N-allyloxycarbonyl-N'-benzylethylenediamine | 289905-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-allyloxycarbonyl-N'-benzylethylenediamine
• 英文别名: Carbamic acid, [2-[(phenylmethyl)amino]ethyl]-, 2-propenyl ester；prop-2-enyl N-[2-(benzylamino)ethyl]carbamate
• CAS: 289905-94-8
• 化学式: C₁₃H₁₈N₂O₂
• 分子量: 234.298
• InChiKey: VTDHGXZXDJZNHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-allyloxycarbonyl-N'-benzylethylenediamine 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 三正丁基氢锡 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 4-(Benzyl-{2-[(2,5-diphenyl-oxazole-4-carbonyl)-amino]-ethyl}-carbamoyl)-2-((9Z,12Z)-octadeca-9,12-dienoylamino)-butyric acid methyl ester
  参考文献：
  名称：

  在靶向的小分子阵列中鉴定新的Cdc25双特异性磷酸酶抑制剂。

  摘要：

  双重特异性蛋白磷酸酶（DSPase）是信号转导，肿瘤发生和细胞周期的关键调节因子。然而，很少有有效的或特异性的DSPase抑制剂可用于这些药理靶标。我们已经使用了组合/平行合成的方法来硬化可变核心区域，并修改4-（苄基-（2- [2- [2,5-二苯基-恶唑-4-羰基）-氨基]-乙基）-氨基甲酰基的侧链）-2-癸酰氨基丁酸（或SC-alphaalphadelta9），它是先前描述的磷酸酶抑制剂文库（Rice，RL; Rusnak，JM; Yokokawa，F .; Yokokawa，S .; Messner，DJ）中最活跃的元素； Boynton，AL； Wipf，P。； Lazo，JS Biochemistry 1997，36，15965）。几种类似物被鉴定为蛋白酪氨酸磷酸酶（PTPase）PTP1B和DSPases VHR和Cdc25B2的有效抑制剂。FY3-alphaalpha09和

  DOI：

  10.1016/s0968-0896(00)00069-9
• 作为产物：
  描述：

  N-allyloxycarbonyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamide 、 N-苄基乙二胺 反应 24.0h， 以89%的产率得到N-allyloxycarbonyl-N'-benzylethylenediamine
  参考文献：
  名称：

  Studies on Development of Sufficiently Chemoselective N-Acylation Reagents: N-Acyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamides

  摘要：

  A variety of storable N-acyl-N-(2,3,4,5,6-pentafluorophenyl)met (4a-e) prepared from N-2,3,4,5,6-pentafluorophenylmethanesulfonamide (3), have been developed after systematic research on the structure-reactivity relationship and were found to serve as N-acylation reagents exhibiting sufficiently good chemoselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00549-4

文献信息

• Combinatorial synthesis and biological evaluation of Library of small-molecule Ser/Thr-protein phosphatase inhibitors
  作者：Peter Wipf、April Cunningham、Robert L. Rice、John S. Lazo

  DOI：10.1016/s0968-0896(96)00199-x

  日期：1997.1

  In eukaryotes, phosphorylation of serine, threonine, and tyrosine residues on proteins is a fundamental posttranslational regulatory process for such functions as signal transduction, gene transcription, RNA splicing, cellular adhesion, apoptosis, and cell cycle control. Based on functional groups present in natural product serine/threonine protein phosphatase (PSTPase) inhibitors, we have designed pharmacophore model 1 and demonstrated the feasibility of a combinatorial chemistry approach for the preparation of functional analogues of 1. preliminary biological testing of 18 structural variants of 1 has identified two compounds with growth inhibitory activity against cultured human breast cancer cells. In vitro inhibition of the PSTPase PP2A was demonstrated with compound 1d. Using flow cytometry we observed that compound If caused prominent inhibition in the G1 phase of the cell cycle. Thus, the combinatorial modifications of the minimal pharmacophore 1 can generate biologically interesting antiproliferative agents. Copyright (C) 1997 Elsevier Science Ltd.
• Studies on Development of Sufficiently Chemoselective N-Acylation Reagents: N-Acyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamides
  作者：Kazuhiro Kondo、Erika Sekimoto、Junko Nakao、Yasuoki Murakami

  DOI：10.1016/s0040-4020(00)00549-4

  日期：2000.8

  A variety of storable N-acyl-N-(2,3,4,5,6-pentafluorophenyl)met (4a-e) prepared from N-2,3,4,5,6-pentafluorophenylmethanesulfonamide (3), have been developed after systematic research on the structure-reactivity relationship and were found to serve as N-acylation reagents exhibiting sufficiently good chemoselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Identification of new Cdc25 dual specificity phosphatase inhibitors in a targeted small molecule array
  作者：Alexander P Ducruet、Robert L Rice、Kenji Tamura、Fumiaki Yokokawa、Shiho Yokokawa、Peter Wipf、John S Lazo

  DOI：10.1016/s0968-0896(00)00069-9

  日期：2000.6

  phosphatase inhibitors (Rice, R. L.; Rusnak, J. M.; Yokokawa, F.; Yokokawa, S.; Messner, D. J.; Boynton, A. L.; Wipf, P.; Lazo, J. S. Biochemistry 1997, 36, 15965). Several analogues were identified as effective inhibitors of the protein tyrosine phosphatase (PTPase) PTP1B and the DSPases VHR and Cdc25B2. Two compounds, FY3-alphaalpha09 and FY21-alphaalpha09, were partial competitive inhibitors of Cdc25B2

  双重特异性蛋白磷酸酶（DSPase）是信号转导，肿瘤发生和细胞周期的关键调节因子。然而，很少有有效的或特异性的DSPase抑制剂可用于这些药理靶标。我们已经使用了组合/平行合成的方法来硬化可变核心区域，并修改4-（苄基-（2- [2- [2,5-二苯基-恶唑-4-羰基）-氨基]-乙基）-氨基甲酰基的侧链）-2-癸酰氨基丁酸（或SC-alphaalphadelta9），它是先前描述的磷酸酶抑制剂文库（Rice，RL; Rusnak，JM; Yokokawa，F .; Yokokawa，S .; Messner，DJ）中最活跃的元素； Boynton，AL； Wipf，P。； Lazo，JS Biochemistry 1997，36，15965）。几种类似物被鉴定为蛋白酪氨酸磷酸酶（PTPase）PTP1B和DSPases VHR和Cdc25B2的有效抑制剂。FY3-alphaalpha09和