(+/-)-aerophobin-1 | 103667-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: (+/-)-aerophobin-1
• 英文别名: (5R,10S)-N-(2-(1H-Imidazol-4-yl)ethyl)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide；(5R,6S)-7,9-dibromo-6-hydroxy-N-[2-(1H-imidazol-5-yl)ethyl]-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxamide
• CAS: 103667-67-0
• 化学式: C₁₅H₁₆Br₂N₄O₄
• 分子量: 476.124
• InChiKey: MDUQIEXQKMPARD-HIFRSBDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 7,9-dibromo-8-methoxy-6-oxo-1-oxa-2-azaspiro<4.5>deca-2,7,9-triene-3-carboxylate 在 zinc(II) tetrahydroborate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 为溶剂， 反应 0.12h， 生成 (+/-)-aerophobin-1
  参考文献：
  名称：

  (±)-Aerothionin、(±)-Homoaerothionin 和 (±)-Aerophobin-1 的全合成

  摘要：

  (±)-Aerothionin、(±)-homoaerothionin 和 (±)-aerophobin-1 已成功合成，使用三氟乙酸铊 (III) 对丙酮酸甲酯肟衍生物的酚氧化作为关键步骤。通过将 1H NMR 光谱与相关化合物的光谱进行比较，还确定了 Aerophobin-2 的立体结构。

  DOI：

  10.1246/bcsj.58.3453

文献信息

• Marine Compounds with Calcium Channel Blocking Properties for the Treatment of Cognitive or Neurodegenerative Diseases
  申请人：Gil Ana Martinez

  公开号：US20080039513A1

  公开（公告）日：2008-02-14

  The invention provides compounds having a spiro heterocyclic unit connected through a linker of a certain length to another spiro cycle, an imidazole ring or an amide group. Some of these compounds have been obtained from Aplysinia cavernicola and a mixture of Aplysina fulva and Oceanapia . The compounds exhibit VDCC blocker activity; some also show acetylcholinesterase and butyrylcholinesterase inhibition activities. Therefore they are useful in the treatment of cognitive and neurodegenerative disorders, such as brain ischemia, stroke, cognitive disorders as senile dementia, cerebrovascular dementia, mild recognition impairment, attention deficit disorder, and/or neurodegenerative dementing disease with aberrant protein aggregations as specially Alzheimers's disease or condition, or prion disease as Creutzfeld-Jakob disease or Gerstmann-Straussler-Scheinker disease.
• [EN] MARINE COMPOUNDS WITH CALCIUM CHANNEL BLOCKING PROPERTIES FOR THE TREATMENT OF COGNITIVE OR NEURODEGENERATIVE DISEASES<br/>[FR] COMPOSES MARINS POSSEDANT DES PROPRIETES BLOQUANT LES CANAUX CALCIQUES, DESTINES AU TRAITEMENT DE MALADIES COGNITIVES OU NEURODEGENERATIVES
  申请人：NEUROPHARMA SA

  公开号：WO2005123073A1

  公开（公告）日：2005-12-29

  The invention provides compounds having a spiro heterocyclic unit connected through a linker of a certain length to another spiro cycle, an imidazole ring or an amide group. Some of these compounds have been obtained from Aplysinia cavernicola and a mixture of Aplysina fulva and Oceanapia. The compounds exhibit VDCC blocker activity; some also show acetylcholinesterase and butyrylcholinesterase inhibition activities. Therefore they are useful in the treatment of cognitive and neurodegenerative disorders, such as brain ischemia, stroke, cognitive disorders as senile dementia, cerebrovascular dementia, mild recognition impairment, attention deficit disorder, and/or neurodegenerative dementing disease with aberrant protein aggregations as specially Alzheimers's disease or condition, or prion disease as Creutzfeld-Jakob disease or Gerstmann-Straussler-Scheinker disease.
• Total Syntheses of (±)-Aerothionin, (±)-Homoaerothionin, and (±)-Aerophobin-1
  作者：Shigeru Nishiyama、Shosuke Yamamura

  DOI：10.1246/bcsj.58.3453

  日期：1985.12

  (±)-aerophobin-1 have been successfully synthesized using phenolic oxidation of the methyl pyruvate oxime derivative with thallium(III) trifluoroacetate as a key step. The stereostructure of aerophobin-2 has been also established by comparison of the 1H NMR spectrum with those of related compounds.

  (±)-Aerothionin、(±)-homoaerothionin 和 (±)-aerophobin-1 已成功合成，使用三氟乙酸铊 (III) 对丙酮酸甲酯肟衍生物的酚氧化作为关键步骤。通过将 1H NMR 光谱与相关化合物的光谱进行比较，还确定了 Aerophobin-2 的立体结构。