boromycin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: boromycin
• 英文别名: [(2R)-1-[(1R)-1-[(1R,2R,5S,7Z,11S,13S,16R,17R,21R,24S,25R,27R,31R,33S,36R)-11,31-dihydroxy-12,12,16,25,32,32,36-heptamethyl-3,22-dioxo-4,18,20,23,26,37,38,40,41-nonaoxa-19-boranuidaheptacyclo[17.17.1.11,33.12,19.113,17.124,27.017,21]hentetracont-7-en-5-yl]ethoxy]-3-methyl-1-oxobutan-2-yl]azanium
• 化学式: C₄₅H₇₃BNO₁₅*H
• 分子量: 879.891
• InChiKey: OOBFYEMEQCZLJL-IIWQOWOFSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  62
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  212
• 氢给体数：
  3
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  boromycin 在 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 (R)-4-((4S,6R)-6-{3-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-propyl}-2,2,5,5-tetramethyl-[1,3]dioxan-4-yl)-2-methyl-butyric acid
  参考文献：
  名称：

  区域选择性，分子内氧硒酸化为通向硼霉素和阿霉素的四氢呋喃单元的途径

  摘要：

  已经合成了具有硼霉素的C（1'）-C（17'）半部的功能和绝对构型的物质，采用分子内氧硒化从烯烃二醇构造四氢呋喃部分，从而合成了豆。

  DOI：

  10.1016/0040-4039(84)80101-x

文献信息

• Boromycin Derivatives: Synthesis and Antimalarial Activity in vitro and in vivo
  作者：Toshiaki Sunazuka、Satoshi Ōmura、Ayumi Tsutsui、Yujiro Furuya、Tomoyasu Hirose、Riyon Kim、Rokurou Masuma、Atsuko Matsumoto、Yoko Takahashi、Aki Ishiyama、Miyuki Namatame、Kazuhiko Otoguro

  DOI：10.3987/com-10-s(e)55

  日期：——

  Derivatives of boromycin, which has significant antimalarial properties both in vitro and in vivo, were examined for similar the efficacy against both drug-resistance strain and drug-sensitive strain of malaria and as a means to elucidate structure-activity relationships. More potent in vitro compounds tended to lose their properties in vivo when administered orally. Some novel 16-O-acyl derivatives were found to be more potent and selective antimalarial compounds compared to boromycin. Furthermore, alkyne-bearing 16-O-alkylacyl compounds retained reasonably good efficacy in vivo when given per os.
• Regioselective, intramolecular oxyselenation as a route to the tetrahydrofuran units of boromycin and aplasmomycin
  作者：James D. White*、Satish C. Choudhry、Myung-chol Kang

  DOI：10.1016/0040-4039(84)80101-x

  日期：1984.1

  A substance possessing the functionality and absolute configuration of the C(1′)-C(17′) half of boromycin has bean synthesized, employing an intra-molecular oxyselenation for construction of the tetrahydrofuran moiety from an olefinic diol.

  已经合成了具有硼霉素的C（1'）-C（17'）半部的功能和绝对构型的物质，采用分子内氧硒化从烯烃二醇构造四氢呋喃部分，从而合成了豆。