4-methaneyl-2-chlorobenzenethanoic acid methyl ester | 871477-05-3

• 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: 4-methaneyl-2-chlorobenzenethanoic acid methyl ester
• 英文别名: (2-chloro-4-methylphenyl)ethanoic acid methyl ester；4-methyl-2-chlorobenzenethanoic acid methyl ester；Methyl 2-(2-chloro-4-methylphenyl)acetate
• CAS: 871477-05-3
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: DAOKQKFXOZURGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  263.2±25.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methaneyl-2-chlorobenzenethanoic acid methyl ester 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 丙酮 为溶剂， 生成 sodium 2-{2-chloro-4-[(2-oxocyclopentyl)methyl]-phenyl}propanoate
  参考文献：
  名称：

  Synthesis and biological evaluation of loxoprofen derivatives

  摘要：

  Non-steroidal anti-inflammatory drugs (NSAIDs) achieve their anti-inflammatory actions through an inhibitory effect on cyclooxygenase (COX). Two COX subtypes, COX-1 and COX-2, are responsible for the majority of COX activity at the gastrointestinal mucosa and in tissues with inflammation, respectively. We previously suggested that both gastric mucosal cell death due to the membrane permeabilization activity of NSAIDs and COX-inhibition at the gastric mucosa are involved in NSAID-induced gastric lesions. We have also reported that loxoprofen has the lowest membrane permeabilization activity among the NSAIDs we tested. In this study, we synthesized a series of loxoprofen derivatives and examined their membrane permeabilization activities and inhibitory effects on COX-1 and COX-2. Among these derivatives, 2-{4'-hydroxy-5-[(2-oxocyclopentyl)methyl]biphenyl-2-yl}propanoate 31 has a specificity for COX-2 over COX-1. Compared to loxoprofen, oral administration of 31 to rats produced fewer gastric lesions but showed an equivalent anti-inflammatory effect. These results suggest that 31 is likely to be a therapeutically beneficial and safer NSAID. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.050
• 作为产物：
  描述：

  2-(2-Chloro-4-methylphenyl)acetaldehyde 在 盐酸 、 高碘酸 作用下， 以 水 、 乙腈 为溶剂， 生成 4-methaneyl-2-chlorobenzenethanoic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of loxoprofen derivatives

  摘要：

  Non-steroidal anti-inflammatory drugs (NSAIDs) achieve their anti-inflammatory actions through an inhibitory effect on cyclooxygenase (COX). Two COX subtypes, COX-1 and COX-2, are responsible for the majority of COX activity at the gastrointestinal mucosa and in tissues with inflammation, respectively. We previously suggested that both gastric mucosal cell death due to the membrane permeabilization activity of NSAIDs and COX-inhibition at the gastric mucosa are involved in NSAID-induced gastric lesions. We have also reported that loxoprofen has the lowest membrane permeabilization activity among the NSAIDs we tested. In this study, we synthesized a series of loxoprofen derivatives and examined their membrane permeabilization activities and inhibitory effects on COX-1 and COX-2. Among these derivatives, 2-{4'-hydroxy-5-[(2-oxocyclopentyl)methyl]biphenyl-2-yl}propanoate 31 has a specificity for COX-2 over COX-1. Compared to loxoprofen, oral administration of 31 to rats produced fewer gastric lesions but showed an equivalent anti-inflammatory effect. These results suggest that 31 is likely to be a therapeutically beneficial and safer NSAID. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.050

文献信息

• [EN] NON NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS<br/>[FR] INHIBITEURS NON NUCLÉOSIDIQUES DE LA TRANSCRIPTASE INVERSE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2005118575A1

  公开（公告）日：2005-12-15

  The invention relates to compounds of formula (I) wherein Ar, X, R1, R2, R3 and R4 are as defined herein and pharmaceutical compositions thereof useful, either alone or in combination with other therapeutic agents as reverse transcriptase inhibitors against wild type and single or double mutant strains of HIV for the treatment or prophylaxis of HIV infection.

  这项发明涉及式(I)的化合物，其中Ar、X、R1、R2、R3和R4如本文所定义，并且它们的药物组合物，可单独使用或与其他治疗剂联合使用，作为针对HIV的野生型和单一或双重突变株的逆转录酶抑制剂，用于治疗或预防HIV感染。
• Methods Of Modulating Uric Acid Levels
  申请人：De La Rosa Martha

  公开号：US20120135929A1

  公开（公告）日：2012-05-31

  Described herein are compounds useful in the reduction of blood uric acid levels, formulations containing them and methods of making and using them. In some embodiments, a compound disclosed herein are used in the treatment or prevention of disorders related to aberrant levels of uric acid.

  本文描述了一些有用于降低血尿酸水平的化合物，包含它们的配方以及制备和使用它们的方法。在某些实施例中，本文所披露的化合物被用于治疗或预防与尿酸异常水平相关的疾病。
• Non-nucleoside Reverse Transcriptase Inhibitors
  申请人：DeROY Patrick

  公开号：US20090143370A1

  公开（公告）日：2009-06-04

  Compounds of formula (I): wherein Ar, X, R 1 , R 2 , R 3 and R 4 are as defined herein. The compounds are useful as reverse transcriptase inhibitors against wild type and single or double mutant strains of HIV.
• US7517998B2
  申请人：——

  公开号：US7517998B2

  公开（公告）日：2009-04-14
• US8198458B2
  申请人：——

  公开号：US8198458B2

  公开（公告）日：2012-06-12