6-hydroxy-8-mercapto-3,4-dihydro-1H-pyrano[3,4-c]pyridine-5-carbonitrile | 1001088-45-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: 6-hydroxy-8-mercapto-3,4-dihydro-1H-pyrano[3,4-c]pyridine-5-carbonitrile
• 英文别名: 6-Oxo-8-sulfanyl-1,3,4,7-tetrahydropyrano[3,4-c]pyridine-5-carbonitrile
• CAS: 1001088-45-4
• 化学式: C₉H₈N₂O₂S
• 分子量: 208.241
• InChiKey: GRRYMCMPFWCCQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-hydroxy-8-mercapto-3,4-dihydro-1H-pyrano[3,4-c]pyridine-5-carbonitrile 、 2-氯苄溴 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 8-(2-chlorobenzylthio)-6-hydroxy-3,4-dihydro-1H-pyrano[3,4-c]pyridine-5-carbonitrile
  参考文献：
  名称：

  Discovery of 3-hydroxy-4-cyano-isoquinolines as novel, potent, and selective inhibitors of human 11β-hydroxydehydrogenase 1 (11β-HSD1)

  摘要：

  Derived from the HTS hit 1, a series of hydroxyisoquinolines was discovered as potent and selective 11 beta-HSD1 inhibitors with good cross species activity. Optimization of substituents at the 1 and 4 positions of the isoquinoline group in addition to the core modifications, with a special focus on enhancing metabolic stability and aqueous solubility, resulted in the identification of several compounds as potent advanced leads. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.058
• 作为产物：
  描述：

  四氢吡喃酮 在 三乙胺 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 8-mercapto-3,4-dihydro-1H-pyrano[3,4-c]pyridin-6-ol 、 6-hydroxy-8-mercapto-3,4-dihydro-1H-pyrano[3,4-c]pyridine-5-carbonitrile
  参考文献：
  名称：

  Discovery of 3-hydroxy-4-cyano-isoquinolines as novel, potent, and selective inhibitors of human 11β-hydroxydehydrogenase 1 (11β-HSD1)

  摘要：

  Derived from the HTS hit 1, a series of hydroxyisoquinolines was discovered as potent and selective 11 beta-HSD1 inhibitors with good cross species activity. Optimization of substituents at the 1 and 4 positions of the isoquinoline group in addition to the core modifications, with a special focus on enhancing metabolic stability and aqueous solubility, resulted in the identification of several compounds as potent advanced leads. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.058

文献信息

• PYRIDONE/HYDROXYPYRIDINE 11-BETA HYDROXYSTEROID DEHYDROGENASE TYPE I INHIBITORS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20140128365A1

  公开（公告）日：2014-05-08

  Novel compounds are provided which are 11-beta-hydroxysteroid dehydrogenase type I inhibitors. 11-beta-hydroxysteroid dehydrogenase type I inhibitors are useful in treating, preventing, or slowing the progression of diseases requiring 11-beta-hydroxysteroid dehydrogenase type I inhibitor therapy. These novel compounds have the structure: enantiomers, diastereomers, solvates, salts, tautomers or prodrugs thereof wherein, A, W, X, Y and R 1 are defined herein.

  提供了一种新型化合物，这些化合物是11-β-羟基类固醇脱氢酶I型抑制剂。11-β-羟基类固醇脱氢酶I型抑制剂在治疗、预防或减缓需要11-β-羟基类固醇脱氢酶I型抑制剂治疗的疾病的进展方面是有用的。这些新型化合物具有结构：对映体、顺反异构体、溶剂化合物、盐、互变异构体或其前药，其中A、W、X、Y和R1在此处有定义。
• WO2008/5910
  申请人：——

  公开号：——

  公开（公告）日：——
• US8318941B2
  申请人：——

  公开号：US8318941B2

  公开（公告）日：2012-11-27
• [EN] PYRIDONE/HYDROXYPYRIDINE 11-BETA HYDROXYSTEROID DEHYDROGENASE TYPE I INHIBITORS<br/>[FR] INHIBITEURS DE TYPE I DE LA 11-BÊTA HYDROXYSTÉROÏDE DÉSHYDROGÉNASE PYRIDONE/HYDROXYPYRIDINE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2008005910A2

  公开（公告）日：2008-01-10

  [EN] Novel compounds are provided which are 11-beta-hydroxysteroid dehydrogenase type I inhibitors. 11-beta-hydroxysteroid dehydrogenase type I inhibitors are useful in treating, preventing, or slowing the progression of diseases requiring 11-beta-hydroxysteroid dehydrogenase type I inhibitor therapy. These novel compounds have the structure formula (I) enantiomers, diastereomers, solvates, salts, tautomers or prodrugs thereof wherein, A, W, X, Y and R₁ are defined herein.
  [FR] La présente invention concerne des composés atypiques qui sont des inhibiteurs de type I de la 11-bêta hydroxystéroïde déshydrogénase (11ß-HSD). Ces inhibiteurs de type I de la 11ß-HSD sont utiles dans le traitement, la prévention ou le ralentissement de la progression de maladies demandant une thérapie par inhibiteur de type I de la 11ß-HSD. Ces composés atypiques ont la formule de structure (I) ainsi que leurs énantiomères, diastéréoisomères, solvates, sels, tautomères ou promédicaments dérivés sachant que A, W,X et R₁ sont définis dans la présente invention.
• Discovery of 3-hydroxy-4-cyano-isoquinolines as novel, potent, and selective inhibitors of human 11β-hydroxydehydrogenase 1 (11β-HSD1)
  作者：Shung C. Wu、David Yoon、Janice Chin、Katy van Kirk、Ramakrishna Seethala、Rajasree Golla、Bin He、Thomas Harrity、Lori K. Kunselman、Nathan N. Morgan、Randolph P. Ponticiello、Joseph R. Taylor、Rachel Zebo、Timothy W. Harper、Wenying Li、Mengmeng Wang、Lisa Zhang、Bogdan G. Sleczka、Akbar Nayeem、Steven Sheriff、Daniel M. Camac、Paul E. Morin、John G. Everlof、Yi-Xin Li、Cheryl A. Ferraro、Kasia Kieltyka、Wilson Shou、Marianne B. Vath、Tatyana A. Zvyaga、David A. Gordon、Jeffrey A. Robl

  DOI：10.1016/j.bmcl.2011.09.058

  日期：2011.11

  Derived from the HTS hit 1, a series of hydroxyisoquinolines was discovered as potent and selective 11 beta-HSD1 inhibitors with good cross species activity. Optimization of substituents at the 1 and 4 positions of the isoquinoline group in addition to the core modifications, with a special focus on enhancing metabolic stability and aqueous solubility, resulted in the identification of several compounds as potent advanced leads. (C) 2011 Elsevier Ltd. All rights reserved.