Ethyl 3-isopropoxybenzoate | 205045-49-4

• 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-isopropoxybenzoate
• 英文别名: ethyl 3-propan-2-yloxybenzoate
• CAS: 205045-49-4
• 化学式: C₁₂H₁₆O₃
• mdl: MFCD11555059
• 分子量: 208.257
• InChiKey: GBISPESJLXKRGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 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-isopropoxybenzoate 在 甲酸 、 硫酸 、 sodium hydride 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 9.5h， 生成 6-bromo-8-ethoxycarbonyl-3'-hydroxyflavone
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Carboxyflavones as Structurally Rigid CysLT₁ (LTD₄) Receptor Antagonists

  摘要：

  The synthesis and CysLT(1) receptor affinities of a new series of highly rigid 3'- and 4'-(2-quinolinylmethoxy)- or 3'- and 4'-[2-(2-quinolinyl)ethenyl]-substituted 6-, 7-, or 8-carboxylated flavones are described. CysLT(1) receptor affinities of the flavones (down to 11 nM) were determined by their ability to displace [H-3]LTD4 from its receptor in guinea pig lung membranes. Structure-affinity relationship studies showed that the relative positions of the carboxylic acid and the quinoline moiety were critical for CysLT(1) affinities. While the carboxyl is optimal in the 8 position but tolerated in the 6 position, only the 6- and not the 8-tetrazole has significant activity. The quinoline moiety may be connected to the flavone skeleton by an ethenyl or a methoxy linker, but the substitution position is important for high affinity, especially in the 6-carboxylated flavones. 4'-Substituted 6-carboxyflavones are essentially inactive, whereas the 3'-substituted analogues have submicromolar CysLT(1) affinity. Replacement of the quinoline by other heteroaromates generally leads to decreased affinities, with the phenyl and naphthyl analogues displaying only little or no affinity, while the 7-chloroquinoline analogue is comparable in activity to the quinoline. Flavones having CysLT(1) receptor affinities of 10-30 nM were selected for determination of their inhibitory effects on the LTD4-induced contraction of guinea pig ileum in vitro. The IC50 values ranged between 15 and 100 nM. Compound 5d (8-carboxy-6-chloro-3'-(2-quinolinylmethoxy)flavone, VUF 5087) was selected for further research because of its high potency in the functional assay. This series contains the most rigid CysLT(1) receptor antagonists known to date, and they are useful in the development of a CysLT(1) antagonist model, which is discussed in the companion paper.

  DOI：

  10.1021/jm970179x
• 作为产物：
  描述：

  间羟基苯甲酸 在 盐酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 Ethyl 3-isopropoxybenzoate
  参考文献：
  名称：

  Structure Activity Relationship of Brevenal Hydrazide Derivatives

  摘要：

  Brevenal是一种由 dinoflagellate Karenia brevis 产生的梯级框架聚醚。这种生物体也负责生成被称为 brevetoxins 的神经毒素化合物。摄入或吸入这些神经毒素会导致不良反应，如胃肠疾病和支气管收缩。Brevenal 对 brevetoxins 显示出拮抗作用，并且在单独使用时显示出有益特性。例如，在哮喘羊模型中，Brevenal 显示出能够增加气管黏膜速度，这一特性促使其被开发为潜在的囊性纤维化治疗药物。Brevenal 的作用机制尚不清楚，具体的结合位点尚未阐明。为进一步理解 brevenal 的作用机制并可能开发第二代药物候选物，通过对醛基部分进行修改，合成了一系列 brevenal 衍生物。这些衍生物包括脂肪族、芳香族和杂芳香族肼衍生物。使用体外突触体结合实验测试了这些 brevenal 衍生物，以确定它们对原生受体的 brevetoxin 和 brevenal 的置换能力。采用羊的吸入模型来确定 brevenal 衍生物的滴入是否导致支气管收缩。仅允许小幅度修改，较大的官能团则导致对 brevenal 受体的亲和力下降，并在羊模型中导致支气管收缩。

  DOI：

  10.3390/md12041839

文献信息

• Design, synthesis, and evaluation of 2-aryl-7-(3′,4′-dialkoxyphenyl)-pyrazolo[1,5-a]pyrimidines as novel PDE-4 inhibitors
  作者：Ikyon Kim、Jong Hwan Song、Chang Min Park、Joon Won Jeong、Hyung Rae Kim、Jin Ryul Ha、Zaesung No、Young-Lan Hyun、Young Sik Cho、Nam Sook Kang、Dong Ju Jeon

  DOI：10.1016/j.bmcl.2009.12.070

  日期：2010.2

  is design, synthesis, and biological evaluation of novel series of 2-aryl-7-(3′,4′-dialkoxyphenyl)-pyrazolo[1,5-a]pyrimidines acting as inhibitors of type 4 phosphodiesterase (PDE4) which is known as a good target for the treatment of asthma and COPD. For this purpose, structure optimization was conducted with the aid of structure-based drug design using the known X-ray crystallography. Also, biological

  本文描述了新颖的2-芳基-7-（3'，4'-二烷氧基苯基）-吡唑并[1,5- a ]嘧啶系列的新颖系列的设计，合成和生物学评估，该抑制剂可作为4型磷酸二酯酶（PDE4）的抑制剂被认为是治疗哮喘和COPD的好靶标。为此目的，使用已知的X射线晶体学，借助于基于结构的药物设计进行结构优化。此外，通过使用体外测定法评估了这些化合物对目标酶的生物学作用，从而产生了有效且选择性的PDE-4抑制剂（IC 50  <10 nM）。
• Aminoethanol derivatives
  申请人：——

  公开号：US20040127574A1

  公开（公告）日：2004-07-01

  The present invention provides a pharmaceutical agent having cholesteryl ester transfer protein inhibitory action and useful as a blood lipid lowering agent and the like. The present invention relates to a compound represented by the formula 1 wherein Ar 1 is an aromatic ring group optionally having substituents, Ar 2 is an aromatic ring group having substituents, OR″ is an optionally protected hydroxyl group, R is an acyl group, R′ is a hydrogen atom or a hydrocarbon group optionally having substituents, or a salt thereof, and a pharmaceutical composition containing a compound of the formula (I) or a salt thereof or a prodrug thereof.

  本发明提供了一种具有胆固醇酯转移蛋白抑制作用的药物剂，可用作降低血脂等方面的药物。本发明涉及一种由式1表示的化合物，其中Ar1是一个带有取代基的芳香环基团，Ar2是一个带有取代基的芳香环基团，OR″是一个可选保护的羟基，R是一个酰基，R′是一个氢原子或一个可选带有取代基的碳氢基团，或其盐，以及含有式(I)的化合物或其盐或前药的药物组合物。
• ISOMANNIDE DERIVATIVES AND THEIR USE AS TASTANTS
  申请人：Tachdjian Catherine

  公开号：US20120183660A1

  公开（公告）日：2012-07-19

  The present invention provides isomannide derivatives having structural formula (I) as shown below and certain subgenera or species thereof, as flavoring agents or tastants, flavor or taste modifiers, and/or flavor/taste enhancers, particularly, savory (“umami”) flavoring agent or tastant, savory taste modifiers, and/or savory flavor enhancers, for ingestible compositions. The present invention also provides methods of preparing isomannide derivatives having the structural formula (II) shown below and certain subgenera or species thereof.

  本发明提供了具有如下所示的结构式(I)及其某些亚属或种类的异曼尼糖衍生物，作为风味剂或味觉剂，风味或味觉调节剂，以及/或风味/味觉增强剂，特别是咸味（"鲜味"）风味剂或味觉剂，咸味调节剂和/或咸味风味增强剂，用于可食用组合物。本发明还提供了制备具有如下所示的结构式(II)及其某些亚属或种类的异曼尼糖衍生物的方法。
• AMINOETHANOL DERIVATIVES
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1362846A1

  公开（公告）日：2003-11-19

  The present invention provides a pharmaceutical agent having cholesteryl ester transfer protein inhibitory action and useful as a blood lipid lowering agent and the like. The present invention relates to a compound represented by the formula wherein Ar1 is an aromatic ring group optionally having substituents, Ar2 is an aromatic ring group having substituents, OR'' is an optionally protected hydroxyl group, R is an acyl group, R' is a hydrogen atom or a hydrocarbon group optionally having substituents, or a salt thereof, and a pharmaceutical composition containing a compound of the formula (I) or a salt thereof or a prodrug thereof.

  本发明提供了一种具有胆固醇酯转移蛋白抑制作用的药剂，可用作降血脂药等。本发明涉及一种由式表示的化合物 其中 Ar1 是可选具有取代基的芳香环基，Ar2 是可选具有取代基的芳香环基，OR''是可选保护的羟基，R 是酰基，R'是氢原子或可选具有取代基的烃基，或其盐，以及含有式（I）化合物或其盐或其原药的药物组合物。
• US6982348B2
  申请人：——

  公开号：US6982348B2

  公开（公告）日：2006-01-03