(2-乙基-4-甲氧基苯基)硼酸 | 342899-07-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (2-乙基-4-甲氧基苯基)硼酸
• 英文名称: 4-methoxy-2-ethylphenylboronic acid
• 英文别名: (2-ethyl-4-methoxy)phenylboronic acid；(2-Ethyl-4-methoxyphenyl)boronic acid
• CAS: 342899-07-4
• 化学式: C₉H₁₃BO₃
• 分子量: 180.011
• InChiKey: JHTURCRYQLGBFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.06
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-乙基-4-甲氧基苯基)硼酸 、 N-叔丁氧羰基-O-三氟甲烷磺酰基-L-酪氨酸甲酯 在 钯 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 生成 (S)-2-(tert-butoxycarbonylamino)-3-(2'-ethyl-4'-methoxylbiphenyl-4-yl)propanoic acid methyl ester
  参考文献：
  名称：

  Process for the preparation of amino acids useful in the preparation of peptide receptor modulators

  摘要：

  本发明提供了一种有用的过程，用于制备在制备氨基酸时有用的中间体，这些氨基酸在制备肽受体调节剂时非常有用，例如这些肽受体的激动剂或部分激动剂。这种肽受体调节剂包括例如类胰高血糖素样肽-1受体调节剂，对改善糖尿病状况非常有用。

  公开号：

  US20060004222A1
• 作为产物：
  描述：

  1-溴-2-乙基-4-甲氧基苯 在 正丁基锂 、 硼酸三丁酯 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以82%的产率得到(2-乙基-4-甲氧基苯基)硼酸
  参考文献：
  名称：

  Process for the preparation of amino acids useful in the preparation of peptide receptor modulators

  摘要：

  本发明提供了一种有用的过程，用于制备在制备氨基酸时有用的中间体，这些氨基酸在制备肽受体调节剂时非常有用，例如这些肽受体的激动剂或部分激动剂。这种肽受体调节剂包括例如类胰高血糖素样肽-1受体调节剂，对改善糖尿病状况非常有用。

  公开号：

  US20060004222A1

文献信息

• Process for the preparation of amino acids useful in the preparation of peptide receptor modulators
  申请人：Mathur Arvind

  公开号：US20060004222A1

  公开（公告）日：2006-01-05

  The present invention provides process useful for the preparation of intermediates which are useful in the preparation of amino acids useful in preparing peptide receptor modulators, for example agonists or partial agonists of such peptide receptors. Such peptide receptor modulators include, for example glucagon like peptide-1 receptor modulators which are useful for the amelioration of the diabetic condition.

  本发明提供了一种有用的过程，用于制备在制备氨基酸时有用的中间体，这些氨基酸在制备肽受体调节剂时非常有用，例如这些肽受体的激动剂或部分激动剂。这种肽受体调节剂包括例如类胰高血糖素样肽-1受体调节剂，对改善糖尿病状况非常有用。
• Synthesis of Chiral-Bridged Atropisomeric Monophosphine Ligands with Tunable Dihedral Angles and their Applications in Asymmetric Suzuki-Miyaura Coupling Reactions
  作者：Wang Xia、Yongsu Li、Zihong Zhou、Huixuan Chen、Hao Liang、Sifan Yu、Xuefeng He、Yaqi Zhang、Jiyan Pang、Zhongyuan Zhou、Liqin Qiu

  DOI：10.1002/adsc.201700020

  日期：2017.5.17

  construction of diastereomeric biaryl monophosphines by means of the substrate-directed asymmetric annulation reactions. A series of new chiral-bridged atropisomeric biphenyl monophosphine ligands with tunable dihedral angles was accordingly synthesized successfully without a resolution step being needed. Using these ligands, different kinds of axially chiral 1,1′-biaryl-2-phosphonates including the first

  在非对映体联芳基单膦化合物的构建中，首先通过底物定向的不对称环化反应实现了精确的手性识别。因此，成功地合成了具有可调二面角的一系列新的手性桥联的阻转异构联苯单膦配体，而无需拆分步骤。使用这些配体，通过钯催化的不对称Suzuki偶联反应，可以制备42-97％的产率的轴向手性1,1'-联芳基-2-膦酸酯，包括首次报道的喹啉基联芳基膦酸酯，最高可达96％ee。
• N-TERMINALLY MODIFIED GLP-1 RECEPTOR MODULATORS
  申请人：Ewing R. William

  公开号：US20080045461A1

  公开（公告）日：2008-02-21

  The subject matter described herein provides novel human glucagon-like peptide-1 (GLP-1) receptor modulators that have biological activity similar or superior to native GLP-1 peptide and thus are useful for the treatment or prevention of diseases or disorders associated with GLP activity. The described compounds include chemically modified peptides that may stimulate insulin secretion in type II diabetics, but also produce other beneficial insulinotropic responses. These synthetic peptide GLP-1 receptor modulators exhibit increased stability to proteolytic cleavage making them ideal therapeutic candidates for oral or parenteral administration. The disclosed and claimed peptides show desirable pharmacokinetic properties and desirable potency in efficacy models of diabetes.

  本文所述主题提供了新颖的人类胰高血糖素样肽-1（GLP-1）受体调节剂，其生物活性类似或优于天然GLP-1肽，因此可用于治疗或预防与GLP活性相关的疾病或疾病。所述化合物包括化学修饰的肽，可以刺激2型糖尿病患者的胰岛素分泌，但也产生其他有益的胰岛素促分泌反应。这些合成肽GLP-1受体调节剂表现出对蛋白酶解的稳定性增加，使它们成为口服或静脉注射的理想治疗候选药物。所披露和声称的肽显示出理想的药代动力学特性和糖尿病疗效模型的理想效力。
• N-terminally modified GLP-1 receptor modulators
  申请人：Bristol-Myers Squibb Company

  公开号：US07960349B2

  公开（公告）日：2011-06-14

  The subject matter described herein provides novel human glucagon-like peptide-1 (GLP-1) receptor modulators that have biological activity similar or superior to native GLP-1 peptide and thus are useful for the treatment or prevention of diseases or disorders associated with GLP activity. The described compounds include chemically modified peptides that may stimulate insulin secretion in type II diabetics, but also produce other beneficial insulinotropic responses. These synthetic peptide GLP-1 receptor modulators exhibit increased stability to proteolytic cleavage making them ideal therapeutic candidates for oral or parenteral administration. The disclosed and claimed peptides show desirable pharmacokinetic properties and desirable potency in efficacy models of diabetes.

  本文描述了一种新型的人类胰高血糖素样肽-1（GLP-1）受体调节剂，其生物活性类似或优于天然GLP-1肽，因此可用于治疗或预防与GLP活性相关的疾病或障碍。所描述的化合物包括化学修饰的肽，可以刺激2型糖尿病患者的胰岛素分泌，但也产生其他有益的胰岛素促进反应。这些合成肽GLP-1受体调节剂表现出对蛋白酶水解的稳定性增加，使它们成为口服或静脉注射的理想治疗候选药物。所披露和索要的肽具有理想的药代动力学特性和在糖尿病的疗效模型中显示出理想的效力。
• Eleven Amino Acid Glucagon-like Peptide-1 Receptor Agonists with Antidiabetic Activity
  作者：Claudio Mapelli、Sesha I. Natarajan、Jean-Philippe Meyer、Margarita M. Bastos、Michael S. Bernatowicz、Ving G. Lee、Jelka Pluscec、Douglas J. Riexinger、Ellen S. Sieber-McMaster、Keith L. Constantine、Constance A. Smith-Monroy、Rajasree Golla、Zhengping Ma、Daniel A. Longhi、Dan Shi、Li Xin、Joseph R. Taylor、Barry Koplowitz、Cecilia L. Chi、Ashish Khanna、Gordon W. Robinson、Ramakrishna Seethala、Ildiko A. Antal-Zimanyi、Robert H. Stoffel、Songping Han、Jean M. Whaley、Christine S. Huang、John Krupinski、William R. Ewing

  DOI：10.1021/jm900752a

  日期：2009.12.10

  Glucagon-like peptide 1 (GLP-1) is a 30 or 31 amino acid peptide hormone that contributes to the physiological regulation of glucose homeostasis and food intake. Herein, we report the discovery of a novel class of 11 amino acid GLP-1 receptor agonists. These peptides consist of a structurally optimized 9-mer, which is closely related to the N-terminal 9 amino acids of GLP-1, linked to a substituted C-terminal biphenylalanine (BIP) dipeptide. SAR studies resulted in 11-mer GLP-1R agonists with similar in vitro potency to the native 30-mer. Peptides 21 and 22 acutely reduced plasma glucose excursions and increased plasma insulin concentrations in a Mouse model of diabetes. These peptides also showed sustained exposures over several hours in mouse and dog models. The described 11-mer GLP-1 receptor agonists represent a new tool in further understanding GLP-1 receptor pharmacology that may lead to novel antidiabetic agents.