2-[(E)-Hydroxyimino]-1a,2-dihydro-1H-7-oxa-cyclopropa[b]naphthalene-7a-carboxylic acid methyl-phenyl-amide | 177610-88-7

• 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: 2-[(E)-Hydroxyimino]-1a,2-dihydro-1H-7-oxa-cyclopropa[b]naphthalene-7a-carboxylic acid methyl-phenyl-amide
• 英文别名: (7E)-7-hydroxyimino-N-methyl-N-phenyl-1,7a-dihydrocyclopropa[b]chromene-1a-carboxamide
• CAS: 177610-88-7
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: OXCHNAWHIAXEFF-MNDPQUGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-methyl-N-phenyl-4-oxochromen-2-carboxamide 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(E)-Hydroxyimino]-1a,2-dihydro-1H-7-oxa-cyclopropa[b]naphthalene-7a-carboxylic acid methyl-phenyl-amide
  参考文献：
  名称：

  A novel class of antagonists for metabotropic glutamate receptors, 7-(Hydroxyimino)cyclopropa[b]chromen-1a-carboxylates

  摘要：

  7-(Hydroxyimino)cyclopropa[b] chromen-1a-carboxylates (4a-c), highly potent antagonists for a phospholipase C-linked metabotropic glutamate receptor, mGluR1, were synthesized through cyclopropanation onto 4-oxo-4H-1-benzopyran-2-carboxylates (5a-c) utilizing dimethyloxosulfonium methylid followed by treatment with hydroxylamine. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00104-7

文献信息

• CYCLOPROPACHROMENECARBOXYLATE DERIVATIVES
  申请人：SUNTORY LIMITED

  公开号：EP0787723A1

  公开（公告）日：1997-08-06

  The present invention provides novel cyclopropachromencarboxylic acid derivatives having an antagonistic activity against metabotropic glutamate receptors and its pharmaceutically acceptable salts. Cyclopropachromencarboxylic acid derivatives and its pharmaceutically acceptable salts represented by the following general formula (1): [wherein A denotes an oxygen atom, hydroxyimino group, an alkyloxyimino group having 1 to 5 carbon atoms, or the group =N-O-(CH2)n-NR1R2 (where n represents an integer of 2 to 8, and each of R1 and R2 independently represents a hydrogen atom or alkyl group having 1 to 5 carbon atoms, respectively); B denotes the group -COOR3(where R3 represents a hydrogen atom or alkyl group having 1 to 5 carbon atoms) or the group -CONR4R5 (where R4 and R5 independently represent a hydrogen atom, alkyl group having 1 to 5 carbon atoms, alkenyl group having 2 to 5 carbon atoms, aminoalkyl group having 1 to 5 carbon atoms wherein N may be substituted, nitrogen-containing saturated heterocycle of which N may be substituted, phenyl group which may be substituted with a halogen atom or hydroxyl group which in turn may be substituted, 2-pyridyl group, or aralkyl group having 7 to 10 carbon atoms, or R4and R5 taken together with the nitrogen atom to which they are attached form a nitrogen-containing heterocyclic ring-system which may be substituted); and X is a halogen atom or the group -OR6(where R6 represents a hydrogen atom, alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms)].

  本发明提供了对代谢型谷氨酸受体具有拮抗活性的新型环丙色羧酸衍生物及其药学上可接受的盐类。由以下通式（1）代表的环丙基色羧酸衍生物及其药学上可接受的盐： [其中 A 表示氧原子、羟基亚氨基、具有 1 至 5 个碳原子的烷氧基亚氨基或基团 =N-O-(CH2)n-NR1R2（其中 n 代表 2 至 8 的整数，R1 和 R2 分别独立地代表氢原子或具有 1 至 5 个碳原子的烷基）； B 表示基团 -COOR3（其中 R3 代表氢原子或具有 1 至 5 个碳原子的烷基）或基团 -CONR4R5（其中 R4 和 R5 分别独立地代表氢原子、具有 1 至 5 个碳原子的烷基、具有 2 至 5 个碳原子的烯基、具有 1 至 5 个碳原子的氨基烷基，其中 N 可被取代、其中 N 可被取代的含氮饱和杂环，可被卤素原子或羟基取代的苯基，可被取代的 2-吡啶基，或具有 7 至 10 个碳原子的芳烷基，或 R4 和 R5 与它们所连接的氮原子一起形成可被取代的含氮杂环环系）；和 X 是卤素原子或基团-OR6（其中 R6 代表氢原子、具有 1 至 5 个碳原子的烷基、具有 3 至 6 个碳原子的烯基或具有 7 至 10 个碳原子的芳基）]。
• A novel class of antagonists for metabotropic glutamate receptors, 7-(Hydroxyimino)cyclopropa[b]chromen-1a-carboxylates
  作者：Hirokazu Annoura、Atsuko Fukunaga、Mayumi Uesugi、Toshio Tatsuoka、Yoshiko Horikawa

  DOI：10.1016/0960-894x(96)00104-7

  日期：1996.4

  7-(Hydroxyimino)cyclopropa[b] chromen-1a-carboxylates (4a-c), highly potent antagonists for a phospholipase C-linked metabotropic glutamate receptor, mGluR1, were synthesized through cyclopropanation onto 4-oxo-4H-1-benzopyran-2-carboxylates (5a-c) utilizing dimethyloxosulfonium methylid followed by treatment with hydroxylamine. Copyright (C) 1996 Elsevier Science Ltd