4-[4-(5-methoxypyridin-2-yl)phenoxymethyl]-5-methylfuran-2-carboxylic acid | 736182-71-1

• 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: 4-[4-(5-methoxypyridin-2-yl)phenoxymethyl]-5-methylfuran-2-carboxylic acid
• 英文别名: 4-[4-(5-Methoxy-pyridin-2-yl)-phenoxymethyl]-5-methyl-furan-2-carboxylic acid；4-[[4-(5-methoxypyridin-2-yl)phenoxy]methyl]-5-methylfuran-2-carboxylic acid
• CAS: 736182-71-1
• 化学式: C₁₉H₁₇NO₅
• 分子量: 339.348
• InChiKey: OWOSQIZIJWIJDC-UHFFFAOYSA-N

物化性质

• 沸点：
  544.3±50.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  81.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[4-(5-methoxypyridin-2-yl)phenoxymethyl]-5-methylfuran-2-carboxylic acid 生成 4-[[4-(5-methoxy-2-pyridinyl)phenoxy]methyl]-5-methyl-N-[(2-methylphenyl)sulphonyl]-2-furancarboxamide
  参考文献：
  名称：

  [EN] EP4 RECEPTOR ANTAGONISTS
  [FR] ANTAGONISTES AUX RECEPTEURS EP4

  摘要：

  式(I)的化合物：其中：R2为H或可选择地取代的C1-4烷基基团；Y为-(CH2)n-X-，其中n为1或2，X为O、S、S(=O)、S(=O)2或NRN1，其中RN1从H或可选择地取代的C1-4烷基中选择，或Y为-C(=O)NRN2-，其中RN2从H、可选择地取代的C1-7烷基或C5-20芳基中选择；R3为可选择地取代的C6芳基基团，连接到另一个可选择地取代的C6芳基基团，如果两个C6芳基基团均为苯环，则两个环之间可能有氧桥，在两个环上的连接处相邻结合；A为单键或C1-3烷基基团；R5为以下之一：(i)羧基；(ii)式(II)的基团；或(iii)式(III)的基团：其中R为可选择地取代的C1-7烷基、C5-20芳基或NRN3RN4，其中RN3和RN4独立地从可选择地取代的C1-4烷基中选择；(iv)四唑-5-基。

  公开号：

  WO2004067524A1
• 作为产物：
  描述：

  2-甲基-3-呋喃甲醇 在 咪唑 、 正丁基锂 、 水 、 甲基磺酰氯 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 4-[4-(5-methoxypyridin-2-yl)phenoxymethyl]-5-methylfuran-2-carboxylic acid
  参考文献：
  名称：

  From virtual to clinical: The discovery of PGN-1531, a novel antagonist of the prostanoid EP4 receptor

  摘要：

  In this Letter, we present the results of a hit-finding and lead optimization programme against the EP4 receptor (EP4R). In a short time period, we were able to discover five structurally diverse series of hit compounds using a combination of virtual screening methods. The most favoured hit, compound 6, was demonstrated to be a competitive antagonist of the EP4R. Compound 73 was identified following several rounds of optimization, which centred on improving both the primary EP4R affinity and selectivity against the related EP2R as well as the aqueous solubility. This work culminated in the preparation of PGN-1531, the sodium salt of 73, which showed a marked improvement in solubility (>10 mg/mL). PGN-1531 is a potent and selective antagonist at EP(4)Rs in vitro and in vivo, with the potential to alleviate the symptoms of migraine that result from cerebral vasodilatation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.068

文献信息

• EP4 receptor antagonists
  申请人：Asterand UK Limited

  公开号：US07196089B2

  公开（公告）日：2007-03-27

  Compounds of formula (I): wherein: R2 is H or an optionally substituted C1-4 alkyl group; Y is either —(CH2)n—X—, where n is 1 or 2 and X is O, S, S(═O), S(═O)2, or NRN1, where RN1 is selected from H or optionally substituted C1-4 alkyl, or Y is —C(═O)NRN2—, where RN2 is selected from H, and optionally substituted C1-7 alkyl or C5-20 aryl; R3 is an optionally substituted C6 aryl group linked to a further optionally substituted C6 aryl group, wherein if both C6 aryl groups are benzene rings, there may be an oxygen bridge between the two rings, bound adjacent the link on both rings; A is a single bond or a C1-3 alkylene group; and R5 is either: (i) carboxy; (ii) a group of formula (II): or (iii) a group of formula (III):  wherein R is optionally substituted C1-7 alkyl, C5-20 aryl or NRN3RN4, where RN3 and RN4 are independently selected from optionally substituted C1-4 alkyl; (iv) tetrazol-5-yl.

  化合物的化学式为（I）：其中：R2为H或可选择性取代的C1-4烷基；Y为—（CH2）n—X—，其中n为1或2，X为O，S，S（═O），S（═O）2或NRN1，其中RN1为H或可选择性取代的C1-4烷基，或Y为—C（═O）NRN2—，其中RN2为H，可选择性取代的C1-7烷基或C5-20芳基；R3为可选择性取代的C6芳基基团，与另一个可选择性取代的C6芳基基团相连，如果两个C6芳基基团都是苯环，则两个环之间可能有一个氧桥，与两个环上的连接相邻；A为单键或C1-3烷基；R5为：（i）羧基；（ii）式（II）的基团：或（iii）式（III）的基团：其中R为可选择性取代的C1-7烷基，C5-20芳基或NRN3RN4，其中RN3和RN4独立地选择可选择性取代的C1-4烷基；（iv）四唑-5-基基团。
• EP4 RECEPTOR ANTAGONISTS
  申请人：Oxford W. Alexander

  公开号：US20070123575A1

  公开（公告）日：2007-05-31

  Compounds of formula (I): wherein: R 2 is H or an optionally substituted C 1-4 alkyl group; Y is either —(CH 2 ) n —X—, where n is 1 or 2 and X is O, S, S(═O), S(═O) 2 , or NR N1 , where R N1 is selected from H or optionally substituted C 1-4 alkyl, or Y is —C(═O)NR N2 —, where R N2 is selected from H, and optionally substituted C 1-7 alkyl or C 5-20 aryl; R 3 is an optionally substituted C 6 aryl group linked to a further optionally substituted C 6 aryl group, wherein if both C 6 aryl groups are benzene rings, there may be an oxygen bridge between the two rings, bound adjacent the link on both rings; A is a single bond or a C 1-3 alkylene group; and R 5 is either: (i) carboxy; (ii) a group of formula (II): ; or (iii) a group of formula (III): wherein R is optionally substituted C 1-7 alkyl, C 5-20 aryl or NR N3 R N4 , where R N3 and R N4 are independently selected from optionally substituted C 1-4 alkyl; (iv) tetrazol-5-yl.

  式(I)的化合物：其中：R2为H或可选取代的C1-4烷基基团；Y为—(CH2)n—X—或—C(═O)NRN2—，其中n为1或2，X为O、S、S(═O)、S(═O)2或NRN1，其中RN1为选自H或可选取代的C1-4烷基的基团，或Y为—C(═O)NRN2—，其中RN2为选自H、可选取代的C1-7烷基或C5-20芳基基团；R3为可选取代的C6芳基基团，连接到另一个可选取代的C6芳基基团，如果两个C6芳基基团都是苯环，则两个环之间可能有一个氧桥，在两个环上都与连接点相邻；A为单键或C1-3烷基基团；R5为：(i)羧基；(ii)式(II)的基团；或(iii)式(III)的基团；其中R为可选取代的C1-7烷基、C5-20芳基或NRN3RN4，其中RN3和RN4独立选自可选取代的C1-4烷基；(iv)四唑-5-基团。
• US7196089B2
  申请人：——

  公开号：US7196089B2

  公开（公告）日：2007-03-27
• US7507754B2
  申请人：——

  公开号：US7507754B2

  公开（公告）日：2009-03-24
• US7528157B2
  申请人：——

  公开号：US7528157B2

  公开（公告）日：2009-05-05