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Molecular structures and antiproliferative activity of side-chain saturated and homologated analogs of 2-chloro-3-(n-alkylamino)-1,4-napthoquinone

Pal, Sanjima and Jadhav, Mahesh and Weyhermueller, Thomas and Patil, Yogesh and Nethaji, M and Kasabe, Umesh and Kathawate, Laxmi and Konkimalla, Badireenath V and Salunke-Gawali, Sunita (2013) Molecular structures and antiproliferative activity of side-chain saturated and homologated analogs of 2-chloro-3-(n-alkylamino)-1,4-napthoquinone. In: JOURNAL OF MOLECULAR STRUCTURE, 1049 . pp. 355-361.

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Official URL: http://dx.doi.org/10.1016/j.molstruc.2013.06.062

Abstract

Side chain homologated derivatives of 2-chloro-3-(n-alkylamino)-1,4-naphthoquinone {n-alkyl: pentyl; L-5, hexyl; L-6, heptyl; L-7 and octyl; L-8} have been synthesized and characterized by elemental analysis, FT-IR, H-1 NMR, UV-visible spectroscopy and LC-MS. Compounds, L-4, n-alkyl: butyl; L-4}, L-6 and L-8 have been characterized by single crystal X-ray diffraction studies. The single crystal X-ray structures reveal that L-4 and L-8 crystallizes in P2(1) space group, while L-6 in P2(1)/c space group. Molecules of L-4 and L-8 from polymeric chains through C-H center dot center dot center dot O and N-H center dot center dot center dot O close contacts. L-6 is a dimer formed by N-H center dot center dot center dot O interaction. Slipped pi-pi stacking interactions are observed between quinonoid and benzenoid rings of L-4 and L-8. Orientations of alkyl group in L-4 and L-8 is on same side of the chain and polymeric chains run opposite to one another to form zip like structure to the alkyl groups. Antiproliferative activities of L-1 to L-8{n-alkyl: methyl; L-1, ethyl; L-2, propyl; L-3 and butyl; L-4} were studied in cancer cells of colon (COLO205), brain (U87MG) and pancreas (MIAPaCa2) where L-1, L-2 and L-3 were active in MIAPaCa2 (L-1 = 1-2 > L-3) and COLO205 (L-2 = L-3 > L-1) and inactive in U87MG. From antiproliferative studies with compounds L-1 to L-8 it can be concluded that homologation of 2-chloro-3-(n-alkylamino)-1,4-napthoquinone with saturated methyl groups yielded tissue specific compounds such as L-2 (for MIAPaCa2) and L-3 (for COLO205) with optimal activity. (c) 2013 Elsevier B.V. All rights reserved.

Item Type: Journal Article
Additional Information: copyright for this article belongs to Elesvier
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 01 Nov 2013 09:47
Last Modified: 01 Nov 2013 09:47
URI: http://eprints.iisc.ac.in/id/eprint/47634

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