3-<2-<<<<2-(trimethylsilyl)ethyl>oxy>carbonyl>(allyloxy)amino>ethyl>indole | 142564-25-8

• 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: 3-<2-<<<<2-(trimethylsilyl)ethyl>oxy>carbonyl>(allyloxy)amino>ethyl>indole
• 英文别名: 2-trimethylsilylethyl N-[2-(1H-indol-3-yl)ethyl]-N-prop-2-enoxycarbamate
• CAS: 142564-25-8
• 化学式: C₁₉H₂₈N₂O₃Si
• 分子量: 360.528
• InChiKey: RQJVIHADLUARFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-<2-<<<<2-(trimethylsilyl)ethyl>oxy>carbonyl>(allyloxy)amino>ethyl>indole 在 palladium diacetate 、 氢氧化钾 、 甲酸:三乙胺 1:1 、 三苯基膦 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 1.5h， 生成 1-methyl-3-<2-<<<<2-(trimethylsilyl)ethyl>oxy>carbonyl>hydroxyamino>ethyl>indole
  参考文献：
  名称：

  Antiviral and antitumor structure-activity relationship studies on tetracyclic eudistomines

  摘要：

  The in vitro antiviral and antitumor activities of (-)-debromoeudistomin K (1a) and 10 structural analogues (1b-1j and 11) were evaluated. The synthesis was accomplished with an intramolecular Pictet-Spengler condensation reaction as the key step. This examination revealed some structural and stereochemical features that are important for both the antiviral and antitumor activities. The most striking points for activity are the necessity to have the correct natural stereochemistry at both C(1) and C(13b) and the presence of the C(1)-NH2 substituent. As was revealed before with naturally isolated eudistomins a substituent in the indole ring greatly influences the biological activity. The 5-OMe derivative Ih shows high potency in both antiviral and antitumor models.

  DOI：

  10.1021/jm00095a019
• 作为产物：
  描述：

  3-{2-[N-({[2-(Trimethylsilyl)ethyl]oxy}carbonyl)-N-hydroxylamino]ethyl}indole 、 3-溴丙烯 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 2.0h， 以100%的产率得到3-<2-<<<<2-(trimethylsilyl)ethyl>oxy>carbonyl>(allyloxy)amino>ethyl>indole
  参考文献：
  名称：

  Antiviral and antitumor structure-activity relationship studies on tetracyclic eudistomines

  摘要：

  The in vitro antiviral and antitumor activities of (-)-debromoeudistomin K (1a) and 10 structural analogues (1b-1j and 11) were evaluated. The synthesis was accomplished with an intramolecular Pictet-Spengler condensation reaction as the key step. This examination revealed some structural and stereochemical features that are important for both the antiviral and antitumor activities. The most striking points for activity are the necessity to have the correct natural stereochemistry at both C(1) and C(13b) and the presence of the C(1)-NH2 substituent. As was revealed before with naturally isolated eudistomins a substituent in the indole ring greatly influences the biological activity. The 5-OMe derivative Ih shows high potency in both antiviral and antitumor models.

  DOI：

  10.1021/jm00095a019

文献信息

• An approach to canthine derivatives using the intramolecular Pictet-Spengler condensation
  作者：Jan H van Maarseveen、Suzanne J.E Mulders、RenéW.M Aben、Chris G Kruse、Hans W Scheeren

  DOI：10.1016/0040-4020(95)00169-9

  日期：1995.4

  mild conditions. With Na-propanal chains, only dimeric and oligomeric compounds were isolated. With the Na-pentanal chain (unidentified) oligomeric compounds were formed as well. The monomeric canthine-like products have not been detected in these cases, probably because formation has to proceed via conformationally disfavored intermediate cyclic iminium ions. Cyclization of Na-butanal functionalized Nb-formyl-

  所述canthine衍生物1b中通过处理N个有效地合成一个（4,4-二乙氧基丁基）-N - b -allyloxytryptamine 9B用TFA / H 2 ö氯仿。该结果表明，在温和条件下，通过中间亚胺离子上吲哚2-位的直接攻击确实可以发生PS环化。用N-一-丙醛链，只有二聚和低聚化合物中分离得到。与N一还形成了-戊醛链（未鉴定的）低聚化合物。在这些情况下，未检测到单体类鸟氨酸产物，可能是因为形成必须通过构象不利的中间环亚胺离子进行。N个环化一-丁醛官能化的N- b甲酰基或N b -benzyltryptamines图9c和9d中，这是已知的速率在PS缩合增强取代基，意外地得到3,4-二氢嘧啶并[1,2一]吲哚16C ，d高产。产物16c，d是通过质子化醛在吲哚2-位上的直接亲电进攻而形成的。