Synthesis and evaluation of novel 4-amino-4,6-androstadiene-3,17-dione: An analog of formestane

Synthesis of 4-amino-4,6-androstadiene-3,17-dione 7, an analog of formestane used in breast cancer therapy as an aromatase inhibitor, from 4-acetoxy-4-androstene-3,17-dione 2 is described. This is the first report of a 4-amino diene (4,6) system in this series of molecules. The new and reported mole...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2008-10, Vol.18 (20), p.5563-5566
Main Authors: Sharma, Sanjay K., Zheng, Weizhong, Joshua, Alummoottil V., Abrams, Douglas N., McEwan, Alexander J.B.
Format: Article
Language:English
Subjects:
4-OHA
Androstadienes - chemistry
Androstenedione - analogs & derivatives
Androstenedione - chemical synthesis
Androstenedione - chemistry
Androstenedione - pharmacology
Antineoplastic agents
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - pharmacology
Aromatase
Aromatase - metabolism
Aromatization
Biological and medical sciences
Breast cancer
Breast Neoplasms - drug therapy
Cell Line, Tumor
Chemistry, Pharmaceutical - methods
Drug Design
Drug Screening Assays, Antitumor
Formestane
General aspects
Humans
Medical sciences
Models, Chemical
Pharmacology. Drug treatments
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Summary:Synthesis of 4-amino-4,6-androstadiene-3,17-dione 7, an analog of formestane used in breast cancer therapy as an aromatase inhibitor, from 4-acetoxy-4-androstene-3,17-dione 2 is described. This is the first report of a 4-amino diene (4,6) system in this series of molecules. The new and reported molecules were screened by the National Cancer Institute (NCI, Bethesda, USA) for in vitro antitumor activity against 60 human cancer cell lines. Compound 7 showed best activity against breast cancer cell line (MCF-7). Synthesis of 4-amino-4,6-androstadiene-3,17-dione 7, an analog of formestane used in breast cancer therapy as an aromatase inhibitor, from 4-acetoxy-4-androstene-3,17-dione 2 is described. This is the first report of a 4-amino diene (4,6) system in this series of molecules. The new ( 7) and reported molecules were screened by the National Cancer Institute (NCI, Bethesda, USA) for in vitro antitumor activity against 60 human cancer cell lines. Molecule 7 showed best activity against breast cancer cell line (MCF-7).
ISSN:0960-894X
0968-0896
1464-3405
1464-3391
DOI:10.1016/j.bmcl.2008.09.018