8-O-pivaloyl-3-rifamycin S | 123812-46-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 8-O-pivaloyl-3-rifamycin S
• 英文别名: [(9E,19E,21Z)-13-acetyloxy-15,17-dihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-26-[4-[(2,4,6-trimethylphenyl)methyl]piperazin-1-yl]-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1,3,5(28),9,19,21,25-heptaen-2-yl] 2,2-dimethylpropanoate
• CAS: 123812-46-4
• 化学式: C₅₆H₇₃N₃O₁₃
• 分子量: 996.208
• InChiKey: NCBMFJNHLOXYEF-PXUBFJSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  72
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  208
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  、 三甲基乙酰氯 在 吡啶 作用下， 反应 2.0h， 生成 8-O-pivaloyl-3-rifamycin S 、 8-O,N-dipivaloyl-3-rifamycin S
  参考文献：
  名称：

  Hypolipidemic activity of rifamycin derivatives

  摘要：

  Series of 3-piperidinyl- and 3-piperazinylrifamycins and to a certain extent 3-hydrazonorifamycins all bearing lipophilic side chains were found to exert potent hypolipidemic activity in lowering both serum cholesterol and LDL-cholesterol in rats. Starting from 3-[N'-(2,4,6-trimethylbenzyl)-N-piperazinyl]rifamycin SV (compound 25), a series of derivatives were synthesized with the aim of dissociating the hypolipidemic from the antibacterial activity, leading to the 8-O,N-dipivaloyl derivative of 25 (compound 48), which is devoid of any antibacterial activity but shows about 50-60% reduction of LDL-cholesterol and 20-30% reduction of serum cholesterol at a dose of 10 mg/kg. Compound 48 was selected for further pharmacological evaluation.

  DOI：

  10.1021/jm00164a013