(1S,2S,7S,8S,9S,12S,13R,16S)-7,9,13-trimethyl-6-(2-methylphenyl)-5,6-diazapentacyclo[10.8.0.02,9.04,8.013,18]icosa-4,18-dien-16-ol | 1133720-75-8

• 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: (1S,2S,7S,8S,9S,12S,13R,16S)-7,9,13-trimethyl-6-(2-methylphenyl)-5,6-diazapentacyclo[10.8.0.02,9.04,8.013,18]icosa-4,18-dien-16-ol
• CAS: 1133720-75-8
• 化学式: C₂₈H₃₈N₂O
• 分子量: 418.623
• InChiKey: LMGYFDYAESSHDZ-RFBYSTSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  31
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3'S,17S)-3'-methyl-2'-(2-methylphenyl)-3',4'-dihydro-2'H-pyrazolo[4',5':17,16]androst-5-ene 3β-acetate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以97%的产率得到(1S,2S,7S,8S,9S,12S,13R,16S)-7,9,13-trimethyl-6-(2-methylphenyl)-5,6-diazapentacyclo[10.8.0.02,9.04,8.013,18]icosa-4,18-dien-16-ol
  参考文献：
  名称：

  Efficient Approach to Androstene-Fused Arylpyrazolines as Potent Antiproliferative Agents. Experimental and Theoretical Studies of Substituent Effects on BF₃-Catalyzed Intramolecular [3 + 2] Cycloadditions of Olefinic Phenylhydrazones

  摘要：

  Highly diastereoselective Lewis acid induced intramolecular 1,3-dipolar cycloadditions of alkenyl phenylhydrazones (containing various substituents on the aromatic ring) obtained from a D-secopregnene aldehyde were carried out under fairly mild conditions to furnish androst-5-ene-fused arylpyrazolines in good to excellent yields. The ability of phenylhydrazones to undergo cyclization was found to be affected significantly by the electronic features of the substituents on the aromatic moiety. The rates of the ring-closure reactions were observed to be increased by electron-donating and decreased by electron-withdrawing groups. The experimental findings on the BF3-catalyzed transformations were supported by calculations of the proposed mechanism at the BLYP/6-31G(d) level of theory, indicating a noteworthy dependence, mainly of the initial complexation step, and hence of the whole process, on the character of the substituent. The cycloaddition was estimated to occur via a zwitterionic intermediate rather than involving a pure concerted mechanism. The antiproliferative activities of the structurally related pyrazoline derivatives were tested in vitro on three malignant human cell lines (HeLa, MCF7, and A431): the microculture tetrazolium assay revealed that several compounds exerted marked cell growth-inhibitory effects. The highest cytotoxic activities, displayed by the p-methoxyphenylpyrazoline derivative 7d (IC50 values: 2.01, 2.16, and 1.41 mu M on HeLa, MCF7, and A341 cells, respectively), were better than those of cisplatin (IC50 values: 12.43, 9.63, and 2.84 mu M, respectively).

  DOI：

  10.1021/ja808636e