Synthesis, pharmacological evaluation and molecular docking studies of indanone derivatives
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- 作者：Ankur Patel (1)
D. Giles (1)
Guru Basavarajaswamy (1)
C. Sreedhar (1)
Avani Patel (1) - 关键词：Analgesic ; Anti ; inflammatory ; Antimicrobial ; Docking ; Indanone ; Isoxazole
- 刊名：Medicinal Chemistry Research
- 出版年：2012
- 出版时间：December 2012
- 年：2012
- 卷：21
- 期：12
- 页码：4403-4411
- 全文大小：403KB
- 参考文献：1. Albrecht R, Kessler HJ, Schroder E (1972) Antimicrobial indanones. US Patent 3,671,520
2. Basappa, Sadashiva MP, Mantelingu K, Swamy SN, Rangappa KS (2003) Solution-phase synthesis of novel 螖2-isoxazoline libraries via 1,3-dipolar cycloaddition and their antifungal properties. Bioorg Med Chem 11:4539鈥?544 CrossRef
3. Basappa Kumar MS, Swamy SN, Mahendra M, Prasad JS, Viswanath BS, Rangappa KS (2004a) Novel 未2-isoxazolines as group II phospholipase A2 inhibitors. Bioorg Med Chem 14:3679鈥?681 CrossRef
4. Basappa MK, Sadashiva MP, Rangappa KS (2004b) A simple and efficient method for the synthesis of 1,2-benzsioxazoles: a series of its potent acetylcholinesterase inhibitors. Indian J Chem 43B:1954鈥?957
5. Black WC, Chung-Sung LI, Guay D, Prasit P (1995) Alkanesulfonamido-1-indanone derivatives as inhibitors of cyclooxygenase. US Patent 5,409,944
6. Charris JE, Lobo GM, Camacho J, Ferrer R, Barazarte A, Dominguez JN, Gamboa N, Robrigure JR, Angel JE (2007) Synthesis and antimalarial activity of (E) 2-(2鈥?chloro-3鈥?quinolinylmethylidene)-5,7-dimethoxyindanones. Lett Drug Des Discov 4(1):49鈥?4 CrossRef
7. Chun-Sing Li W, Black C, Chan C, Ford-Hutchinson AW, Gauthier JY, Gordon R, Guay D, Kargman S, Lau CK (1995) Cyclooxygenase-2 inhibitors. Synthesis and pharmacological activities of 5-methoanesulfonamido-1-indanone derivatives. J Med Chem 38(25):4897鈥?905 CrossRef
8. Deady LW, Desneves J, Kaye AJ, Finlay GJ, Baguley BC, Denny WA (2001) Positioning of the carboxamide side chain in 11- / oxo-11 / H-indeno[1,2- / b]quinolinecarboxamide anticancer agents: effects on cytotoxicity. Bioorg Med Chem 9:445鈥?52 CrossRef
9. Deng BL, Zhao Y, Hartman TL, Watson K, Buckheit RW, Pannecouque C, Clercq ED, Cushmen M (2009) Syntheisis of alkenyldiarylmethanes (ADAMs) containing benzo[ / d]isoxazole and oxazolidine-2-one rings, a new series of potent non-nucleoside HIV-1 reverse transcriptase inhibitors. Eur J Med Chem 44(3):1210鈥?214 CrossRef
10. Desai JT, Deasi CK, Desai KR (2008) A convenient, rapid and eco-friendly synthesis of isoxazoline heterocyclic moiety containing bridge at 2掳 amine as potential pharmacological agent. J Iran Chem Soc 5(1):67鈥?3 CrossRef
11. Eddy NB, Leimbach D (1953) Synthetic analgesics. II. Dithienylbutenyl and dithienylbutylamines. J Pharmacol Exp Ther 107:385鈥?93
12. Finkieisztein LM, Castro EF, Fabian LE, Moltrasio GY, Campos RH, Cavallaro LV, Moglioni AG (2008) New 1-indanone thiosemicarbazone derivatives active against BVDV. Eur J Med Chem 43(8):1767鈥?773 CrossRef
13. Gaba M, Singh D, Singh S, Sharma V, Gaba P (2010) Synthesis and pharmacological evaluation of novel 5-substituted-1-(phenylsulfonyl)-2-methylbenzimidazole derivatives as anti-inflammatory and analgesic agents. Eur J Med Chem 45(6):2245鈥?249 CrossRef
14. Gaud RS, Gupta GD (2004) Practical microbiology, 2nd edn. Nirali Prakashan, Pune, p 111
15. Hammen PD, Mine GM (1979) 2-aminomethyleneindanone analgesic agents US Patent 4,164,514
16. Kalirajan R, Sivakumar SU, Jubie S, Gowramma B, Suresh B (2009) Synthesis and biological evaluation of some heterocyclic derivatives of chalcones. Int J Chemtech Res 1(1):27鈥?4
17. Karabasanagouda T, Adhikari AV, Girisha M (2009) Synthesis of some new pyrazolines and isoxazoles carrying 4-methylthiophenyl moiety as potential analgesic and antiinflammatory agents. Indian J Chem 48B:430鈥?37
18. Kulkarni SK (1999) Handbook of experimental pharmacology, 3rd edn. Vallabh Publications, New Delhi, p 128
19. Meena S, Shankar D, Ramseshu KV, Giles D, Prakash MS, Venkataraman S (2006) Synthesis of 2-(arylmethylene)-(1 / H)-indane-1,3-(2 / H)-diones as potential fungicidal and bactericidal agents. Indian J Chem 45B:1572鈥?573
20. Omran Z, Cailly T, Lescot E, Lisowski V (2005) Synthesis and biological evaluation as AChE inhibitors of new indanones and thiaindanones related to donepezil. Eur J Med Chem 40:1222鈥?245 CrossRef
21. Panara MR, Greco A, Santini G, Sciulli MG (1995) Systematic biosynthesis of prostacyclin by cyclooxygenase (COX)-2: the human pharmacology of a selective inhibitor of COX-2. Br J Pharmacol 116:2429鈥?434 CrossRef
22. Perrone R, Berardi F, Bettoni G, Tortorella V (1987) Monophenolic 2-amino-1-indanone and 2-amino-1-tetralone derivatives: synthesis and assessment of dopaminergic activity. J Med Chem 22:417鈥?19 CrossRef
23. Ring CS, Sun E, McKerrow JH, Lee GK (1993) Structure-based inhibitor design by using protein models for the development of antiparasitic agents. Proc Natl Acad Sci 90:3583 CrossRef
24. Saravanan VS, Selvan PS, Gopal N, Gupta JK (2006) Synthesis and pharmacological evaluation of some indanone-3-acetic acid derivatives. Asian J Chem 18(4):2597鈥?604
25. Saxena HO, Faridi U, Srivastava S, Kumar JK (2008) Gallic acid-based indanone derivatives as anticancer agents. Bioorg Med Chem lett 18:3914鈥?918 CrossRef
26. Shen Y, Sheng R, Zhang J, He Q (2008) 2-Phenoxy-indan-1-one derivatives as acetylcholinesterase inhibitors: a study on the importance of modifications at the side chain on the activity. Bioorg Med Chem 16:7646鈥?653 CrossRef
27. Tao P, Lai L (2001) Protein ligand docking based on empirical method for binding affinity estimation. J Comp Aided Mol Design 15:429鈥?36 CrossRef - 作者单位：Ankur Patel (1)
D. Giles (1)
Guru Basavarajaswamy (1)
C. Sreedhar (1)
Avani Patel (1)
1. Department of Pharmaceutical Chemistry, Acharya & B. M. Reddy College of Pharmacy, Soldevanahalli, Chikkabanavara Post, Bangalore, 560090, Karnataka, India
文摘
A new series of isoxazole fused indanones were synthesized form indane-1,3-dione. The newly synthesized derivatives were confirmed by IR, 1H NMR, and mass spectral data. The synthesized title compounds were evaluated for analgesic, anti-inflammatory, and antimicrobial activities. The modifications carried out in indanone had a positive effect in anti-inflammatory activity when compared to that of other pharmacological activities. The compounds BD 6 , BD 7 , BD 9 , BD 10 , and BD 11 showed good anti-inflammatory activity when compared to that of standard indomethacin. BD 3 , BD 4 , and BD 5 compounds possess moderate anti-inflammatory activity. Some compounds possess moderate analgesic and antimicrobial activity. Docking study reveals that isoxazole nucleus is essential for biological activity. It was concluded that the fusion of isoxazole with indanone nucleus will increase anti-inflammatory activity than analgesic and antimicrobial activity.