Aerothionin | 28714-26-3

• 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: Aerothionin
• 英文别名: (+)-aerothionin；(5S,6R)-7,9-dibromo-N-[4-[[(5S,6R)-7,9-dibromo-6-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carbonyl]amino]butyl]-6-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxamide
• CAS: 28714-26-3
• 化学式: C₂₄H₂₆Br₄N₄O₈
• 分子量: 818.108
• InChiKey: BJWQSQOWGBUSFC-UWXQAFAOSA-N

物化性质

• 熔点：
  134～137
• 密度：
  2.05±0.1 g/cm3(Predicted)
• 溶解度：
  溶于乙醇；溶于DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  160
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 Aerothionin 在 吡啶 作用下， 生成
  参考文献：
  名称：

  New Bioactive Bromotyrosine-Derived Alkaloid from a Marine Sponge Aplysinella sp.

  摘要：

  一种新的溴酪氨酸衍生生物碱(+)-a-plysinillin (1)与七种已知化合物一起，从收集自密克罗尼西亚联邦的海绵Aplysinella sp.的粗有机提取物中分离出来。通过核磁共振(NMR)和质谱技术推测了化合物1的结构。化合物1至8的抑制活性通过链霉菌85E的菌丝形成抑制实验进行了评估。化合物1和8对人类乳腺腺癌细胞系MCF-7表现出抗增殖活性。

  DOI：

  10.1055/s-2008-1074506
• 作为产物：
  描述：

  (5S,10R)-7,9-Dibromo-8-methoxy-10-((1S,4R)-4,7,7-trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carbonyloxy)-1-oxa-2-aza-spiro[4.5]deca-2,6,8-triene-3-carboxylic acid methyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 Aerothionin
  参考文献：
  名称：

  Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative

  摘要：

  Successful first synthesis of optically pure (+)- and (-)-aerothionins (1) from the racemic spiroisoxazoline derivative 8 has been accomplished. The absolute configuration of natural (+)-1 was determined by comparison of (+)- and (-)-8 with related derivatives. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.097

文献信息

• Asymmetric Oxidative Cyclization of <i>o</i>-Phenolic Oxime-Esters:  First Synthesis of Enantiomerically Enriched Spiroisoxazoline Methyl Esters
  作者：Masatoshi Murakata、Masafumi Tamura、Osamu Hoshino

  DOI：10.1021/jo970082i

  日期：1997.6.1

  A new method for the synthesis of enantiomerically enriched cyclohexadienone spiroisoxazoline (-)-2a has been described. Asymmetric intramolecular oxidative cyclization of the o-phenolic oxime-ester 1c using a novel optically active tertiary alcohol (-)-3 as a chiral auxiliary proceeded smoothly to afford cyclohexadienone spiroisoxazoline 2c in 83% yield. Opitcally active tertiary alcohol (-)-3 was

  已经描述了一种合成对映体富集的环己二酮螺异恶唑啉（-）-2a的新方法。使用新型旋光性叔醇（-）-3作为手性助剂，对邻苯酚肟酯1c的不对称分子内氧化环化反应顺利进行，从而以83％的收率得到环己二酮螺异异唑啉2c。通过光学拆分，由外消旋（1S，8R，9R，10R）-8-苯基-1-癸醇（4）合成了具有活性的叔醇（-）-3。用CF（3）COOH除去2c中的手性助剂，然后进行甲基化，得到具有S-构型的74％ee（化学收率71％）的甲酯（-）-2a。2awas的绝对构型由海洋天然产物（+）-aeroothionin的合成决定。
• Cytotoxic dibromotyrosine-derived metabolites from the sponge Aplysina gerardogreeni
  作者：Claudia J. Hernández-Guerrero、Eva Zubía、María J. Ortega、J. Luis Carballo

  DOI：10.1016/j.bmc.2007.05.014

  日期：2007.8

  The chemical study of the sponge Aplysina gerardogreeni collected at the Gulf of California has led to the isolation of four new dibromotyrosine-derived metabolites, aplysinones A-D, whose structures were determined by spectroscopic analysis and chemical methods. The new compounds and four semisynthetic analogues prepared in this study have shown cytotoxic activity against human tumor cell lines.

  对在加利福尼亚湾收集的海绵Aplysina gerardogreeni的化学研究导致分离出四种新的由二溴酪氨酸衍生的代谢物，aplysinones AD，其结构是通过光谱分析和化学方法确定的。在这项研究中制备的新化合物和四种半合成类似物已显示出对人肿瘤细胞系的细胞毒活性。
• 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.
• Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative
  作者：Takahisa Ogamino、Rika Obata、Shigeru Nishiyama

  DOI：10.1016/j.tetlet.2005.11.097

  日期：2006.1

  Successful first synthesis of optically pure (+)- and (-)-aerothionins (1) from the racemic spiroisoxazoline derivative 8 has been accomplished. The absolute configuration of natural (+)-1 was determined by comparison of (+)- and (-)-8 with related derivatives. (c) 2005 Elsevier Ltd. All rights reserved.