6-O-methylfumagillol | 129298-97-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 6-O-methylfumagillol
• 英文别名: (3R,4S,5S,6R)-5,6-dimethoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octane
• CAS: 129298-97-1
• 化学式: C₁₇H₂₈O₄
• 分子量: 296.407
• InChiKey: WJDOBTXNTCTJSY-KPLDXPABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  43.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲氧基-4-[2-甲基-3-(3-甲基丁-2-烯基)环氧乙烷-2-基]-1-氧杂螺[2.5]辛烷-6-醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以95%的产率得到6-O-methylfumagillol
  参考文献：
  名称：

  Chemical Modification of Fumagillin. I. 6-O-Acyl, 6-O-Sulfonyl, 6-O-Alkyl, and 6-O-(N-Substituted-carbamoyl)fumagillols.

  摘要：

  烟曲霉素（1）的降解产物烟曲霉醇（3）的羟基被酰化、磺酰化、烷基化或氨基甲酰化，并考察了所得产物的抗血管生成活性。这些化合物抑制了在大鼠角膜微囊中由碱性成纤维细胞生长因子诱导的血管生成以及体外血管内皮细胞的生长。其中，化合物2（AGM-1470）被发现对血管内皮细胞生长具有最强的抑制作用，并被选为这一系列的候选药物进一步开发。

  DOI：

  10.1248/cpb.40.96

文献信息

• [EN] OXASPIRO [2.5] OCTANE DERIVATIVES AND ANALOGS<br/>[FR] DÉRIVÉS D'OXASPIRO[2.5]OCTANE ET ANALOGUES
  申请人：ZAFGEN CORP

  公开号：WO2012122264A1

  公开（公告）日：2012-09-13

  The invention provides oxaspiro[2.5]octane derivatives and analogs, methods for preparation thereof, intermediates thereto, pharmaceutical compositions, and uses thereof in the treatment of various disorders and conditions, such as overweight and obesity.

  这项发明提供了氧杂螺[2.5]辛烷衍生物和类似物，其制备方法，中间体，药物组合物以及在治疗各种疾病和状况中的用途，例如超重和肥胖。
• Oxaspiro[2.5]octane derivatives and analogs
  申请人：Zafgen, Inc.

  公开号：US10259796B2

  公开（公告）日：2019-04-16

  The invention provides oxaspiro[2.5]octane derivatives and analogs, methods for preparation thereof, intermediates thereto, pharmaceutical compositions, and uses thereof in the treatment of various disorders and conditions, such as overweight and obesity.

  本发明提供了噁螺[2.5]辛烷衍生物和类似物、其制备方法、中间体、药物组合物及其在治疗超重和肥胖等各种疾病和病症中的用途。
• HETEROCYCLIC COMPOUND
  申请人：TOHOKU UNIVERSITY

  公开号：US20200163970A1

  公开（公告）日：2020-05-28

  Provided is a novel compound or salt thereof that induces degradation by autophagy of an intracellular molecule. In this compound, a ligand having activity to bind to an intracellular molecule and a structure having activity to induce autophagy of an intracellular molecule are linked via a linker without loss of the activity of the ligand and the structure.
• [EN] NEW SPIROEPOXIDE TETRAHYDROBENZOTRIAZOLES AND THEIR USE AS METAP-II INHIBITORS<br/>[FR] NOUVEAUX COMPOSÉS TÉTRAHYDROBENZOTRIAZOLE SPIROÉPOXYDES ET LEUR UTILISATION COMME INHIBITEURS DE METAP-II
  申请人：DEUTSCHES KREBSFORSCH

  公开号：WO2014044399A1

  公开（公告）日：2014-03-27

  The present invention relates to new spiroepoxide tetrahydrobenzotriazole compounds, a method for their production and their use as MetAP-II inhibitors, which are particularly useful as inhibitors of angiogenesis. The compounds are characterized by formula (I) R1 = OC(O)R2 where R2 is alkyl, cycloalkyl, aryl, heteroaryl, or cinnamyl or R1 = OC(0)NHR3 where R3 is alkyl, cycloalkyl, aryl, or heteroaryl or R1 = NHC(0)OR4 where R4 is alkyl or R1 = OH, NH2 R5 = alkyl, cycloalkyl, CH2R6 where R6 is aryl or heteroaryl
• Chemical Modification of Fumagillin. I. 6-O-Acyl, 6-O-Sulfonyl, 6-O-Alkyl, and 6-O-(N-Substituted-carbamoyl)fumagillols.
  作者：Shogo MARUI、Fumio ITOH、Yoshio KOZAI、Katsuichi SUDO、Shoji KISHIMOTO

  DOI：10.1248/cpb.40.96

  日期：——

  The hydroxy group of fumagillol (3), a degradation product of fumagillin (1), was acylated, sulfonylated, alkylated or carbamoylated, and the anti-angiogenic activity of the resulting products was examined. These compounds inhibited the angiogenesis induced by basic fibroblast growth factor in the rat corneal micropocket assay and the growth of vascular endothelial cells in vitro. Among them, compound 2 (AGM-1470) was found to show the most potent inhibitory effect on the growth of vascular endothelial cells and was selected form this series as a candidate for further development.

  烟曲霉素（1）的降解产物烟曲霉醇（3）的羟基被酰化、磺酰化、烷基化或氨基甲酰化，并考察了所得产物的抗血管生成活性。这些化合物抑制了在大鼠角膜微囊中由碱性成纤维细胞生长因子诱导的血管生成以及体外血管内皮细胞的生长。其中，化合物2（AGM-1470）被发现对血管内皮细胞生长具有最强的抑制作用，并被选为这一系列的候选药物进一步开发。