bacillcoumacin A

• 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: bacillcoumacin A
• 英文别名: Bacillcoumacin A；2-hydroxy-N-[(1S)-1-[(3S)-8-hydroxy-1-oxo-3,4-dihydroisochromen-3-yl]-3-methylbutyl]acetamide
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: LXFNXENYQUUHMT-AAEUAGOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bacillcoumacin A 在 盐酸 、 水 作用下， 反应 48.0h， 生成 羟基乙酸 、 (3S)-3-<(1'S)-1'-amino-3'-methylbutyl>-3,4-dihydro-8-hydroxy-1H-2-benzopyran-1-one
  参考文献：
  名称：

  Amicoumacins from the marine-derived bacterium Bacillus sp. with the inhibition of NO production

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2014.09.100
• 作为产物：
  描述：

  (S)-3-((S)-1-amino-3-methylbutyl)-8-methoxyisochroman-1-one 在 三溴化硼 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 苯甲醚 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 bacillcoumacin A
  参考文献：
  名称：

  Pd催化的C-H烷基化反应在十二种阿米考霉素类天然产物全合成中的应用

  摘要：

  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。

  DOI：

  10.1021/acs.orglett.1c02576

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.