{3-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-((R)-4-Amino-1-methyl-butyl)-3,7-bis-(3-tert-butoxycarbonylamino-propoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-12-yloxy]-propyl}-carbamic acid tert-butyl ester | 804551-45-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: {3-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-((R)-4-Amino-1-methyl-butyl)-3,7-bis-(3-tert-butoxycarbonylamino-propoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-12-yloxy]-propyl}-carbamic acid tert-butyl ester
• CAS: 804551-45-9
• 化学式: C₄₈H₈₈N₄O₉
• 分子量: 865.248
• InChiKey: DVOPJCLAQAOVOP-FQCVLXPVSA-N

反应信息

• 作为反应物：
  描述：

  {3-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-((R)-4-Amino-1-methyl-butyl)-3,7-bis-(3-tert-butoxycarbonylamino-propoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-12-yloxy]-propyl}-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 4-(6-Dimethylamino-naphthalen-2-yl)-4-oxo-N-{(R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-tris-(3-amino-propoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentyl}-butyramide
  参考文献：
  名称：

  Origins of Cell Selectivity of Cationic Steroid Antibiotics

  摘要：

  A key factor in the potential clinical utility of membrane-active antibiotics is their cell selectivity (i.e., prokaryote over eukaryote). Cationic steroid antibiotics were developed to mimic the lipid A binding character of polymyxin 6 and are shown to bind lipid A derivatives with affinity greater than that of polymyxin B. The outer membranes of Gram-negative bacteria are comprised primarily of lipid A, and a fluorophore-appended cationic steroid antibiotic displays very high selectivity for Gram-negative bacterial membranes over Gram-positive bacteria and eukaryotic cell membranes. This cell selectivity of cationic steroid antibiotics may be due, in part, to the affinity of these compounds for lipid A.

  DOI：

  10.1021/ja046909p
• 作为产物：
  描述：

  {3-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-((R)-4-Azido-1-methyl-butyl)-3,7-bis-(3-tert-butoxycarbonylamino-propoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-12-yloxy]-propyl}-carbamic acid tert-butyl ester 在 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到{3-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-((R)-4-Amino-1-methyl-butyl)-3,7-bis-(3-tert-butoxycarbonylamino-propoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-12-yloxy]-propyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Origins of Cell Selectivity of Cationic Steroid Antibiotics

  摘要：

  A key factor in the potential clinical utility of membrane-active antibiotics is their cell selectivity (i.e., prokaryote over eukaryote). Cationic steroid antibiotics were developed to mimic the lipid A binding character of polymyxin 6 and are shown to bind lipid A derivatives with affinity greater than that of polymyxin B. The outer membranes of Gram-negative bacteria are comprised primarily of lipid A, and a fluorophore-appended cationic steroid antibiotic displays very high selectivity for Gram-negative bacterial membranes over Gram-positive bacteria and eukaryotic cell membranes. This cell selectivity of cationic steroid antibiotics may be due, in part, to the affinity of these compounds for lipid A.

  DOI：

  10.1021/ja046909p