methyl 3-isothiocyanatopyridine-2-carboxylate | 898908-81-1

• 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: methyl 3-isothiocyanatopyridine-2-carboxylate
• CAS: 898908-81-1
• 化学式: C₈H₆N₂O₂S
• 分子量: 194.214
• InChiKey: KEDYZDAIAWNOJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-isothiocyanatopyridine-2-carboxylate 在 氨 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 mineral oil 为溶剂， 反应 9.0h， 生成 2-(methylsulfanyl)-3H,4H-pyrido[3,2-d]pyrimidin-4-one
  参考文献：
  名称：

  [EN] COMPOUNDS AS ASIC INHIBITORS AND USES THEREOF
  [FR] COMPOSÉS UTILISÉS EN TANT QU'INHIBITEURS D'ASIC ET UTILISATIONS DE CEUX-CI

  摘要：

  本发明涉及化合物及其药用可接受的组合物，用作ASIC抑制剂。

  公开号：

  WO2017045750A1
• 作为产物：
  描述：

  硫光气 、 3-氨基吡啶-2-羧酸甲酯 在 碳酸氢钠 作用下， 以 氯仿 、 水 为溶剂， 以89.3%的产率得到methyl 3-isothiocyanatopyridine-2-carboxylate
  参考文献：
  名称：

  [EN] COMPOUNDS AS ASIC INHIBITORS AND USES THEREOF
  [FR] COMPOSÉS UTILISÉS EN TANT QU'INHIBITEURS D'ASIC ET UTILISATIONS DE CEUX-CI

  摘要：

  本发明涉及化合物及其药用可接受的组合物，用作ASIC抑制剂。

  公开号：

  WO2017045750A1

文献信息

• Discovery of a Novel 5-HT₃ Antagonist/5-HT_1A Agonist 3-Amino-5,6,7,8-tetrahydro-2-{4-[4-(quinolin-2-yl)piperazin-1-yl]butyl}quinazolin-4(3<i>H</i>)-one (TZB-30878) as an Orally Bioavailable Agent for Irritable Bowel Syndrome
  作者：Akira Asagarasu、Teruaki Matsui、Hiroyuki Hayashi、Satoru Tamaoki、Yukinao Yamauchi、Kouichi Minato、Michitaka Sato

  DOI：10.1021/jm1002292

  日期：2010.11.11

  We have prepared a series of quinazolinone derivatives linked with piperazinylquinoline for the treatment of irritable bowel syndrome (IBS). Using pharmacophore analysis, we designed and synthesized compounds which bind to both serotonin receptor subtype 1A (5-HT1A) and subtype 3 (5-HT3). Quinazolinone derivatives with a sulfur atom in the linker showed high affinity in in vitro assays, but low in vivo activity. Focusing on the linker to improve the pharmacokinetic profile, the sulfur atom in the linker was replaced with a methylene group. Further optimization led to the discovery of compound 17m (TZB-30878) (J. Pharmacol. Exp. Ther. 2007, 322, 1315-1323, Patent WO2005082887 (A1), 2005), a novel 5-HT1A agonist/5-HT3 antagonist in the 3-aminoquinazolinone series. In in vivo functional assays, 17m dose dependently inhibited the Bezold-Jarisch reflex and induced 5-HT1A-mediated behaviors, and in an IBS animal model, 17m significantly inhibited stress-induced defecation. Pretreatment by WAY-100635 (5-HT1A antagonist) significantly attenuated but did not abolish the inhibitory effects of 17m. These results suggested that 17m exerted inhibitory effects via both 5-HT1A agonistic and 5-HT3 antagonistic activities and that 17m would be useful as a therapeutic agent for IBS.
• Structural Basis for Highly Selective Class II Alpha Phosphoinositide-3-Kinase Inhibition
  作者：Murat Kücükdisli、Hassen Bel-Abed、Davide Cirillo、Wen-Ting Lo、Nina-Louisa Efrém、André Horatscheck、Liudmila Perepelittchenko、Polina Prokofeva、Theresa A. L. Ehret、Silke Radetzki、Martin Neuenschwander、Edgar Specker、Guillaume Médard、Susanne Müller、Stephanie Wilhelm、Bernhard Kuster、Jens Peter von Kries、Volker Haucke、Marc Nazaré

  DOI：10.1021/acs.jmedchem.3c01319

  日期：2023.10.26
• NOVEL MOLECULES FOR REGULATING CELL DEATH
  申请人：Nunnari Jodi

  公开号：US20080287473A1

  公开（公告）日：2008-11-20

  The present invention provides compounds capable of regulating apoptosis, e.g., via regulating mitochondrial fission or fusion. The present invention also provides methods of screening for compounds capable of regulating apoptosis and methods of treating conditions association with apoptosis.
• US8450333B2
  申请人：——

  公开号：US8450333B2

  公开（公告）日：2013-05-28
• [EN] COMPOUNDS AS ASIC INHIBITORS AND USES THEREOF<br/>[FR] COMPOSÉS UTILISÉS EN TANT QU'INHIBITEURS D'ASIC ET UTILISATIONS DE CEUX-CI
  申请人：MERCK PATENT GMBH

  公开号：WO2017045750A1

  公开（公告）日：2017-03-23

  The present invention relates to compounds, and pharmaceutically acceptable compositions thereof, useful as ASIC inhibitors.

  本发明涉及化合物及其药用可接受的组合物，用作ASIC抑制剂。