Synthesis, Characterization, and Docking Studies of 1,4-dien as a Potential Impurity in Bimatoprost Drug.

IF 1.7 4区化学 Q3 CHEMISTRY, ORGANIC

Current organic synthesis Pub Date : 2025-01-09 DOI:10.2174/0115701794327619240924100026

Nagarjuna Reddy Guttikonda, Muvvala Venkatanarayana, Sharath Babu Haridasyam

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引用次数: 0

Abstract

Introduction: The origin, synthesis, characterization and docking studies of (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R,1E,4E)-3-hydroxy-5-phenylpenta-1,4-dien-1-yl)cyclopentyl)-N-ethylhept-5-enamide, an impurity generated in the preparation of an anti-glaucoma agent-Bimatoprost has been described.

Methods: This impurity was controlled by employing 30% Pd/C, and the impurity level was brought to the permissible level, i.e., 0.03% (ICH guidelines) in the final drug preparation of Bimatoprost.

Results: Finally, induced-fit docking calculations were performed to theoretically evaluate the binding efficiencies of these inhibitors in the crystal structure of Prostaglandin F syn-thase (PGFS).

Conclusion: There are negligible differences in RMSD and docking scores between the two ligands, which amount to only 0.18 Å and 0.313 kcal/mol, respectively. These findings strongly indicate that both ligands are likely to exhibit similar biological functions and effi-ciencies.

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比马前列素中潜在杂质1,4-二烯的合成、表征及对接研究。

导言：介绍了抗青光眼药物比马前列素制备过程中产生的杂质(Z)-7-((1R,2R,3R,5S)-3,5-二羟基-2-((R,1E,4E)-3-羟基-5-苯基戊-1,4-二烯-1-基)环戊基)-N-乙基庚-5-烯酰胺的来源、合成、表征和对接研究：方法：通过使用30%的Pd/C来控制该杂质，并将比马前列素最终药物制剂中的杂质含量控制在允许水平，即0.03%（ICH指南）：最后，进行了诱导拟合对接计算，从理论上评估了这些抑制剂在前列腺素F合成酶（PGFS）晶体结构中的结合效率：结论：两种配体之间的 RMSD 和对接得分差异微乎其微，分别仅为 0.18 Å 和 0.313 kcal/mol。这些发现有力地表明这两种配体可能具有相似的生物功能和功效。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Current organic synthesis 化学-有机化学

CiteScore

3.40

自引率

5.60%

发文量

审稿时长

6-12 weeks

期刊介绍： Current Organic Synthesis publishes in-depth reviews, original research articles and letter/short communications on all areas of synthetic organic chemistry i.e. asymmetric synthesis, organometallic chemistry, novel synthetic approaches to complex organic molecules, carbohydrates, polymers, protein chemistry, DNA chemistry, supramolecular chemistry, molecular recognition and new synthetic methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by experts who are internationally known for their eminent research contributions. The journal is essential reading to all synthetic organic chemists. Current Organic Synthesis should prove to be of great interest to synthetic chemists in academia and industry who wish to keep abreast with recent developments in key fields of organic synthesis.