cadiolide C | 1414518-14-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: cadiolide C
• 英文别名: Cadiolide C；(5Z)-4-(3-bromo-4-hydroxyphenyl)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-(3,5-dibromo-4-hydroxybenzoyl)furan-2-one
• CAS: 1414518-14-1
• 化学式: C₂₄H₁₂Br₄O₆
• 分子量: 715.972
• InChiKey: KKSJLDNZJFUGNY-SWNXQHNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cadiolide C 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以4.2 mg的产率得到(5Z)-4-(3-bromo-4-methoxyphenyl)-5-[(3-bromo-4-methoxyphenyl)methylidene]-3-(3,5-dibromo-4-methoxybenzoyl)furan-2-one
  参考文献：
  名称：

  Antibacterial Butenolides from the Korean Tunicate Pseudodistoma antinboja

  摘要：

  Six new (1, 2, and 5-8) and three known (3, 4, and 9) butenolide metabolites were isolated from the tunicate Pseudodistoma antinboja by activity-guided fractionations. The structures were elucidated by combined NMR and MS spectroscopic methods. These compounds were evaluated for their antibacterial activity, and most of them exhibited moderate to significant activity that selectively targeted Gram-positive strains and did not exhibit cytotoxicity in the MTT assay at 100 mu M. Cadiolides 5-9 in particular exhibited significant antibacterial activity that was comparable to or even better than those of marketed drugs such as vancomycin and linezolid against all of the drug-resistant strains tested.

  DOI：

  10.1021/np300544a
• 作为产物：
  描述：

  3,5-dibromo-4-methoxybenzoyl chloride 在 正丁基锂 、 硫酸 、 乙酸酐 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 24.5h， 生成 cadiolide C
  参考文献：
  名称：

  Synthesis and antibacterial activities of cadiolides A, B and C and analogues

  摘要：

  The one-pot multicomponent synthesis of natural butenolides named cadiolides A, B, C and analogues has been realized. The antibacterial structure activity relationship shows that the presence of phenolic hydroxyl groups and the number and position of bromine atoms on the different aromatic rings are important features for antibacterial activity, besides it was demonstrated the tolerance of both benzene and furan ring at position 3 of the butenolide nucleus. Furthermore, none of the most relevant antibacterial compounds showed any cytotoxicity in freshly isolated human neutrophils. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.010

文献信息

• Synthesis and antibacterial activities of cadiolides A, B and C and analogues
  作者：Agathe Boulangé、Javier Parraga、Abraham Galán、Nuria Cabedo、Stéphane Leleu、Maria Jesus Sanz、Diego Cortes、Xavier Franck

  DOI：10.1016/j.bmc.2015.04.010

  日期：2015.7

  The one-pot multicomponent synthesis of natural butenolides named cadiolides A, B, C and analogues has been realized. The antibacterial structure activity relationship shows that the presence of phenolic hydroxyl groups and the number and position of bromine atoms on the different aromatic rings are important features for antibacterial activity, besides it was demonstrated the tolerance of both benzene and furan ring at position 3 of the butenolide nucleus. Furthermore, none of the most relevant antibacterial compounds showed any cytotoxicity in freshly isolated human neutrophils. (C) 2015 Elsevier Ltd. All rights reserved.
• Antibacterial Butenolides from the Korean Tunicate <i>Pseudodistoma antinboja</i>
  作者：Weihong Wang、Hiyoung Kim、Sang-Jip Nam、Boon Jo Rho、Heonjoong Kang

  DOI：10.1021/np300544a

  日期：2012.12.28

  Six new (1, 2, and 5-8) and three known (3, 4, and 9) butenolide metabolites were isolated from the tunicate Pseudodistoma antinboja by activity-guided fractionations. The structures were elucidated by combined NMR and MS spectroscopic methods. These compounds were evaluated for their antibacterial activity, and most of them exhibited moderate to significant activity that selectively targeted Gram-positive strains and did not exhibit cytotoxicity in the MTT assay at 100 mu M. Cadiolides 5-9 in particular exhibited significant antibacterial activity that was comparable to or even better than those of marketed drugs such as vancomycin and linezolid against all of the drug-resistant strains tested.