Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids

Martínez, Mario David; Edelsztein, Valeria Carolina; Durán, Fernando Javier; Chenna, Pablo H. Di; Burton, Gerardo

doi:10.1016/j.steroids.2012.10.012

Cited by 2 publications

(1 citation statement)

References 19 publications

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“…presence of 4-en-3-one function and 17β-side chain having one or more oxygen functionalities. Molecules possessing these features act as competitive inhibitors of 5AR, therefore, all of them could be regarded as a substrate of the enzyme 4-en-3-one steroids [83]. The clinically approved first inhibitor was Steroidal 5α-Reductase: A Therapeutic Target for Prostate Disorders DOI: http://dx.doi.org /10.5772/intechopen.95809 prepared by modification of the structure of naturally existing substrates.…”

Section: Mechanism Based Analoguesmentioning

confidence: 99%

Steroidal 5α-Reductase: A Therapeutic Target for Prostate Disorders

Dhingra¹

2021

Oxidoreductase

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Steroidal 5α-reductase is a system of NADPH dependent enzyme that catalyzes the irreversible conversion of Δ4–3-ketosteroid precursor (testosterone) to its corresponding 5α-reduced metabolite (dihydrotestosterone). Initial role of DHT was discovered through males pseudohermaphroditism, a genetic disorder with complete or partial 5α-reductase deficiency accompanied with features at critical juncture of fetal and postnatal development. However, excessive DHT production, has brought a revolution in revealing the etiology of complications like prostate cancer and benign prostatic hyperplasia. Over the last two decades, converging lines of evidences have highlighted the role of 5α-reductase inhibitors in the treatment of these androgen dependent disorders. Finasteride and Dutasteride, are the two clinically approved inhibitors available in the market, that helps in reducing the prostate volume by blocking the 5a-reductase enzyme.

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Section: Mechanism Based Analoguesmentioning

confidence: 99%

Steroidal 5α-Reductase: A Therapeutic Target for Prostate Disorders

Dhingra¹

2021

Oxidoreductase

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Synthesis, Characterization and Evaluation of 5α, 6β-Dihalo Androsterone Derivatives as 5α-Reductase Inhibitors

Sharma

Rana

Arora

et al. 2022

CEI

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Background and Objective: Testosterone under the influence of 5α-reductase enzyme gets converted to dihydrotestosterone and high levels are found to be causative for androgen dependent disease like benign prostatic hyperplasia. Thus, 5α-reductase has been recognised as an important target for discovering new drugs against Benign Prostatic Hyperplasia and Prostate Cancer. Methods: In the present study, a series of 5α, 6β-Dichloro-17-Oxoandrostan-3β-yl esters (7a-7f) were synthesized and characterized by analytical and spectroscopic methods. The compounds were evaluated for their 5α-reductase inhibitory activity in-vivo by their effect on serum androgen level. Results: The target compounds (7a-7f) showed increased anti-androgenic activity as compared to finasteride and control, which implies that the target compounds are effective in inhibiting 5α-reductase. Particularly, compound 7b showing highest inhibitory activity and noteworthy D-Score was further sorted by performing solubility and dissolution studies. Results of these studies when compared with finasteride showed increased solubility and dissolution of target compound 7b. Conclusion: These results demonstrated that enhancement of activity by the presence of electronegative group at position 3 of the steroidal nucleus makes 7b a lead compound for further exploration and optimal formulation.

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Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids

Cited by 2 publications

References 19 publications

Steroidal 5α-Reductase: A Therapeutic Target for Prostate Disorders

Steroidal 5α-Reductase: A Therapeutic Target for Prostate Disorders

Synthesis, Characterization and Evaluation of 5α, 6β-Dihalo Androsterone Derivatives as 5α-Reductase Inhibitors

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