(2S)-6-nitro-2-methyl-2-dimethoxymethyl-3,4-epoxy-3,4-dihydro-2H-1-benzopyran | 335382-13-3

• 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: (2S)-6-nitro-2-methyl-2-dimethoxymethyl-3,4-epoxy-3,4-dihydro-2H-1-benzopyran
• 英文别名: (2S)-2-(dimethoxymethyl)-2-methyl-6-nitro-1a,7b-dihydrooxireno[2,3-c]chromene
• CAS: 335382-13-3
• 化学式: C₁₃H₁₅NO₆
• 分子量: 281.265
• InChiKey: IUCVZCYPEDRIRJ-XIVSLSHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  86
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-6-nitro-2-methyl-2-dimethoxymethyl-3,4-epoxy-3,4-dihydro-2H-1-benzopyran 、 4-trifluoromethoxyphenyl-1H-imidazol-2-ylmethylamine 在 CoCl₂ 作用下， 以 乙腈 为溶剂， 生成 (2S,3R,4S)-2-Dimethoxymethyl-4-[(1H-imidazol-2-ylmethyl)-(4-trifluoromethoxy-phenyl)-amino]-2-methyl-6-nitro-chroman-3-ol
  参考文献：
  名称：

  Identification of a novel antiangiogenic agent; 4-(N-Imidazol-2-ylmethyl)amino benzopyran analogues

  摘要：

  A series of 4-(N-imidazol-2-ylmethyl)aminobenzopyran analogues, originally designed as K-ATP openers for ischemic diseases, showed antiangiogenic properties through the inhibition of HUVEC tube formation. Especially one of p-Cl substituted analogues (4c) completely inhibited HUVEC tube formation at 10 muM. The compound 4c significantly inhibited tumor growth by 52% on A549 (human non small cell lung carcinoma) in nude mice xenografts without any significant side effects. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00248-8
• 作为产物：
  描述：

  (2S)-2-dimethoxymethyl-2-methyl-6-nitro-2H-1-benzopyran 在 Oxone 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 0.17h， 以97%的产率得到(2S)-6-nitro-2-methyl-2-dimethoxymethyl-3,4-epoxy-3,4-dihydro-2H-1-benzopyran
  参考文献：
  名称：

  BENZOPYRANYL GUANIDINE DERIVATIVES, PROCESS FOR PREPARATION THEREOF, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

  摘要：

  公开号：

  EP1228058B1

文献信息

• US6323238B1
  申请人：——

  公开号：US6323238B1

  公开（公告）日：2001-11-27
• Identification of a novel antiangiogenic agent; 4-(N-Imidazol-2-ylmethyl)amino benzopyran analogues
  作者：Nakjeong Kim、Sunkyung Lee、Kyu Yang Yi、Sung-eun Yoo、Guncheol Kim、Chong Ock Lee、Sung Hee Park、Byung Ho Lee

  DOI：10.1016/s0960-894x(03)00248-8

  日期：2003.5

  A series of 4-(N-imidazol-2-ylmethyl)aminobenzopyran analogues, originally designed as K-ATP openers for ischemic diseases, showed antiangiogenic properties through the inhibition of HUVEC tube formation. Especially one of p-Cl substituted analogues (4c) completely inhibited HUVEC tube formation at 10 muM. The compound 4c significantly inhibited tumor growth by 52% on A549 (human non small cell lung carcinoma) in nude mice xenografts without any significant side effects. (C) 2003 Elsevier Science Ltd. All rights reserved.
• BENZOPYRANYL GUANIDINE DERIVATIVES, PROCESS FOR PREPARATION THEREOF, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Dongbu Hannong Chemical Co., Ltd.

  公开号：EP1228058B1

  公开（公告）日：2003-12-10