ethyl 3-(2,4-dichlorophenyl)-3-hydroxy propanoate | 62547-76-6

• 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: ethyl 3-(2,4-dichlorophenyl)-3-hydroxy propanoate
• 英文别名: Ethyl 3-(2,4-Dichlorophenyl)-3-hydroxypropanoate
• CAS: 62547-76-6
• 化学式: C₁₁H₁₂Cl₂O₃
• 分子量: 263.12
• InChiKey: YBRUTBNRYJYVDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-(2,4-dichlorophenyl)-3-hydroxy propanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 1-(2,4-二氯苯基)-1,3-丙二醇
  参考文献：
  名称：

  Pradefovir: A Prodrug That Targets Adefovir to the Liver for the Treatment of Hepatitis B

  摘要：

  Adefovir dipivoxil, a marketed drug for the treatment of hepatitis B, is dosed at submaximally efficacious doses because of renal toxicity. In an effort to improve the therapeutic index of adefovir, 1-aryl-1,3-propanyl prodrugs were synthesized with the rationale that this selectively liver-activated prodrug class would enhance liver levels of the active metabolite adefovir diphosphate (ADV-DP) and/or decrease kidney exposure. The lead prodrug (14, MB06866, pradefovir), identified from a variety of in vitro and in vivo assays, exhibited good oral bioavailability (F = 42%, mesylate salt, rat) and rate of prodrug conversion to ADV-DP. Tissue distribution studies in the rat using radiolabeled materials showed that cyclic 1-aryl-1,3-propanyl prodrugs enhance the delivery of adefovir and its metabolites to the liver, with pradefovir exhibiting a 12-fold improvement in the liver/kidney ratio over adefovir dipivoxil.

  DOI：

  10.1021/jm7012216
• 作为产物：
  描述：

  2,4-二氯苯甲醛 、 溴乙酸乙酯 生成 ethyl 3-(2,4-dichlorophenyl)-3-hydroxy propanoate
  参考文献：
  名称：

  SNYDER H. R.; BURROUS S. E.; TREEDMAN R.; HEBERT T. J., J. PHARM. SCI., 1978, 67, NO 3, 413-415

  摘要：

  DOI：

文献信息

• Reformatsky Reaction in Water:  Evidence for a Radical Chain Process
  作者：Lothar W. Bieber、Ivani Malvestiti、Elisabeth C. Storch

  DOI：10.1021/jo970827k

  日期：1997.12.1

  The Reformatsky reaction of 2-bromo esters and carbonyl compounds in the presence of zinc can be carried out in concentrated aqueous salt solutions without any cosolvent. The reaction of bromoacetates is greatly enhanced by catalytic amounts of benzoyl peroxide or peracids and gives satisfactory yields with aromatic aldehydes. Preparative yields comparable to those of the traditional procedure are obtained with ethyl 2-bromoisobutyrate. This ester needs no catalyst and reacts even with saturated aldehydes and aromatic ketones, although in law yields. A radical chain mechanism, initiated by electron abstraction from the organometallic Reformatsky reagent, is proposed. Two nonchain pathways, involving radicals directly produced od the metal surface, may compete, especially in the case of secondary and tertiary halides.
• Candida Rugosa lipase-catalyzed kinetic resolution of β-hydroxy-β-arylpropionates and δ-hydroxy-δ-aryl-β-oxo-pentanoates
  作者：Chengfu Xu、Chengye Yuan

  DOI：10.1016/j.tet.2004.12.059

  日期：2005.2

  A simple and convenient method was reported for the preparation of optically active beta-hydroxy-beta-arylpropionates, delta-hydroxy-delta-aryl-beta-oxo-pentanoates and their butyryl derivatives via CRL-catalyzed hydrolysis. The optically active products are potential precursors of some chiral pharmaceuticals and natural products. (C) 2005 Elsevier Ltd. All rights reserved.
• Deracemisation of aromatic β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330 and determination of absolute configuration by 1H NMR
  作者：Santosh Kumar Padhi、Anju Chadha

  DOI：10.1016/j.tetasy.2005.07.017

  日期：2005.8

  Deracemisation of aryl and substituted aryl P-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330 yields the corresponding (S)-enantiomer in >99% enantiomeric excess and good yield (up to 68%). The absolute configuration of ethyl 3-(2,4-dichlorophenyl)-3-hydroxy propanoate and ethyl 3-hydroxy-5-phenyl-pent-4-enoate as determined by H-1 NMR using MTPA chloride was found to be 'S'. The chemical shifts of the methoxy groups of the two diastereomeric MTPA esters were used as diagnostic signals to determine the absolute configuration. (c) 2005 Elsevier Ltd. All rights reserved.
• SNYDER H. R.; BURROUS S. E.; TREEDMAN R.; HEBERT T. J., J. PHARM. SCI., 1978, 67, NO 3, 413-415
  作者：SNYDER H. R.、 BURROUS S. E.、 TREEDMAN R.、 HEBERT T. J.

  DOI：——

  日期：——
• 3-Arylpropionylhydroxamic acid derivatives as Helicobacter pylori urease inhibitors: Synthesis, molecular docking and biological evaluation
  作者：Wei-Kang Shi、Rui-Cheng Deng、Peng-Fei Wang、Qin-Qin Yue、Qi Liu、Kun-Ling Ding、Mei-Hui Yang、Hong-Yu Zhang、Si-Hua Gong、Min Deng、Wen-Run Liu、Qiu-Ju Feng、Zhu-Ping Xiao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2016.07.052

  日期：2016.10

  Helicobacter pylori urease is involved in several physiologic responses such as stomach and duodenal ulcers, adenocarcinomas and stomach lymphomas. Thus, inhibition of urease is taken for a good chance to treat H. pylori-caused infections, we have therefore focused our efforts on seeking novel urease inhibitors. Here, a series of arylpropionylhydroxamic acids were synthesized and evaluated for urease inhibition. Out of these compounds, 3-(2-benzyloxy-5-chlorophenyl)-3-hydroxypropionylhydroxamic acid (d24) was the most active inhibitor with IC50 of 0.15 +/- 0.05 mu M, showing a mixed inhibition with both competitive and uncompetitive aspects. Non-linear fitting of kinetic data gives kinetics parameters of 0.13 and 0.12 mu g.mL(-1) for K-i and K-i', respectively. The plasma protein binding assays suggested that d24 exhibited moderate binding to human and rabbit plasma proteins. (C) 2016 Elsevier Ltd. All rights reserved.