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Journal of Spectroscopy
Volume 2013, Article ID 128149, 7 pages
http://dx.doi.org/10.1155/2013/128149
Research Article

Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction

1Department of Kulliyat, Faculty of Unani Medicine, Aligarh Muslim University, Aligarh 202002, India
2Department of Chemistry, Dongguk University, Gyeongju 780-714, Republic of Korea
3Department of Chemistry, Aligarh Muslim University, Aligarh 202002, India
4Division of Bioscience, Dongguk University, Gyeongju 780-714, Republic of Korea

Received 5 June 2012; Accepted 11 July 2012

Academic Editor: Mircea Cotlet

Copyright © 2013 Shahab A. A. Nami et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

The present paper reports the synthesis and spectroscopic characterization of few N-2′-hydroxyethyl-substituted azacholestanes using BF3-OEt2, TiCl4, SnCl4, and H2SO4 as catalysts in moderate yields by a modified version of Schmidt reaction. A notable feature is the passivity of SnCl4 in case of 3β-acetoxy-N-2′-hydroxyethyl-6-aza-B-homo-5α-cholestan-7-one and 3β-chloro-N-2′-hydroxyethyl-6-aza-B-homo-5α-cholestan-7-one. However, the reaction was unsuccessful in case of N-2′-Hydroxyethyl-6-aza-B-homo-5α-cholestan-7-one. Another striking aspect is the attainment of high yield in case of H2SO4 as catalyst. The semisolid compounds are characterized using various spectroscopic techniques such as FT-IR, 1H-NMR and mass spectra, and microanalytical data. A reaction mechanism has been proposed on the basis of previous studies. Moreover, the compounds have also been screened for their in vitro cytotoxicity against human colon carcinoma cell line, HCT116, and human liver hepatocellular carcinoma cell line, HepG2, using doxorubicin as standard. On the basis of IC50 values, 3β-chloro-N-2′-hydroxyethyl-6-aza-B-homo-5α-cholestan-7-one (5) was found to inhibit the cancer cells most effectively.