16,17,18,19,28,29-hexahydro-3-rifamycin SV | 123812-43-1

• 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: 16,17,18,19,28,29-hexahydro-3-rifamycin SV
• 英文别名: [2,15,17,27,29-Pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-26-[4-[(2,4,6-trimethylphenyl)methyl]piperazin-1-yl]-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,25(29),26-pentaen-13-yl] acetate
• CAS: 123812-43-1；123878-73-9；127760-02-5
• 化学式: C₅₁H₇₃N₃O₁₂
• 分子量: 920.154
• InChiKey: XXFOAPPKFXENRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  66
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  208
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  1-(2,4,6-三甲基苄基)哌嗪 在 platinum(IV) oxide 氢气 、 sodium ascorbate 、 柠檬酸 作用下， 以 乙醇 为溶剂， 反应 14.08h， 生成 16,17,18,19,28,29-hexahydro-3-rifamycin SV
  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

文献信息

• Hypolipidemic activity of rifamycin derivatives
  作者：Peter Traxler、Wilhelm Kump、Klaus Mueller、Werner Tosch

  DOI：10.1021/jm00164a013

  日期：1990.2

  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.