(3S,4R)-3-hydroxy-4-[(2S)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile | 129655-17-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (3S,4R)-3-hydroxy-4-[(2S)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile
• 英文别名: 2H-1-Benzopyran-6-carbonitrile, 3,4-dihydro-3-hydroxy-4-((2S)-2-(hydroxymethyl)-5-oxo-1-pyrrolidinyl)-2,2-dimethyl-, (3S,4R)-
• CAS: 129655-17-0
• 化学式: C₁₇H₂₀N₂O₄
• 分子量: 316.35
• InChiKey: PBEGNZBJXJTFMB-XZJROXQQSA-N

物化性质

• 沸点：
  538.1±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  93.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-hydroxy-4-[(2S)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 (3S,4R)-3-Hydroxy-4-[4-(2-methyl-benzyloxy)-benzenesulfonyl]-tetrahydro-pyran-3-carboxylic acid
  参考文献：
  名称：

  3-Hydroxy-4-arylsulfonyltetrahydropyranyl-3-hydroxamic acids are novel inhibitors of MMP-13 and aggrecanase

  摘要：

  N-Hydroxy-3-hydroxy-4-arylsulfonyltetrahydropyranyl-3-carboxamides were designed as novel inhibitors of MMP-13 and aggrecanase based on known endocyclic hydroxamate inhibitors of matrix metalloproteinases. These compounds offer favorable physicochemical properties and low metabolic clearance. Synthesis and structure-activity relationships are reported. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.081
• 作为产物：
  描述：

  4-Methoxy-benzoic acid 5,6-dihydro-2H-pyran-3-ylmethyl ester 在 potassium carbonate 过氧乙酸 、 ruthenium trichloride 、 potassium osmate(VI) 、 sodium periodate 、 氯化亚砜 、 Hydroquinone 1,4-phthalazinediyl diether 、 sodium acetate 、 sodium hydride 、 caesium carbonate 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 3.0h， 生成 (3S,4R)-3-hydroxy-4-[(2S)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile
  参考文献：
  名称：

  3-Hydroxy-4-arylsulfonyltetrahydropyranyl-3-hydroxamic acids are novel inhibitors of MMP-13 and aggrecanase

  摘要：

  N-Hydroxy-3-hydroxy-4-arylsulfonyltetrahydropyranyl-3-carboxamides were designed as novel inhibitors of MMP-13 and aggrecanase based on known endocyclic hydroxamate inhibitors of matrix metalloproteinases. These compounds offer favorable physicochemical properties and low metabolic clearance. Synthesis and structure-activity relationships are reported. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.081

文献信息

• Nouveaux dérivés de l'amino chromanol, leur procédé de préparation et les compositions pharmaceutiques les renfermant
  申请人：ADIR ET COMPAGNIE

  公开号：EP0365416B1

  公开（公告）日：1993-09-15
• JPH02149578A
  申请人：——

  公开号：JPH02149578A

  公开（公告）日：1990-06-08
• Intranasal administration of modulators of hypothalamic ATP-sensitive potassium channels
  申请人：Herlands Louis

  公开号：US20070026079A1

  公开（公告）日：2007-02-01

  Provided are methods of increasing K ATP channel activity in the hypothalamus of a mammal, methods of reducing glucose production in a mammal, methods of reducing peripheral glucose levels in a mammal, methods of reducing triglyceride levels in a mammal, methods of reducing very low density lipoprotein (VLDL) levels in a mammal, methods of methods of reducing gluconeogenesis in the liver of a mammal, methods of treating metabolic disorders such as diabetes, hyperglycemia, insulin resistance, glucose intolerance, metabolic syndrome and/or obesity, and methods of increasing glucose production and peripheral glucose levels in a mammal. Also provided are methods of treating heart failure, ischemia, coronary heart disease, familial lipoprotein lipase deficiency, hypopituitarism, hyperlipidemia, hypertriglyceridemia, hyperVLDLemia, atherosclerosis, hypercholesterolemia, hypertension, polycystic ovary syndrome, gonadotropin deficiency and/or amenorrhea.
• Modulation of Hypothalamic Atp-Sensitive Potassium Channels
  申请人：Rossetti Luciano

  公开号：US20090012067A1

  公开（公告）日：2009-01-08

  Provided are methods of increasing K ATP activity in the hypothalamus of a mammal, methods of reducing glucose production and peripheral blood glucose levels in a mammal, methods of inhibiting gluconeogenesis in the liver of a mammal, and methods of increasing glucose production and peripheral blood glucose levels in a mammal.
• US4999372A
  申请人：——

  公开号：US4999372A

  公开（公告）日：1991-03-12