2-溴-N-(3,5-二甲基苯基)乙酰胺 | 349120-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-溴-N-(3,5-二甲基苯基)乙酰胺
• 英文名称: 2-bromo-N-(3,5-dimethylphenyl)acetamide
• CAS: 349120-86-1
• 化学式: C₁₀H₁₂BrNO
• mdl: MFCD02974354
• 分子量: 242.115
• InChiKey: TXCXOCFROXZADI-UHFFFAOYSA-N

物化性质

• 沸点：
  351.7±30.0 °C(Predicted)
• 密度：
  1.439±0.06 g/cm3(Predicted)

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：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-溴-N-(3,5-二甲基苯基)乙酰胺 在 sodium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 trans,trans-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-1-(N-[3,5-dimethylphenyl]acetamido)-pyrrolidino-3-carboxylic acid
  参考文献：
  名称：

  Pyrrolidine-3-carboxylic Acids as Endothelin Antagonists. 4. Side Chain Conformational Restriction Leads to ET_B Selectivity

  摘要：

  When the dialkylacetamide side chain of the ETA-selective antagonist ABT-627 is replaced with a 2,6-dialkylacetanilide, the resultant analogues show a complete reversal of receptor selectivity, preferring ETB over ETA. By optimizing the aniline substitution pattern, as well as the alkoxy group on the 2-aryl substituent, it is possible to prepare antagonists with subnanomolar affinity for ETB and with selectivities in excess of 4000-fold. A number of these compounds also show promising pharmacokinetic profiles; a useful balance of properties is found in A-192621 (38). Pharmacology studies with A-192621 serve to reveal the role of the ETB receptor in modulating blood pressure; the observed hypertensive response to persistent ETB blockade is consistent with previous postulates and indicates that ETB-selective antagonists may not be suitable as agents for long-term systemic therapy.

  DOI：

  10.1021/jm990170q
• 作为产物：
  描述：

  1-氨基-3,5-二甲苯 、 溴乙酰溴 在 sodium carbonate 作用下， 以 水 为溶剂， 反应 1.0h， 生成 2-溴-N-(3,5-二甲基苯基)乙酰胺
  参考文献：
  名称：

  光谱技术合成1,2,4-三唑含氮杂嗪乙酰胺衍生物及其与牛血清白蛋白的结合相互作用

  摘要：

  合成了一系列新的含1,2,4-三唑和氮杂部分的乙酰胺衍生物，并使用$ ^ {1} $ H NMR，$ ^ {13} $ C NMR，IR和EI-MS光谱分析对其进行了表征。中间体三唑是通过羧酸盐和碳酰肼的顺序合成而合成的。评价了新合成的1,2,4-三唑衍生物与牛血清白蛋白（BSA）的结合以及热力学，位点选择性结合和同步研究。通过BSA结合以及热力学研究获得的结果证明，所有化合物均显示出与BSA的自发相互作用，并且可以有效地分布并从体内清除。因此，基于三唑的类似物可能是设计新药系统的有用策略。

  DOI：

  10.3906/kim-1801-95

文献信息

• Structure–activity relationship and biological evaluation of 12 N-substituted aloperine derivatives as PD-L1 down-regulatory agents through proteasome pathway
  作者：Qing–Xuan Zeng、Kun Wang、Xin Zhang、Yu-Long Shi、Yue–Ying Dou、Zhi–Hao Guo、Xin–Tong Zhang、Na Zhang、Hong–Bin Deng、Ying–Hong Li、Dan–Qing Song

  DOI：10.1016/j.bioorg.2021.105432

  日期：2021.12

  aloperine derivatives were synthesized and screened for suppression on PD-L1 expression in H460 cells, as a continuation of our work. Systematic structural modifications led to the identification of compound 6b as the most active PD-L1 modulator. Compound 6b could significantly down-regulate both constitutive and inductive PD-L1 expression in NSCLC cells, and successively enhance the cytotoxicity of co-cultured

  作为我们工作的继续，我们合成了29 个 12  N-取代的 aloperine 衍生物，并筛选了其对 H460 细胞中 PD-L1 表达的抑制作用。系统的结构修饰导致化合物6b被鉴定为最活跃的 PD-L1 调节剂。化合物6b在 20 μM 浓度下可显着下调 NSCLC 细胞中组成型和诱导型 PD-L1 的表达，并依次增强共培养 T 细胞对肿瘤细胞的细胞毒性。此外，它对 Lewis 肿瘤异种移植物表现出中等的体内抗癌功效，具有稳定的 PK 和安全性。机理研究表明，6b通过蛋白酶体途径而不是溶酶体途径介导PD-L1的降解。这些结果通过靶向PD-L1激活免疫细胞杀死癌细胞，为具有独特内环骨架的aloperine衍生物的癌症免疫治疗提供了强有力的信息。
• Synthesis, biological evaluation, and in silico study of some unique multifunctional 1,2,4-triazole acetamides
  作者：ALMAS SATTAR、AZIZ UR REHMAN、MUHAMMAD ATHAR ABBASI、SABAHAT ZAHRA SADDIQUI、SHAHID RASOOL、HIRA KHALID、MUHAMMAD ARIF LODHI、FARMAN ALI KHAN

  DOI：10.3906/kim-1706-50

  日期：——

  The imperative demand for antibacterial agents and enzyme inhibitors prompted us to synthesize some new compounds, 6a-6k, bearing multifunctional moieties. The target acetamides were derived from 4-phenyl-5-(1-tosylpiperidin-4-yl)-4$H$-1,2,4-triazole-3-thiol (3). The structural analysis was carried out using modern spectroscopic techniques including IR, NMR, and EIMS spectral analysis. The antibacterial activity was screened against five bacterial strains including three gram-negative and two gram-positive ones. Enzyme inhibition was carried out against lipoxygenase enzyme and results were supported by in silico study. The synthesized compounds were proved to be potent antibacterial agents and enzyme inhibitors.

  抗菌剂和酶抑制剂的迫切需求促使我们合成了一系列含有多功能团的新化合物6a-6k。这些目标乙酰胺衍生物来自于4-苯基-5-(1-对甲苯磺酰基哌啶-4-基)-4H-1,2,4-三唑-3-硫醇(3)。结构分析采用了包括红外光谱(IR)、核磁共振(NMR)和电子轰击质谱(EIMS)在内的现代光谱技术。抗菌活性筛选针对五种细菌菌株，包括三种革兰氏阴性和两种革兰氏阳性菌株。酶抑制作用针对脂氧合酶进行了测试，并得到了计算机辅助研究的支持。合成的化合物被证明是强效的抗菌剂和酶抑制剂。
• Probing phenylcarbamoylazinane-1,2,4-triazole amides derivatives as lipoxygenase inhibitors along with cytotoxic, ADME and molecular docking studies
  作者：Saima Muzaffar、Wardah Shahid、Naheed Riaz、Muhammad Saleem、Muhammad Ashraf、Aziz-ur-Rehman、Bushra Bashir、Ayesha Kaleem、Mariya al-Rashida、Bikash Baral、Keshab Bhattarai、Harald Gross

  DOI：10.1016/j.bioorg.2020.104525

  日期：2021.2

  N-alkyl/aralky/aryl derivatives (7a-o) of 2-(4-phenyl-5-(1-phenylcarbamoyl)piperidine-4H-1,2,4-triazol-3-ylthio)acetamide was synthesized and screened for their inhibitory potential against the enzyme 15-lipoxygenase. The simple precursor ethyl piperidine-4-carboxylate (a) was successively converted into phenylcarbamoyl derivative (1), hydrazide (2), semicarbazide (3) and N-phenylated 5-(1-phenylcarbamoyl)piperidine-1

  寻找小分子作为抗炎剂/药物是治疗癌症、哮喘、关节炎和牛皮癣等多种炎症性疾病的一种不断扩展且成功的方法。除了其他方法外，还可以通过脂氧合酶抑制剂来治疗炎症性疾病，脂氧合酶抑制剂对炎症的发生和进展有着深远的影响。在本研究中，一系列新的2-(4-苯基-5-(1-苯基氨基甲酰基)哌啶-4H-1,2,4-三唑-3的N-烷基/芳烷基/芳基衍生物( 7a-o )合成并筛选了对 15-脂氧合酶的抑制潜力。简单前体哌啶-4-甲酸乙酯( a )依次转化为苯基氨基甲酰基衍生物( 1 )、酰肼( 2 )、氨基脲( 3 )和N-苯基化5-(1-苯基氨基甲酰基)哌啶-1,2,4-三唑( 4 )，然后与亲电子试剂( 6a-o )结合，通过进一步的多步合成，生成最终产物( 7a-o )。所有合成的化合物均通过 FTIR、 1 H、 13 C NMR 光谱、EIMS 和 HREIMS 光谱进行表征。几乎所有合成的化合物都对
• Synthesis and structure-activity relationship of tyrosinase inhibiting novel bi-heterocyclic acetamides: Mechanistic insights through enzyme inhibition, kinetics and computational studies
  作者：Abdul Rehman Sadiq Butt、Muhammad Athar Abbasi、Aziz-ur-Rehman、Sabahat Zahra Siddiqui、Hussain Raza、Mubashir Hassan、Syed Adnan Ali Shah、Muhammad Shahid、Sung-Yum Seo

  DOI：10.1016/j.bioorg.2019.01.036

  日期：2019.5

  these molecules were recognized as potent inhibitors relative to the standard used. The Kinetics mechanism was analyzed by Lineweaver-Burk plots which explored that compound, 9h, inhibited tyrosinase competitively by forming an enzyme-inhibitor complex. The inhibition constants Ki calculated from Dixon plots for this compound was 0.0027 µM. The computational study was coherent with the experimental records

  本研究旨在用于新型双杂环乙酰胺9a-n的选择性合成及其对酪氨酸酶的抑制作用，从而抑制了黑色素生成问题。通过光谱技术（例如1H NMR，13C NMR和EI-MS）以及元素分析，确认了新合成化合物的结构。评估了这些双杂环乙酰胺（9a-n）对酪氨酸酶的抑制作用，并且相对于所用标准品，所有这些分子均被认为是有效的抑制剂。通过Lineweaver-Burk图分析了动力学机理，该图探索了化合物9h通过形成酶抑制剂复合物竞争性抑制酪氨酸酶。由狄克逊图计算出的该化合物的抑制常数Ki为0.0027μM。计算研究与实验记录一致，并且这些配体表现出良好的结合能值（kcal / mol）。溶血分析揭示了它们对红细胞膜的轻度细胞毒性，因此，这些分子可被认为是用于皮肤色素沉着和相关疾病的无毒药物支架。
• A novel method for the synthesis of 1,2,4-triazole-derived heterocyclic compounds: enzyme inhibition and molecular docking studies
  作者：Naheed Riaz、Muhammad Iftikhar、Muhammad Saleem、Aziz-ur-Rehman、Ishtiaq Ahmed、Muhammad Ashraf、Shahnawaz、Jameel Rehman、Mariya al-Rashida

  DOI：10.1007/s13738-019-01848-3

  日期：2020.5

  N-aryl/aralkyl 1,3,4-triazole. The target compounds (9a–q; 10a–q) were obtained by the reaction of N-aryl/aralkyl 1,3,4-triazole (5, 6) with various electrophiles, (8a–q), in N,N-dimethyl formamide (DMF) and sodium hydroxide at room temperature. The characterization of these compounds was done by FTIR, 1H-, 13C-NMR, EI-MS and HR-EI-MS spectral data. All compounds were evaluated for their enzyme inhibitory

  2-（4-乙基-5-（噻吩-2-基甲基）-4H-1,2,4-三唑-3-基硫基）乙酰胺和N的两个新的N-芳基/芳烷基衍生物系列（9a – q）合成了2-（4-苯基-5-（噻吩-2-基甲基）-4H-1,2,4-三唑-3-基硫基）乙酰胺的-芳基/芳烷基衍生物（10a - q）。该方法包括将噻吩-2-乙酸（a）连续转化成其各自的酯，酰肼和N-芳基/芳烷基1,3,4-三唑。目标化合物（9a – q；10a – q）通过N-芳基/芳烷基1,3,4-三唑（5，6）与各种亲电体，（8A - q），在Ñ，ñ -二甲基甲酰胺（DMF）和氢氧化钠在室温下。这些化合物的表征是通过FTIR，1 H-，13 C-NMR，EI-MS和HR-EI-MS光谱数据完成的。评估了所有化合物对鳗鱼乙酰胆碱酯酶AChE（10f，10d ; IC 50值分别为32.26±0.12，45.72±0.11 µM），马丁酰胆碱酯酶BChE（9d，9l，9b，10d，10小时;