methyl 3-bromomethyl-4,5-dibromothiophene-2-carboxylate | 909011-49-0

• 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-4,5-dibromothiophene-2-carboxylate
• 英文别名: 4,5-dibromo-3-bromomethyl-thiophene-2-carboxylic acid methyl ester；Methyl 4,5-dibromo-3-(bromomethyl)thiophene-2-carboxylate
• CAS: 909011-49-0
• 化学式: C₇H₅Br₃O₂S
• 分子量: 392.894
• InChiKey: GIMCJZCJIXWSJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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-4,5-dibromothiophene-2-carboxylate 在 lithium hydroxide 、 sodium hydride 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(2-carboxy-4,5-dibromothiophen-3-yl-methyl)-5-methyl-1-(tetrahydrofuran-2-yl)pyrimidine-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：

  4,5-二溴-3-甲基噻吩-2-甲酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 18.0h， 以71 g的产率得到methyl 3-bromomethyl-4,5-dibromothiophene-2-carboxylate
  参考文献：
  名称：

  [EN] SUBSTITUTED THIOPHENE CARBOXAMIDES, THIOPHENE CARBOXYLIC ACIDS AND DERIVATIVES THEREOF
  [FR] THIOPHÈNE CARBOXAMIDES SUBSTITUÉS, ACIDES THIOPHÈNE CARBOXYLIQUES ET LEURS DÉRIVÉS

  摘要：

  本公开涉及公式(I)和(II)的取代噻吩羧酰胺衍生物，其用于控制植物病原微生物以及包含它们的组合物。

  公开号：

  WO2021123051A1

文献信息

• [EN] SUBSTITUTED THIOPHENE CARBOXAMIDES, THIOPHENE CARBOXYLIC ACIDS AND DERIVATIVES THEREOF<br/>[FR] THIOPHÈNE CARBOXAMIDES SUBSTITUÉS, ACIDES THIOPHÈNE CARBOXYLIQUES ET LEURS DÉRIVÉS
  申请人：BAYER AG

  公开号：WO2021123051A1

  公开（公告）日：2021-06-24

  The present disclosure relates to substituted thiophene carboxamides derivatives of formula (I) adn (II), their use for controlling phytopathogenic microorganisms and compositions comprising thereof.

  本公开涉及公式(I)和(II)的取代噻吩羧酰胺衍生物，其用于控制植物病原微生物以及包含它们的组合物。
• Novel thienopyridine compounds, and methods of use thereof
  申请人：Turtle D. Eric

  公开号：US20060199836A1

  公开（公告）日：2006-09-07

  The present invention relates to novel compounds capable of modulating the stability and/or activity of hypoxia inducible factor (HIF).

  本发明涉及一种能够调节缺氧诱导因子（HIF）稳定性和/或活性的新化合物。
• NOVEL THIENOPYRIDINE COMPOUNDS, AND METHODS OF USE THEREOF
  申请人：FIBROGEN, INC.

  公开号：US20140221422A1

  公开（公告）日：2014-08-07

  The present invention relates to novel compounds capable of modulating the stability and/or activity of hypoxia inducible factor (HIF).

  本发明涉及一种新型化合物，能够调节缺氧诱导因子（HIF）的稳定性和/或活性。
• THIENOPYRIDINE COMPOUNDS, AND METHODS OF USE THEREOF
  申请人：FIBROGEN, INC.

  公开号：EP1866318A2

  公开（公告）日：2007-12-19
• US8703795B2
  申请人：——

  公开号：US8703795B2

  公开（公告）日：2014-04-22