ethyl N-<2-(bromoacetyl)phenyl>carbamate | 122807-12-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl N-<2-(bromoacetyl)phenyl>carbamate
• 英文别名: ethyl [2-(bromoacetyl)phenyl]carbamate；ethyl N-[2-(2-bromoacetyl)phenyl]carbamate
• CAS: 122807-12-9
• 化学式: C₁₁H₁₂BrNO₃
• 分子量: 286.125
• InChiKey: ZSWXIOXAKDEZNE-UHFFFAOYSA-N

物化性质

• 熔点：
  102-104 °C(Solv: ethanol (64-17-5))
• 沸点：
  325.2±22.0 °C(Predicted)
• 密度：
  1.505±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  ethyl N-<2-(bromoacetyl)phenyl>carbamate 在 sodium hydroxide 、 sodium tetrahydroborate 、 四丁基碘化铵 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.75h， 生成 2-氨基喹啉
  参考文献：
  名称：

  N- [2-（1-羟基-2-Y-乙基）苯基]氨基甲酸乙酯的基本介质行为（Y = SMe，SOMe，SO 2 Me，H，Br，CN）

  摘要：

  从一些共同结构为（2→tOOCNH-C6H4）-CHOH-CH2Y的硫代衍生物化合物的氨基甲酸酯基团的水解反应中获得的结果，提出了机理来解释产物，以及相对构型之间的关系。非对映异构体亚砜（Y = SOMe）与反应速率和立体化学结果。当进行其他氨基甲酸酯（Y = H，Br，CN）的水解反应时，还会产生其他有趣且出乎意料的产物。在当前情况下，氨基甲酸酯官能团的表现为非常通用的基团，能够轻松地转化为几种杂环。

  DOI：

  10.1016/0040-4020(89)80047-x
• 作为产物：
  描述：

  (2-acetylphenyl)carbamic acid ethyl ester 在 溴 作用下， 以 乙醚 为溶剂， 生成 ethyl N-<2-(bromoacetyl)phenyl>carbamate
  参考文献：
  名称：

  N- [2-（1-羟基-2-Y-乙基）苯基]氨基甲酸乙酯的基本介质行为（Y = SMe，SOMe，SO 2 Me，H，Br，CN）

  摘要：

  从一些共同结构为（2→tOOCNH-C6H4）-CHOH-CH2Y的硫代衍生物化合物的氨基甲酸酯基团的水解反应中获得的结果，提出了机理来解释产物，以及相对构型之间的关系。非对映异构体亚砜（Y = SOMe）与反应速率和立体化学结果。当进行其他氨基甲酸酯（Y = H，Br，CN）的水解反应时，还会产生其他有趣且出乎意料的产物。在当前情况下，氨基甲酸酯官能团的表现为非常通用的基团，能够轻松地转化为几种杂环。

  DOI：

  10.1016/0040-4020(89)80047-x

文献信息

• 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.
• Ruano, Jose Luis Garcia; Pedregal, Concepcion; Rodriguez, Jesus H., Heterocycles, 1991, vol. 32, # 11, p. 2151 - 2159
  作者：Ruano, Jose Luis Garcia、Pedregal, Concepcion、Rodriguez, Jesus H.

  DOI：——

  日期：——
• RUANO, JOSE LUIS GARCIA;PEDREGAL, CONCEPCION;RODRIGUEZ, JESUS H., TETRAHEDRON, 45,(1989) N, C. 203-214
  作者：RUANO, JOSE LUIS GARCIA、PEDREGAL, CONCEPCION、RODRIGUEZ, JESUS H.

  DOI：——

  日期：——
• GARCIA, RUANO J. L.;PEDREGAL, C.;RODRIGUEZ, J. H., AN. QUIM. C/REAL SOC. ESP. QUIM., 84,(1988) N, C. 297-305
  作者：GARCIA, RUANO J. L.、PEDREGAL, C.、RODRIGUEZ, J. H.

  DOI：——

  日期：——
• Basic media behavior of N-[2-(1-hydroxy-2-Y-ethyl)phenyl] ethyl carbamates (Y = SMe, SOMe, SO2Me, H, Br, CN)
  作者：Jose Luis Garcia Ruano、Concepción Pedregal、Jesús H. Rodriguez

  DOI：10.1016/0040-4020(89)80047-x

  日期：1989.1

  From the results obtained in the hydrolysis reaction of the carbamate group of some thioderivatives compounds whose common structure is (2 → tOOCNH-C6H4)-CHOH-CH2Y a mechanism is suggested to explain the products, as well as the relationship between the relative configuration of diastereoisomeric sulfoxides (Y = SOMe) with the reaction rate and with the stereochemical outcome. Other interesting and

  从一些共同结构为（2→tOOCNH-C6H4）-CHOH-CH2Y的硫代衍生物化合物的氨基甲酸酯基团的水解反应中获得的结果，提出了机理来解释产物，以及相对构型之间的关系。非对映异构体亚砜（Y = SOMe）与反应速率和立体化学结果。当进行其他氨基甲酸酯（Y = H，Br，CN）的水解反应时，还会产生其他有趣且出乎意料的产物。在当前情况下，氨基甲酸酯官能团的表现为非常通用的基团，能够轻松地转化为几种杂环。