来自Physochlainae Radix的两个新胺基
Jin-Yan Tan1, Jian-Li Li1, Pei Li1
1Shanxi Modern Chinese Medicine Engineering Laboratory, Shanxi University of Chinese Medicine, Jinzhong, 030619, P. R. China.
Chemistry & biodiversity
|July 20, 2023
概括
来自Physochlainae Radix的两种新型胺基具有显著的抗炎性质. 这些化合物有效地抑制了脂多糖诱导的RAW 264.7细胞中氧化 (NO) 的产生.
科学领域:
- 自然产品化学 自然产品化学
- 药理学 药理学 是一个学科.
背景情况:
- 生物活性化合物的潜在来源是Physochlainae Radix.
- 了解药用植物的化学成分和生物活动至关重要.
研究的目的:
- 从Physochlainae Radix.中分离和描述新的化学化合物.
- 为了评估分离的化合物的抗炎潜力.
主要方法:
- 使用色谱技术分离化合物.
- 通过综合光谱分析 (NMR,HR-ESI-MS) 阐明结构.
- 在体外抗炎测定使用脂聚糖 (LPS) 诱导的RAW 264.7细胞来测量氧化 (NO) 生产.
主要成果:
- 两种新的胺,指定1和2,具有独特的 (2-formyl-5-hydroxymethyl) pyrroyl-butylamine部分,已成功分离出来.
- 这两种化合物都显著抑制了NO生产.
- 化合物1和2的IC50值分别为17.52±1.68微米和20.37±2.42微米.
结论:
- Physochlainae Radix产生了具有抗炎活性的新型胺基.
- 已识别的化合物代表了作为抗炎药物的进一步研究的有希望的候选者.
相关概念视频
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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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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Amines to Amides: Acylation of Amines
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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
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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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Physical Properties of Amines
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Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
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Nomenclature of Aryl and Heterocyclic Amines
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The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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