(-)-S-{5-[(3S,9S,14aR)-9-benzyl-6,6-dimethyl-1,4,7,10-tetraoxotetradecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-3-yl]pentyl} octanethioate | 1429340-71-5

• 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: (-)-S-{5-[(3S,9S,14aR)-9-benzyl-6,6-dimethyl-1,4,7,10-tetraoxotetradecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-3-yl]pentyl} octanethioate
• 英文别名: S-[5-[(3S,9S,12R)-3-benzyl-6,6-dimethyl-2,5,8,11-tetraoxo-1,4,7,10-tetrazabicyclo[10.3.0]pentadecan-9-yl]pentyl] octanethioate
• CAS: 1429340-71-5
• 化学式: C₃₃H₅₀N₄O₅S
• 分子量: 614.85
• InChiKey: XQAPPMPAFRLPLN-GMQQYTKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-S-{5-[(3S,9S,14aR)-9-benzyl-6,6-dimethyl-1,4,7,10-tetraoxotetradecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-3-yl]pentyl} octanethioate 在 甲醇 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以62%的产率得到(-)-S-{5-[(2S,8S)-8-benzyl-5,5-dimethyl-3,6,9,15-tetraoxo-1,4,7,10-tetraazacyclopentadecan-2-yl]pentyl} octanethioate
  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
• 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 、 偶氮二异丁腈 、 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 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 97.0h， 生成 (-)-S-{5-[(3S,9S,14aR)-9-benzyl-6,6-dimethyl-1,4,7,10-tetraoxotetradecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-3-yl]pentyl} octanethioate
  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

• 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.