cycloart-24-en-3-one | 511-63-7

• 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: cycloart-24-en-3-one
• 英文别名: 9β,19-cyclolanostane-24-en-3-oxo；(17R,20R)-cycloart-24-en-3-one；cycloartenone；(9β)-9,19-cyclolanost-24-en-3-one；9β,19-cyclo-lanost-24-en-3-one；9β,19-Cyclo-lanost-24-en-3-on；(1S,3R,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methylhept-5-en-2-yl]pentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-one
• CAS: 511-63-7
• 化学式: C₃₀H₄₈O
• 分子量: 424.711
• InChiKey: NAJCQAAOHKVCES-ZZOQNIIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  cycloart-24-en-3-one 在 溶剂黄146 、 铂 作用下， 生成 9,19-cyclolanostan-3-one
  参考文献：
  名称：

  Nath, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1937, vol. 247, p. 9,20, 22

  摘要：

  DOI：
• 作为产物：
  描述：

  环阿屯醇 在 镍 4-异丙基甲苯 作用下， 生成 cycloart-24-en-3-one
  参考文献：
  名称：

  高沸点溶剂中的反应II：阮内镍对三萜类化合物的影响

  摘要：

  研究了阮内镍对沸腾对甲基苯丙醚中三萜类化合物的影响。已经观察到以下三种不同类型的反应：（a）3-OH基团的脱氢（氧化），（b）易还原双键的饱和，以及（c）双键转移至相邻位置在盟友转移中。这种转变具有可逆性。通过该反应，将3-羟基三萜烯盐酸盐转化为3-酮-三萜烯，通过氢解除去Cl原子。还提出了一种机制。

  DOI：

  10.1016/s0040-4020(01)92409-3

文献信息

• Oxidation of ozonides with chromic acid
  作者：A.S. Narula、Sukh Dev

  DOI：10.1016/s0040-4039(01)87996-x

  日期：1969.1
• Bentley et al., Journal of the Chemical Society, 1953, p. 3673,3676
  作者：Bentley et al.

  DOI：——

  日期：——
• Biotransformation of Cycloartane-Type Triterpenes by the Fungus <i>Glomerella </i><i>f</i><i>usarioides</i>
  作者：Toshihiro Akihisa、Kenji Watanabe、Risa Yoneima、Takashi Suzuki、Yumiko Kimura

  DOI：10.1021/np058120d

  日期：2006.4.1

  Biotransformation of three cycloartane-type triterpenes, cycloartenol (1), 24-methylenecycloartanol (2), and cycloartenone (3), by the fungus Glomerella fusarioides was studied. Compound 1 was converted to 3, cycloart-25-ene-3 beta, 24-diol (4), and cycloartane-3 beta, 24,25-triol (5). Compound 2 was metabolized to cycloeucalenol (6) and two new compounds, 24-methylcycloartane-3 beta,24,24(1)-triol (7) and 24(1)-methoxy-24-methylcycloartane-3 beta, 24-diol (8). Compound 3 was converted into two new metabolites, 4 alpha,4 beta,14 alpha-trimethyl-9 beta, 19-cyclopregnane-3,20-dione (9) and 25-hydroxy-24-methoxycycloartan-3-one (14), and four known compounds, viz., cycloartane-3,24-dione (10), 24-hydroxycycloart-25-en-3-one (11), (23E)-25-hydroxycycloart-23-en-3-one (12), and 24,25-dihydroxycycloartan-3-one (13). The structures of four new metabolites, 7, 8, 9, and 14, were established by spectroscopic methods.
• 3β-Amino-verbindungen der cycloartan- und lanostanreihe
  作者：G. Adam、B. Voigt、K. Schreiber

  DOI：10.1016/s0040-4020(01)82910-0

  日期：——
• Cancer Chemopreventive Effects of Cycloartane-Type and Related Triterpenoids in in Vitro and in Vivo Models
  作者：Takashi Kikuchi、Toshihiro Akihisa、Harukuni Tokuda、Motohiko Ukiya、Kenji Watanabe、Hoyoku Nishino

  DOI：10.1021/np068044u

  日期：2007.6.1

  Forty-eight natural and semisynthetic cycloartane-type and related triterpenoids have been evaluated for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells as a primary screening test for anti-tumor promoters. In addition, these triterpenoids have been tested for their inhibitory effects on activation of (+/-)-(E)-methtyl-2-[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitric oxide (NO) donor, as a primary screening test for anti-tumor initiators. All of the compounds tested exhibited inhibitory effects on both EBV-EA and NOR 1 activation. Six of these compounds having a C-24 hydroxylated side chain, viz., (24R)-cycloart-25-ene-3 beta,24-diol (9), (24R)-cycloartane-3 beta,24,25-triol (11), (24S)-cycloartane-3 beta,24,25-triol (12), (24 xi)-24-methylcycloartane-3 beta,24,24(1)-triol (14), (24 xi)-24(1)-methoxy-24-methylcycloartane-3 beta,24-diol (15), and (24 xi)-24,25-dihydroxycycloartan-3-one (27), showed higher inhibitory effects than the others tested on both EBV-EA (IC50 values of 6.1-7.4 nM) and NOR 1 activation. Furthermore, compounds 14 and 15 exhibited inhibitory effects on skin tumor promotion in an in vivo two-stage mouse skin carcinogenesis test using 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter.