sodium 1-amino-4-[4-phenylamino-3-carboxyphenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate | 1052087-99-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: sodium 1-amino-4-[4-phenylamino-3-carboxyphenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate
• 英文别名: PSB-0702；1-amino-4-[4-phenylamino-3-sulfophenylamino]-9,10-dioxo-9,10-ihydroanthracene-2-carboxylic acid sodium salt；Sodium;5-[(4-amino-3-carboxy-9,10-dioxoanthracen-1-yl)amino]-2-anilinobenzenesulfonate
• CAS: 1052087-99-6
• 化学式: C₂₇H₁₈N₃O₇S*Na
• 分子量: 551.512
• InChiKey: PZRXTTYJQMKSRF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  187
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1-氨基-4-溴-9,10-二氧代-9,10-二氢蒽-2-羧酸 、 4-氨基二苯胺-2-磺酸 在 铜 作用下， 反应 0.08h， 以55%的产率得到sodium 1-amino-4-[4-phenylamino-3-carboxyphenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate
  参考文献：
  名称：

  High-Affinity, Non-Nucleotide-Derived Competitive Antagonists of Platelet P2Y₁₂ Receptors

  摘要：

  Anthraquinone derivatives related to the moderately potent, nonselective P2Y(12) receptor antagonist reactive blue 2 (6) have been synthesized and optimized with respect to P2Y(12) receptor affinity. A radioligand binding assay utilizing human blood platelet membranes and the P2Y(12) receptor-selective antagonist radioligand [H-3]2-propylthioadenosine-5'-adenylic acid (1,1-dichloro-1-phosphonomethyl-1-phosphonyl) anhydride ([H-3]PSB-0413) was applied for compound testing. 1-Amino-2-sulfoanthraquinone derivatives bearing a (p-phenylamino)anilino substitution in the 4-position and an additional acidic function in the meta-position of the aniline ring showed high P2Y(12) receptor affinity. These new anthraquinone derivatives became accessible by a recently developed copper(0)-catalyzed Ullmann coupling reaction of 1-amino-4-bromoanthraquinone derivatives with anilines in phosphate buffer under microwave irradiation. The most potent compounds exhibited K-i values of 24.9 nM (1-amino-4-[4-phenylamino-3-sulfophenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate, PSB-0739, 39), and 2 1.0 nM (1-amino-4-[4-phenylamino-3-carboxyphenylamino]- 9,10-dioxo-9,10-dihydroanthracene-2-sulfonate, PSB-0702, 41), respectively. 1-Amino-2-sulfo-4-anilinoanthraquinone derivatives appeared to be noncytotoxic, as shown for selected derivatives at two human cell lines (melanoma and astrocytoma). Compounds 39 and 41 represent new lead structures for the development of antithrombotic drugs.

  DOI：

  10.1021/jm9003297