(1S,4aS,5R)-5-[2-(3-Furyl)ethyl]-1,4a-dimethyl-6-methylenedecahydro-1-naphthalenecarboxylic acid | 1235-76-3

• 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: (1S,4aS,5R)-5-[2-(3-Furyl)ethyl]-1,4a-dimethyl-6-methylenedecahydro-1-naphthalenecarboxylic acid
• 英文别名: Polyalthinsaeure；(1S,4aS,5R)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• CAS: 1235-76-3；1235-77-4；4966-13-6；10267-14-8
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: ZQHJXKYYELWEOK-RNHVSHAASA-N

物化性质

• 熔点：
  100 °C
• 沸点：
  428.6±38.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,4aS,5R)-5-[2-(3-Furyl)ethyl]-1,4a-dimethyl-6-methylenedecahydro-1-naphthalenecarboxylic acid 在 四氯化碳 、 三苯基膦 作用下， 反应 0.5h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of polyalthic acid derivatives for the treatment of neglected diseases

  摘要：

  Polyalthic acid is a naturally occurring diterpene found in copaiba oil, one of the most popular natural medicines in the Amazon. Based on the reported antileishmanial activity of copaiba oil, a series of amides and diols derivatives of polyalthic acid were synthesized and tested against Leishmania donovani and Trypanosoma brucei. Polyalthic acid was active in both assays with IC50 ranging from 3.87 to 8.68 mu g/mL. The compound with best antileishmanial activity was 2h (IC50 = 3.84 mu g/mL) and compound 2c showed the best antitrypanosomal activity with an IC50 of 2.54 mu g/mL. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.062

文献信息

• Acid-Mediated Highly Regioselective Oxidation of Substituted Furans: A Simple and Direct Entry to Substituted Butenolides
  作者：Victor Martín、Juan Ceñal、Carlos Carreras、Carlos Tonn、Juan Padrón、Miguel Ramírez、David Díaz、Fernando García-Tellado

  DOI：10.1055/s-2005-869865

  日期：——

  The scope and limitations of an expeditious synthesis of substituted butenolides from 3-substituted or 3,4-disubstituted furans is described. The entire process embodies a controlled oxidation of the furan core to a 2,5-dialkoxy-dihydrofuran intermediate and a regioselective acid-catalyzed hydrolysis to the butenolide derivative. 3-Substituted furans yield exclusively 2-substituted butenolides. Calculations

  描述了从 3-取代或 3,4-二取代呋喃快速合成取代丁烯内酯的范围和限制。整个过程包括呋喃核受控氧化为 2,5-二烷氧基-二氢呋喃中间体和区域选择性酸催化水解为丁烯内酯衍生物。3-取代的呋喃仅产生2-取代的丁烯内酯。计算研究为提议的机制提供了证据。
• Synthesis and biological evaluation of polyalthic acid derivatives for the treatment of neglected diseases
  作者：Cassia S. Mizuno、Ariana B. Souza、Babu L. Tekwani、Sérgio R. Ambrósio、Rodrigo C.S. Veneziani

  DOI：10.1016/j.bmcl.2015.10.062

  日期：2015.12

  Polyalthic acid is a naturally occurring diterpene found in copaiba oil, one of the most popular natural medicines in the Amazon. Based on the reported antileishmanial activity of copaiba oil, a series of amides and diols derivatives of polyalthic acid were synthesized and tested against Leishmania donovani and Trypanosoma brucei. Polyalthic acid was active in both assays with IC50 ranging from 3.87 to 8.68 mu g/mL. The compound with best antileishmanial activity was 2h (IC50 = 3.84 mu g/mL) and compound 2c showed the best antitrypanosomal activity with an IC50 of 2.54 mu g/mL. (C) 2015 Elsevier Ltd. All rights reserved.