N-[4-(3-aminophenyl)-3-cyano-6-(2-hydroxyphenyl)-pyridin-2-yl]thiophene-2-carboxamide | 712350-29-3

• 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-aminophenyl)-3-cyano-6-(2-hydroxyphenyl)-pyridin-2-yl]thiophene-2-carboxamide
• 英文别名: N-[4-(3-aminophenyl)-3-cyano-6-(2-hydroxyphenyl)-2-pyridinyl]thiophene-2-carboxamide；N-[4-(3-Aminophenyl)-3-cyano-6-(2-hydroxyphenyl)-pyridin-2-yl]thiophene-2-carboxamide；N-[4-(3-aminophenyl)-3-cyano-6-(2-hydroxyphenyl)pyridin-2-yl]thiophene-2-carboxamide
• CAS: 712350-29-3
• 化学式: C₂₃H₁₆N₄O₂S
• 分子量: 412.472
• InChiKey: XGNPENONKBZCME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[4-(3-aminophenyl)-3-cyano-6-(2-hydroxyphenyl)-pyridin-2-yl]thiophene-2-carboxamide 、 甲氧基乙酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以61%的产率得到N-(3-cyano-6-(2-hydroxyphenyl)-4-{3-[(methoxyacetyl)amino]phenyl}-2-pyridinyl)thiophene-2-carboxamide
  参考文献：
  名称：

  [DE] SUBSTITUIERTE 4-ARYL-PYRIDINE ALS KISS-1 ANTAGONISTEN
  [EN] SUBSTITUTED 4-ARYL PYRIDINES USED AS KISS-1 ANTAGONISTS
  [FR] 4-ARYL-PYRIDINES SERVANT D'ANTAGONISTES DE KISS-1

  摘要：

  这项发明涉及新的具有公式（I）中R1-R4的含义的4-芳基吡啶，如权利要求1所述，以及制备它们的方法和它们用于治疗和/或预防疾病的用途以及用于制造治疗和/或预防疾病的药物的用途，特别是用于治疗和/或预防疼痛和/或泌尿系统功能障碍。

  公开号：

  WO2004058716A1
• 作为产物：
  描述：

  N-[4-(3-aminophenyl)-6-(2-{[tert-butyl(dimethyl)silyl]-oxy}phenyl)-3-cyanopyridin-2-yl]thiophene-2-carboxamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以17%的产率得到N-[4-(3-aminophenyl)-3-cyano-6-(2-hydroxyphenyl)-pyridin-2-yl]thiophene-2-carboxamide
  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。
• Synthesis and structure–activity relationships of 2-acylamino-4,6-diphenylpyridine derivatives as novel antagonists of GPR54
  作者：Toshitake Kobayashi、Satoshi Sasaki、Naoki Tomita、Seiji Fukui、Noritaka Kuroda、Masaharu Nakayama、Atsushi Kiba、Yoshihiro Takatsu、Tetsuya Ohtaki、Fumio Itoh

  DOI：10.1016/j.bmc.2010.04.036

  日期：2010.6.1

  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.
• [DE] SUBSTITUIERTE 4-ARYL-PYRIDINE ALS KISS-1 ANTAGONISTEN<br/>[EN] SUBSTITUTED 4-ARYL PYRIDINES USED AS KISS-1 ANTAGONISTS<br/>[FR] 4-ARYL-PYRIDINES SERVANT D'ANTAGONISTES DE KISS-1
  申请人：BAYER HEALTHCARE AG

  公开号：WO2004058716A1

  公开（公告）日：2004-07-15

  Die Erfindung betrifft neue 4-Aryl-Pyridine Der Formel (I) mit den Bedeutungen von R1-R4 gemäss Ansprüche 1, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung und/oder Prophylaxe von Krankheiten sowie ihre Verwendung zur Herstellung von Arzneimitteln zur Behandlung und/oder Prophylaxe von Krankheiten, insbesondere zur Behandlung und/oder Prophylaxe von Schmerzzuständen und/oder urologischen Funktionsstörungen.

  这项发明涉及新的具有公式（I）中R1-R4的含义的4-芳基吡啶，如权利要求1所述，以及制备它们的方法和它们用于治疗和/或预防疾病的用途以及用于制造治疗和/或预防疾病的药物的用途，特别是用于治疗和/或预防疼痛和/或泌尿系统功能障碍。