1,7-dihydroxy-3-methyl-6,11-dioxo-6,11-dihydro-5H-benzo[b]carbazole-5-carbonitrile | 200508-06-1

• 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: 1,7-dihydroxy-3-methyl-6,11-dioxo-6,11-dihydro-5H-benzo[b]carbazole-5-carbonitrile
• 英文别名: Pre-kinamycin；1,7-dihydroxy-3-methyl-6,11-dioxobenzo[b]carbazole-5-carbonitrile
• CAS: 200508-06-1
• 化学式: C₁₈H₁₀N₂O₄
• 分子量: 318.288
• InChiKey: ICZJRSZSGQYRIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1,7-dihydroxy-3-methyl-6,11-dioxo-6,11-dihydro-5H-benzo[b]carbazole-5-carbonitrile 在 硫酸 作用下， 生成 Acetic acid 7-acetoxy-5-cyano-3-methyl-6,11-dioxo-6,11-dihydro-5H-benzo[b]carbazol-1-yl ester
  参考文献：
  名称：

  Synthesis of benzo[b]carbazoloquinones by coupling of organostannanes with bromoquinones

  摘要：

  The synthesis of 5-carbonitrile-1,7-dihydroxy-3-methyl-5H-benzo[b]carbazole-6,11-dione, the quinone originally proposed as prekinamycin, was completed by using a palladium and copper catalyzed Stille reaction as the key step. A subsequent heterocyclization afforded a mixture of para(benzo[b]carbazole-6,11-dione) and ortho (benzo[a]carbazole-6,11-dione) quinones. A procedure for the N-cyanation of model indoles is also described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10085-0
• 作为产物：
  描述：

  1,5-二羟基萘 在 tris-(dibenzylideneacetone)dipalladium(0) 、 ammonium cerium (IV) nitrate 、 5%-palladium/activated carbon 、 溴 、 甲酸铵 、 palladium diacetate 、 三溴化硼 、 potassium carbonate 、 对甲苯磺酸 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三乙胺 、 间氯过氧苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium hydroxide 、 sodium t-butanolate 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 溶剂黄146 、 二甲基亚砜 、 丙酮 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 81.51h， 生成 1,7-dihydroxy-3-methyl-6,11-dioxo-6,11-dihydro-5H-benzo[b]carbazole-5-carbonitrile
  参考文献：
  名称：

  Prekinamycin and an isosteric-isoelectronic analogue exhibit comparable cytotoxicity towards K562 human leukemia cells

  摘要：

  金霉素的二氮氧基官能团对生物活性可能不是绝对必需的。

  DOI：

  10.1039/c4md00197d

文献信息

• Synthesis of the benzo[b]carbazoloquinone with the structure proposed for prekinamycin
  作者：Antonio M. Echavarren、Nuria Tamayo、M. Carmen Paredes

  DOI：10.1016/s0040-4039(00)60664-0

  日期：1993.9

  synthesis of the N-cyano benzo[b]carbazolequinone with the structure proposed for prekinamycin has been achieved by palladium and copper catalyzed coupling of a 2-bromonaphthoquinone with an arylstannane followed by ring closure, N-cyanation, and demethylation. Unexpectedly, the ring closure reaction gave also a regioisomer by an unprecedented rearrangement reaction.

  通过钯和铜催化的2-溴萘甲醌与芳基锡烷的偶联，然后闭环，N-氰化和去甲基化，可以合成具有拟用于前激霉素的结构的N-氰基苯并[ b ]咔唑醌。出乎意料的是，闭环反应通过空前的重排反应也产生了区域异构体。
• SEATON, PAMELA J.;GOULD, STEVEN J., J. ANTIBIOTICS, 42,(1989) N, C. 189-197
  作者：SEATON, PAMELA J.、GOULD, STEVEN J.

  DOI：——

  日期：——
• Synthesis of benzo[b]carbazoloquinones by coupling of organostannanes with bromoquinones
  作者：Antonio M Echavarren、Nuria Tamayo、Óscar de Frutos、Alicia García

  DOI：10.1016/s0040-4020(97)10085-0

  日期：1997.12

  The synthesis of 5-carbonitrile-1,7-dihydroxy-3-methyl-5H-benzo[b]carbazole-6,11-dione, the quinone originally proposed as prekinamycin, was completed by using a palladium and copper catalyzed Stille reaction as the key step. A subsequent heterocyclization afforded a mixture of para(benzo[b]carbazole-6,11-dione) and ortho (benzo[a]carbazole-6,11-dione) quinones. A procedure for the N-cyanation of model indoles is also described. (C) 1997 Elsevier Science Ltd.
• Prekinamycin and an isosteric-isoelectronic analogue exhibit comparable cytotoxicity towards K562 human leukemia cells
  作者：Glenn L. Abbott、Xing Wu、Zhufeng Zhao、Lei Guo、Vladimir B. Birman、Brian B. Hasinoff、Gary I. Dmitrienko

  DOI：10.1039/c4md00197d

  日期：——

  The diazo functionality of the kinamycins may not be an absolute requirement for bioactivity.

  金霉素的二氮氧基官能团对生物活性可能不是绝对必需的。