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Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction
Joint Authors
Khan, Suraiya
Alam, Mahboob
Park, Soonheum
Lee, Dong-Ung
Nami, Shahab A. A.
Mushfiq, M.
Source
Issue
Vol. 2013, Issue 2013 (31 Dec. 2013), pp.1-7, 7 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2012-08-28
Country of Publication
Egypt
No. of Pages
7
Main Subjects
Abstract EN
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.
American Psychological Association (APA)
Nami, Shahab A. A.& Khan, Suraiya& Alam, Mahboob& Mushfiq, M.& Lee, Dong-Ung& Park, Soonheum. 2012. Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction. Journal of Spectroscopy،Vol. 2013, no. 2013, pp.1-7.
https://search.emarefa.net/detail/BIM-447868
Modern Language Association (MLA)
Nami, Shahab A. A.…[et al.]. Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction. Journal of Spectroscopy No. 2013 (2013), pp.1-7.
https://search.emarefa.net/detail/BIM-447868
American Medical Association (AMA)
Nami, Shahab A. A.& Khan, Suraiya& Alam, Mahboob& Mushfiq, M.& Lee, Dong-Ung& Park, Soonheum. Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction. Journal of Spectroscopy. 2012. Vol. 2013, no. 2013, pp.1-7.
https://search.emarefa.net/detail/BIM-447868
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-447868