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Synthesis and Antiproliferative Activity of 3-aza Steroids as 5α-reductase Inhibitors

[ Vol. 14 , Issue. 11 ]


Milanpreet Kaur, Richa Dhingra, T. R. Bhardwaj and Neelima Dhingra*   Pages 1335 - 1346 ( 12 )


Background: Dihyrdotestosterone (DHT), the most potent circulating androgen hormone, is produced by stereoselective reduction of testosterone (T) under catalysis of NADPH dependent enzyme steroid 5α-reductase (5AR). The DHT production is related to many pathological conditions and endocrine diseases such as Benign Prostatic Hyperplasia (BPH). Many years ago, the use of 5AR inhibitors for the possible control or suppression of DHT formation has become years ago a therapeutic target for the treatment of BPH. During last two decades, several non steroidal and steroidal compounds have been synthesized as reversible and irreversible 5AR inhibitors.

Methods: Present study describes the synthesis of 17β-substituted amides of 3-aza-A-homo-4aandrosten- 4-one starting from 16-Dehydropregnelone acetate (16-DPA). The structure of newly synthesized compounds was established on the basis of TLC and various spectroscopic studies and compounds were subjected for their in vitro cytotoxicity studies using prostate cancer cell lines PC-3.

Results and Conclusion: Synthesized compounds (13a to 13h) showed better cytotoxicity as compared to reference drug and 3-Aza-A-homo-17β-(4-nitrobenzamido)-4a-androsten-4-one (13b) showed an excellent antiproliferative activity as compared to Dutasteride.


Azasteroids, benign prostatic hyperplasia, dihydrotestosterone, testosterone, steroids, 5α-reductase enzyme.


CT Institute of Pharmaceutical Sciences, Shahpur, Jalandhar, Punjab 144001, Department of Pharmaceutical Chemistry, University Institute of Pharmaceutical Sciences, Panjab University, Chandigarh 160014, School of Pharmacy and Emerging Sciences, Baddi University of Emerging Sciences and Technology, Baddi (Solan), Himachal Pradesh 173205, University Institute of Pharmaceutical Sciences, Department of Pharmaceutical Chemistry, Panjab University, Chandigarh 160014

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