2-cyano-N-[2-(bromo)phenyl]acetamide | 80277-87-8

• 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: 2-cyano-N-[2-(bromo)phenyl]acetamide
• 英文别名: N-(2-bromophenyl)-2-cyanoacetamide
• CAS: 80277-87-8
• 化学式: C₉H₇BrN₂O
• mdl: MFCD03383383
• 分子量: 239.071
• InChiKey: IBHCCLKPASINHW-UHFFFAOYSA-N

物化性质

• 熔点：
  140-141 °C
• 沸点：
  437.2±30.0 °C(Predicted)
• 密度：
  1.608±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2-cyano-N-[2-(bromo)phenyl]acetamide 在 盐酸羟胺 、 sodium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以77%的产率得到3-amino-3-(hydroxyimino)-N-[2-(bromo)phenyl]propanamide
  参考文献：
  名称：

  Low Molecular Weight Amidoximes that Act as Potent Inhibitors of Lysine-Specific Demethylase 1

  摘要：

  The recently discovered enzyme lysine-specific demethylase 1 (LSD1) plays an important role in the epigenetic control of gene expression, and aberrant gene silencing secondary to LSD1 dysregulation is thought to contribute to the development of cancer. We reported that (bis)guanidines, (bis)biguanides, and their urea- and thiourea isosteres are potent inhibitors of LSD1 and induce the re-expression of aberrantly silenced tumor suppressor genes in tumor cells in vitro. We now report a series of small molecule amidoximes that are moderate inhibitors of recombinant LSD1 but that produce dramatic changes in methylation at the histone 3 lysine 4 (H3K4) chromatin mark, a specific target of LSD1, in Calu-6 lung carcinoma cells. In addition, these analogues increase cellular levels of secreted frizzle-related protein (SFRP) 2, H-cadherin (HCAD), and the transcription factor GATA4. These compounds represent leads for an important new series of drug-like epigenetic modulators with the potential for use as antitumor agents.

  DOI：

  10.1021/jm3002845
• 作为产物：
  描述：

  氰乙酸 、 2-溴苯胺 在 五氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以95%的产率得到2-cyano-N-[2-(bromo)phenyl]acetamide
  参考文献：
  名称：

  Low Molecular Weight Amidoximes that Act as Potent Inhibitors of Lysine-Specific Demethylase 1

  摘要：

  The recently discovered enzyme lysine-specific demethylase 1 (LSD1) plays an important role in the epigenetic control of gene expression, and aberrant gene silencing secondary to LSD1 dysregulation is thought to contribute to the development of cancer. We reported that (bis)guanidines, (bis)biguanides, and their urea- and thiourea isosteres are potent inhibitors of LSD1 and induce the re-expression of aberrantly silenced tumor suppressor genes in tumor cells in vitro. We now report a series of small molecule amidoximes that are moderate inhibitors of recombinant LSD1 but that produce dramatic changes in methylation at the histone 3 lysine 4 (H3K4) chromatin mark, a specific target of LSD1, in Calu-6 lung carcinoma cells. In addition, these analogues increase cellular levels of secreted frizzle-related protein (SFRP) 2, H-cadherin (HCAD), and the transcription factor GATA4. These compounds represent leads for an important new series of drug-like epigenetic modulators with the potential for use as antitumor agents.

  DOI：

  10.1021/jm3002845

文献信息

• 3,4-Disubstituted isothiazoles: Novel potent inhibitors of VEGF receptors 1 and 2
  作者：Alexander S. Kiselyov、Marina Semenova、Victor V. Semenov

  DOI：10.1016/j.bmcl.2008.12.078

  日期：2009.2

  Novel derivatives of isothiazoles are described as potent ATP-competitive inhibitors of vascular endothelial growth factor receptors I and II (VEGFR-1/2). A number of compounds exhibited VEGFR-2 inhibitory activity comparable to that of Vatalanib™ in both HTRF enzymatic and cellular assays. Several derivatives featuring bulky meta-substituents in the amide portion of the molecule displayed 4- to 8-fold

  异噻唑的新型衍生物被描述为血管内皮生长因子受体I和II（VEGFR-1 / 2）的有效ATP竞争性抑制剂。在HTRF酶和细胞分析中，许多化合物均具有与Vatalanib™相当的VEGFR-2抑制活性。几种在分子的酰胺部分具有较大的间位取代基的衍生物显示出对VEGFR-2的特异性是VEGFR-1的4到8倍。活性分子 在整个Caco-2细胞单层上也表现出高的固有渗透性（> 30×10 -5 cm / min）。
• Substituted phenyl-5-aminopyrazoles
  申请人：American Cyanamid Company

  公开号：US04393217A1

  公开（公告）日：1983-07-12

  This disclosure describes novel substituted phenyl-5-aminopyrazoles useful as anxiolytic and/or anti-depressant agents.

  这份披露描述了新型的取代苯基-5-氨基吡唑，可用作抗焦虑和/或抗抑郁药物。
• Synthesis of highly functionalized dihydroquinolinones via a tandem benzylation/intramolecular C–N coupling strategy
  作者：Pei-Sen Gao、Chang-Wang Pan、Yan Sui、Hui-Xian Ye、Cheng Liu、Dong-Sheng Liu、Wen-Tong Chen

  DOI：10.1016/j.tet.2024.133865

  日期：2024.4

  This study reported a tandem strategy on sequential base-controlled benzylation/Pd-catalyzed secondary amide arylation for one-pot synthesis of highly functionalized hydroquinolin-2-ones. This strategy involves creation of 3 bonds, 1 ring, and 1 quaternary carbon center while synthesizing diverse 3-cyano substituted hydroquinolin-2-ones in 41–83% yields.

  本研究报道了连续碱基控制的苄基化/Pd 催化的仲酰胺芳基化的串联策略，用于一锅合成高功能化的氢喹啉-2-酮。该策略涉及创建 3 个键、1 个环和 1 个季碳中心，同时合成多种 3-氰基取代的氢喹啉-2-酮，产率为 41-83%。
• US4393217A
  申请人：——

  公开号：US4393217A

  公开（公告）日：1983-07-12