methyl 3-bromomethyl-5-phenylthiophene-2-carboxylate | 936095-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: methyl 3-bromomethyl-5-phenylthiophene-2-carboxylate
• 英文别名: methyl 3-(bromomethyl)-5-phenyl-thiophene-2-carboxylate；methyl 3-(bromomethyl)-5-phenylthiophene-2-carboxylate
• CAS: 936095-32-8
• 化学式: C₁₃H₁₁BrO₂S
• 分子量: 311.199
• InChiKey: FXUUNXCQYXMIDE-UHFFFAOYSA-N

物化性质

• 沸点：
  428.2±45.0 °C(Predicted)
• 密度：
  1.470±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-bromomethyl-5-phenylthiophene-2-carboxylate 在 lithium hydroxide 、 sodium hydride 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 198.0h， 生成 (S)-1-(2-Amino-2-carboxyethyl)-3-(2-carboxy-5-phenylthiophene-3-yl-methyl)-5-methylpyrimidine-2, 4-dione
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization of N³-Substituted Willardiine Derivatives:  Role of the Substituent at the 5-Position of the Uracil Ring in the Development of Highly Potent and Selective GLU_K5 Kainate Receptor Antagonists

  摘要：

  Some N-3-substituted analogues of willardiine such as 11 and 13 are selective kainate receptor antagonists. In an attempt to improve the potency and selectivity for kainate receptors, a range of analogues of 11 and 13 were synthesized with 5-substituents on the uracil ring. An X-ray crystal structure of the 5-methyl analogue of 13 bound to GLU(K5) revealed that there was allowed volume around the 4- and 5-positions of the thiophene ring, and therefore the 4,5-dibromo and 5-phenyl (67) analogues were synthesized. Compound 67 (ACET) demonstrated low nanomolar antagonist potency on native and recombinant GLU(K5)-containing kainate receptors (K-B values of 7 +/- 1 and 5 +/- 1 nM for antagonism of recombinant human GLU(K5) and GLU(K5)/GLU(K2), respectively) but displayed IC50 values > 100 mu M for antagonism of GLU(A2), GLU(K6), or GLU(K6)/GLU(K2).

  DOI：

  10.1021/jm061041u
• 作为产物：
  描述：

  methyl 3-methyl-5-phenylthiophene-2-carboxylate 在 偶氮二异丁腈 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 以80%的产率得到methyl 3-bromomethyl-5-phenylthiophene-2-carboxylate
  参考文献：
  名称：

  [EN] PHOSPHOTHIOPHENE AND PHOSPHOTHIAZOLE HCV POLYMERASE INHIBITORS
  [FR] INHIBITEURS DE PHOSPHOTHIOPHÈNE ET PHOSPHOTHIAZOLE VHC POLYMÉRASE

  摘要：

  公开号：

  WO2010101967A3

文献信息

• PHOSPHOTHIOPHENE AND PHOSPHOTHIAZOLE HCV POLYMERASE INHIBITORS
  申请人：Dousson Cyril

  公开号：US20100233123A1

  公开（公告）日：2010-09-16

  Provided herein are phosphothiophene and phosphothiazole compounds, for example, of any of Formulae I, IA, IIA, IIIA, IVA, VA, VIA, VIIA, IB, IIB, IIIB, IVB, VB, VIIB and VIIB disclosed herein, pharmaceutical compositions comprising the compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host infected with HCV.

  本文提供了磷硫杂苯和磷硫杂唑化合物，例如公式I、IA、IIA、IIIA、IVA、VA、VIA、VIIA、IB、IIB、IIIB、IVB、VB、VIIB和VIIB中的任何一种，以及包含这些化合物的制药组合物和其制备方法。同时提供了这些化合物用于治疗HCV感染的方法，该方法适用于HCV感染的宿主。
• PHOSPHOTHIOPHENE AND PHOSPHOTHIAZOLE AS HCV POLYMERASE INHIBITORS
  申请人：IDENIX Pharmaceuticals, Inc.

  公开号：EP2403860B1

  公开（公告）日：2015-11-04
• US8193372B2
  申请人：——

  公开号：US8193372B2

  公开（公告）日：2012-06-05
• [EN] PHOSPHOTHIOPHENE AND PHOSPHOTHIAZOLE HCV POLYMERASE INHIBITORS<br/>[FR] INHIBITEURS DE PHOSPHOTHIOPHÈNE ET PHOSPHOTHIAZOLE VHC POLYMÉRASE
  申请人：IDENIX PHARMACEUTICALS INC

  公开号：WO2010101967A3

  公开（公告）日：2010-11-11
• Synthesis and Pharmacological Characterization of N³-Substituted Willardiine Derivatives:  Role of the Substituent at the 5-Position of the Uracil Ring in the Development of Highly Potent and Selective GLU_K5 Kainate Receptor Antagonists
  作者：Nigel P. Dolman、Julia C. A. More、Andrew Alt、Jody L. Knauss、Olli T. Pentikäinen、Carla R. Glasser、David Bleakman、Mark L. Mayer、Graham L. Collingridge、David E. Jane

  DOI：10.1021/jm061041u

  日期：2007.4.1

  Some N-3-substituted analogues of willardiine such as 11 and 13 are selective kainate receptor antagonists. In an attempt to improve the potency and selectivity for kainate receptors, a range of analogues of 11 and 13 were synthesized with 5-substituents on the uracil ring. An X-ray crystal structure of the 5-methyl analogue of 13 bound to GLU(K5) revealed that there was allowed volume around the 4- and 5-positions of the thiophene ring, and therefore the 4,5-dibromo and 5-phenyl (67) analogues were synthesized. Compound 67 (ACET) demonstrated low nanomolar antagonist potency on native and recombinant GLU(K5)-containing kainate receptors (K-B values of 7 +/- 1 and 5 +/- 1 nM for antagonism of recombinant human GLU(K5) and GLU(K5)/GLU(K2), respectively) but displayed IC50 values > 100 mu M for antagonism of GLU(A2), GLU(K6), or GLU(K6)/GLU(K2).