2-bromo-N-(4-bromophenyl)propanamide | 42276-46-0

• 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-bromo-N-(4-bromophenyl)propanamide
• CAS: 42276-46-0
• 化学式: C₉H₉Br₂NO
• 分子量: 306.985
• InChiKey: FJXNJUQSLIKVOC-UHFFFAOYSA-N

物化性质

• 沸点：
  397.8±27.0 °C(Predicted)
• 密度：
  1.818±0.06 g/cm3(Predicted)
• 保留指数：
  1837

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  2-bromo-N-(4-bromophenyl)propanamide 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 2-(2,3-dihydro-1,4-benzodioxin-6-ylamino)-N-(4-pyridin-3-ylphenyl)propanamide
  参考文献：
  名称：

  Identification of 2-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)amino)-N-phenylpropanamides as a novel class of potent DprE1 inhibitors

  摘要：

  The identification of a novel series of DprE1 inhibitors based on a 2((2,3-dihydrobenzo [b][1,4]dioxin-6-yl) amino)-N-phenylpropanamide scaffold is described herein. SAR exploration around the HTS hit 1 led to the identification of multiple analogues with potent DprE1 inhibition and good whole-cell antimycobacterial activity.

  DOI：

  10.1016/j.bmcl.2020.127192
• 作为产物：
  描述：

  4-溴苯胺 、 2-溴丙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-bromo-N-(4-bromophenyl)propanamide
  参考文献：
  名称：

  取代Pyridazin-3（2 H）-ones作为高度有效和偏向的甲酰基肽受体激动剂。

  摘要：

  在这里，我们描述了重点功能化的哒嗪-3（2 H）-一基甲酰肽受体（FPR）激动剂系列的开发，这些激动剂显示出高效力和偏向激动性。所描述的化合物通过减少有害的FPR1 / 2介导的细胞内钙（Cai2 +）动员，证明了生存信号的活化偏向激活，ERK1 / 2磷酸化。对于ERK1 / 2的磷酸化，化合物50的EC50为0.083μM，在hFPR1处距Cai2 +动员约20倍。

  DOI：

  10.1021/acs.jmedchem.8b01912

文献信息

• Design and synthesis of new 8-anilide theophylline derivatives as bronchodilators and antibacterial agents
  作者：Alaa K. M. Hayallah、Ahmad A. Talhouni、Abdel Alim M. Abdel Alim

  DOI：10.1007/s12272-012-0805-4

  日期：2012.8

  Theophylline derivatives have long been recognized as potent bronchodilators for the relief of acute asthma. Recently, it was found that bacterial infection has a role in asthma pathogenesis. The present work involves the design and synthesis of 8-substituted theophylline derivatives as bronchodilators and antibacterial agents. The chemical structures of these compounds were elucidated by IR, 1H-NMR

  长期以来，茶碱衍生物被认为是缓解急性哮喘的有效支气管扩张剂。最近，发现细菌感染在哮喘发病机制中起作用。目前的工作涉及作为支气管扩张剂和抗菌剂的 8-取代茶碱衍生物的设计和合成。这些化合物的化学结构通过IR、1H-NMR、质谱和元素分析阐明。使用乙酰胆碱诱导的豚鼠支气管痉挛评估支气管扩张剂活性，与标准氨茶碱相比，大多数化合物显示出显着的抗支气管收缩活性。此外，使用氨苄青霉素作为参考药物，在体外研究了所有目标化合物对革兰氏阳性菌和革兰氏阴性菌的抗菌活性。结果表明，一些测试化合物具有显着的抗菌活性。计算药效团模型以获得对支气管扩张剂活性的基本结构特征的有用洞察。还讨论了构效关系。
• Copper-Catalyzed Cross-Coupling of Secondary α-Haloamides with Terminal Alkynes: Access to Diverse 2,3-Allenamides
  作者：Yunhe Lv、Weiya Pu、Xueli Zhu、Tiantian Zhao、Feifei Lin

  DOI：10.1002/adsc.201701556

  日期：2018.4.3

  A copper‐catalyzed C(sp)−C(sp3) cross‐coupling of terminal alkynes with readily available secondary α‐haloamides for the efficient synthesis of 2,3‐allenamides is realized. The methodology is characterized by its wide substrate scope, which makes it an important complement to traditional methods for synthesizing allenes. A mechanism involving an alkynylcopper species is proposed.

  实现了末端炔与易于获得的仲α-卤代酰胺的铜催化C（sp）-C（sp 3）交叉偶联，可有效合成2,3-烯丙基酰胺。该方法的特点是具有广泛的底物范围，这使其成为了传统合成丙二烯方法的重要补充。提出了一种涉及炔铜物种的机制。
• Synthesis and Antimicrobial Activity of 2-(4-(Hydroxyalkyl)-1<i>H</i> -1,2,3-triazol-1-yl)-<i>N</i> -substituted propanamides
  作者：C.P. Kaushik、Raj Luxmi

  DOI：10.1002/jhet.2988

  日期：2017.11

  2,3‐triazoles having amide linkage and hydroxyl group) have been synthesized from click reaction between terminal alkyne and 2‐azido‐N‐substituted propanamide (generated in situ from reaction of 2‐bromo‐N‐substituted propanamide and sodium azide) and characterized by FTIR, 1H NMR, 13C NMR spectroscopy, and HRMS. All the newly synthesized triazoles were tested in vitro for antimicrobial activity against

  一系列21 21 2-（4-（羟烷基）-1 H -1,2,3-三唑-1-基）-N-取代的丙酰胺（1,4-二取代的1,2,3-三唑具有酰胺键和羟基是由末端炔烃与2-叠氮基-N-取代的丙酰胺（由2-溴-N - N取代的丙酰胺和叠氮化钠的反应原位生成）之间的点击反应合成的，其特征在于FTIR，1 H NMR，13 C NMR光谱和HRMS。所有新合成的三唑均在体外测试了对四种细菌培养物（大肠杆菌，产气肠杆菌，肺炎克雷伯菌，金黄色葡萄球菌和两种真菌培养物：白色念珠菌和黑曲霉。合成的1,4-二取代的1,2,3-三唑类对被测菌株显示出中等至良好的抗菌潜力。
• Amine derivative
  申请人：Ishihara Yuji

  公开号：US20060128690A1

  公开（公告）日：2006-06-15

  The present invention provides a compound represented by the formula wherein Ar 1 is a cyclic group optionally having substituent(s); R is a hydrogen atom, an optionally halogenated C 1-6 alkyl, a phenyl optionally having substituent(s) or a pyridyl optionally having substituent(s); Ra 1 , Ra 2 , Ra 3 and Ra 4 are the same or different and each is a hydrogen atom, an optionally halogenated C 1-6 alkyl or the like; Ar is a monocyclic aromatic ring optionally having substituent(s); Y is an optionally halogenated alkylene group; and R 1 and R 2 are (1) the same or different and each is a hydrogen atom or a C 1-6 alkyl, (2) R 1 and R 2 form a nitrogen-containing heterocycle optionally having substituent(s) together with the adjacent nitrogen atom, or (3) R 1 and Y form a nitrogen-containing heterocycle optionally having substituent(s) together with the adjacent nitrogen atom, and R 2 is a hydrogen atom or a C 1-6 alkyl; provided that when the nitrogen-containing heterocycle formed by R 1 and R 2 together with the adjacent nitrogen atom is a piperazine, or when R is a C 1-4 alkyl, Ar 1 is a cyclic group having substituent(s), or a salt thereof, having a melanin-concentrating hormone antagonistic action and useful as an agent for the prophylaxis or treatment of obesity and the like.

  本发明提供了一种化合物，其表示为式子： 其中，Ar1是一个环状基团，可以具有取代基；R是氢原子，可选卤代的C1-6烷基，苯环，可以具有取代基，或者吡啶环，可以具有取代基；Ra1，Ra2，Ra3和Ra4相同或不同，每个都是氢原子，可选卤代的C1-6烷基或类似物；Ar是一个单环芳香环，可以具有取代基；Y是可选卤代的脂肪族烷基；R1和R2是（1）相同或不同，每个都是氢原子或C1-6烷基，（2）R1和R2与相邻的氮原子一起形成含氮杂环，可以具有取代基，或（3）R1和Y与相邻的氮原子一起形成含氮杂环，可以具有取代基，并且R2是氢原子或C1-6烷基；但是当R1和R2与相邻的氮原子一起形成哌嗪环，或当R是C1-4烷基，Ar1是具有取代基的环状基团或其盐时，该化合物具有黑色素浓集激素拮抗作用，可用作预防或治疗肥胖症等药物。
• AMINE DERIVATIVE
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1593667A1

  公开（公告）日：2005-11-09

  The present invention provides a compound represented by the formula wherein Ar1 is a cyclic group optionally having substituent(s); R is a hydrogen atom, an optionally halogenated C1-6 alkyl, a phenyl optionally having substituent(s) or a pyridyl optionally having substituent(s); Ra1, Ra2, Ra3 and Ra4 are the same or different and each is a hydrogen atom, an optionally halogenated C1-6 alkyl or the like; Ar is a monocyclic aromatic ring optionally having substituent(s); Y is an optionally halogenated alkylene group; and R1 and R2 are (1) the same or different and each is a hydrogen atom or a C1-6 alkyl, (2) R1 and R2 form a nitrogen-containing heterocycle optionally having substituent(s) together with the adjacent nitrogen atom, or (3) R1 and Y form a nitrogen-containing heterocycle optionally having substituent(s) together with the adjacent nitrogen atom, and R2 is a hydrogen atom or a C1-6 alkyl; provided that when the nitrogen-containing heterocycle formed by R1 and R2 together with the adjacent nitrogen atom is a piperazine, or when R is a C1-4 alkyl, Ar1 is a cyclic group having substituent(s), or a salt thereof, having a melanin-concentrating hormone antagonistic action and useful as an agent for the prophylaxis or treatment of obesity and the like.

  本发明提供了一种由式表示的化合物 其中 Ar1 是任选具有取代基的环状基团； R 是氢原子、任选卤化的 C1-6 烷基、任选具有取代基的苯基或任选具有取代基的吡啶基； Ra1、Ra2、Ra3 和 Ra4 相同或不同，各自为氢原子、任选卤代的 C1-6 烷基或类似物； Ar 是单环芳香环，可选择具有取代基； Y 是任选卤代亚烷基；以及 R1 和 R2 (1) 相同或不同，且各自为氢原子或 C1-6 烷基；(2) R1 和 R2 组成含氮杂环，可选择与相邻氮原子一起具有取代基；或 (3) R1 和 Y 组成含氮杂环，可选择与相邻氮原子一起具有取代基，且 R2 为氢原子或 C1-6 烷基； 条件是当 R1 和 R2 与相邻氮原子一起形成的含氮杂环是哌嗪时，或当 R 是 C1-4 烷基时，Ar1 是具有取代基的环状基团或其盐，具有黑色素浓缩激素拮抗作用，可用作预防或治疗肥胖症等的药物。