Efficient entry to diversely functionalized spirooxindoles from isatin and their biological activity

Medicinal Chemistry Research

Volumn 22, Issue 6, 2013, Pages 2717-2723

  Kidwai, Mazaahir ^a,b   Jain, Arti ^b   Nemaysh, Vishal ^c   Kumar, Rakesh ^c   Luthra, Pratibha Mehta ^c  

^a JIWAJI UNIVERSITY   (India)

^b UNIVERSITY OF DELHI   (India)

^c UNIVERSITY OF DELHI   (India)

Author keywords

Diversified series of spirooxindoles; Green methodology; Novel compounds; Pharmacological activity; Two step multicomponent reaction

Indexed keywords

ANTINEOPLASTIC AGENT; ISATIN DERIVATIVE; LEWIS ACID; SPIROOXINDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS;

EID: 84879654893     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0249-x     Document Type: Article

References (35)

1. Bonsignore L, Loy G, Secci D, Calignano A (1993) Synthesis and pharmacological activity of 2-oxo(2H)1-benzopyran-3-carboxamide derivatives. Eur J Med Chem 28:517-520
2. Chandrasekhar S, Narsihmulu C, Sultana SS, Reddy NR (2002) Poly(ethylene glycol) (PEG) as a reusable solvent medium for organic synthesis. Application in the Heck reaction. Org Lett 4:4399. doi: 10.1021/ol0266976
3. Cornils B, Herrmann WA (1998) Aqueous phase organometallic catalysis - concepts and applications. Wiley-VCH, Weinheim
4. Cui CB, Kakeya H, Osada H (1996a) Spirotryprostatin B, a novel mammalian cell cycle inhibitor produced by Aspergillus fumigatus. J Antibiot 49:832
5. Cui CB, Kakeya H, Osada H (1996b) Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. II. Physico-chemical properties and structures. J Antibiot 49:534-540
6. DeSimone RW, Mitchell KS, Currie SA, Darrow JW, Pippin DA (2004) Privileged structures: applications in drug discovery. Comb Chem High Throughput Screen 7:473-493
7. Elguero J, Goya P, Jagerovic N, Silva AMS (2002) Pyrazoles as drugs: facts and fantasies. Targets Heterocycl Syst 6:52-98
8. Evans BE, Rittle KE, Bock MG, DiPardo RM, Freidinger RM, Whitter WL, Lundell GF, Veber DF, Anderson PS, Chang RSL, Lotti VJ, Cerino DJ, Chen TB, Kling PJ, Kunkel KA, Springer JP, Hirshfield J (1988) Methods for drug discovery: development of potent, selective, orally effective cholecystokinin antagonists. J Med Chem 31:2235-2246
9. Galliford CV, Scheidt KA (2007) Pyrrolidinyl-spirooxindole natural products as inspiration for the development of potential therapeutic agents. Angew Chem Int Ed 46:8748. doi: 10.1002/anie.200701342
10. Haimov A, Neumann R (2002) Polyethylene glycol as a non-ionic liquid solvent for polyoxometalate catalyzed aerobic oxidation. Chem Commun 21:876-877. doi: 10.1039/b200559j
11. Hansch C, Steward AR, Iwasa J, Deutsh EW (1965) The use of a hydrophobic bonding constant for structure-activity correlations. Mol Pharmacol 1:207. doi: 10.1124/mol.1.3.205
12. Jain SC, Kumar R, Goswami R, Pandey MK, Khurana S, Rohtagi L, Gyanda K (2005) Synthesis of novel non-isoprenoid phenolic acids and 3-alkylpyridines. Pure Appl Chem 77:185-193. doi: 10.1351/pac200577010185
13. Joshi KC, Jain R, Sharma K (1988) J Indian Chem Soc 115:202
14. Kang T-H, Matsumoto K, Murakami Y, Takayama H, Kitajima M, Aimi N, Watanabe H (2002) Pteropodine and isopteropodine positively modulate the function of rat muscarinic M(1) and 5-HT(2) receptors expressed in Xenopus oocyte. Eur J Pharmacol 444:39-45
15. Kauzmann W (1959) Some factors in the interpretation of protein denaturation. Adv Protein Chem 14:37
16. Kidwai M, Jain A, Bhardwaj S (2012a) Magnetic nanoparticles catalyzed synthesis of diverse N-heterocycles. Mol Divers 16:121-128. doi: 10.1007/s11030-011-9336-z
17. Kidwai M, Jain A, Sharma A, Kuhad RC (2012b) First time reported enzymatic synthesis of new series of quinoxalines - A green approach. J Mol Catal B Enzym 74:236-240. doi: 10.1016/j.molcatb.2011.11.002
18. Konkoy CS, Fick DB, Cai SX, Lan NC, Keana JFW (2000) PCT Int. Appl.WO0075123.
19. Chem Abstr 2001(134):29313a
20. Kubo I, Muroi H, Himejima M (1993) Structure-antibacterial activity relationships of anarcadic acids. J Agric Food Chem 41:1016-1019
21. Kulkarni SK, Kaul PN (1980) Substances of marine origin affecting pentobarbital pharmacokinetics. Indian J Exp Biol 13:270-272
22. Leitner W (2002) Supercritical carbon dioxide as a green reaction medium for catalysis. Acc Chem Res 35:746-756. doi: 10.1021/ar010070q
23. Marina O, Shibinskaya SA, Lyakhov AV, Mazepa SA, Andronati AV, Turov NM, Zholobak NYS (2010) Synthesis, cytotoxicity, antiviral activity and interferon inducing ability of 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxalines. Eur J Med Chem 45:1237-1243. doi: 10.1016/j.ejmech.2009.12.014
24. Nandakumar A, Thirumurugan P, Perumal PT, Vembu P, Ponnuswamy MN, Ramesh P (2010) One-pot multicomponent synthesis and anti-microbial evaluation of 2′-(indol-3-yl)-2-oxospiro(indoline-3,4′-pyran) derivatives. Bioorg Med Chem Lett 20:4252-4258. doi: 10.1016/j.bmcl.2010.05.025
25. Patchett AA, Nargund RP (2000) Section IV. Topics in drug design and discovery. Annu Rep Med Chem 35:289-298. doi: 0065-7743/00
26. Penning TD, Talley JJ, Bertanshaw SR, Carter JS, Collins PW, Docter S, Graneto MJ, Lee IF, Malecha JW, Miyashiro JM, Roger RS, Rogier DJ, Yu SS, Anderson GD, Burton EG, Cogburn JN, Gregory SA, Koboldt CM, Perkins EW, Seibert K, Veenbuizen AW, Zhang YY, Isakson PC (1997) Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl] benzenesulfonamide (SC-58635, celecoxib). J Med Chem 40:1347-1365
27. b- demethylalstophylline oxindole, an oxindole alkaloid from the leaves of Alstonia macrophylla. Phytochemistry 26:865
28. Schreiber SL (2000) Target-oriented and diversity-oriented organic synthesis discovery. Science 287:1964-1969. doi: 10.1126/science.287.5460.1964
29. Sheldon RA (2001) Catalytic reactions in ionic liquids. Chem Commun 23:2399-2407. doi: 10.1039/B107270F
30. Sheldon RA (2005) Green solvents for sustainable organic synthesis: state of the art. Green Chem 7:267. doi: 10.1039/b418069k
31. Skommer J, Wlodkowic D, Matto M, Eray M, Pelkonen J (2006) HA14-1, a small molecule Bcl-2 antagonist, induces apoptosis and modulates action of selected anticancer drugs in follicular lymphoma B cells. Leuk Res 30:322-331
32. Togo H, Lida S (2006) Synthetic use of molecular iodine for organic synthesis. Synlett 14:2159-2176. doi: 10.1055/s-2006-950405
33. Wang X, Quan Z, Zhang Z (2007) Michael additions of dihydropyrimidines and 2-amino-1,3,4-thiadiazoles to a,b-ethylenic compounds: using polyethylene glycols as a green reaction media. Tetrahedron 63:8227-8233. doi: 10.1016/j.tet.2007.05.108
34. Williams RM, Cox RJ (2003) Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report. Acc Chem Res 36:127-139. doi: 10.1021/ar020229e
35. Yanagida S, Takahashi K, Okahama M (1978) Metal-ion complexation of noncyclic poly(oxyethylene) derivatives. II. PMR studies of the complexation with alkali and alkaline earth metal cations. Bull Chem Soc Jpn 51:1294-1299