(2R, 4S, 5S) 1-(4-(4-(((7-Chloroquinolin-4-yl)amino)methyl)-1H-1,2,3-triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

IF 0.4 Q4 CHEMISTRY, ORGANIC

Molbank Pub Date : 2023-07-03 DOI:10.3390/m1681

Houin Kuan, Yuhan Xie, Yuzhu Guo, Alessandra Gianoncelli, G. Ribaudo, P. Coghi

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引用次数: 1

Abstract

1,2,3-triazole pharmacophore is a widely recognized motif used for a variety of applications, including drug discovery, chemical biology, and materials science. We herein report the synthesis of a derivative of azidothymidine (AZT), which was combined with the 7-chloro quinoline scaffold through a 1,4-disubstituted 1,2,3-triazole. The chemical structure of the new molecule was fully characterized by Fourier transform infrared (FTIR) spectroscopy, proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC) distortionless enhancement by polarization transfer (DEPT), correlation spectroscopy (1H-1H-COSY), ultraviolet (UV) spectroscopy, and high-resolution mass spectrometry (HRMS). Computational studies were used to predict the interaction of the synthesized compound with HIV reverse transcriptase, a target of relevance for developing new therapeutics against AIDS. The drug-likeness of the compound was also investigated by computing the physico-chemical properties that are important for the pharmacokinetic profile.

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(2R, 4S, 5S) 1-(4-(4-(7-氯喹啉-4-基)氨基)甲基)-1H-1,2,3-三唑-1-基)-5-(羟甲基)四氢呋喃-2-基)-5-甲基嘧啶-2,4(1H,3H)-二酮

1,2,3-三唑药效团是一种被广泛认可的基序，用于各种应用，包括药物发现、化学生物学和材料科学。本文报道了叠氮噻嗪（AZT）衍生物的合成，该衍生物通过1,4-二取代的1,2,3-三唑与7-氯喹啉支架结合。通过傅里叶变换红外光谱（FTIR）、质子核磁共振（1H-NMR）、碳-13核磁共振（13C-NMR）、异核单量子相干（HSQC）、偏振转移无畸变增强（DEPT）对新分子的化学结构进行了全面表征，相关光谱（1H-1H-COSY）、紫外线（UV）光谱和高分辨率质谱（HRMS）。计算研究被用来预测合成的化合物与HIV逆转录酶的相互作用，HIV逆转录酶是开发新的艾滋病治疗方法的相关靶点。还通过计算对药代动力学特征很重要的物理化学性质来研究该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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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.)