Medicinal Chemistry Research

, Volume 23, Issue 4, pp 1950–1955

Synthesis, characterization, and cytotoxicity of N-2′-hydroxyethyl-substituted azastigmastanes

Original Research

DOI: 10.1007/s00044-013-0795-x

Cite this article as:
Alam, M., Nami, S.A.A., Rehman, S. et al. Med Chem Res (2014) 23: 1950. doi:10.1007/s00044-013-0795-x

Abstract

The in vitro cytotoxicity of N-2′-hydroxyethyl-substituted azastigmastanes and its precursor steroidal ketones against cancer cell lines: MCF-7, HepG2, and HCT 116; has been carried out using MTT assay. The N-2′-hydroxyethyl-substituted azastigmastanes were synthesized by bespoke version of Schmidt reaction using common Lewis acids like BF3–OEt2, SnCl4 and H2SO4 as catalysts in substantial yields. Sulphuric acid was found to be the most suitable catalyst in terms of reaction yield and time, while SnCl4 was found to be the weakest in case of 3β-acetoxy-N-2′-hydroxyethyl-6-aza-B-homo-5α-stigmastan-7-one and 3β-chloro-N-2′-hydroxyethyl-6-aza-B-homo-5α-stigmastan-7-one and almost inactive in case of N-2′-hydroxyethyl-6-aza-B-homo-5α-stigmastan-7-one. The products were obtained in semi-solid state and characterized by spectroscopic techniques and microanalytical data. Moreover, on the basis of IC50, compound 5 was found to inhibit the cancer cells most effectively in conformity with our previous findings.

Keywords

CytotoxicitySteroidal ketoneStigmastaneLewis acidsSchmidt reaction

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  1. 1.Division of BioscienceDongguk UniversityGyeongjuRepublic of Korea
  2. 2.Department of Kulliyat, Faculty of Unani MedicineAligarh Muslim UniversityAligarhIndia
  3. 3.Department of Ilmul Advia, Faculty of Unani MedicineAligarh Muslim UniversityAligarhIndia
  4. 4.Department of ChemistryDongguk UniversityGyeongjuRepublic of Korea