(5R,11aS)-2-(5-azido-pentyl)-5-(3-hydroxyphenyl)-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione | 1223077-59-5

• 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: (5R,11aS)-2-(5-azido-pentyl)-5-(3-hydroxyphenyl)-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione
• 英文别名: (5R,11aS)-2-(5-azidopentyl)-5-(3-hydroxyphenyl)-6H-1,2,3,5,11,11a-hexahydroimidazo[1,5-b]-β-carboline-1,3-dione；(10R,15S)-13-(5-azidopentyl)-10-(3-hydroxyphenyl)-8,11,13-triazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(9),2,4,6-tetraene-12,14-dione
• CAS: 1223077-59-5
• 化学式: C₂₄H₂₄N₆O₃
• 分子量: 444.493
• InChiKey: SDFLYPKEGLHWQL-RBBKRZOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5R,11aS)-2-(5-azido-pentyl)-5-(3-hydroxyphenyl)-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 以94%的产率得到(5R,11aS)-2-(5-aminopentyl)-5-(3-hydroxyphenyl)-6H-1,2,3,5,11,11a-hexahydroimidazo[1,5-b]-β-carboline-1,3-dione
  参考文献：
  名称：

  The first highly stereoselective approach to the mitotic kinesin Eg5 inhibitor HR22C16 and its analogues

  摘要：

  A general method for the synthesis of the mitotic kinesin Eg5 inhibitor HR22C16 1 and its analogues based on protecting group (PG)-modulated highly diastereoselective Pictet-Spengler reaction of L-tryptophan methyl ester hydrochloride with meta-(RO)-benzaldehyde is described. By using the enantiomerically pure (1R,3S)-1,3-disubstituted tetrahydro-beta-carboline trans-4c as a common chiral synthon, HR22C16 1 and its analogues 2 and 3 were synthesized in 90.1%, 90.2%, and 86.5% overall yields, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.029
• 作为产物：
  描述：

  D-色氨酸甲酯 在 甲醇 、 氢溴酸 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 异丙醇 为溶剂， 反应 21.77h， 生成 (5R,11aS)-2-(5-azido-pentyl)-5-(3-hydroxyphenyl)-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione
  参考文献：
  名称：

  A general strategy for the highly stereoselective synthesis of HR22C16-like mitotic kinesin Eg5 inhibitors from both l- and d-tryptophans

  摘要：

  An efficient and general strategy for the highly stereoselective synthesis of HR22C16-like mitotic kinesin Eg5 inhibitors 1 from both L- and D-tryptophan methyl ester hydrohalides is described. (1R,35)-trans-1,3-Disubstituted 1,2,3,4-tetrahydro-beta-carbolines (1R,3S)-trans-2 could be obtained in high yields and with high stereoselectivities from the Pictet-Spengler reaction of L-tryptophan methyl ester hydrohalide with some 3-acyloxyl benzaldehydes via a CIAT (crystal induced asymmetric transformation) process, whereas (1R,3R)-cis-1,3-disubstituted 1,2,3,4-tetrahydro-beta-carbolines (1R,3R)-cis-2 could also be obtained in high yields and with high stereoselectivities from a Pictet-Spengler reaction of D-tryptophan methyl ester hydrohalide with some other 3-acyloxyl benzaldehydes via a CIAT process. Both compounds (1R,35)-trans-2 and (1R,3R)-cis-2 were efficiently converted into HR22C16-like mitotic kinesin Eg5 inhibitors 1 by the same one-pot procedure through tandem reactions. A total of eighteen target compounds 1 were obtained from six intermediate compounds 2 in 87-95% yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.011