（2R，4aS，6aS，12bR，14aS，14bR）10-羟基-N-（4-（（6-甲氧基喹啉-8-基）氨基）戊基）-2,4a，6a，9,12b，14a-六甲基-11-氧代-1,2,3,4,4a，5,6,6a，11,12b，13,14,14a，14b-十四氢冰-2-甲酰胺

IF 0.6 Q4 CHEMISTRY, ORGANIC

Molbank Pub Date : 2023-08-29 DOI:10.3390/m1716

Yuhan Xie, Houin Kuan, Qin Wei, Alessandra Gianoncelli, G. Ribaudo, P. Coghi

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引用次数: 0

摘要

我们在此报道了一种天然化合物celastrol的衍生物的合成与抗疟药伯氨喹通过一个酰胺活化羧酸与HOBt/EDC。利用质子核磁共振(1H-NMR)、碳-13核磁共振(13C-NMR)、异核单量子相干(HSQC)、相关光谱(1H-1H-COSY)、极化转移无畸变增强(DEPT)、质谱、傅里叶变换红外(FTIR)和紫外(UV)光谱对新分子的化学结构进行了全面表征。计算研究被纳入预测合成化合物与肌内质网(SR) Ca2+转运atp酶(SERCA)的相互作用，SERCA是开发关节炎新疗法的相关靶点。通过预测其药代动力学性质，考察了化合物的药物相似性。

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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(2R,4aS,6aS,12bR,14aS,14bR)10-Hydroxy-N-(4-((6-methoxyquinolin-8-yl)amino)pentyl)-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxamide

We herein report the synthesis of a derivative of the natural compound celastrol linked to the antimalarial drug primaquine through an amide obtained by the activation of the carboxylic acid with HOBt/EDC. The chemical structure of the new molecule was fully characterized by proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), heteronuclear single quantum coherence (HSQC), correlation spectroscopy (1H-1H-COSY), distortionless enhancement by polarization transfer (DEPT), mass spectrometry, Fourier-transform infrared (FTIR), and ultraviolet (UV) spectroscopies. Computational studies were enrolled to predict the interaction of the synthesized compound with sarco-endoplasmic reticulum (SR) Ca2+ transport ATPase (SERCA), a target of relevance for developing new therapeutics against arthritis. The drug-likeness of the compound was also investigated by predicting its pharmacokinetic properties.

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来源期刊

Molbank Chemistry-Physical and Theoretical Chemistry

CiteScore

0.70

自引率

33.30%

发文量

174

审稿时长

11 weeks

期刊介绍： •organic synthesis •biosynthesis •extraction and purification •natural product derivatives •structural elucidation (X-ray crystallography, NMR, etc.)