3-(3-bromophenylamino)-4-ethoxycyclobut-3-ene-1,2-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3-bromophenylamino)-4-ethoxycyclobut-3-ene-1,2-dione
• 英文别名: 3-(3-Bromo phenylamino)-4-ethoxy-3-cyclobuten-1,2-dione；3-(3-Bromophenylamino)-4-ethoxy-3-cyclobuten-1,2-dione；3-[(3-Bromophenyl)amino]-4-ethoxycyclobut-3-ene-1,2-dione；3-(3-bromoanilino)-4-ethoxycyclobut-3-ene-1,2-dione
• 化学式: C₁₂H₁₀BrNO₃
• mdl: MFCD14281297
• 分子量: 296.12
• InChiKey: VFHRIIVWOBSOAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氨基-4-氯苯甲酸 、 3-(3-bromophenylamino)-4-ethoxycyclobut-3-ene-1,2-dione 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以0.30 g的产率得到2-[2-(3-bromo-phenylamino)-3,4-dioxo-cyclobut-1-enylamino]-4-chloro-benzoic acid
  参考文献：
  名称：

  Bioisosteric Modifications of 2-Arylureidobenzoic Acids:  Selective Noncompetitive Antagonists for the Homomeric Kainate Receptor Subtype GluR5

  摘要：

  2-Arylureidobenzoic acids (AUBAs) have recently been presented as the first series of selective noncompetitive GluR5 antagonists. In this paper we have modified the acidic moiety of the AUBAs by introducing different acidic and neutral groups, and similarly, we have replaced the urea linker of the AUBAs with other structurally related linkers. Replacing the acid with neutral substituents led to inactive compounds in all instances, showing that an acidic moiety is necessary for activity. Replacing the carboxylic moiety in 2a with a sulfonic acid (5c) or a tetrazole ring (5d) improved the potency at GluR5 receptors (compounds 5c and 5d showed IC50 values of 1.5 and 2.0 muM, respectively, compared to compound 2a with IC50 = 4.8 muM). Compound 5c did not show improved in vivo activity in the ATPA rigidity test compared to 2a, whereas compound 5d was 4 times more potent than 2a. All compounds wherein the urea linker had been replaced showed lower or no activity. The results described extend the knowledge of structure-activity relationships for the AUBAs, and compound 5d may prove to be a good candidate for studying GluR5 receptors in vitro and in vivo.

  DOI：

  10.1021/jm030638w
• 作为产物：
  描述：

  方酸二乙酯 、 间溴苯胺 以 乙醇 为溶剂， 反应 68.0h， 生成 3-(3-bromophenylamino)-4-ethoxycyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Diaminocyclobutene-3,4-dione derivatives, their preparation and use

  摘要：

  本发明涉及具有式(I)或其药学上可接受的盐的化合物。在式(I)中，X代表具有结构式(II)的基团，而Y代表O或S。本发明的化合物可用作氯离子通道阻滞剂。

  公开号：

  US20010056092A1

文献信息

• DIAMINOCYCLOBUTENE-3,4-DIONE DERIVATIVES, THEIR PREPARATION AND USE
  申请人：NEUROSEARCH A/S

  公开号：EP1117633B1

  公开（公告）日：2002-09-18
• US6413996B2
  申请人：——

  公开号：US6413996B2

  公开（公告）日：2002-07-02
• [EN] DIAMINOCYCLOBUTENE-3,4-DIONE DERIVATIVES, THEIR PREPARATION AND USE<br/>[FR] DERIVES DE DIAMINOCYCLOBUTENE-3,4-DIONE, LEUR PREPARATION ET UTILISATION
  申请人：NEUROSEARCH AS

  公开号：WO2000020378A1

  公开（公告）日：2000-04-13

  The present invention discloses compounds having formula (1) or a pharmaceutically acceptable salt thereof, wherein X represents (2), Y represents O or S. The meaning of R', R'', R''', R?2, R3, R4, R5, and R6¿ are specified in the application. The compounds are useful as chloride channel blockers.