从醇及其衍生物合成功能化金字胺:二十年的发展
Surabhi Mishra1, Sumran Raikwar1, Beeraiah Baire1
1Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, INDIA.
Chemistry, an Asian journal
|May 29, 2023
概括
本综述详细介绍了在药物化学中至关重要的胺基衍生物的合成方法. 甲基醇和相关化合物是制造这些生物活性分子的关键构件.
科学领域:
- 有机化学 有机化学
- 药用化学 医学化学
- 异环化学 异环化学
背景情况:
- 胺 (1,3-氨酸) 是核酸,天然产品和药品中发现的重要异环基架.
- 胺衍生物具有广泛的生物活性,包括抗结核,抗菌,抗真菌,抗病毒,抗炎症,抗疟疾和抗癌性质.
- 这些特权结构的合成在药物发现和开发中具有重要意义.
研究的目的:
- 审查用于金字素支架的合成策略.
- 为了突出使用propargylic酒精及其衍生物作为三碳synthons.
- 涵盖了从2000年到2022年的胺合成发展情况.
主要方法:
- 在文献中报告的合成方法的总结.
- 专注于使用基醇,基和基的反应.
- 分析2000年至2022年间开发的合成方法.
主要成果:
- 编制各种合成路径以访问金字素构建块.
- 在pyrimidine环形形成中证明了propargylic衍生物的多功能性.
- 在23年的时间里,综合方法的进展概述.
结论:
- 甲基醇及其衍生物是合成生物相关金胺的有效前体.
- 审查的合成方法为药物化学家提供了有价值的工具.
- 继续在这一领域的研究对于开发新型治疗剂至关重要.
相关概念视频
02:27Preparation of Alkynes: Alkylation Reaction
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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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02:34Preparation of Alkynes: Dehydrohalogenation
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Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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01:38Preparation of Alcohols via Substitution Reactions
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Overview
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
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01:33Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes
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Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...
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02:29Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis
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Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
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02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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