10β-Bromo-3α,4β,8α-triacetoxy-9α,15:12,13-diepoxytrichothecane | 118170-25-5

• 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: 10β-Bromo-3α,4β,8α-triacetoxy-9α,15:12,13-diepoxytrichothecane
• 英文别名: [(1R,2S,3S,4R,5R,7S,8S,9S,13S,14S)-3,4-diacetyloxy-8-bromo-2,9-dimethylspiro[6,10-dioxatetracyclo[7.2.2.12,5.01,7]tetradecane-14,2'-oxirane]-13-yl] acetate
• CAS: 118170-25-5
• 化学式: C₂₁H₂₇BrO₉
• 分子量: 503.344
• InChiKey: NIUZDUYNWTXCMZ-SYTAUTQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  10β-Bromo-3α,4β,8α-triacetoxy-9α,15:12,13-diepoxytrichothecane 在 银 、 锌 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 16.0h， 以20%的产率得到3α,4β,8α-Triacetoxy-15-hydroxy-12,13-epoxytrichothec-9-ene
  参考文献：
  名称：

  Structure-activity studies of trichothecenes: cytotoxicity of analogs and reaction products derived from T-2 toxin and neosolaniol

  摘要：

  Forty-two analogues and reaction products derived from T-2 toxin or neosolaniol were assayed for their cytotoxicity to cultured mouse lymphoma cells. Structure-activity relationships confirmed the stereospecific nature of the cytotoxic action of T-2. Cytotoxicity was particularly susceptible to changes at C3, C4, C9, and C10 but was relatively unaffected by changes at C8, which appears to represent a region of steric tolerance in the interaction of T-2 with a cellular constituent. The most potent compounds were T-2, diacetoxyscirpenol, and a series of C8 ester analogues 11 and 31-35.

  DOI：

  10.1021/jm00123a008
• 作为产物：
  描述：

  T-2 tetraol 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 生成 10β-Bromo-3α,4β,8α-triacetoxy-9α,15:12,13-diepoxytrichothecane
  参考文献：
  名称：

  Structure-activity studies of trichothecenes: cytotoxicity of analogs and reaction products derived from T-2 toxin and neosolaniol

  摘要：

  Forty-two analogues and reaction products derived from T-2 toxin or neosolaniol were assayed for their cytotoxicity to cultured mouse lymphoma cells. Structure-activity relationships confirmed the stereospecific nature of the cytotoxic action of T-2. Cytotoxicity was particularly susceptible to changes at C3, C4, C9, and C10 but was relatively unaffected by changes at C8, which appears to represent a region of steric tolerance in the interaction of T-2 with a cellular constituent. The most potent compounds were T-2, diacetoxyscirpenol, and a series of C8 ester analogues 11 and 31-35.

  DOI：

  10.1021/jm00123a008

文献信息

• ANDERSON, D. W.;BLACK, R. M.;LEE, C. G.;POTTAGE, C.;RICKARD, R. L.;SANDFO+, J. MED. CHEM., 32,(1989) N, C. 555-562
  作者：ANDERSON, D. W.、BLACK, R. M.、LEE, C. G.、POTTAGE, C.、RICKARD, R. L.、SANDFO+

  DOI：——

  日期：——