6-methyl-12--6,7,12,13-tetrahydroindolo<2,3-a>pyrrolo<3,4-c>carbazole-5,7-dione | 236750-84-8

• 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: 6-methyl-12--6,7,12,13-tetrahydroindolo<2,3-a>pyrrolo<3,4-c>carbazole-5,7-dione
• 英文别名: 6-methyl-12-[O-(α-D-glucopyranosyl)-(1->4)-β-D-glucopyranosyl]-6,7,12,13-tetrahydroindolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione；3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-13-methyl-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4,6,8,10,15,17,19,21-nonaene-12,14-dione
• CAS: 236750-84-8
• 化学式: C₃₃H₃₃N₃O₁₂
• 分子量: 663.638
• InChiKey: DSAWHWMQJLKIBS-SGWHAXCLSA-N

物化性质

• 沸点：
  974.4±65.0 °C(Predicted)
• 密度：
  1.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  48
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  227
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 6-methyl-12--6,7,12,13-tetrahydroindolo<2,3-a>pyrrolo<3,4-c>carbazole-5,7-dione 以 吡啶 为溶剂， 反应 38.0h， 以58%的产率得到6-methyl-12--6,7,12,13-tetrahydroindolo<2,3-a>pyrrolo<3,4-c>carbazole-5,7-dione
  参考文献：
  名称：

  Conformational Control in the Rebeccamycin Class of Indolocarbazole Glycosides

  摘要：

  Indolocarbazole glycosides are balanced between two conformations: a "closed" conformation containing a cyclic hydrogen bond between the indolocarbazole NH and the pyranose oxygen and an "open" conformation in which the indolocarbazole NH is hydrogen bonded to solvent. The open conformation never has a commanding advantage, even in DMSO, but in nonpolar environments the cyclic conformation predominates.

  DOI：

  10.1021/jo990296v
• 作为产物：
  描述：

  麦芽糖 在 硫酸氢铵 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 110.0h， 生成 6-methyl-12--6,7,12,13-tetrahydroindolo<2,3-a>pyrrolo<3,4-c>carbazole-5,7-dione
  参考文献：
  名称：

  Conformational Control in the Rebeccamycin Class of Indolocarbazole Glycosides

  摘要：

  Indolocarbazole glycosides are balanced between two conformations: a "closed" conformation containing a cyclic hydrogen bond between the indolocarbazole NH and the pyranose oxygen and an "open" conformation in which the indolocarbazole NH is hydrogen bonded to solvent. The open conformation never has a commanding advantage, even in DMSO, but in nonpolar environments the cyclic conformation predominates.

  DOI：

  10.1021/jo990296v

文献信息

• Regiocontrolled Synthesis of the Antitumor Antibiotic AT2433-A1
  作者：John D. Chisholm、David L. Van Vranken

  DOI：10.1021/jo000911r

  日期：2000.11.1

  The indolo[2,3-a]carbazole glycosides are potent antitumor antibiotics currently undergoing clinical trials for the treatment of numerous types of cancer. AT2433-A1 is the most complex member of this family of compounds possessing a unique disaccharide with a sensitive aminodeoxysugar and an unsymmetric aglycon. The synthesis of this natural product requires a method for glycosylation that sets the

  吲哚[2，3-a]咔唑糖苷是有效的抗肿瘤抗生素，目前正接受临床试验以治疗多种类型的癌症。AT2433-A1是该化合物家族中最复杂的成员，具有独特的二糖以及敏感的氨基脱氧糖和不对称糖苷配基。这种天然产物的合成需要糖基化的方法，该方法设定异头异构中心的立体化学和糖苷配基的区域化学。这些目标是通过对bis-3，4-（3-吲哚基）琥珀酰亚胺进行曼尼希环化反应而得到的，主要的二氢吲哚中间体可以与复杂的碳水化合物被立体选择性地糖基化，而没有羟基的保护或活化。通过在动力学或热力学条件之间进行选择，可以精确地控制曼尼希环化反应的区域化学。该策略最终导致抗肿瘤抗生素AT2433-A1的首次合成。
• Conformational Control in the Rebeccamycin Class of Indolocarbazole Glycosides
  作者：Eric J. Gilbert、John D. Chisholm、David L. Van Vranken

  DOI：10.1021/jo990296v

  日期：1999.7.1

  Indolocarbazole glycosides are balanced between two conformations: a "closed" conformation containing a cyclic hydrogen bond between the indolocarbazole NH and the pyranose oxygen and an "open" conformation in which the indolocarbazole NH is hydrogen bonded to solvent. The open conformation never has a commanding advantage, even in DMSO, but in nonpolar environments the cyclic conformation predominates.