Open Access
Subscription Access
Open Access
Subscription Access
A Facile and An Efficient Synthesis of 3,3-Disubstituted Oxindole Scaffolds and their Cytotoxic Properties
Subscribe/Renew Journal
A facile and an efficient synthesis of 3,3-disubstituted oxindole derivatives were synthesised by treating isatins with electron rich benzene derivatives at room temperature. The compounds were evaluated for cytotoxic activity against human breast cancer cells (MCF7) and human ovarian carcinoma cells (SKVO3) by using MTT assay. Compounds 5(9.2μM and 9.5μM) and 7(8.0μM and 10.4μM) exhibited relatively higher cytotoxic activity against both MCF7 and SKVO3 cell lines, respectively.
Keywords
Isatins, Methoxy Benzenes, Boron Trifluoride Diethyl Etherate, MCF7 and SKVO3.
Subscription
Login to verify subscription
User
Font Size
Information
- Naresh Kumar R, et al. Synthesis of novel nicotinohydrazide and (1,3,4-oxadiazol-2-yl)-6-(trifluromethyl)pyridine derivatives as potential anticancer agents. Bioorganic Medicinal Chemistry Letters. 26; 2016: 4829-4831.
- Ibrahim HS et al. Isatin-pyrazole benzenesulfonamide hybrids potently inhibit tumor-associated carbonic anhydrase isoforms IX and XII. European Jounal of Medicinal Chemistry. 103; 2015: 583-593.
- Rohini R et al. Synthesis of mono, bis-2-(2-arylideneaminophenyl) indole azomethines as potential antimicrobial agents. Archives of Pharmcol Research 34; 2011: 1077-1084.
- Verma M et al. Anticonvulsant activity of Schiff bases of isatin derivatives. Acta Pharmaceutica. 54; 2004: 49-56.
- Pandeya SN et al. Synthesis, antibacterial and antifungal activities of N-mannich bases of 3-[N2-pyrimethaminylimino] isatin. Indian Journal of Pharmaceutical Sciences. 64; 2002: 209-212.
- Selvam P et al. Synthesis and anti HIV activity of Novel Isatin-Sulphonamides. Indian Journal of Pharmaceutical Sciences. 70; 2008: 779-782.
- Sridhar SK and Ramesh A. Synthesis and pharmacological activities of hydrazones, Schiff and Mannich bases of isatin derivatives. Biological and Pharmaceutical Bulletin. 24; 2001: 1149-1152.
- Eldehna WM et al. Design, synthesis and QSAR study of certain isatin-pyridine hybrids as potential anti-proliferative agents. European. Journal of Medicinal Chemistry. 90; 2015: 684-694.
- Sharma P et al. H2O-mediated isatin spiroepoxide ring opening with NaCN: Synthesis of novel 3-tetrazolylmethyl-3-hydroxy-oxindole hybrids and their anticancer evaluation. European Journal of Medicinal Chemistry. 104; 2015: 11-24.
- Pervez H et al. Cytotoxic and Phytotoxic Effects of Some New N4-Aryl Substituted Isatin-3-thiosemicarbazones. Medicinal Chemistry. 2012, 8, 505-514.
- Hamdy AM et al. Regioselective synthesis Suziki-Miyaura reaction of 4,7-dichloro-N-methylisatin. Synthesis, anti-HIV activity and modelling studies. Rsc. Advances. 5; 2015: 107360-107369.
- Bandgar BP and Shaikh AK. Molecular iodine catalyzed efficient and highly rapid synthesis of bis(indolyl) methanes under mild conditions. Tetrahedron letters. 44; 2003: 1959-1961.
- Bandgar BP, Bettigeri SA and Joshi N S. Hexamethylenetetramine-Bromine Catalysed Rapid and Efficient synthesis of bis(indolyl) methanes. Monatshefte fur Chemie. 135; 2004: 1265-1273.
- Silveira CC et al. Glycerine and CeCl3 7H2O:A new and efficient recyclable medium for the synthesis of bis (indolyl) methanes. Tetrahedron letters. 50; 2009: 6060-6063.
- Xia M, Wang SB and Yuan WB. Lewis acid catalysed electrophillic substitution of indole with schiffs bases under microwave solvent free irradiation. Synthetic Communications. 34; 2004: 3175-3182.
- Babu G Sridhar N and Perumal PT. A convenient method of synthesis of bis(indolyl)methanes: Indium trichloride catalysed reaction of indoles with aldehydes and schiffs bases. Synthetic Communications. 30; 2000: 1609-1614.
- Bandgar BP and Shaikh KA. Organic reactions in aqueous media: In F3 catalysed synthesis of bis(indolyl)methanes in water under mild conditions. Journal of Chemistry Research. Synopses. 34; 2004: 72-74.
- Reddy YT et al. Efficient synthesis of Bis(indolyl)methanes catalysed byTiCl4. Indian Journal of Chemistry. 44B; 2005: 2393-2395.
- Kamal A and Qureshi AA. Synthesis of some substituted Di Indolyl methanes in aqueous medium at room temperature. Tetrahedron letters. 19; 1963: 513-520.
- Chen D, Yu L and Wang PG. Lewis acid catalysed reactions in protic media, Lanthanides-catalyzed reaction of indoles with aldehydes or ketones. Tetrahedron letters. 37; 1996: 4467-4470.
- Ji SJ et al. Efficient synthesis of Bis(indolyl)methanes catalysed by Lewis acids in ionic liquids. Synlett. 13; 2003: 2077-2079.
- ME XL et al. Simple and efficient method for synthesis of Bis(indolyl)methanes with Cu(BF4).SiO2 Under mild conditions. Tetrahedron letters. 45; 2004: 4567-4570.
- Yadav JS et al. Novel use of selectfluorTM for th synthesis of cis- fused pyrano- and furano-tetrahydro quinoline. Advanced Synthesis and Catalysis.2003: 345-349.
- Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of Immunological Methods. 65; 1983: 55-63.
Abstract Views: 237
PDF Views: 0