Synthesis, anti-proliferative and genotoxicity studies of 6-chloro-5-(2-substituted-ethyl)-1,3-dihydro-2H-indol-2-ones and 6-chloro-5-(2-chloroethyl)-3-(alkyl/ary-2-ylidene)indolin-2-ones

• Published in: European journal of medicinal chemistry Vol. 121; pp. 221 - 231
• Main Authors: Meti, Gangadhar Y., Kamble, Atulkumar A., Kamble, Ravindra R., Somagond, Shilpa M., Devarajegowda, H.C., Kumari, Sandhya, Kalthur, Guruprasad, Adiga, Satish K.
• Format: Journal Article
• Language: English
• Published: PARIS Elsevier Masson SAS 04.10.2016; Elsevier
• Subjects: 2H-Indol-2-ones; Anti-proliferative activity; Antineoplastic Agents - chemistry; Cell line; Cell Line, Tumor; Cell Proliferation - drug effects; Chemistry, Medicinal; Dose-Response Relationship, Drug; Genotoxicity; Humans; Indoles - chemistry; Indoles - pharmacology; Life Sciences & Biomedicine; Mutagens - chemistry; Mutagens - pharmacology; Pharmacology & Pharmacy; Science & Technology; Cell line; 2H-Indol-2-ones; Anti-proliferative activity; Genotoxicity; DESIGN; POTENTIAL ANTICANCER ACTIVITY; INHIBITORS; DERIVATIVES
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2016.05.028

A series of 6-chloro-5-(2-substituted-ethyl)-1,3-dihydro-2H-indol-2-ones (3a-h) and 6-chloro-5-(2-chloroethyl)-3-(alkyl/aryl-2-ylidene)indolin-2-ones (5i-x) were synthesized. Compounds 3a-e, 5i-l and 5q-r were selected by NIH, USA for in vitro anti-proliferative screening. Based on the impressive growth inhibitory (GI %) effect by the compounds 3a-b and 3e which showed growth inhibition in the range 1.22–76.30%, 2.85–76.03% and 10.98–82.05% respectively at 10−5 concentration, these compounds were further analyzed for anti-proliferative activity at 5 dose concentration and genotoxicity. A series of 6-chloro-5-(2-substituted-ethyl)-1,3-dihydro-2H-indol-2-ones (3a-h) and 6-chloro-5-(2-chloroethyl)-3-(alkyl/aryl-2-ylidene)indolin-2-ones (5i-x) were synthesized. Compounds 3a-e, 5i-l and 5q-r were selected by NIH, USA for in vitro anti-proliferative screening. Based on the impressive growth inhibitory (GI%) effect, the compounds 3a-b and 3e were further analyzed for anti-proliferative (at 5 dose concentration) and genotoxic activity. [Display omitted] •Indolin-2-one derivatives 3a-h and 5i-x were synthesized.•Compounds 3a-e, 5i-l, 5q-r were screened for in vitro anti-proliferation and genotoxicity.•Growth inhibition was up to 82.05 at 10−5 M concentration.•Among the tested compounds 3a-b, 3e exhibited promising anti-proliferative and genotoxic activity.