caracasine acid

• 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: caracasine acid
• 英文别名: 3-[(1R,4R,5R,6S,9R)-5-methyl-10-methylidene-11-oxo-4-prop-1-en-2-yl-5-tricyclo[7.2.1.01,6]dodecanyl]propanoic acid
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: YXUUMMCRJVEJDN-AOHSKODXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  caracasine acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以84.3%的产率得到ent-3,4-seco-15-oxokaur-4(19)-en-3-oic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of caracasine acid derivatives

  摘要：

  A series of caracasine acid (1) derivatives were synthesized and evaluated for their in vitro cytotoxicity on human cancer-derived cell lines MCF-7 and PC-3, as well as for other activities such as antibacterial, antileishmanial and antitrypanosomal activity. Compound 1 was more effective than any of its derivatives against tested human cancer cell lines. PC-3 cells were more sensitive than MCF-7 to all compounds, particularly the methyl ester (2), the amide (9) and the epoxide (10).The evaluation of antiparasitic activity revealed that ester derivatives (2-8) and the amide derivative (9) were the most effective antileishmanial and antitrypanosomal compounds, even though their effect on Trypanosoma cruzi was modest. Finally, compound 1 and the derivatives evidenced a broad spectrum of antibacterial activity, as assayed against Gram-positive and Gram-negative bacteria. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.015

文献信息

• Synthesis and biological evaluation of caracasine acid derivatives
  作者：Katiuska Chávez、Reinaldo S. Compagnone、Annamil Álvarez、Katherine Figarella、Iván Galindo-Castro、Sabrina Marsiccobetre、Jennifer Triviño、Irina Arocha、Antonieta Taddei、Giovannina Orsini、Stephen Tillett、Alírica I. Suárez

  DOI：10.1016/j.bmc.2015.04.015

  日期：2015.7

  A series of caracasine acid (1) derivatives were synthesized and evaluated for their in vitro cytotoxicity on human cancer-derived cell lines MCF-7 and PC-3, as well as for other activities such as antibacterial, antileishmanial and antitrypanosomal activity. Compound 1 was more effective than any of its derivatives against tested human cancer cell lines. PC-3 cells were more sensitive than MCF-7 to all compounds, particularly the methyl ester (2), the amide (9) and the epoxide (10).The evaluation of antiparasitic activity revealed that ester derivatives (2-8) and the amide derivative (9) were the most effective antileishmanial and antitrypanosomal compounds, even though their effect on Trypanosoma cruzi was modest. Finally, compound 1 and the derivatives evidenced a broad spectrum of antibacterial activity, as assayed against Gram-positive and Gram-negative bacteria. (C) 2015 Elsevier Ltd. All rights reserved.