(R,S)-2-<4-(isopropoxy)phenyl>propanoic acid methyl ester | 158816-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R,S)-2-<4-(isopropoxy)phenyl>propanoic acid methyl ester
• 英文别名: methyl 2-(4-isopropoxyphenyl)propanoate；Methyl 2-(4-isopropoxyphenyl)propionate；methyl 2-(4-propan-2-yloxyphenyl)propanoate
• CAS: 158816-13-8
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: HYPXWNQVDTXYKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R,S)-2-<4-(isopropoxy)phenyl>propanoic acid methyl ester 在 sodium hydroxide 、 phosphate buffer 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 32.0h， 生成 (S)-2-<4-(isopropoxy)phenyl>-N'-(2-chlorophenyl)propanohydrazide
  参考文献：
  名称：

  Chemoenzymic Synthesis of Optically Pure 1,3,4-Oxadiazol-2(3H)-ones with Acaricidal Activity

  摘要：

  Both enantiomers of 5-[1-(4-isopropoxy)phenyl]ethyl-3-(2-chlorophenyl)-1,3,4-oxadiazol-2(3H)-one (1a), a new compound with high ovicidal activity against Tetranychus urticae (Koch), were synthesized starting from enzymatically prepared optically pure 2-[4-(isopropoxy)phenyl]propanoic acid (3). Laboratory tests have shown that the biological activity of the R isomer is at least 400-fold higher than that of the S form.

  DOI：

  10.1021/jf00047a042
• 作为产物：
  描述：

  4-羟基苯乙酸甲酯 在 potassium tert-butylate 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 (R,S)-2-<4-(isopropoxy)phenyl>propanoic acid methyl ester
  参考文献：
  名称：

  5-脂氧合酶的异羟肟酸抑制剂的体内表征。

  摘要：

  可以将异羟肟酸功能性地掺入简单分子中以产生有效的5-脂氧合酶抑制剂。已经直接使用大鼠腹膜过敏模型测量了许多这些异羟肟酸酯在体内抑制白三烯合成的能力。尽管它们在体外具有强大的酶抑制活性，但许多口服异羟肟酸在体内仅能弱抑制白三烯的合成。这种差异至少部分归因于异羟肟酸酯快速代谢为相应的羧酸，而该羧酸对酶无活性。对影响这种代谢的结构特征的研究表明，2-芳基丙氧基异羟肟酸相对抗代谢水解。

  DOI：

  10.1021/jm00394a032

文献信息

• 2-Arylpropionic CXC Chemokine Receptor 1 (CXCR1) Ligands as Novel Noncompetitive CXCL8 Inhibitors
  作者：Marcello Allegretti、Riccardo Bertini、Maria Candida Cesta、Cinzia Bizzarri、Rosa Di Bitondo、Vito Di Cioccio、Emanuela Galliera、Valerio Berdini、Alessandra Topai、Giuseppe Zampella、Vincenzo Russo、Nicoletta Di Bello、Giuseppe Nano、Luca Nicolini、Massimo Locati、Piercarlo Fantucci、Saverio Florio、Francesco Colotta

  DOI：10.1021/jm049082i

  日期：2005.6.1

  The CXC chemokine CXCL8/IL-8 plays a major role in the activation and recruitment of polymorphonuclear (PMN) cells at inflammatory sites. CXCL8 activates PMNs by binding the seven-transmembrane (7-TM) G-protein-coupled receptors CXC chemokine receptor 1 (CXCR1) and CXC chemokine receptor 2 (CXCR2). (R)-Ketoprofen (1) was previously reported to be a potent and specific noncompetitive inhibitor of CXCL8-induced human PMNS chemotaxis. We report here molecular modeling studies showing a putative interaction site of 1 in the TM region of CXCR1. The binding model was confirmed by alanine scanning mutagenesis and photoaffinity labeling experiments. The molecular model driven medicinal chemistry optimization of 1 led to a new class of potent and specific inhibitors of CXCL8 biological activity. Among these, repertaxin (13) was selected as a clinical candidate drug for prevention of post-ischemia reperfusion injury.
• Bosetti Aldo, Bianchi Daniele, La Porta Piero, Bettarini Franco, Massimin+, J. Agr. and Food Chem, 42 (1994) N 11, S 2596- 2599
  作者：Bosetti Aldo, Bianchi Daniele, La Porta Piero, Bettarini Franco, Massimin+

  DOI：——

  日期：——
• In vivo characterization of hydroxamic acid inhibitors of 5-lipoxygenase
  作者：James B. Summers、Bruce P. Gunn、Hormoz Mazdiyasni、Andrew M. Goetze、Patrick R. Young、Jennifer B. Bouska、Richard D. Dyer、Dee W. Brooks、George W. Carter

  DOI：10.1021/jm00394a032

  日期：1987.11

  The hydroxamic acid functionally can be incorporated into simple molecules to produce potent inhibitors of 5-lipoxygenase. The ability of many of these hydroxamates to inhibit leukotriene synthesis in vivo has been measured directly with a rat peritoneal anaphylaxis model. Despite their potent enzyme inhibitory activity in vitro, many orally dosed hydroxamic acids only weakly inhibited leukotriene

  可以将异羟肟酸功能性地掺入简单分子中以产生有效的5-脂氧合酶抑制剂。已经直接使用大鼠腹膜过敏模型测量了许多这些异羟肟酸酯在体内抑制白三烯合成的能力。尽管它们在体外具有强大的酶抑制活性，但许多口服异羟肟酸在体内仅能弱抑制白三烯的合成。这种差异至少部分归因于异羟肟酸酯快速代谢为相应的羧酸，而该羧酸对酶无活性。对影响这种代谢的结构特征的研究表明，2-芳基丙氧基异羟肟酸相对抗代谢水解。
• Chemoenzymic Synthesis of Optically Pure 1,3,4-Oxadiazol-2(3H)-ones with Acaricidal Activity
  作者：Aldo Bosetti、Daniele Bianchi、Piero La Porta、Franco Bettarini、Sergio Massimini

  DOI：10.1021/jf00047a042

  日期：1994.11

  Both enantiomers of 5-[1-(4-isopropoxy)phenyl]ethyl-3-(2-chlorophenyl)-1,3,4-oxadiazol-2(3H)-one (1a), a new compound with high ovicidal activity against Tetranychus urticae (Koch), were synthesized starting from enzymatically prepared optically pure 2-[4-(isopropoxy)phenyl]propanoic acid (3). Laboratory tests have shown that the biological activity of the R isomer is at least 400-fold higher than that of the S form.