[(4'S,6'S,7'R,8'S)-5'-acetyl-7'-methoxy-12'-nonadecyl-10',13'-dioxospiro[1,3-dioxolane-2,11'-2,5-diazatetracyclo[7.4.0.02,7.04,6]tridec-1(9)-ene]-8'-yl]methyl carbamate

• 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: [(4'S,6'S,7'R,8'S)-5'-acetyl-7'-methoxy-12'-nonadecyl-10',13'-dioxospiro[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: C₃₇H₅₉N₃O₈
• 分子量: 673.891
• InChiKey: VLXVTXZVRQRZFP-MSJZVDRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  48
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  [(4'S,6'S,7'R,8'S)-5'-acetyl-7'-methoxy-12'-nonadecyl-10',13'-dioxospiro[1,3-dioxolane-2,11'-2,5-diazatetracyclo[7.4.0.02,7.04,6]tridec-1(9)-ene]-8'-yl]methyl carbamate 在 氨 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 (4S,6S,7R,8S)-11-amino-8-(hydroxymethyl)-7-methoxy-12-nonadecyl-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-diene-10,13-dione 、 6-demethyl-6-n-nonadecylmitomycin C
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Novel 6-Alkyl-6-demethylmitomycins

  摘要：

  A series of 6-alkyl-6-demethylmitomycins (1-5) was synthesized and evaluated for anticellular and antitumor activities. These novel compounds were prepared by Michael addition of various carbanion species to 6-demethyl-7,7-(ethylenedioxy)-6,7-dihydro-6-methylidenemitosane (6 and 9) followed by treatment with NH3 or MeOH/K2CO3. Alkylation at the C-6 position of 6-demethyl-6-selenide (7) was also useful for the alternative synthesis of 6-alkyl-6-demethylmitomycins. The antitumor activity of these derivatives was evalulated, and 6-demethyl-6-ethylmitomycin A (2a) was found to exhibit excellent activity against S-180 solid tumor in mice. The structure-activity relationship is also discussed.

  DOI：

  10.1021/jm00038a009
• 作为产物：
  描述：

  6-Demethyl-7,7-(ethylenedioxy)-6,7-dihydro-6-methylidenemitosane 、 1-octadecylmagnesium bromide 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 [(4'S,6'S,7'R,8'S)-5'-acetyl-7'-methoxy-12'-nonadecyl-10',13'-dioxospiro[1,3-dioxolane-2,11'-2,5-diazatetracyclo[7.4.0.02,7.04,6]tridec-1(9)-ene]-8'-yl]methyl carbamate
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Novel 6-Alkyl-6-demethylmitomycins

  摘要：

  A series of 6-alkyl-6-demethylmitomycins (1-5) was synthesized and evaluated for anticellular and antitumor activities. These novel compounds were prepared by Michael addition of various carbanion species to 6-demethyl-7,7-(ethylenedioxy)-6,7-dihydro-6-methylidenemitosane (6 and 9) followed by treatment with NH3 or MeOH/K2CO3. Alkylation at the C-6 position of 6-demethyl-6-selenide (7) was also useful for the alternative synthesis of 6-alkyl-6-demethylmitomycins. The antitumor activity of these derivatives was evalulated, and 6-demethyl-6-ethylmitomycin A (2a) was found to exhibit excellent activity against S-180 solid tumor in mice. The structure-activity relationship is also discussed.

  DOI：

  10.1021/jm00038a009

文献信息

• Synthesis and Antitumor Activity of Novel 6-Alkyl-6-demethylmitomycins
  作者：Hitoshi Arai、Yutaka Kanda、Tadashi Ashizawa、Makoto Morimoto、Katsushige Gomi、Motomichi Kono、Masaji Kasai

  DOI：10.1021/jm00038a009

  日期：1994.6

  A series of 6-alkyl-6-demethylmitomycins (1-5) was synthesized and evaluated for anticellular and antitumor activities. These novel compounds were prepared by Michael addition of various carbanion species to 6-demethyl-7,7-(ethylenedioxy)-6,7-dihydro-6-methylidenemitosane (6 and 9) followed by treatment with NH3 or MeOH/K2CO3. Alkylation at the C-6 position of 6-demethyl-6-selenide (7) was also useful for the alternative synthesis of 6-alkyl-6-demethylmitomycins. The antitumor activity of these derivatives was evalulated, and 6-demethyl-6-ethylmitomycin A (2a) was found to exhibit excellent activity against S-180 solid tumor in mice. The structure-activity relationship is also discussed.