ethyl 3-<3-(benzyloxy)phenyl>-2-methylprop-2-enoate | 129649-15-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 3-<3-(benzyloxy)phenyl>-2-methylprop-2-enoate
• 英文别名: ethyl (E)-2-methyl-3-(3-benzyloxyphenyl)propenoate；(E)-Ethyl 3-(3-(benzyloxy)phenyl)-2-methylacrylate；ethyl (E)-2-methyl-3-(3-phenylmethoxyphenyl)prop-2-enoate
• CAS: 129649-15-6
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: YITACXOGJXBAFW-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  ethyl 3-<3-(benzyloxy)phenyl>-2-methylprop-2-enoate 在 potassium hexacyanoferrate(III) 、 potassium osmate(VI) 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 水 、 叔丁醇 为溶剂， 反应 48.0h， 生成 ethyl (2R,3R)-3-(3-benzyloxyphenyl)-2,3-dihydroxy-2-methyl-propanoate
  参考文献：
  名称：

  [EN] ANTIDIABETIC OXAZOLIDINEDIONES AND THIAZOLIDINEDIONES
  [FR] OXAZOLIDINEDIONES ET THIAZOLIDINEDIONES ANTIDIABETIQUES

  摘要：

  公式（I）中的苯氧苯基和苯氧苄基噁唑烷-2,4-二酮和噻唑烷-2,4-二酮是PPAR γ的激动剂或部分激动剂，对于治疗和控制与2型糖尿病症状相关的高血糖，以及常伴随2型糖尿病的血脂异常、高脂血症、高胆固醇血症、高甘油三酯血症和肥胖症具有用处。

  公开号：

  WO2005070905A1
• 作为产物：
  描述：

  三乙基2-膦酰基丙酯 、 3-苄氧基苯甲醛 在 sodium hydride 作用下， 生成 ethyl 3-<3-(benzyloxy)phenyl>-2-methylprop-2-enoate
  参考文献：
  名称：

  The development of a novel series of (quinolin-2-ylmethoxy)phenyl-containing compounds as high-affinity leukotriene receptor antagonists. 3. Structural variation of the acidic side chain to give antagonists of enhanced potency

  摘要：

  This paper is the third in a series outlining the development of orally active sulfido peptide leukotriene antagonists containing a (quinolin-2-ylmethoxy)phenyl moiety. In this work the systematic variation of the acid side chain substituents led to dramatic and reproducible changes in the oral activity of these compounds, presumably due to alterations in their pharmacokinetic properties. The most potent compound identified, 5-[4-[4-(quinolin-2-yl-methoxy)phenyl]-3-methylbutyl]tetrazole (32), represents a convergence of good in vitro antagonist activity and a 3-10-fold improvement in oral potency over the current clinical candidate 2. The new findings from these optimization studies are as follows: oxygen substitution in the acid side chain was not necessary for antagonist activity, in vitro and in vivo activity was enhanced by alkyl or phenyl substitution on the gamma-carbon of the acid side chain of para-substituted (quinolin-2-ylmethoxy)phenyl derivatives, and free rotation about the side chain carbon atom adjacent to the (quinolin-2-ylmethoxy)phenyl ring was required for activity. The lead compound of this report (32) is a competitive inhibitor of [3H]LTD4 binding to receptor membrane purified from guinea pig lung (Ki = 12 +/- 3 nM) and of the spasmogenic activity of LTC4, LTD4, and LTE4 in guinea pig lung strip. Dosed orally in guinea pigs, this compound blocks LTD4-induced bronchoconstriction (ED50 0.8 mg/kg) and antigen-induced systemic anaphylaxis (ED50 = 1.2 mg/kg).

  DOI：

  10.1021/jm00172a024

文献信息

• [EN] ANTIDIABETIC OXAZOLIDINEDIONES AND THIAZOLIDINEDIONES<br/>[FR] OXAZOLIDINEDIONES ET THIAZOLIDINEDIONES ANTIDIABETIQUES
  申请人：MERCK & CO INC

  公开号：WO2005070905A1

  公开（公告）日：2005-08-04

  Phenoxyphenyl and phenoxybenzyl oxazolidine-2,4-diones and thiazolidine-2,4-diones of formula (I) are agonists or partial agonists of PPAR gamma and are useful in the treatment and control of hyperglycemia that is symptomatic of type II diabetes, as well as dyslipidemia, hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, and obesity that are often associated with type 2 diabetes.

  公式（I）中的苯氧苯基和苯氧苄基噁唑烷-2,4-二酮和噻唑烷-2,4-二酮是PPAR γ的激动剂或部分激动剂，对于治疗和控制与2型糖尿病症状相关的高血糖，以及常伴随2型糖尿病的血脂异常、高脂血症、高胆固醇血症、高甘油三酯血症和肥胖症具有用处。
• [EN] SUBSTITUTED BIPHENYL GPR40 MODULATORS<br/>[FR] MODULATEURS DU GPR40 À BIPHÉNYLE SUBSTITUÉ
  申请人：AMGEN INC

  公开号：WO2009048527A1

  公开（公告）日：2009-04-16

  The present invention provides compounds useful, for example, for treating metabolic disorders in a subject. Such compounds have the general formula I: where the definitions of the variables are provided herein. The present invention also provides compositions that include, and methods for using, the compounds in preparing medicaments and for treating metabolic disorders such as, for example, type II diabetes.

  本发明提供了一种有用的化合物，例如，用于治疗受试者的代谢紊乱。这些化合物具有一般公式I：其中变量的定义在此处提供。本发明还提供了包括这些化合物的组合物，以及使用这些化合物制备药物和治疗代谢紊乱的方法，例如II型糖尿病。
• Substituted biphenyl GPR40 modulators
  申请人：Amgen Inc.

  公开号：US08030354B2

  公开（公告）日：2011-10-04

  The present invention provides compounds useful, for example, for treating metabolic disorders in a subject. Such compounds have the general formula I: where the definitions of the variables are provided herein. The present invention also provides compositions that include, and methods for using, the compounds in preparing medicaments and for treating metabolic disorders such as, for example, type II diabetes.

  本发明提供了一些有用的化合物，例如用于治疗受试者的代谢紊乱。这些化合物具有一般式I，其中变量的定义在此提供。本发明还提供包括这些化合物的组合物，并使用这些化合物制备药物和治疗代谢紊乱的方法，例如II型糖尿病。
• WO2007/8501
  申请人：——

  公开号：——

  公开（公告）日：——
• GALEMMO, ROBERT A.;JOHNSON, WILLIAM H. (JR);LEARN, KEITH S.;LEE, THOMAS D+, J. MED. CHEM., 33,(1990) N0, C. 2828-2841
  作者：GALEMMO, ROBERT A.、JOHNSON, WILLIAM H. (JR)、LEARN, KEITH S.、LEE, THOMAS D+

  DOI：——

  日期：——