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含咪唑化合物的合成及其治疗潜力

Synthesis and therapeutic potential of imidazole containing compounds.

作者信息

Siwach Ankit, Verma Prabhakar Kumar

机构信息

Department of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak, Haryana, India.

出版信息

BMC Chem. 2021 Feb 18;15(1):12. doi: 10.1186/s13065-020-00730-1.

Abstract

Imidazole is a five-membered heterocyclic moiety that possesses three carbon, two nitrogen, four hydrogen atoms, and two double bonds. It is also known as 1, 3-diazole. It contains two nitrogen atoms, in which one nitrogen bear a hydrogen atom, and the other is called pyrrole type nitrogen. The imidazole name was reported by Arthur Rudolf Hantzsch (1857-1935) in 1887. 1, 3-diazole is an amphoteric in nature i.e. it shows both acidic and basic properties. It is a white or colorless solid that is highly soluble in water and other polar solvents. Due to the presence of a positive charge on either of two nitrogen atom, it shows two equivalent tautomeric forms. Imidazole was first named glyoxaline because the first synthesis has been made by glyoxal and ammonia. It is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. The derivatives of 1, 3-diazole show different biological activities such as antibacterial, antimycobacterial, anti-inflammatory, antitumor, antidiabetic, anti-allergic, antipyretic, antiviral, antioxidant, anti-amoebic, antihelmintic, antifungal and ulcerogenic activities, etc. as reported in the literature. There are different examples of commercially available drugs in the market which contains 1, 3-diazole ring such as clemizole (antihistaminic agent), etonitazene (analgesic), enviroxime (antiviral), astemizole (antihistaminic agent), omeprazole, pantoprazole (antiulcer), thiabendazole (antihelmintic), nocodazole (antinematodal), metronidazole, nitroso-imidazole (bactericidal), megazol (trypanocidal), azathioprine (anti rheumatoid arthritis), dacarbazine (Hodgkin's disease), tinidazole, ornidazole (antiprotozoal and antibacterial), etc. This present review summarized some pharmacological activities and various kinds of synthetic routes for imidazole and their derived products.

摘要

咪唑是一种五元杂环部分,含有三个碳原子、两个氮原子、四个氢原子和两个双键。它也被称为1,3 - 二唑。它含有两个氮原子,其中一个氮原子带有一个氢原子,另一个被称为吡咯型氮。咪唑这个名称由亚瑟·鲁道夫·汉斯奇(1857 - 1935)于1887年提出。1,3 - 二唑本质上是两性的,即它兼具酸性和碱性。它是一种白色或无色固体,极易溶于水和其他极性溶剂。由于两个氮原子中的任何一个都带有正电荷,它呈现出两种等效的互变异构形式。咪唑最初被命名为乙二醛肟,因为它最初是由乙二醛和氨合成的。它是一些天然产物如组氨酸、嘌呤、组胺和基于DNA的结构等的基本核心。在不同的杂环化合物中,咪唑因其广泛的化学和生物学性质而更为人所知。咪唑已成为新药开发中的重要合成子。文献报道,1,3 - 二唑的衍生物具有不同的生物活性,如抗菌、抗分枝杆菌、抗炎、抗肿瘤、抗糖尿病、抗过敏、解热、抗病毒、抗氧化、抗阿米巴、抗蠕虫、抗真菌和致溃疡活性等。市场上有不同的市售药物含有1,3 - 二唑环,如氯苯甲嗪(抗组胺药)、依托尼秦(镇痛药)、恩韦肟(抗病毒药)、阿司咪唑(抗组胺药)、奥美拉唑、泮托拉唑(抗溃疡药)、噻苯达唑(抗蠕虫药)、诺考达唑(抗线虫药)、甲硝唑、亚硝基咪唑(杀菌剂)、美他唑(杀锥虫药)、硫唑嘌呤(抗类风湿性关节炎药)、达卡巴嗪(霍奇金病药)、替硝唑、奥硝唑(抗原虫和抗菌药)等。本综述总结了咪唑及其衍生产品的一些药理活性和各种合成路线。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e11/7893931/7a735daefd4c/13065_2020_730_Fig1_HTML.jpg

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