7,7-(Ethylenedioxy)-6-(phenylseleno)mitosane

• 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: 7,7-(Ethylenedioxy)-6-(phenylseleno)mitosane
• 英文别名: [(4'S,6'S,7'R,8'S)-5'-acetyl-7'-methoxy-12'-methyl-10',13'-dioxo-12'-phenylselanylspiro[1,3-dioxolane-2,11'-2,5-diazatetracyclo[7.4.0.02,7.04,6]tridec-1(9)-ene]-8'-yl]methyl carbamate
• 化学式: C₂₅H₂₇N₃O₈Se
• 分子量: 576.465
• InChiKey: QMZVPHVOYUDSQV-IKJPLNEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.67
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  7,7-(Ethylenedioxy)-6-(phenylseleno)mitosane 在 氨 、 5,5-二甲基-1,3-环己二酮 作用下， 以 甲醇 为溶剂， 以81%的产率得到丝裂霉素 C
  参考文献：
  名称：

  Facile nucleophilic cleavage of selenide with dimedone. Synthesis of novel 6-demethylmitomycins

  摘要：

  DOI：

  10.1021/jo00067a063
• 作为产物：
  描述：

  丝裂霉素 C 在 氨 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 生成 7,7-(Ethylenedioxy)-6-(phenylseleno)mitosane
  参考文献：
  名称：

  First preparation of mitomycins specifically labeled with deuterium at the C6-methyl position

  摘要：

  DOI：

  10.1021/jo00295a051

文献信息

• Synthesis and Antitumor Activity of Novel Mitomycin Derivatives Containing Functional Groups at the C-6-Methyl Position
  作者：Hitoshi Arai、Yutaka Kanda、Tadashi Ashizawa、Makoto Morimoto、Katsushige Gomi、Motomichi Kono、Masaji Kasai

  DOI：10.1021/jm00038a008

  日期：1994.6

  compounds exhibited remarkable activity against MMC-resistant P388 in mice. FAB-MS spectra of these mitomycin derivatives showed the elimination of the C-6-methyl substituents from the mitomycin skeletons to form quinonemethides. Interestingly, treatment of 6-demethyl-6-[[(2-pyrimidinyl)thio]methyl ]mitomycin C (12v) with diethylamine afforded 6-demethyl-6-[(diethylamino)methyl]mitomycin C (31) in good

  合成了一系列C-6取代的甲基丝裂霉素，并评估了其抗细胞和抗肿瘤活性。这些新颖的化合物是通过将各种醇或硫醇迈克尔加成至6-去甲基-7,7-（乙二氧基）-6,7-二氢-6-亚甲基亚神经松脂中，然后用NH3或MeOH / K2CO3处理而制备的。大多数化合物对HeLa S3均有效，其中一些化合物对小鼠的P388白血病和肉瘤180显示出优于丝裂霉素C（MMC）的活性。此外，某些化合物对小鼠的MMM耐药P388表现出显着活性。这些丝裂霉素衍生物的FAB-MS光谱表明，从丝裂霉素骨架上消除了C-6-甲基取代基，从而形成了醌甲基化物。有趣的是 用二乙胺处理6-去甲基-6-[[[（2-嘧啶基）硫代]甲基]丝裂霉素C（12v）得到6-脱甲基-6-[[（二乙氨基）甲基]丝裂霉素C（31），收率高。这些结果表明，C-6取代的甲基丝裂霉素将具有与MMC不同的生物学特性。
• 6-Demethyl-6-halo- and 6-Demethyl-6-thiomitomycins: Synthesis of Novel Mitomycin Derivatives Involving a Tandem Michael Addition/Retro-Mannich Reaction Sequence
  作者：Hitoshi Arai、Masaji Kasai

  DOI：10.1021/jo00084a028

  日期：1994.3

  Synthesis of novel 6-demethyl-6-halomitomycins (3, 4, 6, and 7) and 6-demethyl-6-thiomitomycins (5 and 8) is described from key intermediates, namely, 6-demethyl-7,7-(ethylenedioxy)-6,6-dihalo- 6,7-dihydromitosanes (18 and 19) and 6-demethyl-7,7- (ethylenedioxy)-6,7-dihydro-6-thiomitosane (20), respectively. Compounds 18-20 were prepared through a tandem Michael addition and a retro-Mannich reaction sequence (N-halosuccinimide or cationic arylsulfenyl species in the presence of Et(2)NH) on 10.
• First synthesis of mitomycins completely labeled at the C-6-methyl by 13CH3 and CD3
  作者：Hitoshi Arai、Yutaka Kanda、Masaji Kasai

  DOI：10.1021/jo00056a022

  日期：1993.2

  The C-6-methyl group of mitomycins was completely labeled with carbon-13 or deuterium for the first time. The synthesis was accomplished by the C-6-methylation of 6-demethyl-7,7-(ethylenedioxy)-6-(phenylseleno)mitosane 8 that was formed by a novel replacement of the methylene moiety of 6-demethyl-7,7-(ethylenedioxy)-6-methylenemitosane 10 by a phenylseleno group, and followed by conversion to the mitomycins. For the synthesis of 8, we found that selenenamide 11 is an excellent reagent for the replacement. We have also determined that the replacement proceeded via the addition of 11 to the methylene of 10 with a subsequent retro-Mannich reaction.
• KASAI, MASADZI;KANDA, YUTAKA;MORIMOTO, MAKOTO;AKINAGA, SIRO;SAJTO, XIROSI+
  作者：KASAI, MASADZI、KANDA, YUTAKA、MORIMOTO, MAKOTO、AKINAGA, SIRO、SAJTO, XIROSI+

  DOI：——

  日期：——
• KANDA, YUTAKA;KOGYO, HAKKO;AKINAGA, SHIRO;KASAI, MASAJI, J. LABELL. COMPOUNDS AND RADIOPHARM., 28,(1990) N, C. 1031-1036
  作者：KANDA, YUTAKA、KOGYO, HAKKO、AKINAGA, SHIRO、KASAI, MASAJI

  DOI：——

  日期：——