benzo[b]thieno[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H,13H)-dione | 174349-80-5

• 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: benzo[b]thieno[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H,13H)-dione
• 英文别名: 6H,12H-benzo[b]thieno[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione；3-Thia-13,23-diazahexacyclo[14.7.0.0^{2,10}.0^{4,9}.0^{11,15}.0^{17,22}]tricosa-1(16),2(10),4(9),5,7,11(15),17(22),18,20-nonaene-12,14-dione；3-thia-13,23-diazahexacyclo[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: 174349-80-5
• 化学式: C₂₀H₁₀N₂O₂S
• 分子量: 342.378
• InChiKey: JJQPROAZGIYDBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzo[b]thieno[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H,13H)-dione 在 盐酸 、 汞 、 锌 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以62%的产率得到6H,12H-benzo[b]thieno[2,3-a]pyrrolo[3,4-c]carbazole-7-one
  参考文献：
  名称：

  苯并[b]噻吩并和苯并[b]呋喃基-[2,3-a]吡咯并[3,4-c]咔唑-5-，-7-和-5,7-二酮的合成

  摘要：

  苯并[b]噻吩并[2,3-a]吡咯并[3,4-c]咔唑和苯并[b]呋喃基[2,3-a]吡咯并[3,4-c]咔唑是从2-（2 -钯（II）-苯并[b]噻吩并）-（8）和2-（2-苯并[b]呋喃基）-3- [3-（2,5-二氧代-1H-吡咯烷基）]吲哚（9）乙酸盐/四氯-1,4-苯醌氧化AE闭环。

  DOI：

  10.1002/jhet.5570380306
• 作为产物：
  描述：

  3-(1-benzothiophen-3-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione 在 碘 作用下， 以 苯 为溶剂， 生成 benzo[b]thieno[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H,13H)-dione
  参考文献：
  名称：

  Aryl[ a ]pyrrolo[3,4- c ]carbazoles as selective cyclin D1-CDK4 inhibitors

  摘要：

  The synthesis of new analogues of Arcyriaflavin A in which one indole ring is replaced by an aryl or heteroaryl ring is described. These new series of aryl[a]pyrrolo[3,4-c]carbazoles were evaluated as inhibitors of Cyclin D1-CDK4. A potent and selective D1-CDK4 inhibitor, 7a (D1-CDK4 IC50=45 nM), has been identified. The potency, selectivity profile against other kinases, and structure-activity relationship (SAR) trends of this class of compounds are discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00791-1

文献信息

• Synthesis of benzo[b]thieno- and benzo[b]furano-[2,3-a]pyrrolo[3,4-c]carbazole-5-, -7- and -5,7-dione
  作者：Robert L. Hudkins、Neil W. Johnson

  DOI：10.1002/jhet.5570380306

  日期：2001.5

  Benzo[b]thieno[2,3-a]pyrrolo[3,4-c]carbazoles and benzo[b]furano[2,3-a]pyrrolo[3,4-c]carbazoles were prepared from 2-(2-benzo[b]thieno)- (8) and 2-(2-benzo[b]furano)-3-[3-(2,5-dioxo-lH-pyrrolidinyl)]indole (9) by a palladium(II)acetate/tetrachloro-1,4-benzoquinone oxidative A-E ring closure.

  苯并[b]噻吩并[2,3-a]吡咯并[3,4-c]咔唑和苯并[b]呋喃基[2,3-a]吡咯并[3,4-c]咔唑是从2-（2 -钯（II）-苯并[b]噻吩并）-（8）和2-（2-苯并[b]呋喃基）-3- [3-（2,5-二氧代-1H-吡咯烷基）]吲哚（9）乙酸盐/四氯-1,4-苯醌氧化AE闭环。
• Aryl[ a ]pyrrolo[3,4- c ]carbazoles as selective cyclin D1-CDK4 inhibitors
  作者：Concha Sanchez-Martinez、Chuan Shih、Margaret M. Faul、Guoxin Zhu、Michael Paal、Carmen Somoza、Tiechao Li、Christine A. Kumrich、Leonard L. Winneroski、Zhou Xun、Harold B. Brooks、Bharvin K.R. Patel、Richard M. Schultz、Tammy B. DeHahn、Charles D. Spencer、Scott A. Watkins、Eileen Considine、Jack A. Dempsey、Catherine A. Ogg、Robert M. Campbell、Bryan A. Anderson、Jill Wagner

  DOI：10.1016/s0960-894x(03)00791-1

  日期：2003.11

  The synthesis of new analogues of Arcyriaflavin A in which one indole ring is replaced by an aryl or heteroaryl ring is described. These new series of aryl[a]pyrrolo[3,4-c]carbazoles were evaluated as inhibitors of Cyclin D1-CDK4. A potent and selective D1-CDK4 inhibitor, 7a (D1-CDK4 IC50=45 nM), has been identified. The potency, selectivity profile against other kinases, and structure-activity relationship (SAR) trends of this class of compounds are discussed. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of Aryl- and Heteroaryl[<i>a</i>]pyrrolo[3,4-<i>c</i>]carbazoles
  作者：Concha Sanchez-Martinez、Margaret M. Faul、Chuan Shih、Kevin A. Sullivan、John L. Grutsch、Jeremy T. Cooper、Stanley P. Kolis

  DOI：10.1021/jo034207x

  日期：2003.10.1

  Synthesis of aryl- and hetero[a]pyrrolo[3,4-c]carbazoles by photochemical oxidation and Heck cyclization are described. Photochemical oxidation of 2-naphthyl indolyl maleimide affords two different carbazole regioisomers, depending on the reaction conditions. The regiochemistry of the cyclization can be controlled using the Heck reaction.
• Synthesis and Mixed Lineage Kinase Activity of Pyrrolocarbazole and Isoindolone Analogs of (+)K-252a
  作者：Robert L. Hudkins、Neil W. Johnson、Thelma S. Angeles、George W. Gessner、John P. Mallamo

  DOI：10.1021/jm051074u

  日期：2007.2.8

  Structural modification of the indolecarbazole natural product (+)K-252a identified structural requirements for MLK activity and a novel series of potent fused pyrrolocarbazole MLK1/3 inhibitors. The SAR revealed that the lactam regiochemistry, the shape of the heterocycle, and aryl rings B and F are important to MLK activity. Heteroatom and alkyl replacement of the N-12 and/or N-13 indole nitrogen atoms identified the nonplanar dihydronaphthyl[3,4-a]pyrrolo[3,4-c]carbazole-7-one (8) and corresponding 5,7-dione (7) as potent cell-permeable MLK1/3 family-selective leads with in vitro activity comparable to that of (+)K-252a and determined them to be 2- to 3-fold more potent than the aglycone natural product K-252c.