3-(Trifluoromethylsulfonyloxy)-5-(4-biphenylyl)-2-pentenoic acid ethyl ester | 774221-02-2

• 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: 3-(Trifluoromethylsulfonyloxy)-5-(4-biphenylyl)-2-pentenoic acid ethyl ester
• 英文别名: ethyl (Z)-5-(4-phenylphenyl)-3-(trifluoromethylsulfonyloxy)pent-2-enoate
• CAS: 774221-02-2
• 化学式: C₂₀H₁₉F₃O₅S
• 分子量: 428.429
• InChiKey: IQFHOKHOUYLWDK-JXAWBTAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(Trifluoromethylsulfonyloxy)-5-(4-biphenylyl)-2-pentenoic acid ethyl ester 在 N-氯代丁二酰亚胺 、 copper(l) iodide 、 二甲基硫 、 Pd(AsPh₂)2 、 二异丁基氢化铝 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 [(E)-3-methyl-5-(4-phenylphenyl)pent-2-enyl] phosphono hydrogen phosphate
  参考文献：
  名称：

  Aromatic farnesyl diphosphate analogues

  摘要：

  A stereocontrolled vinyl triflate-based synthetic route has been used to prepare four analogues of farnesyl diphosphate (FPP) where the terminal isoprene units have been replaced with aromatic moieties. Two of these analogues exhibit no productive interaction with protein farnesyltransferase, but the 2-naphthyl derivative 2 is a modest inhibitor of the enzyme, and the para-biphenyl derivative 4 is a surprisingly effective alternative substrate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00187-7
• 作为产物：
  描述：

  4-氯甲基联苯 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 生成 3-(Trifluoromethylsulfonyloxy)-5-(4-biphenylyl)-2-pentenoic acid ethyl ester
  参考文献：
  名称：

  Aromatic farnesyl diphosphate analogues

  摘要：

  A stereocontrolled vinyl triflate-based synthetic route has been used to prepare four analogues of farnesyl diphosphate (FPP) where the terminal isoprene units have been replaced with aromatic moieties. Two of these analogues exhibit no productive interaction with protein farnesyltransferase, but the 2-naphthyl derivative 2 is a modest inhibitor of the enzyme, and the para-biphenyl derivative 4 is a surprisingly effective alternative substrate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00187-7

文献信息

• Compounds and methods for use in treating neoplasia and cancer based upon inhibitors of isoprenylcysteine methyltransferase
  申请人：Gibbs A. Richard

  公开号：US20070004803A1

  公开（公告）日：2007-01-04

  The present invention relates to a novel method for the treatment of neoplasia, including cancer and other diseases and conditions in humans and mammals. More particularly, in preferred aspects, the present invention provides a method for the use of prenylcysteine analogs for the treatment of neoplasia, hyperproliferative cell growth including psoriasis, restenosis following cardiovascular surgery, hyperplasia, including renal hyperplasia, chronic inflammatory diseases including rheumatoid and osteoarthritis, among others.

  本发明涉及一种新的治疗肿瘤的方法，包括癌症和其他人类和哺乳动物疾病和病况的治疗。更具体地，在首选方面，本发明提供了一种使用戊二烯基半胱氨酸类似物治疗肿瘤、包括牛皮癣、心血管手术后再狭窄、包括肾脏增生的增生、包括类风湿和骨关节炎等慢性炎症疾病的方法。
• PRODRUGS AND CONJUGATES OF PRENYLATION INHIBITORS
  申请人：Borch Richard Frederic

  公开号：US20100249072A1

  公开（公告）日：2010-09-30

  Described herein are neutral prodrugs of phosphorus-containing inhibitors of farnesyl transferase that include one or more phosphate fragments or analogs of phosphate fragments. Analogs of phosphate fragments include various linkers other than oxygen connecting the phosphate fragment to the remaining portion of the drug, such as but not limited to linkers forming phosphoramidates, phosphonates, difluorophosphonates, phosphordiamidates, and the like.

  本文描述了一种醇化酶磷酸转移酶的中性前药，其中包括一个或多个磷酸盐片段或磷酸盐片段的类似物。磷酸盐片段的类似物包括各种连接磷酸盐片段与药物其余部分的氧以外的连接剂，例如但不限于形成磷酰胺酸盐、膦酸盐、二氟膦酸盐、磷酰二胺酸盐等的连接剂。
• WO2006/99313
  申请人：——

  公开号：——

  公开（公告）日：——
• US8324378B2
  申请人：——

  公开号：US8324378B2

  公开（公告）日：2012-12-04
• Aromatic farnesyl diphosphate analogues
  作者：Chunmei Zhou、Ying Shao、Richard A. Gibbs

  DOI：10.1016/s0960-894x(02)00187-7

  日期：2002.5

  A stereocontrolled vinyl triflate-based synthetic route has been used to prepare four analogues of farnesyl diphosphate (FPP) where the terminal isoprene units have been replaced with aromatic moieties. Two of these analogues exhibit no productive interaction with protein farnesyltransferase, but the 2-naphthyl derivative 2 is a modest inhibitor of the enzyme, and the para-biphenyl derivative 4 is a surprisingly effective alternative substrate. (C) 2002 Elsevier Science Ltd. All rights reserved.