ent-beyer-15-en-18-O-succinate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ent-beyer-15-en-18-O-succinate
• 英文别名: 4-oxo-4-[[(1R,5S,9S,13S)-5,9,13-trimethyl-5-tetracyclo[11.2.1.01,10.04,9]hexadec-14-enyl]methoxy]butanoic acid
• 化学式: C₂₄H₃₆O₄
• 分子量: 388.547
• InChiKey: ARXNJMYASVTMEU-UCGPCWDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ent-beyer-15-en-18-ol 、 丁二酰氯 在 水 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以80%的产率得到ent-beyer-15-en-18-O-succinate
  参考文献：
  名称：

  Structural Elucidation and Antimicrobial Characterization of Novel Diterpenoids from Fabiana densa var. ramulosa

  摘要：

  Novel diterpenoids were isolated from the extracts of Fabiana densa var. ramulosa and found to display a selective activity against Gram-positive bacterial strains with negligible cytotoxicity toward human keratinocytes. This study highlighted the role played by the acidic group at C18 of the tetracyclic ent-beyerene scaffold for antibacterial effects and how the length and flexibility of the alkyl chain between the two carbonyl groups are crucial factors to increase the antimicrobial activity of the molecules, supporting the development of natural products from F. densa and their derivatives for treatment of microbial infections.

  DOI：

  10.1021/acsmedchemlett.9b00605

文献信息

• INHIBITORS OF ANTIBIOTIC RESISTANCE MEDIATED BY ARNT
  申请人：UNIVERSITÀ DEGLI STUDI DI ROMA "LA SAPIENZA"

  公开号：US20220259249A1

  公开（公告）日：2022-08-18

  The present invention relates to diterpene compounds of general formula (I) capable of contrasting the antibiotic-resistance mediated by the ArnT enzyme, to their use as a medicament, in particular for use as an adjuvant of an antibiotic therapy in the treatment of antibiotic-resistant bacterial infections. The invention relates also to associations of one or more of the compounds of formula (I) with at least another active ingredient, in particular an antibacterial agent and/or an antibiotic, and compositions comprising one or more compounds of formula (I) or the association according to the present invention and at least one pharmaceutically acceptable excipient and/or carrier as well as to products, in particular medical devices, comprising at least a compound, an association or a composition according to the present invention. Moreover, the invention relates to the use of compounds of formula (I) to sensitize a bacterium to an antibacterial agent or an antibiotic, for example, colistin (polymyxin E) or polymyxin B and to an in vivo or in vitro method for sensitizing a bacterium to an antibacterial agent or an antibiotic comprising the exposure of said bacterium to one or more compounds of formula (I) together with colistin.
• Structural Elucidation and Antimicrobial Characterization of Novel Diterpenoids from <i>Fabiana densa</i> var. <i>ramulosa</i>
  作者：Deborah Quaglio、Silvia Corradi、Silvia Erazo、Valeria Vergine、Simone Berardozzi、Fabio Sciubba、Floriana Cappiello、Maria Elisa Crestoni、Fiorentina Ascenzioni、Francesco Imperi、Franco Delle Monache、Mattia Mori、Maria Rosa Loffredo、Francesca Ghirga、Bruno Casciaro、Bruno Botta、Maria Luisa Mangoni

  DOI：10.1021/acsmedchemlett.9b00605

  日期：2020.5.14

  Novel diterpenoids were isolated from the extracts of Fabiana densa var. ramulosa and found to display a selective activity against Gram-positive bacterial strains with negligible cytotoxicity toward human keratinocytes. This study highlighted the role played by the acidic group at C18 of the tetracyclic ent-beyerene scaffold for antibacterial effects and how the length and flexibility of the alkyl chain between the two carbonyl groups are crucial factors to increase the antimicrobial activity of the molecules, supporting the development of natural products from F. densa and their derivatives for treatment of microbial infections.