conicasterone | 76758-20-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: conicasterone
• 英文别名: (5R,9R,10R,13R,17R)-17-[(2R,5R)-5,6-dimethylheptan-2-yl]-10,13-dimethyl-4-methylidene-2,5,6,7,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 76758-20-8
• 化学式: C₂₉H₄₆O
• 分子量: 410.684
• InChiKey: JZUYDQLGXDUUKE-ZKDZLAFLSA-N

物化性质

• 沸点：
  501.7±50.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  conicasterone 在 sodium tetrahydroborate 、 5%-palladium/activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 4β-methyl-24(R)-methylcholest-8(14)-en-3β-ol
  参考文献：
  名称：

  Insights on pregnane-X-receptor modulation. Natural and semisynthetic steroids from Theonella marine sponges

  摘要：

  Pregnane-X-receptor (PXR) is a member of nuclear receptors superfamily that activates gene transcription by binding to responsive elements in the promoter of target genes. PXR is a master gene orchestrating the expression/activity of genes involved in the metabolism of endobiotics including bilirubin, bile acids, glucose and lipid. In addition PXR oversights the metabolism of the large majority of xenobiotics including a large amount of prescribing drugs. Thus, developing PXR ligands represents a great opportunity for a therapeutic intervention on human diseases including diabetes, obesity, dyslipidemias and liver disorders. To this end, natural compounds represent an arsenal of new chemical scaffolds useful for the identification of novel PXR ligands. Here, we report a series of 4-methylenesteroid derivatives isolated from Theonella marine sponges as novel PXR modulators. In addition, combining medicinal chemistry, pharmacological experiments and computational studies, we have investigated the effects of different modifications on ring A and on the side chain of 4-methylenesteroid derivatives toward PXR modulation. This study provides the molecular bases of ligand/PXR interaction useful for designing novel PXR modulators. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.005
• 作为产物：
  描述：

  conicasterol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以28 mg的产率得到conicasterone
  参考文献：
  名称：

  Marine Natural Products. XXX. Two New 3-Keto-4-methylene Steroids, Theonellasterone and Conicasterone, and a Diels-Alder Type Dimeric Steroid Bistheonellasterone, from the Okinawan Marine Sponge Theonella swinhoei.

  摘要：

  从冲绳海洋海绵Theonella swinhoei中分离出两种新的3-酮-4-亚甲基类固醇，即theonellasterone（3）和conicasterone（4），以及一种Diels-Alder型二聚类固醇，即bistheonellasterone（5），以及两种已知的4-亚甲基固醇，即theonellasterol（1）和conicasterol（2）。这些类固醇的结构已经根据化学和物理化学证据得到阐明。Bistheonellasterone（5）被认为是通过theonellasterone（3）及其Δ4-异构体的Diels-Alder环加成生物合成的。非常有趣的是，在光学显微镜下，theonellasterone（3）和conicasterone（4）被看作是沉积在新鲜海洋海绵组织中的晶体。

  DOI：

  10.1248/cpb.40.1773

文献信息

• Sterols in marine invertebrates. 22. Isolation and structure elucidation of conicasterol and theonellasterol, two new 4-methylene sterols from the Red Sea sponges Theonella conica and Theonella swinhoei
  作者：Ernest Kho、David K. Imagawa、Michel Rohmer、Yoel Kashman、Carl Djerassi

  DOI：10.1021/jo00322a019

  日期：1981.4