4-{3-cyano-6-[2-(methoxymethoxy)phenyl]-2-[(thiophen-2-ylcarbonyl)amino]pyridin-4-yl}benzoic acid | 925932-61-2

• 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-{3-cyano-6-[2-(methoxymethoxy)phenyl]-2-[(thiophen-2-ylcarbonyl)amino]pyridin-4-yl}benzoic acid
• 英文别名: 4-{3-cyano-6-[2-(methoxymethoxy)phenyl]-2-[(2-thienylcarbonyl)amino]pyridin-4-yl} benzoic acid；4-[3-Cyano-6-[2-(methoxymethoxy)phenyl]-2-(thiophene-2-carbonylamino)pyridin-4-yl]benzoic acid
• CAS: 925932-61-2
• 化学式: C₂₆H₁₉N₃O₅S
• 分子量: 485.52
• InChiKey: DNDVXXANCBJLPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  150
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-{3-cyano-6-[2-(methoxymethoxy)phenyl]-2-[(thiophen-2-ylcarbonyl)amino]pyridin-4-yl}benzoic acid 、 N-叔丁氧羰基-1,2-乙二胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以64%的产率得到tert-butyl (2-{[(4-{3-cyano-6-[2-(methoxymethoxy)-phenyl]-2-[(thiophen-2-ylcarbonyl)amino]pyridin-4-yl}-phenyl)carbonyl]amino}ethyl)carbamate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 2-acylamino-4,6-diphenylpyridine derivatives as novel antagonists of GPR54

  摘要：

  GPR54 is a G protein-coupled receptor (GPCR) which was formerly an orphan receptor. Recent functional study of GPR54 revealed that the receptor has an essential role to modulate sex-hormones including GnRH. Though antagonists of GPR54 are expected to be novel drugs for sex-hormone dependent diseases such as prostate cancer or endometriosis, small molecule GPR54 antagonists have not been reported. We have synthesized a series of 2-acylamino-4,6-diphenylpyridines to identify potent GPR54 antagonists. Detailed structure-activity relationship studies led to compound 9l with an IC50 value of 3.7 nM in a GPR54 binding assay, and apparent antagonistic activity in a cellular functional assay. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.036
• 作为产物：
  描述：

  2-噻吩甲酰氯 、 methyl 4-{2-amino-3-cyano-6-[2-(methoxymethoxy)-phenyl]pyridin-4-yl}benzoate 在 吡啶 、 sodium hydroxide 、 水 、 盐酸 作用下， 反应 19.0h， 以81%的产率得到4-{3-cyano-6-[2-(methoxymethoxy)phenyl]-2-[(thiophen-2-ylcarbonyl)amino]pyridin-4-yl}benzoic acid
  参考文献：
  名称：

  EP1921066

  摘要：

  公开号：

文献信息

• PYRIDYLPHENOL COMPOUND AND USE THEREOF
  申请人：Sasaki Satoshi

  公开号：US20090156646A1

  公开（公告）日：2009-06-18

  The present invention provides a compound which has metastin receptor antagonist activity and is useful for preventing and treating hormone-dependent cancer, benign prostatomegaly, endometriosis, precocious puberty, uterine myoma or the like. More specifically, the present invention provides a compound, represented by the formula: or a salt thereof, a prodrug thereof, and a pharmaceutical agent containing the same; wherein Ring A represents a 5- to 8-membered homocyclic or heterocyclic group optionally having a substituent other than formula —X-R 1 wherein X represents a bond or a spacer, and R 1 represents optionally substituted amino or an optionally substituted nitrogen-containing heterocyclic group; Ring B represents an optionally substituted benzene ring; R 2 represents an optionally substituted homocyclic or heterocyclic group; and R 3 and R 4 independently represent a hydrogen atom, cyano, acyl or an optionally substituted hydrocarbon group.

  本发明提供了一种具有转移素受体拮抗活性的化合物，可用于预防和治疗激素依赖性癌症、良性前列腺增生、子宫内膜异位症、早熟、子宫肌瘤等。更具体地，本发明提供了一种化合物，其表示为以下公式：或其盐、前药及含有该化合物的药物制剂；其中环A表示一个5-至8-成员的同环或异环族群，可选地具有除公式—X-R1以外的取代基，其中X表示键或空间组分，而R1表示可选地取代的氨基或可选地取代的含氮杂环族群；环B表示可选地取代的苯环；R2表示可选地取代的同环或异环族群；而R3和R4独立地表示氢原子、氰基、酰基或可选地取代的碳氢基团。