N-{4-[3-(β-alanylamino)phenyl]-3-cyano-6-(2-hydroxy-4-methoxyphenyl)pyridin-2-yl}benzamide trifluoroacetate | 925924-85-2

• 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: N-{4-[3-(β-alanylamino)phenyl]-3-cyano-6-(2-hydroxy-4-methoxyphenyl)pyridin-2-yl}benzamide trifluoroacetate
• 英文别名: N-[4-[3-(3-aminopropanoylamino)phenyl]-3-cyano-6-(2-hydroxy-4-methoxyphenyl)pyridin-2-yl]benzamide;2,2,2-trifluoroacetic acid
• CAS: 925924-85-2
• 化学式: C₂HF₃O₂*C₂₉H₂₅N₅O₄
• 分子量: 621.573
• InChiKey: JLWLGSVYCBQZHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  45
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  188
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  tert-butyl {3-[(3-{3-cyano-6-[4-methoxy-2-(methoxymethoxy)phenyl]-2-[(phenylcarbonyl)amino]pyridin-4-yl}phenyl)-amino]-3-oxopropyl}carbamate 、 三氟乙酸 反应 1.5h， 以86%的产率得到N-{4-[3-(β-alanylamino)phenyl]-3-cyano-6-(2-hydroxy-4-methoxyphenyl)pyridin-2-yl}benzamide trifluoroacetate
  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

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。