Synthesis, NMR and X-ray characterization of dibenzoannulated dimeric steroid spiroketals. Evaluation of cytotoxicity and anti-inflammatory activity

IF 2.1 4区医学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Steroids Pub Date : 2025-04-13 DOI:10.1016/j.steroids.2025.109614

Rsuini U. Gutiérrez-Aguilar , Juan A. Antolín-González , Nimsi Campos-Xolalpa , Salud Perez-Gutierrez , Marcos Flores-Álamo , Josué Vazquez-Chavez , Martín A. Iglesias-Arteaga

引用次数: 0

Abstract

Two dibenzoannulated dimeric steroid spiroketals were obtained from cholesterol and 1,4-phenylenedimethanol. The key step in synthetic protocol is a Pd-catalyzed double spiroketalization in an adduct obtained from the double Sonogashira coupling of the 5α and 5β diastereomers of 4,5-secocholestan-5-ol. A detailed NMR characterization supported by Single Crystal X-ray Diffraction studies corroborated the obtained structures. While no cytotoxic effect was observed, the obtained compounds produced a significant reduction in the production of nitric oxide in macrophages stimulated with Lipopolysaccharide (LPS), indicating a potential anti-inflammatory activity.

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二苯并环二聚体甾体螺旋酮的合成、核磁共振和x射线表征。细胞毒性和抗炎活性的评价

我们从胆固醇和 1,4-亚苯基二甲醇中获得了两种二苯并annulated 二聚甾类螺酮。合成方案的关键步骤是在 4,5-secocholestan-5-醇的 5α 和 5β 非对映异构体双 Sonogashira 偶联得到的加合物中进行钯催化双螺酮化。详细的核磁共振表征和单晶 X 射线衍射研究证实了所获得的结构。虽然没有观察到细胞毒性作用，但获得的化合物能显著减少巨噬细胞在脂多糖（LPS）刺激下产生的一氧化氮，这表明它们具有潜在的抗炎活性。

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来源期刊

Steroids 医学-内分泌学与代谢

CiteScore

5.10

自引率

3.70%

发文量

120

审稿时长

73 days

期刊介绍： STEROIDS is an international research journal devoted to studies on all chemical and biological aspects of steroidal moieties. The journal focuses on both experimental and theoretical studies on the biology, chemistry, biosynthesis, metabolism, molecular biology, physiology and pharmacology of steroids and other molecules that target or regulate steroid receptors. Manuscripts presenting clinical research related to steroids, steroid drug development, comparative endocrinology of steroid hormones, investigations on the mechanism of steroid action and steroid chemistry are all appropriate for submission for peer review. STEROIDS publishes both original research and timely reviews. For details concerning the preparation of manuscripts see Instructions to Authors, which is published in each issue of the journal.