N-(diphenyl)carbamoyl-4-piperidone | 292059-33-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(diphenyl)carbamoyl-4-piperidone
• 英文别名: 4-oxo-N,N-diphenylpiperidine-1-carboxamide
• CAS: 292059-33-7
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: GOEGHTRBHIEZEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(diphenyl)carbamoyl-4-piperidone 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 3.25h， 生成 4-(1-Diphenylcarbamoyl-piperidin-4-ylidenemethyl)-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：

  4,4-哌啶二醇盐酸盐 、 二苯氨基甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以61%的产率得到N-(diphenyl)carbamoyl-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

• DISPIRO TETRAOXANE COMPOUNDS AND THEIR USE IN THE TREATMENT OF MALARIA AND/OR CANCER
  申请人：Amewu Richard

  公开号：US20100113436A1

  公开（公告）日：2010-05-06

  A compound having the formula (I) wherein ring A represents a substituted or unsubstituted monocyclic or multicyclic ring; m=any positive integer; n=0-5; X=CH and Y=—C(O)NR 1 R 2 , —NR 1 R 2 or —S(O) 2 R 4 , where R 1 , R 2 and R 4 are each individually selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amine, substituted or unsubstituted carbocyclic ring, substituted or unsubstituted heterocyclic ring, or any combination thereof, or R 1 and R 2 are linked so as to form part of a substituted or unsubstituted heterocyclic ring, or X=N and Y=—S(O) 2 R 3 or —C(O)R 3 , where R 3 is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amine, substituted or unsubstituted carbocyclic ring, substituted or unsubstituted heterocyclic ring or any combination thereof.

  化合物的式子为（I），其中环A代表取代或未取代的单环或多环环；m=任何正整数；n=0-5；X=CH，Y=—C（O）NR1R2，—NR1R2或—S（O）2R4，其中R1，R2和R4分别从H，取代或未取代的烷基，取代或未取代的芳基，取代或未取代的胺基，取代或未取代的碳环，取代或未取代的杂环，或任何这些的组合中单独选择，或R1和R2被连接起来形成取代或未取代的杂环的一部分，或X=N且Y=—S（O）2R3或—C（O）R3，其中R3从H，取代或未取代的烷基，取代或未取代的芳基，取代或未取代的胺基，取代或未取代的碳环，取代或未取代的杂环，或任何这些的组合中选择。
• DISPIRO TETRAOXANE COMPOUNDS
  申请人：Amewu Richard

  公开号：US20130023551A1

  公开（公告）日：2013-01-24

  A compound having the formula (I) wherein ring A represents a substituted or unsubstituted monocyclic or multicyclic ring; m=any positive integer; n=0-5; X═CH and Y═—C(O)NR 1 R 2 , —NR 1 R 2 or —S(O) 2 R 4 , where R 1 , R 2 and R 4 are each individually selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amine, substituted or unsubstituted carbocyclic ring, substituted or unsubstituted heterocyclic ring, or any combination thereof, or R 1 and R 2 are linked so as to form part of a substituted or unsubstituted heterocyclic ring, or X═N and Y═—S(O) 2 R 3 or —C(O)R 3 , where R 3 is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amine, substituted or unsubstituted carbocyclic ring, substituted or unsubstituted heterocyclic ring or any combination thereof.

  化合物的化学式为（I），其中环A代表取代或未取代的单环或多环环；m = 任何正整数；n = 0-5；X = CH，Y = -C（O）NR1R2，-NR1R2或-S（O）2R4，其中R1，R2和R4分别选自H，取代或未取代的烷基，取代或未取代的芳基，取代或未取代的胺基，取代或未取代的碳环，取代或未取代的杂环，或任何组合，或R1和R2连接成为取代或未取代的杂环的一部分；或X = N，Y = -S（O）2R3或-C（O）R3，其中R3选自H，取代或未取代的烷基，取代或未取代的芳基，取代或未取代的胺基，取代或未取代的碳环，取代或未取代的杂环或任何组合。
• DISPIRO TETRAOXANE COMPOUNDS AND THEIR USE IN THE TREATMENT OF MALARIA AND/OR CANCER
  申请人：Liverpool School of Tropical Medicine

  公开号：EP2233479A1

  公开（公告）日：2010-09-29

  A compound having the formula (I) wherein ring A represents a substituted or unsubstituted monocyclic or multicyclic ring; m=any positive integer; n=0-5; X=CH and Y=-C(O)NR1R2, -NR1R2 or -S(O)2R4, where R1, R2 and R4 are each individually selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amine, substituted or unsubstituted carbocyclic ring, substituted or unsubstituted heterocyclic ring, or any combination thereof, or R1 and R2 are linked so as to form part of a substituted or unsubstituted heterocyclic ring; or X=N and Y=-S(O)2R3 or -C(O)R3, where R3 is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amine, substituted or unsubstituted carbocyclic ring, substituted or unsubstituted heterocyclic ring or any combination thereof.

  具有式 (I) 的化合物 其中 环 A 代表取代或未取代的单环或多环； m= 任何正整数； n=0-5； X=CH和Y=-C(O)NR1R2、-NR1R2或-S(O)2R4，其中R1、R2和R4各自单独选自由H、取代或未取代的烷基、取代或未取代的芳基、取代或未取代的胺、取代或未取代的碳环环、取代或未取代的杂环或它们的任意组合组成的组，或R1和R2连接以形成取代或未取代的杂环的一部分； 或 X=N 和 Y=-S(O)2R3 或-C(O)R3，其中 R3 选自 H、取代或未取代的烷基、取代或未取代的芳基、取代或未取代的胺、取代或未取代的碳环、取代或未取代的杂环或它们的任何组合组成的组。
• [EN] DISPIRO TETRAOXANE COMPOUNDS<br/>[FR] COMPOSÉS DISPIROTÉTRAOXANE
  申请人：UNIV LIVERPOOL

  公开号：WO2008038030A2

  公开（公告）日：2008-04-03

  [EN] A compound having the formula (I) wherein ring A represents a substituted or unsubstituted monocyclic or multicyclic ring; m=any positive integer; n=0-5; X=CH and Y=-C(O)NR¹R², -NR¹R² or -S(O)₂R⁴, where R¹, R² and R⁴ are each individually selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amine, substituted or unsubstituted carbocyclic ring, substituted or unsubstituted heterocyclic ring, or any combination thereof, or R¹ and R² are linked so as to form part of a substituted or unsubstituted heterocyclic ring, or X=N and Y=-S(O)₂R³ or -C(O)R³, where R³ is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amine, substituted or unsubstituted carbocyclic ring, substituted or unsubstituted heterocyclic ring or any combination thereof.
  [FR] L'invention concerne un composé répondant à la formule (I), dans laquelle le noyau A représente un noyau monocyclique ou polycyclique substitué ou non substitué; m = n'importe quel nombre entier positif; n = 0-5; X = CH et Y = -C(O)NR¹R², -NR¹R² ou -S(O)₂R⁴, où R¹, R² et R⁴ sont chacun individuellement sélectionnés dans le groupe constitué de H, d'alkyles substitués ou non substitués, d'aryles substitués ou non substitués, d'amines substituées ou non substituées, de noyaux carbocycliques substitués ou non substitués, de noyaux hétérocycliques substitués ou non substitués ou de n'importe quelle combinaison de ceux-ci ou bien R¹ et R² sont reliés de façon à former une partie d'un noyau hétérocyclique substitué ou non substitué ou bien X = N et Y = -S(O)₂R³ ou -C(O)R³, où R³ est sélectionné dans le groupe constitué de H, d'alkyles substitués ou non substitués, d'aryles substitués ou non substitués, d'amines substituées ou non substituées, de noyaux carbocycliques substitués ou non substitués, de noyaux hétérocycliques substitués ou non substitués ou de n'importe quelle combinaison de ceux-ci.
• Synthesis of N -substituted piperidine-4-(benzylidene-4-carboxylic acids) and evaluation as inhibitors of steroid-5α-reductase type 1 and 2
  作者：Franck Picard、Eckhard Baston、Wolfgang Reichert、Rolf W. Hartmann

  DOI：10.1016/s0968-0896(00)00070-5

  日期：2000.6

  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.