3α,15-Diacetoxy-4β-hydroxy-8α-<(3-methylbutyryl)oxy>-12,13-epoxytrichothec-9-ene | 34084-03-2

• 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: 3α,15-Diacetoxy-4β-hydroxy-8α-<(3-methylbutyryl)oxy>-12,13-epoxytrichothec-9-ene
• 英文别名: 3-acetyl HT-2 toxin；3-A HT-2；Iso-T-2 toxin；[(1S,2R,4S,7R,9R,10R,11S,12S)-10-acetyloxy-2-(acetyloxymethyl)-11-hydroxy-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-yl] 3-methylbutanoate
• CAS: 34084-03-2
• 化学式: C₂₄H₃₄O₉
• 分子量: 466.529
• InChiKey: SBEUAAIAYCUUJR-QYWOHJEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3α,15-Diacetoxy-4β-hydroxy-8α-<(3-methylbutyryl)oxy>-12,13-epoxytrichothec-9-ene 在 吡啶 、 chromium(VI) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以82%的产率得到3α,15-Diacetoxy-8α-<(3-methylbutyryl)oxy>-12,13-epoxytrichothec-9-en-4-one
  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：

  乙酸酐 、 HT-2 toxin 在 吡啶 作用下， 以64%的产率得到3α,15-Diacetoxy-4β-hydroxy-8α-<(3-methylbutyryl)oxy>-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

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：——
• Structure-activity studies of trichothecenes: cytotoxicity of analogs and reaction products derived from T-2 toxin and neosolaniol
  作者：D. W. Anderson、R. M. Black、C. G. Lee、C. Pottage、R. L. Rickard、M. S. Sandford、T. D. Webber、N. E. Williams

  DOI：10.1021/jm00123a008

  日期：1989.3

  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.