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IN373388: 2-benzyltetralin compounds as anticancer agents and the process of preparing the same

This invention provides 2-benzyltetralin compounds as anticancer agents and the process of preparing the same. The series is represented by structure 1, possessing potential anticancer activity against human liver cancer cells. 2-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydro-6- methoxynaphthalene (2) is a representative example of the series possessing molecular formulae as C21H2604 exhibits potential in-vivo anticancer activity. In safety studies, compound 2 was found to be safe in acute oral toxicity in Swiss albino mice up to 300mg/kg oral dose. More particularly, the invention relates to the potent anticancer and tubulin polymerisation inhibition activity of a new benzyltetralin (2) synthesized from 6-methoxytetralone and a gallic acid derivative. Spectral details of 2: Compound 2 is a yellow solid with m.p. 106-108 0C. In-"HNMR (CDC13): 51.46 (m,lH, CH), 2.02 (m, 2H, CH2), 2.43 (t, 1H, CH of 4-CH2), 2.61 (d, 2H, CH2), 2.79 (bs, 3H, CH of 4-CH2and 1-CH2), 3.84 (s, 3H, OCH3), 3.94 (s, 9H, 3xOCH3), 6.41 (s/2H, CH aromatic), 6.65 (m, 2H, CH aromatic), 6.97 (m, 1H, CH aromatic); l3C NMR (CDC13): 8 29.56, 29.74, 35.56, 36.92, 43.63, 55.63, 56.51, 56.61, 61.28, 106.48, 112.32, 113.87, 128.96, 130.37, 136.66, 137.02, 138.10, 153.46, 158.01. In electrospray ionization mass (ESI-MS, MeOH) it gives adducts ions at 365 [M+Na]+, 381 [M+K]+ for its molecular formulae as C21H2604, further confirmed by High resolution mass (ESI-HRMS) Calcd. 343.1909; found 343.1917 for C21H27.04 [M+H]+.
Patent No:
IN373388
Application No:
201711009095
Filing Date:
16-03-2017
Issue Date:
06-08-2021
Applicant:
CSIR-Central Institute of medicinal and Aromatic Plants (CSIR-CIMAP), Lucknow
Inventor(s):
Negi Arvind Singh; Gautam Yashveer; Luqman Suaib; Fatima Kaneez; Chanda Debabrata; Singh Arjun; Wahajuddin; Taneja Isha
IPC Classification:
C01B 25/00
Country:
India
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