1-(4-cyano-3-fluorobenzyl)-5-(hydroxymethyl)-imidazole | 222978-10-1

• 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-(4-cyano-3-fluorobenzyl)-5-(hydroxymethyl)-imidazole
• 英文别名: 2-fluoro-4-[(5-hydroxymethyl)imidazol-1-ylmethyl]benzonitrile；1-(4-cyano-3-fluorobenzyl)-5-(hydroxymethyl) imidazole；1-(4-Cyano-3-fluorobenzyl)-5-(hydroxymethyl)imidazole；2-fluoro-4-[[5-(hydroxymethyl)imidazol-1-yl]methyl]benzonitrile
• CAS: 222978-10-1
• 化学式: C₁₂H₁₀FN₃O
• 分子量: 231.229
• InChiKey: DRJLYHCEQLOIOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-cyano-3-fluorobenzyl)-5-(hydroxymethyl)-imidazole 在 4 A molecular sieve 、 三氧化硫吡啶 、 三乙酰氧基硼氢化钠 、 三乙胺 作用下， 以 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 生成 1-(3-chlorophenyl)-4-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-2-piperazinone
  参考文献：
  名称：

  Aryloxy substituted N-arylpiperazinones as dual inhibitors of farnesyltransferase and geranylgeranyltransferase-I

  摘要：

  A series of aryloxy substituted piperazinones with dual farnesyltransferase/geranylgeranyltransferase-I inhibitory activity was prepared. These compounds were found to have potent inhibitory activity in vitro and are promising agents for the inhibition of Ki-Ras signaling. (C) 2001 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00240-2
• 作为产物：
  描述：

  2-氟-4-甲基苯腈 在 lithium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 乙酸乙酯 为溶剂， 生成 1-(4-cyano-3-fluorobenzyl)-5-(hydroxymethyl)-imidazole
  参考文献：
  名称：

  Aryloxy substituted N-arylpiperazinones as dual inhibitors of farnesyltransferase and geranylgeranyltransferase-I

  摘要：

  A series of aryloxy substituted piperazinones with dual farnesyltransferase/geranylgeranyltransferase-I inhibitory activity was prepared. These compounds were found to have potent inhibitory activity in vitro and are promising agents for the inhibition of Ki-Ras signaling. (C) 2001 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00240-2

文献信息

• Inhibitors of prenyl-protein transferase
  申请人：Merck & Co., Inc.

  公开号：US06441017B1

  公开（公告）日：2002-08-27

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

  本发明涉及抑制萜基-蛋白转移酶（FTase）和致癌基因蛋白Ras的大环化合物。该发明还涉及含有本发明化合物的化疗组合物以及抑制萜基-蛋白转移酶和致癌基因蛋白Ras的方法。
• [EN] INHIBITORS OF PRENYL-PROTEIN TRANSFERASE<br/>[FR] INHIBITEURS DE PRENYL-PROTEINE-TRANSFERASES
  申请人：MERCK & CO., INC.

  公开号：WO1999009985A1

  公开（公告）日：1999-03-04

  (EN) The present invention is directed to compounds which inhibit prenyl-protein transferases, farnesyl-protein transferase and geranylgeranyl-protein transferase type I, 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 farnesyl-protein transferase and geranylgeranyl-protein transferase type I and the prenylation of the oncogene protein RAS.(FR) L'invention concerne des composés qui inhibent les prényl-protéine-transférases, la farnésyl-protéine-transférase et la géranylgéranyl-protéine-transférase de type I, de même que la prénylation de la protéine oncogène Ras. L'invention concerne également des compositions chimiothérapeutiques renfermant les composés considérés, ainsi que des procédés permettant d'inhiber la farnésyl-protéine-transférase, la géranylgéranyl-protéine-transférase de type I et la prénylation de la protéine oncogène Ras.

  该发明涉及抑制异戊二烯基-蛋白质转移酶、法尼基-蛋白质转移酶和生长酰基-蛋白质转移酶I型以及癌基因蛋白Ras的异戊二烯基化的化合物。该发明还涉及含有该发明化合物的化疗组合物以及抑制法尼基-蛋白质转移酶、生长酰基-蛋白质转移酶I型和癌基因蛋白Ras的异戊二烯基化的方法。
• [EN] INHIBITORS OF PRENYL-PROTEIN TRANSFERASE<br/>[FR] INHIBITEURS DE LA PRENYL-PROTEINE TRANSFERASE
  申请人：MERCK & CO INC

  公开号：WO2001017992A1

  公开（公告）日：2001-03-15

  The present invention is directed to 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.

  本发明涉及抑制异戊二烯基-蛋白转移酶及癌基因蛋白Ras的异戊二烯基化的化合物。本发明还涉及包含本发明化合物的化疗组合物以及抑制异戊二烯基-蛋白转移酶及癌基因蛋白Ras的异戊二烯基化的方法。
• Conformational Restriction of Flexible Ligands Guided by the Transferred NOE Experiment:  Potent Macrocyclic Inhibitors of Farnesyltransferase
  作者：Christopher J. Dinsmore、Michael J. Bogusky、J. Christopher Culberson、Jeffrey M. Bergman、Carl F. Homnick、C. Blair Zartman、Scott D. Mosser、Michael D. Schaber、Ronald G. Robinson、Kenneth S. Koblan、Hans E. Huber、Samuel L. Graham、George D. Hartman、Joel R. Huff、Theresa M. Williams

  DOI：10.1021/ja003673q

  日期：2001.3.1
• INHIBITORS OF PRENYL-PROTEIN TRANSFERASE
  申请人：MERCK & CO., INC.

  公开号：EP1014984A1

  公开（公告）日：2000-07-05