N-(3-bromophenyl)propiolamide | 1094224-34-6

• 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-(3-bromophenyl)propiolamide
• 英文别名: N-(3-bromophenyl)prop-2-ynamide
• CAS: 1094224-34-6
• 化学式: C₉H₆BrNO
• mdl: MFCD11132490
• 分子量: 224.057
• InChiKey: OJMHFECEPQYCBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(3-bromophenyl)propiolamide 、 5-azidomethyl-2-methylpyrimidine-4-ylamine 在 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到1-((4-amino-2-methylpyrimidin-5-yl)methyl)-N-(3-bromophenyl)-1H-1,2,3-triazole-4-carboxamide
  参考文献：
  名称：

  1,2,3-三唑氨基嘧啶类抗蓝藻作为PDHc-E1竞争性抑制剂的合成及活性

  摘要：

  蓝藻有害藻华是全球关注的问题，但是市场上目前所有可用的杀藻剂都是非选择性的，并且对非目标物种具有潜在的副作用。在目前的工作中，合理设计并合成了包含16个新的1,2,3-三唑氨基嘧啶的两类化合物（4和6）作为蓝细菌的防治剂。我们的设计重点是通过抑制丙酮酸脱氢酶复合物E1（PDHc-E1）来抑制蓝细菌。化合物4和6显示出对强效抑制大肠杆菌PDHC-E1（IC 50 = 4.13-23.76μM）和对也强杀藻活动集胞藻。PCC 6803（EC50 = 1.7–8.1μM）和微囊藻。FACHB905（EC 50 = 2.1–11.8μM）。特别是6d对4种藻类的杀藻活性不仅高于prometricn。它们也与硫酸铜相当或更高。类似物4c，4d，6d和6e显示出强效的杀藻活性和对大肠杆菌PDHc-E1的抑制作用，但对猪PDHc-E1的抑制作用却可以忽略不计。如分子对接，定点诱变，酶促测定和抑制动力学分

  DOI：

  10.1021/acs.jafc.9b02878
• 作为产物：
  描述：

  3-Trimethylsilanyl-propynoic acid (3-bromo-phenyl)-amide 在 KF-Al₂O₃ (5 mol percent) 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以90%的产率得到N-(3-bromophenyl)propiolamide
  参考文献：
  名称：

  Highly efficient desilylation of 3-trimethylsilylprop-2-ynamides by the action of KF-Al2O3

  摘要：

  A highly effective procedure has been developed for desilylation of 3-trimethylsilylprop-2-ynamides in the presence of KF-Al2O3 as catalyst. The corresponding terminal prop-2-ynamides were obtained in high yield in methanol at 25 C using 5 mol % of the catalyst (reaction time 20 min). Rise in temperature leads to the formation of Z, E-3-methoxyprop-2-enamides or 3,3-dimethoxypropanamides as a result of tandem desilylation-addition of methanol, depending on the conditions.

  DOI：

  10.1134/s1070428011120037

文献信息

• Discovery of <i>N</i>-Phenylpropiolamide as a Novel Succinate Dehydrogenase Inhibitor Scaffold with Broad-Spectrum Antifungal Activity on Phytopathogenic Fungi
  作者：Yu-Hao Zhang、Shan-Shan Yang、Qi Zhang、Tian-Tian Zhang、Tian-Yi Zhang、Bo-Hang Zhou、Le Zhou

  DOI：10.1021/acs.jafc.2c07712

  日期：2023.3.1

  Based on the structural features of both succinate dehydrogenase inhibitors (SDHIs) and targeted covalent inhibitors, a series of N-phenylpropiolamides containing a Michael acceptor moiety were designed to find new antifungal compounds. Nineteen compounds showed potent inhibition activity in vitro on nine species of plant pathogenic fungi. Compounds 9 and 13 showed higher activity on most of the fungi

  基于琥珀酸脱氢酶抑制剂 (SDHI) 和靶向共价抑制剂的结构特征，设计了一系列含有迈克尔受体部分的N-苯基丙酰胺，以寻找新的抗真菌化合物。十九种化合物在体外对九种植物病原真菌显示出有效的抑制活性。化合物9和13对大多数真菌表现出比标准药物嘧菌酯更高的活性。化合物13可完全抑制Physalospora piricola在 200 μg/mL 的浓度下感染苹果超过 7 天，并且在≤100 μg/mL 的浓度下对植物的种子萌发和幼苗生长表现出高度安全性。作用机制表明，13是一种SDH抑制剂，中值抑制浓度IC 50为0.55 μg/mL，与阳性药物啶酰菌胺相当。分子对接研究表明，13可以通过氢键与SDH的泛醌结合区很好地结合，并发生π-烷基相互作用和π-阳离子相互作用。在细胞水平上，1作为母体化合物可以破坏P. piricola的菌丝结构并部分溶解细胞壁和/或细胞膜。构效关系分析表明，乙炔基应该是
• Construction of Multifunctional 3-Amino-2-carbamimidoylacrylamides and Their Crystalline Channel-Type Inclusion Complexes
  作者：Jinjin Wang、Jiyong Liu、Hualong Ding、Jing Wang、Ping Lu、Yanguang Wang

  DOI：10.1021/acs.joc.5b00827

  日期：2015.6.5

  3-Amino-2-carbarmimidoylacrylamides were efficiently prepared via a copper(I)-catalyzed three-component reaction of sulfonylaides, propriolamides, and amidines. The synthesized compounds provided three kinds of crystalline structures based on the position of halogen. Two of them presented channel-type inclusion complexes with ethyl acetate through intermolecular hydrogen bonding, intermolecular C-H center dot center dot center dot pi and pi-pi interactions, and van der Waals forces.
• Synthesis and Activity of 1,2,3-Triazole Aminopyrimidines against Cyanobacteria as PDHc-E1 Competitive Inhibitors
  作者：Yuan Zhou、Jiangtao Feng、Lingling Feng、Dan Xie、Hao Peng、Meng Cai、Hongwu He

  DOI：10.1021/acs.jafc.9b02878

  日期：2019.11.13

  available algicides in the market are nonselective and have potential side effects on nontarget species. In the present work, two series of compounds (4 and 6) comprising 16 novel 1,2,3-triazole aminopyrimidines were rationally designed and synthesized as control agent for cyanobacteria. Our design focus was the inhibiting cyanobacteria by inhibition against pyruvate dehydrogenase complex E1 (PDHc-E1)

  蓝藻有害藻华是全球关注的问题，但是市场上目前所有可用的杀藻剂都是非选择性的，并且对非目标物种具有潜在的副作用。在目前的工作中，合理设计并合成了包含16个新的1,2,3-三唑氨基嘧啶的两类化合物（4和6）作为蓝细菌的防治剂。我们的设计重点是通过抑制丙酮酸脱氢酶复合物E1（PDHc-E1）来抑制蓝细菌。化合物4和6显示出对强效抑制大肠杆菌PDHC-E1（IC 50 = 4.13-23.76μM）和对也强杀藻活动集胞藻。PCC 6803（EC50 = 1.7–8.1μM）和微囊藻。FACHB905（EC 50 = 2.1–11.8μM）。特别是6d对4种藻类的杀藻活性不仅高于prometricn。它们也与硫酸铜相当或更高。类似物4c，4d，6d和6e显示出强效的杀藻活性和对大肠杆菌PDHc-E1的抑制作用，但对猪PDHc-E1的抑制作用却可以忽略不计。如分子对接，定点诱变，酶促测定和抑制动力学分
• Highly efficient desilylation of 3-trimethylsilylprop-2-ynamides by the action of KF-Al2O3
  作者：M. V. Andreev、L. P. Safronova、A. S. Medvedeva

  DOI：10.1134/s1070428011120037

  日期：2011.12

  A highly effective procedure has been developed for desilylation of 3-trimethylsilylprop-2-ynamides in the presence of KF-Al2O3 as catalyst. The corresponding terminal prop-2-ynamides were obtained in high yield in methanol at 25 C using 5 mol % of the catalyst (reaction time 20 min). Rise in temperature leads to the formation of Z, E-3-methoxyprop-2-enamides or 3,3-dimethoxypropanamides as a result of tandem desilylation-addition of methanol, depending on the conditions.