[(1S,4S,7S,9S)-16-(benzenesulfonyl)-9-bromo-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-trien-4-yl]methyl acetate | 1252612-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: [(1S,4S,7S,9S)-16-(benzenesulfonyl)-9-bromo-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-trien-4-yl]methyl acetate
• CAS: 1252612-13-7
• 化学式: C₂₃H₂₂BrN₃O₆S
• 分子量: 548.414
• InChiKey: YCDRELQRWXNCAV-ZZTDLJEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(1S,4S,7S,9S)-16-(benzenesulfonyl)-9-bromo-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-trien-4-yl]methyl acetate 在 cobalt,triphenylphosphane,chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以49%的产率得到[(1S,4S,7S,9R)-9-[(1S,4S,7S,9R)-4-(acetyloxymethyl)-16-(benzenesulfonyl)-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-trien-9-yl]-16-(benzenesulfonyl)-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-trien-4-yl]methyl acetate
  参考文献：
  名称：

  General Approach to Epipolythiodiketopiperazine Alkaloids: Total Synthesis of (+)-Chaetocins A and C and (+)-12,12′-Dideoxychetracin A

  摘要：

  A highly stereoselective and systematic strategy for the introduction of polysulfides in the synthesis of epipolythiodiketopiperazines is described. We report the first total synthesis of dimeric epitri- and epitetrathiodiketopiperazines.

  DOI：

  10.1021/ja106869s
• 作为产物：
  描述：

  (1S,4S,7S,9S)-16-(benzenesulfonyl)-9-bromo-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-methyl-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-triene-3,6-dione 、 乙酰氯 在 pyridine hydrofluoride 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 80.0h， 以85%的产率得到[(1S,4S,7S,9S)-16-(benzenesulfonyl)-9-bromo-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-trien-4-yl]methyl acetate
  参考文献：
  名称：

  General Approach to Epipolythiodiketopiperazine Alkaloids: Total Synthesis of (+)-Chaetocins A and C and (+)-12,12′-Dideoxychetracin A

  摘要：

  A highly stereoselective and systematic strategy for the introduction of polysulfides in the synthesis of epipolythiodiketopiperazines is described. We report the first total synthesis of dimeric epitri- and epitetrathiodiketopiperazines.

  DOI：

  10.1021/ja106869s

文献信息

• Concise Total Synthesis of (+)-Luteoalbusins A and B
  作者：Timothy C. Adams、Joshua N. Payette、Jaime H. Cheah、Mohammad Movassaghi

  DOI：10.1021/acs.orglett.5b02059

  日期：2015.9.4

  The first total synthesis of (+)-luteoalbusins A and B is described. Highly regio- and diastereoselective chemical transformations in our syntheses include a Friedel-Crafts C3-indole addition to a cydotryptophan-derived diketopiperazine, a late-stage diketopiperazine dihydroxylation, and a C11-sulfidation sequence, in addition to congener-specific polysulfane synthesis and cyclization to the corresponding epipolythiodiketopiperazine. We also report the cytoxicity of both alkaloids, and closely related derivatives, against A549, He La, HCT116, and MCF7 human cancer cell lines.