N-(dicyclohexyl)acetyl-4-piperidone | 292059-31-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-(dicyclohexyl)acetyl-4-piperidone
• 英文别名: 1-(2,2-Dicyclohexylacetyl)piperidin-4-one
• CAS: 292059-31-5
• 化学式: C₁₉H₃₁NO₂
• 分子量: 305.461
• InChiKey: YGQPHTQPQBNMKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(dicyclohexyl)acetyl-4-piperidone 在 palladium on activated charcoal 正丁基锂 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 5.25h， 生成 4-[[1-(2,2-Dicyclohexylacetyl)piperidin-4-yl]methyl]benzoic acid
  参考文献：
  名称：

  Synthesis of N -substituted piperidine-4-(benzylidene-4-carboxylic acids) and evaluation as inhibitors of steroid-5α-reductase type 1 and 2

  摘要：

  The synthesis of N-substituted piperidine-4-(benzylidene-4-carboxylic acids) is described [benzoyl (1), benzyl (2), adamantanoyl (3), cyclohexanoyl (4), cyclohexylacetyl (5), diphenylacetyl (6), dicyclohexylacetyl (7), 2-propylpentanoyl (8), diphenylcarbamoyl (9). trimethylacetyl (10), 3,3-dimethylacryloyl (11), dicyclohexylacetyl derivative of the benzyl compound (12)]. Compounds were tested for inhibitory activity toward Scc-reductase isozymes 1 and 2 in human and rat. The test compounds inhibited 5 alpha-reductase, showing a broad range of inhibitory potencies. In rat, compounds 6 (IC50 = 3.44 and 0.37 mu M for type 1 and 2, respectively) and 9 (IC50 = 0.54 and 0.69 mu M for type 1 and 2, respectively) displayed the best inhibition toward both Isozymes. Compound 7 showed a strong inhibition toward type 2 human and rat enzyme (IC50 = 60 and 80 nM) but only a moderate activity versus type 1 enzyme (IC50 approximately 10 mu M for rat and human enzyme). In vivo, selected compounds reduced prostate weights in castrated testosterone treated rats. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00070-5
• 作为产物：
  描述：

  dicyclohexylacetyl chloride 、 4,4-哌啶二醇盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以68%的产率得到N-(dicyclohexyl)acetyl-4-piperidone
  参考文献：
  名称：

  Synthesis of N -substituted piperidine-4-(benzylidene-4-carboxylic acids) and evaluation as inhibitors of steroid-5α-reductase type 1 and 2

  摘要：

  The synthesis of N-substituted piperidine-4-(benzylidene-4-carboxylic acids) is described [benzoyl (1), benzyl (2), adamantanoyl (3), cyclohexanoyl (4), cyclohexylacetyl (5), diphenylacetyl (6), dicyclohexylacetyl (7), 2-propylpentanoyl (8), diphenylcarbamoyl (9). trimethylacetyl (10), 3,3-dimethylacryloyl (11), dicyclohexylacetyl derivative of the benzyl compound (12)]. Compounds were tested for inhibitory activity toward Scc-reductase isozymes 1 and 2 in human and rat. The test compounds inhibited 5 alpha-reductase, showing a broad range of inhibitory potencies. In rat, compounds 6 (IC50 = 3.44 and 0.37 mu M for type 1 and 2, respectively) and 9 (IC50 = 0.54 and 0.69 mu M for type 1 and 2, respectively) displayed the best inhibition toward both Isozymes. Compound 7 showed a strong inhibition toward type 2 human and rat enzyme (IC50 = 60 and 80 nM) but only a moderate activity versus type 1 enzyme (IC50 approximately 10 mu M for rat and human enzyme). In vivo, selected compounds reduced prostate weights in castrated testosterone treated rats. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00070-5

文献信息

• Synthesis and Evaluation of 2‘-Substituted 4-(4‘-Carboxy- or 4‘-carboxymethylbenzylidene)-<i>N</i>-acylpiperidines: Highly Potent and in Vivo Active Steroid 5α-Reductase Type 2 Inhibitors
  作者：Franck Picard、Stephan Barassin、Armand Mokhtarian、Rolf W. Hartmann

  DOI：10.1021/jm0208471

  日期：2002.8.1

  and evaluated for inhibition of rat and human steroid 5alpha-reductase isozymes types 1 and 2. In the dicyclohexylacetyl series, fluorination in the 2-position of the benzene nucleus (15), exchange of the carboxy group by a carboxymethyl moiety (20), and combination of both structural modifications (25) led to highly active inhibitors of the human type 2 isozyme (IC(50) values: 15, 11 nM; 20, 6 nM;

  合成了16种衍生自N-酰基-4-苄叉亚哌啶-4'-羧酸的化合物，并评估了它们对1型和2型大鼠和人类固醇5α-还原酶同工酶的抑制作用。在二环己基乙酰基系列中，氟在2位的位置苯核（15），羧甲基部分的羧基交换（20）和两种结构修饰的组合（25）导致了人类2型同工酶的高活性抑制剂（IC（50）值：15，11 nM ； 20，6 nM; 25，7 nM;非那雄胺，5 nM）。在体内，所有测试化合物均显着降低了去势睾丸激素治疗大鼠的前列腺重量。显示了化合物7的口服活性。从发现化合物15在大鼠中具有活性的发现来看，尽管它是大鼠酶的一种较弱的抑制剂，并且是人类酶的一种强抑制剂，