- 1Rubio, L.; Motilva, M.; Romero, M. Crit Rev Food Sci Nut 2013, 53, 943.
- 2Harman, D. J Gerontol 1956, 11, 298.
- 3Hussain, S. P.; Hofseth, L. J.; Harris, C. C. Nat Rev Cancer 2003, 3, 276.
- 4Esterbauer, H.; Ramos, P. Rev Physiol Biochem Pharmacol 1995, 127, 31.
- 5Detsi, A.; Bouloumbasi, D.; Prousis, K.; Koufaki, M.; Athanasellis, G.; Melagraki, G.; Afantitis, A.; Igglessi-Markopoulou, O.; Kontogiorgis, C.; Hadjipavlou-Litina, D. J Med Chem 2007, 50, 2450.
- 6(a) Garrido, G.; Gonzalez, D.; Delporte, C.; Backhouse, N.; Quintero, G.; Nunez-Selles, A. J.; Morales, M. A. Phytother Res 2001, 15, 18; (b) Weber, V.; Rubat, C.; Duroux, E.; Lartigue, C.; Madesclaire, M.; Coudert, P. Bioorg Med Chem 2005, 13, 4552.
- 7Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine, 2nd ed.; Clarendon: Oxford, 1989.
- 8Orhan, H.; Sahin, G. Exp Toxicol Pathol 2001, 53, 133.
- 9(a) Tapiero, H.; Tew, K. D.; Nguyen Ba, G.; Mathe, G. Biomed Pharmacother 2002, 56, 200; (b) Intra, J.; Kuo, S. Chem Biol Interact 2007, 169, 91; (c) Khan, S. A.; Priyamvada, S.; Arivarasu, N. A.; Khan, S.; Yusufi, A. N. Nutrition 2007, 23, 687; (d) Chen, H.; Zhang, M.; Qu, Z.; Xie, Z. Food Chem 2008, 106, 559.
- 10Weinreb, O.; Amit, T.; Youdim, M. B. Free Radical Biol Med 2007, 43, 546.
- 11(a) Gomes, A.; Neuwirth, O.; Freitas, M.; Couto, D.; Ribeiro, D.; Figueiredo, A.; Silva, A.; Seixas, R.; Pinto, D.; Tome, A.; Cavaleiro, J.; Fernandes, E.; Lima, J. Bioorg Med Chem 2009, 17, 7218; (b) Sheikh, J.; Parvez, A.; Juneja, H.; Ingle, V.; Chohan, Z.; Youssoufi, M.; Hadda, T. Eur J Med Chem 2011, 46, 1390; (c) Nishiyama, T.; Shiotsu, S.; Tsujita, H. Polym Degrad Stab 2002, 76, 435; (d) Cushnie, T. P. T.; Lamb, A. Int J Antimicrob Agents 2005, 26, 343; (e) Havsteen, B. Biochem Pharmacol 1983, 32, 1141; (f) Epstein, J.; Sanderson, I. R.; Macdonald, T. T. Br J Nutr 2010, 103, 1545.
- 12(a) Hassan, G.; Abou-Seri, S.; Kamel, G.; Ali, M. Eur J Med Chem 2014, 76, 482; (b) Aggarwal, R.; Bansal, A.; Rozas, I.; Kelly, B.; Kaushik, P.; Kaushik, D. Eur J Med Chem 2013, 70, 350; (c) El-Moghazy, S.; Barsoum, F.; Abdel-Rahman, H.; Marzouk, A. Med Chem Res 2012, 21, 1722.
- 13Srivastava, A.; Chandra, A.; Singh, R. M. Ind J Chem 2005, 44, 2077.
- 14Prakash Naik, H. R.; Bhojya Naik, H. S.; Ravikumar Naik, T. R.; Bindu, P. J.; Raja Naik, H.; Aravinda, T.; Lamani, D. S. Med Chem 2009, 5, 148.
- 15Harrison, E. A.; Rice, K. C. J Heterocyclic Chem 1977, 14, 909.
- 16El-Gaby, M.; Abdel-Gawad, S.; Ghorab, M.; Heiba, H.; Aly, H. Phosphorus Sulfur Silicon Relat Elem 2006, 181, 279.
- 17Mahajan, P.; Nikam, M.; Chate, A.; Nimbalkar, U.; Patil, V.; Bobade, A.; Chaudhari, A.; Deolankar, D.; Javale, B.; Gill, C. Phosphorus Sulfur Silicon Relat Elem 2015, 190, 1803.
- 18Halimehjnai, A. Z.; Hosseyni, S.; Gholami, H.; Hashemi, M. M. Synth Commun 2013, 43, 191.
- 19(a) Baker, W. J Chem Soc 1933, 1381;
(b) Jain, P. K.; Makrandi, J. K. Synthesis 1982, 3, 221;
10.1055/s-1982-29755 Google Scholar(c) Santos, C. M. M.; Silva, A. M. S.; Cavaleiro, J. A. S. Eur J Org Chem 2003, 23, 4575.
- 20Wang, S. X.; Li, X. W.; Li, J. T. Ultrason Sonochem 2008, 15, 33.
- 21(a) Yu, L. J Agric Food Chem 2001, 49, 3452; (b) Kilclgil, A. H.; Coban, T.; Tuncbilek, M.; Can-Eke, B.; Dundar, O. B.; Ertan, R.; Iscan, M. Arch Pharm Res 2004, 27, 610; (c) Blois, M. S. Nature 1958, 181, 1199.
- 22Nagaharikal, Y.; Kalyani, V.; Ramadosskarthikeyan, S. J Acute Dis 2013, 156.
10.1016/S2221-6189(13)60118-3 Google Scholar
- 23Mahimaidoss, J.; Antony, C.; Vincent, A. R. J Pharm Res 2013, 6, 188.
- 24Hatano, T.; Kagawa, H.; Yasuhara, T.; Okuda, T. Chem Pharm Bull 1988, 36, 2090.
- 25Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. Adv Drug Deliv Rev 2001, 46, 3.
- 26Zhao, Y.; Abraham, M. H.; Lee, J.; Hersey, A.; Luscombe, N. C.; Beck, G.; Sherborne, B.; Cooper, I. Pharm Res 2002, 19, 1446.
- 27Ertl, P.; Rohde, B.; Selzer, P. J Med Chem 2000, 43, 3714.
