6-Formyl-B-norcholesta-3,5-dien | 92944-13-3

• 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: 6-Formyl-B-norcholesta-3,5-dien
• 英文别名: (3R,3aR,5aS,5bR,10aS,10bS)-3a,5b-dimethyl-3-[(2R)-6-methylheptan-2-yl]-1,2,3,4,5,5a,6,7,10a,10b-decahydrocyclopenta[a]fluorene-10-carbaldehyde
• CAS: 92944-13-3
• 化学式: C₂₇H₄₂O
• 分子量: 382.63
• InChiKey: RPDAMVPMUXPKAQ-XWMUOLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  6-Formyl-B-norcholesta-3,5-dien 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 以60 mg的产率得到B-norcholesta-3,5-dien-6-carboxilic acid
  参考文献：
  名称：

  Ahmad, M. S.; Khan, N. Z.; Ansari, I. A., Acta Chimica Hungarica, 1984, vol. 115, # 2, p. 193 - 196

  摘要：

  DOI：
• 作为产物：
  描述：

  3β-acetoxyl-5β-hydroxyl-6β-formyl-B-norcholestane 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以88%的产率得到6-Formyl-B-norcholesta-3,5-dien
  参考文献：
  名称：

  Synthesis and in vitro antiproliferative evaluation of some ring B abeo-sterols

  摘要：

  Using cholesterol, p-sitosterol, dehydroisoandrosterone and pregnenolone as starting materials, a series of 5(6 -> 7)abeo-sterols with different substituted groups and various side chains were synthesized and the antiproliferative activity of these compounds against HeLa, SMMC 7404 and MGC 7901 cells was investigated. The results revealed that the presence of a cholesterol-type side chain was very important for their cytotoxicity, and in particular a thiosemicarbazone at the C-6 position significantly enhanced the antiproliferative activity of these compounds. Although the elimination of 5-hydroxyl has no an obvious effect on their cytotoxic function, removal of the hydroxyl at the C-3 position decreased markedly the antiproliferative activity of the compounds. Some compounds have similar cytotoxic capability as cis-platin does. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.05.005

文献信息

• Synthesis of Novel Ring B Abeo-sterol Derivatives and their Antiproliferative Activities
  作者：Chunfang Gan、Lianghua Fan、Yanmin Huang、Zhiping Liu、Jianguo Cui

  DOI：10.2174/1573406411309060008

  日期：2013.7.1

  Using cholesterol, β-sitosterol, dehydroisoandrosterone and pregnenolone as starting materials, a series of 6- hydroximino analogs of ring B abeo-sterols were synthesized and characterized. The antiproliferative activity of analogs was evaluated against SGC 7901 (human gastric carcinoma), HeLa (human cervical carcinoma) and Bel 7404 (human liver carcinoma) cells. The results showed that the presence of a alkyl side chain was very important for their cytotoxicity. However, the presence of 6-hydroximino cannot increase the cytotoxicity of compounds compared with 6-hydroxy group. The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs.

  以胆固醇、β-谷甾醇、脱氢表雄酮和孕烯醇酮为起始原料，合成并表征了一系列环B断裂甾体的6-羟亚氨类似物。评估了这些类似物对SGC 7901（人胃癌）、HeLa（人宫颈癌）和Bel 7404（人肝癌）细胞的抗增殖活性。结果显示，烷基侧链的存在对其细胞毒性至关重要。然而，与6-羟基相比，6-羟亚氨并不能提高化合物的细胞毒性。这些研究获得的信息可能对设计新型化疗药物有所帮助。
• Steroids. III. Alumina-Induced Reactions of Steroidal Oxime Acetates
  作者：MASAYUKI ONDA、KEIJI TAKEUCHI

  DOI：10.1248/cpb.21.1287

  日期：——

  An alumina-induced reaction of 6-acetoximino-3β-acetoxycholestan-5α-ol nitrite (I) is examined and affords several kinds of compounds. Among them II, III and IV are belong to the same type of compound. From the spectral data and their reactions, the structures containing 5α, 6α-epoxy and 6β, 7β-isonitrosoimino groups are tentatively assumed for them. V and VI are identified to be another type containing 5α-acetoxy and 6-oxo groups. The formation pathways of both types of compounds are deduced by comparison with the reaction products of the relative compounds.

  对 6-乙酰氧亚氨基-3β-乙酰氧基胆甾烷-5α-醇亚硝酸盐（I）的氧化铝诱导反应进行了研究，并得出了几种化合物。其中 II、III 和 IV 属于同一类化合物。根据光谱数据及其反应，初步推测它们的结构中含有 5α，6α-环氧基和 6β，7β-异亚硝基亚氨基。V 和 VI 被确定为含有 5α-乙酰氧基和 6-氧代基团的另一种类型。通过与相关化合物的反应产物进行比较，推断出了这两类化合物的形成途径。
• Cornforth et al., Biochemical Journal, 1953, vol. 54, p. 590,596
  作者：Cornforth et al.

  DOI：——

  日期：——
• Tanabe,K. et al., Chemical and pharmaceutical bulletin, 1961, vol. 9, p. 1 - 6
  作者：Tanabe,K. et al.

  DOI：——

  日期：——
• Yates, Peter; Stiver, Shirley, Canadian Journal of Chemistry, 1988, vol. 66, p. 1209 - 1218
  作者：Yates, Peter、Stiver, Shirley

  DOI：——

  日期：——