thioacetic acid S-(3-chlorobenzyl) ester | 873463-97-9

• 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: thioacetic acid S-(3-chlorobenzyl) ester
• 英文别名: 3-chlorobenzyl thioacetate；Thioacetic acid S-(3-chloro-benzyl) ester；S-[(3-chlorophenyl)methyl] ethanethioate
• CAS: 873463-97-9
• 化学式: C₉H₉ClOS
• 分子量: 200.689
• InChiKey: HEEPGMBOVLMMBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  thioacetic acid S-(3-chlorobenzyl) ester 在 sodium hydroxide 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 5a-(3-chlorobenzylsulfanyl)dihydrobicyclomycin
  参考文献：
  名称：

  Fluorine-substituted dihydrobicyclomycins: Synthesis and biochemical and biological properties

  摘要：

  Many studies show that selective introduction of fluorine within pharmacological agents leads to improved activities. In this study, we determine the effects of aryl fluorine substitution in 5a-(benzylsulfanyl)-dihydrobicyclomycin (3) on the in vitro inhibition of Escherichia coli rho-dependent ATPase activity. Compound 3 is an analog of bicyclomycin (1), which is the only known selective inhibitor of rho, and I and 3 have comparable in vitro inhibitory activities. We demonstrate that aryl fluorine substitution of 3 leads to increase in inhibitory activity but that the beneficial effects due to fluorine were dependent upon the site and number of fluorine substituents. The bioactivitics are rationalized in terms of the bond moment created by the aryl fluoride bond within the 5a-aryl dihydrobicyclomycin-rho-binding pocket. Use of this hypothesis led to file design of dihydrobicyclomycin derivatives with superior in vitro rho inhibitory activities. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.075
• 作为产物：
  描述：

  3-氯苄溴 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙腈 为溶剂， 反应 1.08h， 以86%的产率得到thioacetic acid S-(3-chlorobenzyl) ester
  参考文献：
  名称：

  使用聚合物负载的硫代乙酸钠从烷基卤化物方便地合成硫代乙酸烷基酯

  摘要：

  烷基卤化物被有效地转换成相应的小号温和和非水性的条件下-烷基硫代乙酸酯，使用聚合物承载的硫代乙酸钠作为以高收率和纯度室温一个新的聚合物试剂。用过的聚合试剂可以通过过滤定量除去，并且可以通过蒸发溶剂获得纯产物。废聚合物试剂可以再生和重复使用几次，而其活性不会明显改变。

  DOI：

  10.1007/s13738-012-0093-4

文献信息

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

  公开号：US05780488A1

  公开（公告）日：1998-07-14

  The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation 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 the farnesylation of the oncogene protein Ras.

  本发明涉及抑制法尼基-蛋白转移酶（FTase）和致癌基因蛋白Ras的法尼基化的化合物。该发明还涉及含有本发明化合物的化疗组合物以及用于抑制法尼基-蛋白转移酶和致癌基因蛋白Ras的法尼基化的方法。
• EP0959883A4
  申请人：——

  公开号：EP0959883A4

  公开（公告）日：2001-05-09
• INHIBITORS OF FARNESYL-PROTEIN TRANSFERASE
  申请人：MERCK & CO., INC.

  公开号：EP0959883A1

  公开（公告）日：1999-12-01
• US5780488A
  申请人：——

  公开号：US5780488A

  公开（公告）日：1998-07-14
• [EN] INHIBITORS OF FARNESYL-PROTEIN TRANSFERASE<br/>[FR] INHIBITEURS DE LA FARNESYLE-PROTEINE TRANSFERASE
  申请人：MERCK & CO., INC.

  公开号：WO1997036583A1

  公开（公告）日：1997-10-09

  (EN) The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation 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 the farnesylation of the oncogene protein Ras.(FR) La présente invention concerne des composés inhibiteurs de la farnésyle-protéine transférase (FTase) et de la farnésylation de la protéine oncogène Ras. L'invention concerne également, non seulement des compositions chimiothérapiques contenant les composés de l'invention, mais aussi des procédés d'inhibition de la farnésyle-protéine transférase et de la farnésylation de la protéine oncogène Ras.