Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction
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-...
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| Language: | English |
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Wiley
2013-01-01
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| Series: | Journal of Spectroscopy |
| Online Access: | http://dx.doi.org/10.1155/2013/128149 |
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| author | Shahab A. A. Nami Suraiya Khan Mahboob Alam M. Mushfiq Dong-Ung Lee Soonheum Park |
| author_facet | Shahab A. A. Nami Suraiya Khan Mahboob Alam M. Mushfiq Dong-Ung Lee Soonheum Park |
| author_sort | Shahab A. A. Nami |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-4512e167a7544931bdfae3be28ec846a |
| institution | OA Journals |
| issn | 2314-4920 2314-4939 |
| language | English |
| publishDate | 2013-01-01 |
| publisher | Wiley |
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| series | Journal of Spectroscopy |
| spelling | doaj-art-4512e167a7544931bdfae3be28ec846a2025-08-20T02:37:52ZengWileyJournal of Spectroscopy2314-49202314-49392013-01-01201310.1155/2013/128149128149Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt ReactionShahab A. A. Nami0Suraiya Khan1Mahboob Alam2M. Mushfiq3Dong-Ung Lee4Soonheum Park5Department of Kulliyat, Faculty of Unani Medicine, Aligarh Muslim University, Aligarh 202002, IndiaDepartment of Chemistry, Aligarh Muslim University, Aligarh 202002, IndiaDepartment of Chemistry, Aligarh Muslim University, Aligarh 202002, IndiaDepartment of Chemistry, Aligarh Muslim University, Aligarh 202002, IndiaDivision of Bioscience, Dongguk University, Gyeongju 780-714, Republic of KoreaDepartment of Chemistry, Dongguk University, Gyeongju 780-714, Republic of KoreaThe 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.http://dx.doi.org/10.1155/2013/128149 |
| spellingShingle | Shahab A. A. Nami Suraiya Khan Mahboob Alam M. Mushfiq Dong-Ung Lee Soonheum Park Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction Journal of Spectroscopy |
| title | Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction |
| title_full | Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction |
| title_fullStr | Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction |
| title_full_unstemmed | Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction |
| title_short | Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction |
| title_sort | synthesis spectral characterization and in vitro cytotoxicity of n 2 hydroxyethyl substituted azacholestanes prepared from 6 oxocholestanes by modified schmidt reaction |
| url | http://dx.doi.org/10.1155/2013/128149 |
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