AI-77-C | 77675-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: AI-77-C
• 英文别名: N-acetylamicoumacin C；(2S)-2-[(2S,3S)-3-acetamido-5-oxooxolan-2-yl]-2-hydroxy-N-[(1S)-1-[(3S)-8-hydroxy-1-oxo-3,4-dihydroisochromen-3-yl]-3-methylbutyl]acetamide
• CAS: 77675-00-4
• 化学式: C₂₂H₂₈N₂O₈
• 分子量: 448.473
• InChiKey: UZCRVMORNZRNBV-OLOWNEEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  triethyloxonium fluoroborate 、 AI-77-C 以 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  1H-2-Benzopyran-1-one derivatives, microbial products with pharmacological activity. Conversion into orally active derivatives with antiinflammatory and antiulcer activities

  摘要：

  A novel gastroprotective substance, 6-[[1(S)-[3(S),4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl] -3-methylbutyl]amino]-4(S),5(S)-dihydroxy-6-oxo-3(S)-ammoniohexanoate (AI-77-B, 1), isolated from a culture broth of Bacillus pumilus AI-77, was chemically modified to prodrugs that are active by oral dosing. Compound 1 was lactonized and then monoalkylated at the primary amine position. Six N-alkylated gamma-lactone derivatives of 1 (with alkyl chains being methyl 5a, ethyl 5b, n-propyl 5c, n-butyl 5d, n-pentyl 5e, or n-hexyl 5f) were synthesized and eight compounds including 1 and gamma-lactone derivative 2 were compared for their gastroprotective activities and blood levels after oral administration in rats. Further, chloroform-water partition coefficients of 5a-f were also compared as a measure of lipid solubility. The protective effects of these compounds on stress ulcers were mutually related to blood levels of dealkylated compounds (1 and 2). Parent compound 1 was detected in blood at 1 h after each of 5a-d was administered. When 5b or 5c was administered, high activity and high blood levels of 1 were observed in comparison with those levels obtained with 5a or 5d. Neither 5e nor 5f were detected in any amount in blood by oral administration without special formulation due to extremely low solubilities and agglutinative properties in intestinal fluid. Interestingly, 5b and 5c were found to have antiinflammatory activities in addition to potent antiulcerogenicity action.

  DOI：

  10.1021/jm00379a002
• 作为产物：
  描述：

  amicoumacin C 在 sodium hydroxide 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 生成 AI-77-C
  参考文献：
  名称：

  AI-77s，具有胃肠保护作用的微生物产品的研究。AI-77s的结构和化学性质

  摘要：

  新型胃保护物质AI-77-B（1）及其类似物AI-77-C（2），D（3），F（4）和G（5）的结构和化学性质。描述了短小芽孢杆菌AI-77。证实1的结构为6-[[1（S）-（3（S），4-二氢-8-羟基-1-氧代-1H-1H-2-苯并吡喃-3-基）-3-甲基丁基]。氨基] -4（小号），5（小号） -二羟基-6-氧代-3（小号）-aminohexanoic酸由X射线与化学研究和组合的结构2，3，4和5通过1的化学合成和光谱分析确定。

  DOI：

  10.1016/s0040-4020(01)83504-3

文献信息

• Application of Pd-Catalyzed C–H Alkylation Reaction in Total Syntheses of Twelve Amicoumacin-Type Natural Products
  作者：Hui-Hong Wang、Zhao Li、Yi-Yue Feng、Gao-Feng Yin、Tao Shi、Dian He、Xiao-Dong Wang、Zhen Wang

  DOI：10.1021/acs.orglett.1c02576

  日期：2021.9.3

  Enantioselective total syntheses of 12 amicoumacin-type natural products are accomplished with a palladium(II)-catalyzed C–H alkylation as the key step to furnish the 3,4-dihydroisocoumarin scaffold. The target chemicals are assembled in a convergent protocol by merging 3,4-dihydroisocoumarin derived amine part with categories of acid segments that are efficiently prepared by chemoselective catalytic

  12 种阿米香豆素类天然产物的对映选择性全合成是通过钯 (II) 催化的 C-H 烷基化作为提供 3,4-二氢异香豆素支架的关键步骤完成的。通过将 3,4-二氢异香豆素衍生的胺部分与通过手性 1,2-二羟乙基呋喃-2(5H)-ones 的化学选择性催化氧化有效制备的酸链段类别合并，将目标化学品组装在一个收敛协议中。随后，研究了阿米香霉素对五种癌细胞系和一种正常细胞系的细胞毒性。
• Amicoumacins from the marine-derived bacterium Bacillus sp. with the inhibition of NO production
  作者：Jian Bai、Dong Liu、Siwang Yu、Peter Proksch、Wenhan Lin

  DOI：10.1016/j.tetlet.2014.09.100

  日期：2014.11

  Chemical examination of the fermentation broth of the marine-derived bacterium Bacillus sp. resulted in the isolation of seven new amicoumacin-type isocoumarin derivatives, namely bacillcoumacins A-G (1-7), together with four known analogues. Their structures were elucidated on the basis of extensive spectroscopic analysis, while the absolute configurations of the new compounds were determined by CD, Mosher's method, and chemical conversion. Compounds 7 and 9 showed inhibitory effects against the NO production induced by lipopolysaccharide (LPS) in mouse macrophage RAW 264.7 cells. (C) 2014 Elsevier Ltd. All rights reserved.