1-(3-Chloro-phenyl)-6-({[3-(4-cyano-benzyl)-3H-imidazol-4-ylmethyl]-amino}-methyl)-4-oxo-1,4-dihydro-pyridine-3-carbonitrile | 797783-26-7

• 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: 1-(3-Chloro-phenyl)-6-({[3-(4-cyano-benzyl)-3H-imidazol-4-ylmethyl]-amino}-methyl)-4-oxo-1,4-dihydro-pyridine-3-carbonitrile
• 英文别名: 1-(3-chlorophenyl)-6-[[[3-[(4-cyanophenyl)methyl]imidazol-4-yl]methylamino]methyl]-4-oxopyridine-3-carbonitrile
• CAS: 797783-26-7
• 化学式: C₂₅H₁₉ClN₆O
• 分子量: 454.918
• InChiKey: PRJQZNMTCLOSFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  97.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲基磺酰氯 、 1-(3-Chloro-phenyl)-6-({[3-(4-cyano-benzyl)-3H-imidazol-4-ylmethyl]-amino}-methyl)-4-oxo-1,4-dihydro-pyridine-3-carbonitrile 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以18%的产率得到N-[1-(3-Chloro-phenyl)-5-cyano-4-oxo-1,4-dihydro-pyridin-2-ylmethyl]-N-[3-(4-cyano-benzyl)-3H-imidazol-4-ylmethyl]-methanesulfonamide
  参考文献：
  名称：

  Design, synthesis, and activity of 4-quinolone and pyridone compounds as nonthiol-containing farnesyltransferase inhibitors

  摘要：

  As a part of our efforts to identify potent inhibitors of farnesyltransferase (FTase), modification of the structure of tipifarnib through structure-based design was undertaken by replacing the 2-quinolones with 4-quinolones and pyridones, and subsequent relocation of the D-ring to the N-methyl group on the imidazole ring. This study has yielded a novel series of potent and selective FTase inhibitors. The X-ray structure of tipifarnib (1) in complex with FTase was described.

  DOI：

  10.1016/j.bmcl.2004.08.012
• 作为产物：
  描述：

  3-(dimethylaminomethine)-4-oxo-6-methyl-2-pyrone 在 N-甲基吡咯烷酮 、 selenium(IV) oxide 、 sodium azide 、 水 、 三溴化磷 、 三乙酰氧基硼氢化钠 、 sodium cyanoborohydride 、 溶剂黄146 、 三苯基膦 、 N,N'-羰基二咪唑 、 lithium bromide 、 sodium t-butanolate 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 69.0h， 生成 1-(3-Chloro-phenyl)-6-({[3-(4-cyano-benzyl)-3H-imidazol-4-ylmethyl]-amino}-methyl)-4-oxo-1,4-dihydro-pyridine-3-carbonitrile
  参考文献：
  名称：

  Design, synthesis, and activity of 4-quinolone and pyridone compounds as nonthiol-containing farnesyltransferase inhibitors

  摘要：

  As a part of our efforts to identify potent inhibitors of farnesyltransferase (FTase), modification of the structure of tipifarnib through structure-based design was undertaken by replacing the 2-quinolones with 4-quinolones and pyridones, and subsequent relocation of the D-ring to the N-methyl group on the imidazole ring. This study has yielded a novel series of potent and selective FTase inhibitors. The X-ray structure of tipifarnib (1) in complex with FTase was described.

  DOI：

  10.1016/j.bmcl.2004.08.012

文献信息

• Design, synthesis, and activity of 4-quinolone and pyridone compounds as nonthiol-containing farnesyltransferase inhibitors
  作者：Qun Li、Akiyo Claiborne、Tongmei Li、Lisa Hasvold、Vincent S. Stoll、Steven Muchmore、Clarissa G. Jakob、Wendy Gu、Jerry Cohen、Charles Hutchins、David Frost、Saul H. Rosenberg、Hing L. Sham

  DOI：10.1016/j.bmcl.2004.08.012

  日期：2004.11

  As a part of our efforts to identify potent inhibitors of farnesyltransferase (FTase), modification of the structure of tipifarnib through structure-based design was undertaken by replacing the 2-quinolones with 4-quinolones and pyridones, and subsequent relocation of the D-ring to the N-methyl group on the imidazole ring. This study has yielded a novel series of potent and selective FTase inhibitors. The X-ray structure of tipifarnib (1) in complex with FTase was described.