fradcarbazole A | 1415406-00-6

• 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: fradcarbazole A
• 英文别名: Fradcarbazole A；(2S,3R,4R,6R)-4-[[5-(1H-indol-3-yl)-1,3-thiazol-2-yl]-methylamino]-3-methoxy-2-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-16-one
• CAS: 1415406-00-6
• 化学式: C₃₉H₃₂N₆O₃S
• 分子量: 664.787
• InChiKey: SOGUXZBEONSYNB-LIGDEFGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  49
• 可旋转键数：
  4
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  staurosporine 在 乙醇 、 三乙胺 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 49.0h， 生成 fradcarbazole A
  参考文献：
  名称：

  Biomimetic semi-synthesis of fradcarbazole A and its analogues

  摘要：

  The first synthesis of fradcarbazole A (1) has been accomplished by using a biomimetic intramolecular cyclization/dehydration to construct the staurosporine-thiazole-indole skeleton. The phenyl and oxazole analogues of fradcarbazole A (2-4) were also synthesized using the same strategy. Compounds 1-4 displayed cytotoxicity against A549 cell line with IC50 values of 0.4-3.6 mu M, induction of G(0)/G(1) arrest of A549 cell cycle at 10 mu M, and inhibition of PK-beta kinase with IC50 values of 0.5-0.9 mu W. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.065

文献信息

• Biomimetic semi-synthesis of fradcarbazole A and its analogues
  作者：Liping Wang、Xiangui Mei、Cong Wang、Weiming Zhu

  DOI：10.1016/j.tet.2015.08.065

  日期：2015.10

  The first synthesis of fradcarbazole A (1) has been accomplished by using a biomimetic intramolecular cyclization/dehydration to construct the staurosporine-thiazole-indole skeleton. The phenyl and oxazole analogues of fradcarbazole A (2-4) were also synthesized using the same strategy. Compounds 1-4 displayed cytotoxicity against A549 cell line with IC50 values of 0.4-3.6 mu M, induction of G(0)/G(1) arrest of A549 cell cycle at 10 mu M, and inhibition of PK-beta kinase with IC50 values of 0.5-0.9 mu W. (C) 2015 Elsevier Ltd. All rights reserved.