Synthesis and biological activity of some amino-4'-substituted phenyl(pyridine)androst-4-en-3-one candidates
- Authors: Amr A.E.1,2, Abdalla M.M.3, Hussein M.M.4, Safwat H.M.4, Elgamal M.H.2
-
Affiliations:
- Pharmaceutical Chemistry Department, Drug Exploration and Development Chair, College of Pharmacy
- National Research Center
- Research Unit
- Pharmaceutical Chemistry Departments, Faculty of Pharmacy
- Issue: Vol 87, No 2 (2017)
- Pages: 305-310
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/218438
- DOI: https://doi.org/10.1134/S1070363217020256
- ID: 218438
Cite item
Abstract
A series of substituted androstanopyridine derivatives 2–5 were synthesized using 17-acetyl- 1,7,8,10,11,12,13,15,16,17-decahydro-10,13-dimethyl-2H-cyclopenta[a]-phenanthren-3(6H,9H,14H)-one (progesterone, 1) as a starting material. Reaction of 1a–1d with malononitrile and aldehydes in the presence of ammonium acetate gave the corresponding amino cyanopyridine derivatives 2a–2d. The same compounds 1a–1d reacted with cyanoacetamide and aldehydes in the presence of ammonium acetate to give a mixture of 3a–3d and 4a–4d, that was separated chromatographically. The reaction of compounds 1a–1d with ethyl cyanoacetate and aldehydes led to products 5a–5d. Structures of the newly synthesized compounds were elucidated by physical and spectral methods. The synthesized compounds were tested as 5α-reductase inhibitors and anti-prostate cancer agents.
About the authors
A. E. Amr
Pharmaceutical Chemistry Department, Drug Exploration and Development Chair, College of Pharmacy; National Research Center
Email: mmostafa201120@yahoo.com
Saudi Arabia, Riyadh, 11451; Cairo
M. M. Abdalla
Research Unit
Author for correspondence.
Email: mmostafa201120@yahoo.com
Egypt, 6 October City
M. M. M. Hussein
Pharmaceutical Chemistry Departments, Faculty of Pharmacy
Email: mmostafa201120@yahoo.com
Egypt, Gizza
H. M. Safwat
Pharmaceutical Chemistry Departments, Faculty of Pharmacy
Email: mmostafa201120@yahoo.com
Egypt, Gizza
M. H. Elgamal
National Research Center
Email: mmostafa201120@yahoo.com
Egypt, Cairo