ethyl 6-((5-chloro-2-hydroxyphenyl)methyl)-2-pyridinecarboxylate | 892663-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ethyl 6-((5-chloro-2-hydroxyphenyl)methyl)-2-pyridinecarboxylate
• 英文别名: Ethyl 6-[(5-chloro-2-hydroxyphenyl)methyl]-2-pyridinecarboxylate；ethyl 6-[(5-chloro-2-hydroxyphenyl)methyl]pyridine-2-carboxylate
• CAS: 892663-03-5
• 化学式: C₁₅H₁₄ClNO₃
• 分子量: 291.734
• InChiKey: WRDIVVWKTQUSIA-UHFFFAOYSA-N

物化性质

• 沸点：
  449.8±45.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 6-((5-chloro-2-hydroxyphenyl)methyl)-2-pyridinecarboxylate 在 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 6-[[5-氯-2-[(4-氯-2-氟苯基)甲氧基]苯基]甲基]吡啶-2-羧酸
  参考文献：
  名称：

  Development of an in vivo active, dual EP1 and EP3 selective antagonist based on a novel acyl sulfonamide bioisostere

  摘要：

  Recent preclinical studies demonstrate a role for the prostaglandin E-2 (PGE(2)) subtype 1 (EP1) receptor in mediating, at least in part, the pathophysiology of hypertension and diabetes mellitus. A series of amide and N-acylsulfonamide analogs of a previously described picolinic acid-based human EP1 receptor antagonist (7) were prepared. Each analog had improved selectivity at the mouse EP1 receptor over the mouse thromboxane receptor (TP). A subset of analogs gained affinity for the mouse PGE2 subtype 3 (EP3) receptor, another potential therapeutic target. One analog (17) possessed equal selectivity for EP1 and EP3, displayed a sufficient in vivo residence time in mice, and lacked the potential for acyl glucuronide formation common to compound 7. Treatment of mice with 17 significantly attenuated the vasopressor activity resulting from an acute infusion of EP1 and EP3 receptor agonists. Compound 17 represents a potentially novel therapeutic in the treatment of hypertension and diabetes mellitus. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.046
• 作为产物：
  描述：

  ethyl 6-[(5-chloro-2-hydroxyphenyl)hydroxymethyl]-2-pyridinecarboxylate 在 palladium 10% on activated carbon 、 硫酸 、 氢气 、 zinc dibromide 作用下， 以 乙酸乙酯 为溶剂， 65.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以82%的产率得到ethyl 6-((5-chloro-2-hydroxyphenyl)methyl)-2-pyridinecarboxylate
  参考文献：
  名称：

  Development and Scope of the Phenolic Aldol Reaction of 2-Formylpyridines

  摘要：

  研究表明，2-甲酰基吡啶是镁促进酚醛反应的合适亲电体。研究人员开发了特别温和的反应条件，并对反应范围进行了简要考察。该工艺可通过随后的还原直接获得一系列官能化的 2-羟基苯基-2-吡啶基甲醇和 2-羟基苯基-2-吡啶基甲烷。

  DOI：

  10.1055/s-0029-1217325

文献信息

• Development and Scope of the Phenolic Aldol Reaction of 2-Formylpyridines
  作者：Matthew Whiting、Mark Wilkinson、Kathy Harwood

  DOI：10.1055/s-0029-1217325

  日期：——

  2-Formylpyridines have been shown to be suitable electrophiles for the magnesium-promoted phenolic aldol reaction. Exceptionally mild reaction conditions have been developed and a brief survey of the reaction scope has been conducted. This process gives straightforward access to a range of functionalised 2-hydroxy­phenyl-2-pyridylmethanols and 2-hydroxyphenyl-2-pyridylmethanes via their subsequent reduction.

  研究表明，2-甲酰基吡啶是镁促进酚醛反应的合适亲电体。研究人员开发了特别温和的反应条件，并对反应范围进行了简要考察。该工艺可通过随后的还原直接获得一系列官能化的 2-羟基苯基-2-吡啶基甲醇和 2-羟基苯基-2-吡啶基甲烷。
• Pyridine Compounds For The Treatment Of Prostaglandin Mediated Diseases
  申请人：Martin Paul Giblin Gerard

  公开号：US20080249138A1

  公开（公告）日：2008-10-09

  Compounds of formula (I) or a pharmaceutically acceptable derivative thereof: wherein X, Y, Z, R 2a , R 2b , R 3a , R 3b , R 8 , R 9 , and R x are as defined in the specification, a process for the preparation of such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine.

  化合物的化学式为（I）或其药学上可接受的衍生物： 其中X、Y、Z、R2a、R2b、R3a、R3b、R8、R9和Rx如规范所定义，制备这种化合物的过程，包含这种化合物的药物组合物以及在医学上使用这种化合物。
• BENZOFURAN COMPOUNDS USEFUL IN THE TREATMENT OF CONDITIONS MEDIATED BY THE ACTION OF PGE2 AT THE EP1 RECEPTOR
  申请人：Eatherton Andrew John

  公开号：US20100056527A1

  公开（公告）日：2010-03-04

  A compound of formula (I): wherein R 1 , R 2 , and R 3 are as defined in the specification, a process for the preparation of such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine.

  化合物式（I）：其中R1、R2和R3如规范所定义，制备此类化合物的过程，包含此类化合物的制药组合物以及此类化合物在医学中的使用。
• Benzofuran Compounds As EP1 Receptor Antagonists
  申请人：Gibson Mairi

  公开号：US20090099169A1

  公开（公告）日：2009-04-16

  Compounds of formula (I) or a pharmaceutically acceptable derivative thereof: wherein R 1 , R 2a , R 2b , R 2c , and R 3 are as defined in the specification, a process for the preparation of such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine.

  式(I)的化合物或其药学上可接受的衍生物，其中R1、R2a、R2b、R2c和R3如规范中所定义，制备这种化合物的方法，包含这种化合物的药物组合物以及这种化合物在医药中的用途。
• Pyridine compounds for the treatment of prostaglandin mediated diseases
  申请人：Glaxo Group Limited

  公开号：US07759369B2

  公开（公告）日：2010-07-20

  Compounds of formula (I) or a pharmaceutically acceptable derivative thereof: wherein X, Y, Z, R2a, R2b, R3a, R3b, R8, R9, and Rx are as defined in the specification, a process for the preparation of such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine.

  化合物的公式(I)或其药学上可接受的衍生物：其中X、Y、Z、R2a、R2b、R3a、R3b、R8、R9和Rx的定义如规范所述，制备这种化合物的过程，包括这种化合物的药物组合物以及这种化合物在医学上的用途。