butyl (4-acetylphenyl)carbamate | 72531-04-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: butyl (4-acetylphenyl)carbamate
• 英文别名: butyl N-(4-acetylphenyl)carbamate
• CAS: 72531-04-5
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: BLLWWSFFSNESTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  butyl (4-acetylphenyl)carbamate 在 溴 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以85%的产率得到butyl [4-(bromoacetyl)phenyl]carbamate
  参考文献：
  名称：

  含有 Ethane-1,2-diyl 连接链的新型 N-Arylpiperazines 的合成和体外抗分枝杆菌活性

  摘要：

  新型 1-(2-{3-/4-[(烷氧基羰基)氨基]苯基}-2-羟乙基)-4-(2-氟苯基)-哌嗪-1-鎓氯化物（烷氧基=甲氧基到丁氧基；8a-h ) 已通过多步反应设计和合成，作为正在进行的研究计划的一部分，重点是寻找新的抗分枝杆菌。这些化合物的亲脂性是通过 RP-HPLC 使用甲醇/水流动相和不同体积分数的有机改性剂来评估的。log kw 值是从保留因子 k (log k) 的对数与流动相改性剂的体积分数 (ϕM) 之间的线性关系的截距外推的，从 2.113 (8e) 到 2.930 (8h) 和表明这些盐具有相对较高的亲脂性。通过评估它们的紫外/可见光谱来研究分子 8a-h 的电子特性。在研究的下一阶段，化合物 8a-h 进行了体外筛选，以对抗结核分枝杆菌 CNCTC My 331/88（与 H37Rv 和 ATCC 2794 相同）、堪萨斯分枝杆菌 CNCTC My 235/80（与

  DOI：

  10.3390/molecules22122100
• 作为产物：
  描述：

  4-氨基苯乙酮 、 氯甲酸丁酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 butyl (4-acetylphenyl)carbamate
  参考文献：
  名称：

  作为潜在胆碱酯酶抑制剂的芳氨基丙酮衍生物：合成、对接研究和生物学评价

  摘要：

  观察到乙酰胆碱减少的神经退行性疾病正在世界范围内增加。在本研究中，制备了一系列具有 N-苯基氨基甲酸酯部分 (1-16) 的新型芳基氨基丙酮衍生物作为潜在的乙酰胆碱酯酶和丁酰胆碱酯酶抑制剂。进行了体外酶分析；结果表示为抑制百分比和 IC50 值。将抑制活性与参考药物加兰他敏和卡巴拉汀进行比较，显示哌啶衍生物 (1-3) 是最有效的。通过使用对接、分子动力学模拟和量子力学计算的组合技术，从分子建模研究中确定了这些化合物的可能作用机制。

  DOI：

  10.3390/molecules25071751

文献信息

• Synthesis of Aryl Carbamates <i>via</i> Copper‐Catalyzed Coupling of Aryl Halides with Potassium Cyanate
  作者：Xinye Yang、Yihua Zhang、Dawei Ma

  DOI：10.1002/adsc.201200296

  日期：2012.9.17

  Coupling of aryl halides with potassium cyanate takes place at 100–110 °C in alcohols under the catalysis of CuI (cuprous iodide) and 2‐(2,6‐dimethylphenylamino)‐2‐oxoacetic acid, affording the corresponding aryl carbamates with great diversity.

  在CuI（碘化亚铜）和2-（2,6-二甲基苯基氨基）-2-氧代乙酸的催化下，芳基卤化物与氰酸钾的偶合反应发生在100-110°C的醇中。 。
• Searching new structural scaffolds for BRAF inhibitors. An integrative study using theoretical and experimental techniques
  作者：Ludmila E. Campos、Francisco M. Garibotto、Emilio Angelina、Jiri Kos、Tihomir Tomašič、Nace Zidar、Danijel Kikelj、Tomas Gonec、Pavlina Marvanova、Petr Mokry、Josef Jampilek、Sergio E. Alvarez、Ricardo D. Enriz

  DOI：10.1016/j.bioorg.2019.103125

  日期：2019.10

  The identification of the V600E activating mutation in the protein kinase BRAF in around 50% of melanoma patients has driven the development of highly potent small inhibitors (BRAFi) of the mutated protein. To date, Dabrafenib and Vemurafenib, two specific BRAFi, have been clinically approved for the treatment of metastatic melanoma. Unfortunately, after the initial response, tumors become resistant and patients develop a progressive and lethal disease, making imperative the development of new therapeutic options. The main objective of this work was to find new BRAF inhibitors with different structural scaffolds than those of the known inhibitors. Our study was carried out in different stages; in the first step we performed a virtual screening that allowed us to identify potential new inhibitors. In the second step, we synthesized and tested the inhibitory activity of the novel compounds founded. Finally, we conducted a molecular modelling study that allowed us to understand interactions at the molecular level that stabilize the formation of the different molecular complexes.Our theoretical and experimental study allowed the identification of four new structural scaffolds, which could be used as starting structures for the design and development of new inhibitors of BRAF. Our experimental data indicate that the most active compounds reduced significantly ERK1/2 phosphorylation, a measure of BRAF inhibition, and cell viability. Thus, from our theoretical and experimental results, we propose new substituted hydroxynaphthalenecarboxamides, N-(hetero)aryl-piperazinylhydroxyalkylphenylcarbamates, substituted piperazinylethanols and substituted piperazinylpropandiols as initial structures for the development of new inhibitors for BRAF. Moreover, by performing QTAIM analysis, we are able to describe in detail the molecular interactions that stabilize the different Ligand-Receptor complexes. Such analysis indicates which portion of the different molecules must be changed in order to obtain an increase in the binding affinity of these new ligands.
• An integrative study to identify novel scaffolds for sphingosine kinase 1 inhibitors
  作者：Marcela Vettorazzi、Emilio Angelina、Santiago Lima、Tomas Gonec、Jan Otevrel、Pavlina Marvanova、Tereza Padrtova、Petr Mokry、Pavel Bobal、Lina M. Acosta、Alirio Palma、Justo Cobo、Janette Bobalova、Jozef Csollei、Ivan Malik、Sergio Alvarez、Sarah Spiegel、Josef Jampilek、Ricardo D. Enriz

  DOI：10.1016/j.ejmech.2017.08.017

  日期：2017.10

  Sphingosine kinase 1 (SphK1), the enzyme that produces the bioactive sphingolipid metabolite, sphingosine-1-phosphate, is a promising new molecular target for therapeutic intervention in cancer and inflammatory diseases. In view of its importance, the main objective of this work was to find new and more potent inhibitors for this enzyme possessing different structural scaffolds than those of the known inhibitors. Our theoretical and experimental study has allowed us to identify two new structural scaffolds (three new compounds), which could be used as starting structures for the design and then the development of new inhibitors of SphK1. Our study was carried out in different steps: virtual screening, synthesis, bioassays and molecular modelling. From our results, we propose a new dihydrobenzo[b] pyrimido[5,4-f]azepine and two alkyl3-/4-[-1-hydroxy-2-(4-arylpiperazin-1-yl)ethyliphenyl}carbamates as initial structures for the development of new inhibitors. In addition, our molecular modelling study using QTAIM calculations, allowed us to describe in detail the molecular interactions that stabilize the different Ligand-Receptor complexes. Such analyses indicate that the cationic head of the different compounds must be refined in order to obtain an increase in the binding affinity of these ligands. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Synthesis and In Vitro Antimycobacterial Activity of Novel N-Arylpiperazines Containing an Ethane-1,2-diyl Connecting Chain
  作者：Tomáš Goněc、Ivan Malík、Jozef Csöllei、Josef Jampílek、Jiřina Stolaříková、Ivan Solovič、Peter Mikuš、Stanislava Keltošová、Peter Kollár、Jim O’Mahony、Aidan Coffey

  DOI：10.3390/molecules22122100

  日期：——

  observed for the most effective 1-(2-4-[(butoxycarbonyl)amino]phenyl}-2-hydroxyethyl)-4-(2-fluorophenyl)piperazin-1-ium chloride (8h). In addition, all of them showed low (insignificant) in vitro toxicity against a human monocytic leukemia THP-1 cell line, as observed LD50 values > 30 μM indicated. The structure–antimycobacterial activity relationships of the analyzed 8a–h series are also discussed.

  新型 1-(2-3-/4-[(烷氧基羰基)氨基]苯基}-2-羟乙基)-4-(2-氟苯基)-哌嗪-1-鎓氯化物（烷氧基=甲氧基到丁氧基；8a-h ) 已通过多步反应设计和合成，作为正在进行的研究计划的一部分，重点是寻找新的抗分枝杆菌。这些化合物的亲脂性是通过 RP-HPLC 使用甲醇/水流动相和不同体积分数的有机改性剂来评估的。log kw 值是从保留因子 k (log k) 的对数与流动相改性剂的体积分数 (ϕM) 之间的线性关系的截距外推的，从 2.113 (8e) 到 2.930 (8h) 和表明这些盐具有相对较高的亲脂性。通过评估它们的紫外/可见光谱来研究分子 8a-h 的电子特性。在研究的下一阶段，化合物 8a-h 进行了体外筛选，以对抗结核分枝杆菌 CNCTC My 331/88（与 H37Rv 和 ATCC 2794 相同）、堪萨斯分枝杆菌 CNCTC My 235/80（与
• Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological Evaluation
  作者：Anna Hudcová、Aleš Kroutil、Renata Kubínová、Adriana D. Garro、Lucas J. Gutierrez、Daniel Enriz、Michal Oravec、Jozef Csöllei

  DOI：10.3390/molecules25071751

  日期：——

  acetylcholine is observed are growing worldwide. In the present study, a series of new arylaminopropanone derivatives with N-phenylcarbamate moiety (1–16) were prepared as potential acetylcholinesterase and butyrylcholinesterase inhibitors. In vitro enzyme assays were performed; the results are expressed as a percentage of inhibition and the IC50 values. The inhibitory activities were compared with

  观察到乙酰胆碱减少的神经退行性疾病正在世界范围内增加。在本研究中，制备了一系列具有 N-苯基氨基甲酸酯部分 (1-16) 的新型芳基氨基丙酮衍生物作为潜在的乙酰胆碱酯酶和丁酰胆碱酯酶抑制剂。进行了体外酶分析；结果表示为抑制百分比和 IC50 值。将抑制活性与参考药物加兰他敏和卡巴拉汀进行比较，显示哌啶衍生物 (1-3) 是最有效的。通过使用对接、分子动力学模拟和量子力学计算的组合技术，从分子建模研究中确定了这些化合物的可能作用机制。