secochiliolide acid | 102904-56-3

• 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: secochiliolide acid
• 英文别名: 3-[(3S,5R,6S,10R)-3-(furan-3-yl)-10-methyl-1-oxo-7-propan-2-ylidene-2-oxaspiro[4.5]decan-6-yl]propanoic acid
• CAS: 102904-56-3
• 化学式: C₂₀H₂₆O₅
• 分子量: 346.423
• InChiKey: HXQMNSQWUMHREA-LKCJXIOFSA-N

物化性质

• 沸点：
  544.6±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  secochiliolide acid 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Preparation and antitrypanosomal activity of secochiliolide acid derivatives

  摘要：

  Secochiliolide acid (1) isolated from the Patagonian shrub Nardophyllum biyoides, was used as a scaffold for the preparation of a series of nine derivatives. Compound 1 and its derivatives were tested against Trypanosoma cruzi epimastigotes grown in liquid media. It was first observed that secochiliolide acid (1) inhibited the proliferation of the parasites, with an IC50 of 2 mu g/mL. Six of the synthesized derivatives were also active with IC50's between 2 and 7 mu g/mL which are comparable to that of the commercial drug benznidazole (2.5 mu g/mL). These results indicate that the carboxyl group is not essential for the bioactivity of 1, while the presence of the tetrasubstituted exocyclic double bond seems to be important. Moreover, the presence of the furan and spirolactone rings is not essential for the bioactivity per se, but is important in combination with other structural fragments present in the molecule. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.064

文献信息

• New diterpenes from and
  作者：J. Jakupovic、S. Banerjee、F. Bohlmann、R.M. King、H. Robinson

  DOI：10.1016/s0040-4020(01)87350-6

  日期：1986.1

  From the aerial parts of in addition to known compounds nine diterpenes were isolated, three isolabdanes, three seco-isolabdanes, a cis-clerodane, a rearranged dilactone and a geranyl geraniol derivative. The aerial parts of gave two of the new diterpenes and three further diterpenes which are closely related to those of the species. Further-more two new geranyl geraniol derivatives were present. The

  从已知化合物的地上部分中分离出九种二萜，三种异麦角烷，三种癸二异麦角烷，顺式-环戊烷，重排的二内酯和香叶基香叶醇衍生物。的地上部分产生了两个新的二萜和另外三个与该物种密切相关的二萜。另外，存在两种新的香叶基香叶醇衍生物。通过高场NMR光谱阐明了结构。
• Secochiliolide ester derivatives: Preparation and evaluation of their antitrypanosomal and antimalarial efficacy
  作者：Romina J. Ronchi、Claire Beaufay、Joanne Bero、Juan B. Robirosa、Marcia Mazzuca、Jorge A. Palermo、Joëlle Quetin-Leclercq、Marianela Sánchez

  DOI：10.1111/cbdd.13392

  日期：2019.2

  AbstractIn the present study, a series of new esters of secochiliolide acid (SA), a diterpene isolated from Nardophyllum bryoides, were synthesized in good yield. All compounds were evaluated for their in vitro antiparasitic properties (on Plasmodium falciparum and Trypanosoma brucei brucei) and cytotoxicity (on WI38, normal mammalian cells). They displayed moderate antitrypanosomal activity with IC50 values between 2.55 and 18.14 μm, with selectivity indices >10, and low antiplasmodial effects with IC50 > 29 μm. The only exception was the n‐hexyl ester of SA, which showed a strong and selective antiplasmodial activity (IC50 = 1.99 μm and selectivity index = 117.0). The in vivo antimalarial efficacy of this compound was then assessed according to the 4‐day suppressive test of Peters in mice. An intraperitoneal treatment at 50 mg kg−1 day−1 induced a slight parasitaemia reduction by 56% which was statistically significant on day 4 post‐infection and an increase in the survival time.
• Preparation and antitrypanosomal activity of secochiliolide acid derivatives
  作者：Gastón E. Siless、Esteban Lozano、Marianela Sánchez、Marcia Mazzuca、Miguel A. Sosa、Jorge A. Palermo

  DOI：10.1016/j.bmcl.2013.06.064

  日期：2013.9

  Secochiliolide acid (1) isolated from the Patagonian shrub Nardophyllum biyoides, was used as a scaffold for the preparation of a series of nine derivatives. Compound 1 and its derivatives were tested against Trypanosoma cruzi epimastigotes grown in liquid media. It was first observed that secochiliolide acid (1) inhibited the proliferation of the parasites, with an IC50 of 2 mu g/mL. Six of the synthesized derivatives were also active with IC50's between 2 and 7 mu g/mL which are comparable to that of the commercial drug benznidazole (2.5 mu g/mL). These results indicate that the carboxyl group is not essential for the bioactivity of 1, while the presence of the tetrasubstituted exocyclic double bond seems to be important. Moreover, the presence of the furan and spirolactone rings is not essential for the bioactivity per se, but is important in combination with other structural fragments present in the molecule. (C) 2013 Elsevier Ltd. All rights reserved.