(1R,2S,4R,5R,8R,9S,11R)-9-formyl-5-methyl-2-[[(2R,5R)-5-methylmorpholin-2-yl]oxymethyl]-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylic acid | 561323-54-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S,4R,5R,8R,9S,11R)-9-formyl-5-methyl-2-[[(2R,5R)-5-methylmorpholin-2-yl]oxymethyl]-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylic acid
• CAS: 561323-54-4
• 化学式: C₂₅H₃₇NO₅
• 分子量: 431.572
• InChiKey: CUIIMOCJKZOQAA-ACVNAFQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,3-dibromoacrylaldehyde 、 (1R,2S,4R,5R,8R,9S,11R)-9-formyl-5-methyl-2-[[(2R,5R)-5-methylmorpholin-2-yl]oxymethyl]-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylic acid 在 sodium cyanoborohydride 作用下， 以 乙腈 为溶剂， 生成 (1R,2S,4R,5R,8R,9S,11R)-2-[[(2R,5R)-4-(3,3-difluoroprop-2-enyl)-5-methylmorpholin-2-yl]oxymethyl]-9-formyl-5-methyl-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylic acid
  参考文献：
  名称：

  Identification of a broad-Spectrum azasordarin with improved pharmacokinetic properties

  摘要：

  The synthesis and antifungal activity of 5- and 5'-6'-substituted azasordarin derivatives are described. Modification of the 5'-position led to the discovery of the spirocyclopentyl analogue 7g, which is the first azasordarin to register single-digit MIC values versus Aspergillus spp. Further investigation identified the 5'-i-Pr derivative 7b, which displays superior pharmacokinetic properties compared to other azasordarins. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00161-6
• 作为产物：
  描述：

  在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 生成 (1R,2S,4R,5R,8R,9S,11R)-9-formyl-5-methyl-2-[[(2R,5R)-5-methylmorpholin-2-yl]oxymethyl]-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylic acid
  参考文献：
  名称：

  Identification of a broad-Spectrum azasordarin with improved pharmacokinetic properties

  摘要：

  The synthesis and antifungal activity of 5- and 5'-6'-substituted azasordarin derivatives are described. Modification of the 5'-position led to the discovery of the spirocyclopentyl analogue 7g, which is the first azasordarin to register single-digit MIC values versus Aspergillus spp. Further investigation identified the 5'-i-Pr derivative 7b, which displays superior pharmacokinetic properties compared to other azasordarins. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00161-6