20R,24S-epoxycycloartan-6α,16β,25-triol-3-one 6,16,25-triacetate | 460323-44-8

• 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: 20R,24S-epoxycycloartan-6α,16β,25-triol-3-one 6,16,25-triacetate
• 英文别名: (2aR,3R,4S,5aS,5bS,7S,7aR,11aR,12aS)-3-((2R,5S)-5-(2-acetoxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)-2a,5a,8,8-tetramethyl-9-oxotetradecahydro-1H,12H-cyclopenta[a]cyclopropa[e]phenanthrene-4,7-diyl diacetate；[(1S,3R,8R,9S,11S,12S,14S,15R,16R)-14-acetyloxy-15-[(2R,5S)-5-(2-acetyloxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-oxo-9-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl] acetate
• CAS: 460323-44-8
• 化学式: C₃₆H₅₄O₈
• 分子量: 614.82
• InChiKey: QDJBNKYNSPKWQQ-FCIUJBTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  44.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  20R,24S-epoxycycloartan-6α,16β,25-triol-3-one 6,16,25-triacetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1461.0h， 以26 mg的产率得到cyclopycnanthogenin
  参考文献：
  名称：

  摘要：

  The partial synthesis of cyclopycanthogenin, 20R,24S-epoxycycloartan-6alpha, 16beta,25-triol-3-one, was developed in four steps from cyclosiversigenin.

  DOI：

  10.1023/a:1014864731925
• 作为产物：
  描述：

  cyclosiversigenin 3,6,16,25-tetraacetate 在 jones reagent 、 potassium hydrogencarbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 731.0h， 生成 20R,24S-epoxycycloartan-6α,16β,25-triol-3-one 6,16,25-triacetate
  参考文献：
  名称：

  摘要：

  The partial synthesis of cyclopycanthogenin, 20R,24S-epoxycycloartan-6alpha, 16beta,25-triol-3-one, was developed in four steps from cyclosiversigenin.

  DOI：

  10.1023/a:1014864731925

文献信息

• SERIES OF HALOGENATED TETRACYCLIC TRITERPENE DERIVATIVES AND THEIR PREPARATION AND APPLICATION
  申请人：SHANGHAI KING-X BIOTECH CO., LTD

  公开号：US20220177511A1

  公开（公告）日：2022-06-09

  The invention provides a series of halogenated tetracyclic triterpene derivatives and their preparation and application. It is represented by the following general structural formula: R 1 is halogen, R 2 is H, and the halogen is selected from fluorine, chlorine, bromine or iodine; or R 1 and R 2 are each fluorine, and R 3 is an amine, alcohol, amino acid, peptide or phosphate linked to oxygen through an acyl group. The derivatives are relatively stable in rat whole blood through pharmacokinetic studies. The absolute bioavailability after a single intragastric administration for male and female rats was 15.6% and 28.4% respectively. The mean bioavailability was 22%. The derivatives showed better in vivo activities compared with the existing standard drugs enalapril and sacubitril valsartan sodium. Meanwhile, hydrophilic prodrugs of the tetracyclic triterpenoid derivatives in the present invention were prepared. The derivatives of the present invention can be used for preparing cardiovascular medicines.

  本发明提供了一系列卤代四环三萜衍生物及其制备和应用。其通式如下：R1为卤素，R2为氢，卤素选自氟、氯、溴或碘；或R1和R2均为氟，R3为胺、醇、氨基酸、肽或磷酸，通过酰基连接到氧。通过药代动力学研究，这些衍生物在大鼠全血中相对稳定。单次口服给雄性和雌性大鼠后的绝对生物利用度分别为15.6％和28.4％。平均生物利用度为22％。与现有标准药物依那普利和沙库巴曲钠相比，这些衍生物在体内活性更好。同时，本发明还制备了四环三萜衍生物的亲水性前药。本发明的衍生物可用于制备心血管药物。