(3aRS,8aRS)-2-benzyl-6,6-dimethylhexahydro-[1,3]dioxepino[5,6-d]isoxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: (3aRS,8aRS)-2-benzyl-6,6-dimethylhexahydro-[1,3]dioxepino[5,6-d]isoxazole
• 英文别名: (3aR,8aR)-2-benzyl-6,6-dimethyl-3a,4,8,8a-tetrahydro-3H-[1,3]dioxepino[5,6-d][1,2]oxazole
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: AZKMCCXCDKOGOC-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aRS,8aRS)-2-benzyl-6,6-dimethylhexahydro-[1,3]dioxepino[5,6-d]isoxazole 在 palladium 10% on activated carbon 氢气 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 (5R,6R)-6-(aminomethyl)-2,2-dimethyl-1,3-dioxepan-5-ol
  参考文献：
  名称：

  WO2008/30118

  摘要：

  公开号：
• 作为产物：
  描述：

  钆布醇中间体 在 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 6.75h， 以42.5%的产率得到(3aRS,8aRS)-2-benzyl-6,6-dimethylhexahydro-[1,3]dioxepino[5,6-d]isoxazole
  参考文献：
  名称：

  WO2008/30118

  摘要：

  公开号：

文献信息

• Transition state analogue inhibitors of human methylthioadenosine phosphorylase and bacterial methylthioadenosine/S-adenosylhomocysteine nucleosidase incorporating acyclic ribooxacarbenium ion mimics
  作者：Keith Clinch、Gary B. Evans、Richard F.G. Fröhlich、Shivali A. Gulab、Jemy A. Gutierrez、Jennifer M. Mason、Vern L. Schramm、Peter C. Tyler、Anthony D. Woolhouse

  DOI：10.1016/j.bmc.2012.07.006

  日期：2012.9

  Several acyclic hydroxy-methylthio-amines with 3-5 carbon atoms were prepared and coupled via a methylene link to 9-deazaadenine. The products were tested for inhibition against human MTAP and Escherichia coli and Neisseria meningitidis MTANs and gave K-i values as low as 0.23 nM. These results were compared to those obtained with 1st and 2nd generation inhibitors (1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-methylthio-D-ribitol (MT-Immucillin-A, 3) and (3R,4S)-1-[9-deazaadenin-9-yl)methyl]3-hydroxy-4-methylthiomethylpyrrolidine (MT-DADMe-Immucillin-A, 4). The best inhibitors were found to exhibit binding affinities of approximately 2- to 4-fold those of 3 but were significantly weaker than 4. Cleavage of the 2,3 carbon-carbon bond in MT-Immucillin-A (3) gave an acyclic product (79) with a 21,500 fold loss of activity against E. coli MTAN. In another case, N-methylation of a side chain secondary amine resulted in a 250-fold loss of activity against the same enzyme [(+/-)-65 vs (+/-)-68]. The inhibition results were also contrasted with those acyclic derivatives previously prepared as inhibitors for a related enzyme, purine nucleoside phosphorylase (PNP), where some inhibitors in the latter case were found to be more potent than their cyclic counterparts. (C) 2012 Elsevier Ltd. All rights reserved.
• US8383636B2
  申请人：——

  公开号：US8383636B2

  公开（公告）日：2013-02-26
• WO2008/30118
  申请人：——

  公开号：——

  公开（公告）日：——