12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-6-benzyl-5,7(6H)-dione | 87259-91-4

• 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: 12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-6-benzyl-5,7(6H)-dione
• 英文别名: 12,13-dihydro-6-(phenylmethyl)-5H-indolo<2,3-a>carbazole-5,7(6H)-dione；6-benzylidolo<2,3-a>pyrrolo<3,4-c>carbazole-5,7(6H)-dione；6-benzyl-12,13-dihydro-6H-indolo<2,3-a>pyrrolo<3,4-c>carbazole-5,7-dione；N-Benzylarcyriaflavin A；12,13-dihydro-6-(phenylmethyl)-5H-indolo[2,3-a]pyrrolo[3,4-c]-carbazole-5,7(6H)-dione；6-Benzyl-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione；13-benzyl-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: 87259-91-4
• 化学式: C₂₇H₁₇N₃O₂
• 分子量: 415.451
• InChiKey: BOWKECNQMUSQGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  69
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-6-benzyl-5,7(6H)-dione 以71%的产率得到N-benzylstaurosporinone
  参考文献：
  名称：

  Synthesis of arcyriaflavin B

  摘要：

  DOI：

  10.1016/s0040-4039(00)81677-9
• 作为产物：
  描述：

  dimethyl 3,6-bis(2-nitrophenyl)phthalate 生成 12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-6-benzyl-5,7(6H)-dione
  参考文献：
  名称：

  Synthesis of arcyriaflavin B

  摘要：

  DOI：

  10.1016/s0040-4039(00)81677-9

文献信息

• A facile synthesis of staurosporine aglycone
  作者：Guojian Xie、J. William Lown

  DOI：10.1016/s0040-4039(00)77245-5

  日期：1994.8

  A highly efficient method is described for the synthesis of staurosporine aglycone 3 from the readily available dibromomaleic acid in six steps.

  描述了一种高效的方法，该方法可通过六个步骤从容易获得的二溴马来酸合成星形孢菌素苷元3。
• Coupling reactions of indole-3-acetic acid derivatives. Synthesis of arcyriaflavin A
  作者：Jan Bergman、Eva Koch、Benjamin Pelcman

  DOI：10.1039/b004029k

  日期：——

  The bisindolesuccinic acid methyl ester 10 was obtained by an iodine-promoted coupling of the dianion 9. The diester was converted to the N-benzylimide 12, which was oxidatively cyclized to the indolo[2,3-a]pyrrolo[3,4-c]carbazole 15. The diester 10 could be directly transformed to the known indolocarbazole diester 27via acid-induced intramolecular cyclization in TFA. The same methodology gave arcyriaflavin A 4 from the succinimide 18b.

  双吲哚基琥珀酸甲酯10是通过碘促进的双阴离子9的耦合反应获得的。该二酯被转化为N-苄基亚胺12，随后经过氧化环合得到吲哚[2,3-a]吡咯[3,4-c]咔唑15。二酯10可以直接通过三氟乙酸中的酸诱导分子内环合反应转化为已知的吲哚咔唑二酯27。同样的合成方法从琥珀酰亚胺18b得到了亮菌素A 4。
• Coupling of indoleacetic acid trianion or methyl indoleacetic acid dianion. A biomimetic approach to indolocarbazole alkaloids.
  作者：J. Bergman、B. Pelcman

  DOI：10.1016/s0040-4039(00)96533-x

  日期：1987.1

  obtained as a mixture of diastereomers by iodine promoted coupling of the dianion or via the trianion . The diester was converted to the N-benzylimide which was oxidatively cyclized to the indolo[2,3-a]pyrrolo[3,4-c]carbazole compound .

  双吲哚琥珀酸酯是通过碘促进的二价阴离子或三价阴离子的非对映异构体的混合物。将二酯转化为N-苄基酰亚胺，将其氧化环化为吲哚[2，3-a]吡咯并[3，4-c]咔唑化合物。
• The synthesis of bioactive indolocarbazoles related to K-252a
  作者：David Moffat、Christopher J. Nichols、Dean A. Riley、Nigel S. Simpkins

  DOI：10.1039/b506444a

  日期：——

  n to give a ketone, or by dihydroxylation and cyclic sulfate formation, enable the preparation of diverse indolocarbazole products. Issues of imide nitrogen protection for the indolocarbazole, and opportunities for asymmetric desymmetrisation of key intermediates were also explored. A novel chiral lithium amide base mediated transformation of a cyclic sulfate intermediate gave the anticipated ketone

  从容易获得的桥连环戊烯开始，已制备了一系列与天然产物K-252a有关的功能化吲哚并咔唑。涉及初始氢硼化-氧化以生成酮的转化序列，或通过二羟基化和环状硫酸盐形成的转化序列，使得能够制备各种吲哚并咔唑产物。还探讨了吲哚并咔唑的酰亚胺氮保护问题以及关键中间体的不对称脱对称现象。新型的手性锂酰胺基碱介导的环状硫酸盐中间体的转化产生了预期的酮产物，其收率高达87％ee。筛选了未保护的酰亚胺取代的吲哚并咔唑形式的许多化合物的生物活性，发现它们是多种激酶的有效抑制剂。
• Synthesis of Indolo[2,3-<i>a</i>]pyrrolo[3,4-<i>c</i>]carbazoles by Oxidative Cyclization of Bisindolylmaleimides with a Rhodium(III)-Copper(II) Catalytic System
  作者：Bernhard Witulski、Torsten Schweikert

  DOI：10.1055/s-2005-869977

  日期：——

  A novel catalytic protocol for the synthesis of a series of indolo[2,3-a]pyrrolo[3,4-c]carbazoles based on the bimetallic system RhCl 3 .3H 2 O and Cu(OAc) 2 .H 2 O in the presence of molecular oxygen was investigated. The method was applied to the synthesis of the glycosidated fluoroindolocarbazole 3 that was recently isolated as a metabolite from feeding experiments of Saccharothrix aerocolonigenes

  基于双金属体系 RhCl 3 .3H 2 O 和 Cu(OAc) 2 .H 2 O 合成一系列吲哚[2,3-a]吡咯并[3,4-c]咔唑的新催化方案研究了分子氧的存在。该方法应用于糖苷化的氟吲哚咔唑 3 的合成，该糖苷化的氟吲哚咔唑 3 最近作为一种代谢物从产气结肠糖丝菌 ATCC 39243 与氟色氨酸的喂养实验中分离出来。