Methyl 10-cyano-23-oxo-8-oxa-1,15,17,21-tetrazapentacyclo[19.2.2.13,7.19,13.015,19]heptacosa-3,5,7(27),9,11,13(26),16,18-octaene-4-carboxylate | 254108-04-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 10-cyano-23-oxo-8-oxa-1,15,17,21-tetrazapentacyclo[19.2.2.13,7.19,13.015,19]heptacosa-3,5,7(27),9,11,13(26),16,18-octaene-4-carboxylate
• CAS: 254108-04-8
• 化学式: C₂₅H₂₃N₅O₄
• 分子量: 457.489
• InChiKey: SFKOTJCSIYBZQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-氨基金刚烷 、 Methyl 10-cyano-23-oxo-8-oxa-1,15,17,21-tetrazapentacyclo[19.2.2.13,7.19,13.015,19]heptacosa-3,5,7(27),9,11,13(26),16,18-octaene-4-carboxylate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到N-(2-adamantyl)-10-cyano-23-oxo-8-oxa-1,15,17,21-tetrazapentacyclo[19.2.2.13,7.19,13.015,19]heptacosa-3,5,7(27),9,11,13(26),16,18-octaene-4-carboxamide
  参考文献：
  名称：

  Macrocyclic piperazinones as potent dual inhibitors of farnesyltransferase and geranylgeranyltransferase-I

  摘要：

  A series of macrocyclic piperazinone compounds with dual farnesyltransferase/geranylgeranyltransferase-I inhibitory activity was prepared. These compounds were found to be potent inhibitors of protein prenylation in cell culture. A hypothesis for the binding mode of compound 3o in FPTase is proposed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.051
• 作为产物：
  描述：

  4-Bromo-23-oxo-8-oxa-1,15,17,21-tetrazapentacyclo[19.2.2.13,7.19,13.015,19]heptacosa-3,5,7(27),9,11,13(26),16,18-octaene-10-carbonitrile 在 palladium diacetate 、 1,3-双(二苯基膦)丙烷 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成 Methyl 10-cyano-23-oxo-8-oxa-1,15,17,21-tetrazapentacyclo[19.2.2.13,7.19,13.015,19]heptacosa-3,5,7(27),9,11,13(26),16,18-octaene-4-carboxylate
  参考文献：
  名称：

  Macrocyclic piperazinones as potent dual inhibitors of farnesyltransferase and geranylgeranyltransferase-I

  摘要：

  A series of macrocyclic piperazinone compounds with dual farnesyltransferase/geranylgeranyltransferase-I inhibitory activity was prepared. These compounds were found to be potent inhibitors of protein prenylation in cell culture. A hypothesis for the binding mode of compound 3o in FPTase is proposed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.051

文献信息

• US6562823B1
  申请人：——

  公开号：US6562823B1

  公开（公告）日：2003-05-13
• Macrocyclic piperazinones as potent dual inhibitors of farnesyltransferase and geranylgeranyltransferase-I
  作者：Christopher J Dinsmore、C.Blair Zartman、Jeffrey M Bergman、Marc T Abrams、Carolyn A Buser、J.Christopher Culberson、Joseph P Davide、Michelle Ellis-Hutchings、Christine Fernandes、Samuel L Graham、George D Hartman、Hans E Huber、Robert B Lobell、Scott D Mosser、Ronald G Robinson、Theresa M Williams

  DOI：10.1016/j.bmcl.2003.11.051

  日期：2004.2

  A series of macrocyclic piperazinone compounds with dual farnesyltransferase/geranylgeranyltransferase-I inhibitory activity was prepared. These compounds were found to be potent inhibitors of protein prenylation in cell culture. A hypothesis for the binding mode of compound 3o in FPTase is proposed. (C) 2003 Elsevier Ltd. All rights reserved.