(-)-(3S,9S,14aR)-9-benzyl-3-[(R)-7-(tert-butyldimethylsilyloxy)-6-oxooctyl]-6,6-dimethyldecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10-tetraone | 1247053-01-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (-)-(3S,9S,14aR)-9-benzyl-3-[(R)-7-(tert-butyldimethylsilyloxy)-6-oxooctyl]-6,6-dimethyldecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10-tetraone
• 英文别名: (3S,9S,14aR)-9-benzyl-3-((R)-7-(tert-butyldimethylsilyloxy)-6-oxooctyl)-6,6-dimethyldecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10-tetraone；(3S,9S,12R)-3-benzyl-9-[(7R)-7-[tert-butyl(dimethyl)silyl]oxy-6-oxooctyl]-6,6-dimethyl-1,4,7,10-tetrazabicyclo[10.3.0]pentadecane-2,5,8,11-tetrone
• CAS: 1247053-01-5
• 化学式: C₃₄H₅₄N₄O₆Si
• 分子量: 642.911
• InChiKey: DRRPLDNNWWVJDF-GYUKIKGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-(3S,9S,14aR)-9-benzyl-3-[(R)-7-(tert-butyldimethylsilyloxy)-6-oxooctyl]-6,6-dimethyldecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10-tetraone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以78%的产率得到环[2-甲基丙氨酰基-L-苯丙氨酰基-D-脯氨酰基-(2S,9R)-2-氨基-9-羟基-8-氧代癸酰基]
  参考文献：
  名称：

  CYCLIC PEPTIDES WITH AN ANTI-PARASITIC ACTIVITY

  摘要：

  本发明涉及一种制备具有抗寄生虫活性和抗癌活性的环肽的方法。该发明还涉及将该肽作为抗寄生虫剂，例如在弓形虫病的治疗中以及作为抗癌剂的用途。该发明还涉及将该环肽用于移植前体外处理器官的用途。

  公开号：

  US20120034593A1
• 作为产物：
  描述：

  (S)-2-tert-butoxycarbonylamino-hex-5-enoic acid methyl ester 在 N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide 、 过氧化双月桂酰 、 1-羟基苯并三唑 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 26.5h， 生成 (-)-(3S,9S,14aR)-9-benzyl-3-[(R)-7-(tert-butyldimethylsilyloxy)-6-oxooctyl]-6,6-dimethyldecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10-tetraone
  参考文献：
  名称：

  Flexible Synthesis and Evaluation of Diverse Anti-Apicomplexa Cyclic Peptides

  摘要：

  A modular approach to synthesize anti-Apicomplexa parasite inhibitors was developed that takes advantage of a pluripotent cyclic tetrapeptide scaffold capable of adjusting appendage and skeletal diversities in only a few steps (one to three steps). The diversification processes make use of selective radical coupling reactions and involve a new example of a reductive carbon nitrogen cleavage reaction with SmI2. The resulting bioactive cyclic peptides have revealed new insights into structural factors that govern selectivity between Apicomplexa parasites such as Toxoplasma and Plasmodium and human cells.

  DOI：

  10.1021/jo4001492

文献信息

• CYCLIC PEPTIDES WITH AN ANTI-PARASITIC ACTIVITY
  申请人：Wong Yung-Sing

  公开号：US20120034593A1

  公开（公告）日：2012-02-09

  The present invention relates to a method for preparing a cyclic peptide with antiparasite activity and anticancer activity. The invention also relates to this peptide as an antiparasite agent, for example in the treatment of toxoplasmosis and as an anticancer agent. The invention also relates to the use of this cyclic peptide for treating organs ex vivo before transplantation.

  本发明涉及一种制备具有抗寄生虫活性和抗癌活性的环肽的方法。该发明还涉及将该肽作为抗寄生虫剂，例如在弓形虫病的治疗中以及作为抗癌剂的用途。该发明还涉及将该环肽用于移植前体外处理器官的用途。
• Flexible Synthesis and Evaluation of Diverse Anti-Apicomplexa Cyclic Peptides
  作者：Mariam Traoré、Flore Mietton、Danièle Maubon、Marine Peuchmaur、Flaviane Francisco Hilário、Rossimiriam Pereira de Freitas、Alexandre Bougdour、Aurélie Curt、Marjorie Maynadier、Henri Vial、Hervé Pelloux、Mohamed-Ali Hakimi、Yung-Sing Wong

  DOI：10.1021/jo4001492

  日期：2013.4.19

  A modular approach to synthesize anti-Apicomplexa parasite inhibitors was developed that takes advantage of a pluripotent cyclic tetrapeptide scaffold capable of adjusting appendage and skeletal diversities in only a few steps (one to three steps). The diversification processes make use of selective radical coupling reactions and involve a new example of a reductive carbon nitrogen cleavage reaction with SmI2. The resulting bioactive cyclic peptides have revealed new insights into structural factors that govern selectivity between Apicomplexa parasites such as Toxoplasma and Plasmodium and human cells.