伪IX,其N-氧化物和具有抗菌活性的新型碳胺类同类物的简要合成
Plamen Angelov1, Yordanka Mollova-Sapundzhieva1, Francisco Alonso2
1Department of Organic Chemistry, University of Plovdiv Paisii Hilendarski, 24 Tsar Asen Str., 4000 Plovdiv, Bulgaria.
Molecules (Basel, Switzerland)
|August 10, 2024
概括
研究人员合成了伪素IX及其类似物,发现了具有显著抗菌活性的新型化合物,用于对抗金黄色葡萄球菌. 这些新类型的药物显示出广泛的疗效,与现有治疗方法相比.
科学领域:
- 有机合成 有机合成
- 药品化学 药品化学 是一个
- 自然产品的合成方法
背景情况:
- 伪 IX 是一种具有潜在生物活性的天然产品.
- 开发高效的合成路径对于研究和利用自然产品至关重要.
- 探索天然产品的类似物可以提高治疗性质.
研究的目的:
- 开发一种有效的合成伪素IX.
- 为了合成新型的卡尔博克萨米德类型的伪素IX.
- 为了评估合成化合物的抗菌活性.
主要方法:
- 从3-oxododecanoic酸phenylamide中开发了一个四步合成的伪IX.
- 对基组进行控制的部分减少,产生了伪 IX的N-氧化物 (NQNO).
- 通过三步合成,可以制备新的碳胺类同类物.
主要成果:
- 伪 IX 合成了 52% 的总产量,通过单次色谱净化.
- 已经成功地制备了新型的 karboxamide 类型的 pseudane IX.
- 新型类似物在100μg/mL时表现出显著的抗菌活性,对抗金黄色葡萄球菌.
- 一种类型显示了与NQNO.相当的广泛抗菌活性.
结论:
- 已经建立了一个有效的合成路径到伪素IX及其类似物.
- 新型伪IX类似物具有强大的抗菌特性.
- 这些发现表明,有可能开发新的抗菌剂.
相关概念视频
Preparation of Amides
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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
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Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
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Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
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One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
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