5α-Cycloart-24-ene-3,23-dione | 141946-48-7

• 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: 5α-Cycloart-24-ene-3,23-dione
• 英文别名: cycloart-24-ene-3,23-dione；cycloarta-24-en-3,23-dione；(1S,3R,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methyl-4-oxohept-5-en-2-yl]pentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-one
• CAS: 141946-48-7
• 化学式: C₃₀H₄₆O₂
• 分子量: 438.694
• InChiKey: LQGIBUSCGSTCBO-GBZKQWGVSA-N

物化性质

• 熔点：
  135.8-136.0 °C
• 沸点：
  539.2±23.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5α-Cycloart-24-ene-3,23-dione 在 palladium on activated charcoal 吡啶 、 lithium aluminium tetrahydride 、 氢气 、 对甲苯磺酸 、 三氯氧磷 作用下， 以 甲醇 、 乙醚 、 乙醇 、 苯 为溶剂， 反应 16.5h， 生成 9,19-cyclolanostan-3-one
  参考文献：
  名称：

  Cycloartanes and other terpenoids and phenylpropanoids from Monocyclanthus vignei

  摘要：

  From the petrol extract of the stem bark of Monocyclanthus vignei 30 terpenoids and two phenylpropanoids have been isolated and their structures established, among them 17 new cycloartane-type compounds. Geranic acid and beta-caryophyllene were found to be the major constituents.

  DOI：

  10.1016/0031-9422(92)80456-o
• 作为产物：
  描述：

  3β-Hydroxy-5α-cycloart-24-en-23-one 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以2 mg的产率得到5α-Cycloart-24-ene-3,23-dione
  参考文献：
  名称：

  Cycloartanes and other terpenoids and phenylpropanoids from Monocyclanthus vignei

  摘要：

  From the petrol extract of the stem bark of Monocyclanthus vignei 30 terpenoids and two phenylpropanoids have been isolated and their structures established, among them 17 new cycloartane-type compounds. Geranic acid and beta-caryophyllene were found to be the major constituents.

  DOI：

  10.1016/0031-9422(92)80456-o

文献信息

• Cytotoxic and anti-HIV-1 constituents of Gardenia obtusifolia and their modified compounds
  作者：Patoomratana Tuchinda、Wilart Pompimon、Vichai Reutrakul、Manat Pohmakotr、Chalobon Yoosook、Natedao Kongyai、Samaisukh Sophasan、Kulawee Sujarit、Suchart E Upathum、Thawatchai Santisuk

  DOI：10.1016/s0040-4020(02)00999-7

  日期：2002.9

  5alpha-Cycloart-24-ene-3,23-dione (1), 5alpha-cycloart-24-ene-3,16,23-trione (2) and methyl 3,4-seco-cycloart-4(28),24-diene-29-hydroxy-23-oxo-3-oate (3), together with five known flavones 5,7,4'-tlihydroxy-3,8-dimethoxyflavone (4), 5,7,4'-trihydroxy-3,8,3'-trimethoxyflavone (5), 5,7,4'-trihydroxy-3,6,8-trimethoxyflavone (6), 5,4'-dihydroxy-3,6,7,8-tetramethoxyflavone (7) and 5,3-dihydroxy-3,6,7,8,4'-pentamethoxyflavone (8) have been isolated from the leaves and twigs of Gardenia obtusifolia. The structures were assigned on the basis of spectroscopic methods. Compounds 3-8 and some of the modified compounds showed significant cytotoxic activities in several mammalian cell lines, especially 8 and its diacetate 21 which exhibited potent cytotoxicities (compound 8: P-388 0.05 mug/mL, KB 0.09 mug/mL, BCA-1 0.63 mug/mL, Lu-1 0.09 mug/mL, ASK 0.70 mug/mL; its diacetate: P-388 0.27 mug/mL, KB 0.06 mug/mL, BCA-1 0.53 mug/mL, Lu-1 0.49 mug/mL). It was also found that 5, 8 and 21 showed antimitotic acitivity in the ASK assay. Compounds 2, 4, 6, 7 and some of the modified compounds displayed interesting anti-HIV activity in the syncytium assay, but were inactive or exhibited weak activity in the HIV-1 RT assay; while compound 3 was found to be active in the HIV-1 RT assay (99.9% inhibition at 200 mug/mL), but cytotoxic in the syncytium assay. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Cycloartanes and other terpenoids and phenylpropanoids from Monocyclanthus vignei
  作者：Hans Achenbach、Dieter Frey

  DOI：10.1016/0031-9422(92)80456-o

  日期：1992.12

  From the petrol extract of the stem bark of Monocyclanthus vignei 30 terpenoids and two phenylpropanoids have been isolated and their structures established, among them 17 new cycloartane-type compounds. Geranic acid and beta-caryophyllene were found to be the major constituents.