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Journal of Spectroscopy
30217 Vol.2013, 000(2013)
Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction
Shahab A. A. Nami[1,2]; Suraiya Khan[3]; Mahboob Alam[3,4]; M. Mushfiq[3]; Dong-Ung Lee[4]; and Soonheum Park[2];
[1]Department of Kulliyat, Faculty of Unani Medicine, Aligarh Muslim University, Aligarh 202002, India [2]Department of Chemistry, Dongguk University, Gyeongju 780-714, Republic of Korea [3]Department of Chemistry, Aligarh Muslim University, Aligarh 202002, India [4]Division of Bioscience, Dongguk University, Gyeongju 780-714, Republic of Korea
 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.
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