2-(4-溴苯基)-5-甲基嘧啶 | 174720-38-8

• 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-(4-溴苯基)-5-甲基嘧啶
• 英文名称: 2-(4-bromophenyl)-5-methylpyrimidine
• CAS: 174720-38-8
• 化学式: C₁₁H₉BrN₂
• 分子量: 249.11
• InChiKey: BSUNLHHGZSFMOP-UHFFFAOYSA-N

物化性质

• 沸点：
  251.2±32.0 °C(Predicted)
• 密度：
  1.434±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-甲基哌嗪 、 2-(4-溴苯基)-5-甲基嘧啶 在 palladium diacetate caesium carbonate 、 2-(二叔丁基膦)联苯 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 以81%的产率得到5-methyl-2-[4-(3-(S)-methyl-piperazin-1-yl)-phenyl]-pyrimidine
  参考文献：
  名称：

  WO2007/70398

  摘要：

  公开号：
• 作为产物：
  描述：

  3-羟基-2-甲基丙-2-烯醛 、 4-溴苯甲脒盐酸盐水合物 在 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 2-(4-溴苯基)-5-甲基嘧啶
  参考文献：
  名称：

  Heterocyclic Insecticides Acting at the GABA-Gated Chloride Channel: 5-Alkyl-2-arylpyrimidines and -1,3-thiazines

  摘要：

  5-tert-Butyl-2-(4-ethynylphenyl)pyrimidine and the corresponding 2,5-disubstituted-4H-1,3-thiazine block the GABA-gated chloride channel at c.20 and c.200 nM, respectively, measured as 50% inhibition of the binding of 1-(-4-ethynylphenyl)-4-[H-3]propyl-2,6,7-trioxabicyclo[2.22]octane (4'-ethynyl-4-n-[H-3]propylbicycloorthobenzoate; [H-3]EBOB) in house fly and mouse brain membranes, and they are also toxic to topically-treated dies with LD(50) values of 6-27 mu g g(-1) alone and 2-6 mu g g(-1) with piperonyl butoxide (PB) as synergist. In the pyrimidine series, the general pattern of effectiveness of substituents in the 5-position is tert-butyl > isopropyl approximate to cyclohexyl approximate to cyclopropyl > methyl, phenyl and 3- and 4-fluorophenyl, and in the 2-position is 4-ethynylphenyl much greater than 4-bromophenyl. These planar pyrimidines and nearly-planar 4H-1,3-thiazines with 2-ethynylphenyl or 2-bromophenyl and 5-tert-butyl or 5-isopropyl substituents are more effective than the corresponding 6H-1,3-thiazine, 6-oxo-1,3-thiazines and 4,6-dioxo-1,3-thiazine examined, but they are less active than the analogous conformationally flexible trans-1,3-dioxanes and -1,3-dithianes. The heterocyclic moiety confers a region of high electron density and positions the 2- and 5-substituents in a linear or parallel relationship for optimal affinity at the receptor. Two observations indicate that the new pyrimidines and thiazines probably act as chloride channel blockers. First, the poisoning signs are identical to those of EBOB in both mice and house flies. Second, each of the pyrimidines, thiazines and dioxanes falls on the same correlation line for inhibition of [H-3]EBOB binding and toxicity to house flies (with PB) as that obtained earlier for EBOB analogs, dithianes and polychlorocycloalkanes, suggesting that they all act at the same or closely coupled binding sites in the GABA-gated chloride channel.

  DOI：

  10.1002/(sici)1096-9063(199603)46:3<237::aid-ps359>3.0.co;2-p

文献信息

• Novel compounds that are ERK inhibitors
  申请人：Cooper Alan B.

  公开号：US20090118284A1

  公开（公告）日：2009-05-07

  Disclosed are the ERK inhibitors of formula 1.0: and the pharmaceutically acceptable salts, esters and solvates thereof. Q is a piperidine or piperazine ring that can have a bridge or a fused ring. The piperidine ring can have a double bond in the ring. All other substitutents are as defined herein. Also disclosed are methods of treating cancer using the compounds of formula 1.0.

  本发明公开了式1.0的ERK抑制剂及其药学上可接受的盐、酯和溶剂化物。其中，Q是一个带有桥或融合环的哌啶或哌嗪环。哌啶环中可以在环上具有双键。所有其他取代基如本文所定义。本发明还公开了使用式1.0的化合物治疗癌症的方法。
• Compounds that are ERK inhibitors
  申请人：Cooper Alan B.

  公开号：US08546404B2

  公开（公告）日：2013-10-01

  Disclosed are the ERK inhibitors of formula 1.0: and the pharmaceutically acceptable salts, esters and solvates thereof. Q is a piperidine or piperazine ring that can have a bridge or a fused ring. The piperidine ring can have a double bond in the ring. All other substitutents are as defined herein. Also disclosed are methods of treating cancer using the compounds of formula 1.0.

  本文揭示了式1.0的ERK抑制剂及其药学上可接受的盐、酯和溶剂化物。其中，Q是一个可带有桥或融合环的哌啶或哌嗪环。哌啶环中可以有一个环内双键。所有其他取代基的定义如本文所述。此外，本文还揭示了使用式1.0的化合物治疗癌症的方法。
• HETEROCYCLIC COMPOUNDS AND USE THEREOF AS ERK INHIBITORS
  申请人：Sun Robert

  公开号：US20110038876A1

  公开（公告）日：2011-02-17

  Disclosed are the ERK inhibitors of formula 1.0: [Formula (1.0)] and the pharmaceutically acceptable salts, esters and solvates thereof. Q is a piperidine or piperazine ring that can have a bridge or a fused ring. The piperidine ring can have a double bond in the ring. All other substitutents are as defined herein. Also disclosed are methods of treating cancer using the compounds of formula 1.0.

  本发明涉及公开的ERK抑制剂，其化学式为1.0：[Formula (1.0)]及其药学上可接受的盐、酯和溶剂化物。其中，Q是一个可具有桥或融合环的哌啶或哌嗪环。哌啶环中可以在环中具有双键。所有其他取代基均如所定义。本发明还公开了使用化合物1.0治疗癌症的方法。
• Triazolopyrimidine compounds and their use in treating cancer
  申请人：Dizal (Jiangsu) Pharmaceutical Co., Ltd.

  公开号：US11084827B2

  公开（公告）日：2021-08-10

  The invention concerns compounds of Formula (I): or pharmaceutically acceptable salts thereof, wherein R1, R2, X, Ring A, Ring B and Ring C have any of the meanings hereinbefore defined in the description; process for their preparation; pharmaceutical compositions containing them and their use in treating MCT4 mediated diseases.

  本发明涉及式（I）化合物： 或其药学上可接受的盐，其中 R1、R2、X、环 A、环 B 和环 C 具有本文在描述中定义的任何含义；它们的制备工艺；含有它们的药物组合物以及它们在治疗 MCT4 介导的疾病中的用途。
• WO2007/70398
  申请人：——

  公开号：——

  公开（公告）日：——