4-[2-fluoro-5-(methanesulfonyloxy)-benzyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester | 367268-98-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-[2-fluoro-5-(methanesulfonyloxy)-benzyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester
• 英文别名: 4-[2-Fluoro-5-(methanesulfonyloxy)-benzyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester；tert-butyl 4-[(2-fluoro-5-methylsulfonyloxyphenyl)methyl]-3-oxopiperazine-1-carboxylate
• CAS: 367268-98-2
• 化学式: C₁₇H₂₃FN₂O₆S
• 分子量: 402.444
• InChiKey: CMOXGWYKZZLSLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[2-fluoro-5-(methanesulfonyloxy)-benzyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester 在 盐酸 、 三乙酰氧基硼氢化钠 、 caesium carbonate 作用下， 以 二甲基亚砜 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 生成 4-Fluoro-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
  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-氟-3-甲基苯酚 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium hydride 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-[2-fluoro-5-(methanesulfonyloxy)-benzyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester
  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

• Inhibitors of prenyl-protein transferase
  申请人：——

  公开号：US20020123497A1

  公开（公告）日：2002-09-05

  The present invention is directed to peptidomimetic macrocyclic compounds which inhibit prenyl-protein transferase and the prenylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting prenyl-protein transferase and the prenylation of the oncogene protein Ras.

  本发明涉及抑制蛋白质脂基转移酶和癌基因蛋白Ras的蛋白质肽模拟大环化合物。该发明还涉及包含本发明化合物的化疗组合物以及抑制蛋白质脂基转移酶和癌基因蛋白Ras脂基化的方法。
• US6534506B2
  申请人：——

  公开号：US6534506B2

  公开（公告）日：2003-03-18
• [EN] INHIBITORS OF PRENYL-PROTEIN TRANSFERASE<br/>[FR] INHIBITEURS DE PRENYL-PROTEINE TRANSFERASE
  申请人：MERCK & CO INC

  公开号：WO2001077116A1

  公开（公告）日：2001-10-18

  The present invention is directed to peptidomimetic macrocyclic compounds which inhibit prenyl-protein transferase and the prenylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting prenyl-protein transferase and the prenylation of the oncogene protein Ras.
• 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.