methyl 3-bromophenethylcarbamate | 1279816-33-9

• 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: methyl 3-bromophenethylcarbamate
• 英文别名: methyl N-[2-(3-bromophenyl)ethyl]carbamate
• CAS: 1279816-33-9
• 化学式: C₁₀H₁₂BrNO₂
• 分子量: 258.115
• InChiKey: MONWLTALOPFVDE-UHFFFAOYSA-N

物化性质

• 沸点：
  365.3±25.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3-bromophenethylcarbamate 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四磷十氧化物 、 potassium acetate 、 sodium carbonate 、 对甲苯磺酸 、 三氯氧磷 作用下， 以 乙醇 、 水 、 二甲基亚砜 、 丙酮 、 甲苯 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Exploration of a Series of 5-Arylidene-2-thioxoimidazolidin-4-ones as Inhibitors of the Cytolytic Protein Perforin

  摘要：

  A series of novel 5-arylidene-2-thioxoimidazolidin-4-ones were investigated as inhibitors of the lymphocyte-expressed pore-forming protein perform. Structure activity relationships were explored through variation of an isoindolinone or 3,4-dihydroisoquinolinone subunit on a fixed 2-thioxoimidazolidin-4-one/thiophene core. The ability of the resulting compounds to inhibit the lytic activity of both isolated perform protein and perforin delivered in situ by natural killer cells was determined. A number of compounds showed excellent activity at concentrations that were nontoxic to the killer cells, and several were a significant improvement on previous classes of inhibitors, being substantially more potent and soluble. Representative examples showed rapid and reversible binding to immobilized mouse perforin at low concentrations (<= 2.5 mu M) by surface plasmon resonance and prevented formation of perforin pores in target cells despite effective target cell engagement, as determined by calcium influx studies. Mouse PK studies of two analogues showed T-1/2 values of 1.1-1.2 h (dose of 5 mg/kg iv) and MTDs of 60-80 mg/kg (ip).

  DOI：

  10.1021/jm401604x
• 作为产物：
  描述：

  3-溴氰苄 在 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 methyl 3-bromophenethylcarbamate
  参考文献：
  名称：

  一种6-溴-1,2,3,4-四氢异喹啉-1-甲酸的化 学合成方法

  摘要：

  本发明涉及一种6‑溴‑1,2,3,4‑四氢异喹啉‑1‑甲酸的化学合成方法。本发明以3‑溴苯乙腈为原料，经还原、酰胺化、关环、水解四步反应简易合成了6‑溴‑1,2,3,4‑四氢异喹啉‑1‑甲酸。本发明为该化合物的合成提供了一种高效合成的方法。主要包括如下：将3‑溴苯乙腈和催化剂雷内镍，加入到甲醇或乙醇溶剂中，通入氢气还原得到3‑溴苯乙胺；将3‑溴苯乙胺、氯甲酸甲酯和缚酸剂，溶于有机溶剂中，控制反应温度，得到3‑溴苯乙氨基甲酸甲酯；将3‑溴苯乙氨基甲酸甲酯、2‑羰基乙酸和浓硫酸，加入四氢呋喃溶剂中，反应得到6‑溴‑2‑甲氧羰基‑1,2,3,4‑四氢异喹啉‑1‑甲酸；将6‑溴‑2‑甲氧羰基‑1,2,3,4‑四氢异喹啉‑1‑甲酸，加入一定浓度的硫酸中，反应得到6‑溴‑1,2,3,4‑四氢异喹啉‑1‑甲酸。

  公开号：

  CN103880745B

文献信息

• [EN] COMPOUNDS, PREPARATIONS AND USES THEREOF<br/>[FR] COMPOSÉS, LEURS PRÉPARATIONS ET LEURS UTILISATIONS
  申请人：PETER MACCALLUM CANCER INST

  公开号：WO2011075784A1

  公开（公告）日：2011-06-30

  The present invention provides novel compounds of the Formula (I), pharmaceutical compositions comprising such compounds and methods for using such compounds as agents or drugs for inhibiting perforin activity and for treating a subject at risk of or susceptible to a disease or disorder, or having a disease or disorder associated with undesirable perforin activity.

  本发明提供了式（I）的新化合物，包括这些化合物的药物组合物以及使用这些化合物作为抑制穿孔素活性的药剂或药物，用于治疗患有与不良穿孔素活性相关的疾病或紊乱、或处于患有风险或易感染某种疾病或紊乱的受试者的方法。
• COMPOUNDS, PREPARATION AND USES THEREOF
  申请人：Spicer Julie Ann

  公开号：US20130065897A1

  公开（公告）日：2013-03-14

  The present invention provides novel compounds of the Formula I, pharmaceutical compositions comprising such compounds and methods for using such compounds as agents or drugs for inhibiting perforin activity and for treating a subject at risk of or susceptible to a disease or disorder, or having a disease or disorder associated with undesirable perforin activity.

  本发明提供了公式I的新化合物，包括这些化合物的制药组合物以及使用这些化合物作为抑制穿孔素活性的药剂或药物的方法，以及用于治疗处于风险或易感疾病或紊乱，或具有与不良穿孔素活性相关的疾病或紊乱的受试者。
• COMPOUNDS, PREPARATIONS AND USES THEREOF
  申请人：Peter MacCallum Cancer Institute

  公开号：EP2515903A1

  公开（公告）日：2012-10-31
• Exploration of a Series of 5-Arylidene-2-thioxoimidazolidin-4-ones as Inhibitors of the Cytolytic Protein Perforin
  作者：Julie A. Spicer、Gersande Lena、Dani M. Lyons、Kristiina M. Huttunen、Christian K. Miller、Patrick D. O’Connor、Matthew Bull、Nuala Helsby、Stephen M. F. Jamieson、William A. Denny、Annette Ciccone、Kylie A. Browne、Jamie A. Lopez、Jesse Rudd-Schmidt、Ilia Voskoboinik、Joseph A. Trapani

  DOI：10.1021/jm401604x

  日期：2013.12.12

  A series of novel 5-arylidene-2-thioxoimidazolidin-4-ones were investigated as inhibitors of the lymphocyte-expressed pore-forming protein perform. Structure activity relationships were explored through variation of an isoindolinone or 3,4-dihydroisoquinolinone subunit on a fixed 2-thioxoimidazolidin-4-one/thiophene core. The ability of the resulting compounds to inhibit the lytic activity of both isolated perform protein and perforin delivered in situ by natural killer cells was determined. A number of compounds showed excellent activity at concentrations that were nontoxic to the killer cells, and several were a significant improvement on previous classes of inhibitors, being substantially more potent and soluble. Representative examples showed rapid and reversible binding to immobilized mouse perforin at low concentrations (<= 2.5 mu M) by surface plasmon resonance and prevented formation of perforin pores in target cells despite effective target cell engagement, as determined by calcium influx studies. Mouse PK studies of two analogues showed T-1/2 values of 1.1-1.2 h (dose of 5 mg/kg iv) and MTDs of 60-80 mg/kg (ip).
• 一种6-溴-1,2,3,4-四氢异喹啉-1-甲酸的化 学合成方法
  申请人：南通大学

  公开号：CN103880745B

  公开（公告）日：2018-12-04

  本发明涉及一种6‑溴‑1,2,3,4‑四氢异喹啉‑1‑甲酸的化学合成方法。本发明以3‑溴苯乙腈为原料，经还原、酰胺化、关环、水解四步反应简易合成了6‑溴‑1,2,3,4‑四氢异喹啉‑1‑甲酸。本发明为该化合物的合成提供了一种高效合成的方法。主要包括如下：将3‑溴苯乙腈和催化剂雷内镍，加入到甲醇或乙醇溶剂中，通入氢气还原得到3‑溴苯乙胺；将3‑溴苯乙胺、氯甲酸甲酯和缚酸剂，溶于有机溶剂中，控制反应温度，得到3‑溴苯乙氨基甲酸甲酯；将3‑溴苯乙氨基甲酸甲酯、2‑羰基乙酸和浓硫酸，加入四氢呋喃溶剂中，反应得到6‑溴‑2‑甲氧羰基‑1,2,3,4‑四氢异喹啉‑1‑甲酸；将6‑溴‑2‑甲氧羰基‑1,2,3,4‑四氢异喹啉‑1‑甲酸，加入一定浓度的硫酸中，反应得到6‑溴‑1,2,3,4‑四氢异喹啉‑1‑甲酸。