3-((4-amino-3-bromo-9,10-dioxo-9,10-dihydroanthracen-1-yl)amino)benzoic acid | 1394134-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-((4-amino-3-bromo-9,10-dioxo-9,10-dihydroanthracen-1-yl)amino)benzoic acid
• 英文别名: IPR-855；3-[(4-Amino-3-bromo-9,10-dioxoanthracen-1-yl)amino]benzoic acid
• CAS: 1394134-90-7
• 化学式: C₂₁H₁₃BrN₂O₄
• 分子量: 437.249
• InChiKey: HKBWHAWDSOFDQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-氨基-2,4-二溴蒽醌 、 间氨基苯甲酸 在 potassium acetate 、 copper diacetate 、 铜 、 盐酸 、 水 作用下， 以 戊醇 为溶剂， 反应 24.17h， 生成 3-((4-amino-3-bromo-9,10-dioxo-9,10-dihydroanthracen-1-yl)amino)benzoic acid
  参考文献：
  名称：

  针对尿激酶受体的小分子的设计、合成、生化研究、细胞表征和基于结构的计算研究

  摘要：

  尿激酶受体 (uPAR) 作为丝氨酸蛋白酶尿激酶型纤溶酶原激活剂 (uPA) 的停靠位点，以促进细胞外基质 (ECM) 降解和肿瘤侵袭和转移。之前，我们报道了一种基于结构的虚拟筛选产生的 uPAR·uPA 相互作用的小分子抑制剂。在这里，我们测量了大量来自商业来源的衍生物的亲和力。进行了其他化合物的合成以探测各种基团对母体化合物的作用。广泛的基于结构的计算研究表明这些化合物的结合模式导致了结构-活性关系研究。对包括 A549、H460 和 H1299 在内的非小细胞肺癌 (NSCLC) 细胞系的细胞研究表明，化合物可阻止侵袭、迁移和粘附。对活性化合物侵入的影响与其对uPA和MMP蛋白水解活性的抑制一致。这些化合物显示出微弱的细胞毒性，这与 uPAR 对转移的限制作用一致。

  DOI：

  10.1016/j.bmc.2012.06.002

文献信息

• [EN] PROCESS FOR PREPARING SUBSTITUTED 9,10-DIOXO-9,10-DIOXO-9,10-DIHYDROANTHRECENES AND 6H-ANTHRA(1,9-CD)ISOXAZOL-6-ONES<br/>[FR] PROCÉDÉ POUR PRÉPARER DES 9,10-DIOXO-9,10-DIOXO-9,10-DIHYDROANTHRÉCÈNES ET DES 6H-ANTHRA(1,9-CD)ISOXAZOL-6-ONES SUBSTITUÉS
  申请人：PURDUE PHARMA LP

  公开号：WO2017161235A1

  公开（公告）日：2017-09-21

  The disclosure provides processes of preparing compounds of Formula (I) and Formula (IV), their salts, and intermediates thereof, wherein R1, R2, R3, and R7 are defined as set forth in the specification.

  该披露提供了制备Formula (I)和Formula (IV)化合物、它们的盐以及中间体的过程，其中R1、R2、R3和R7的定义如规范中所述。
• Ullmann reactions of 1-amino-4-bromoanthraquinones bearing various 2-substituents furnishing novel dyes
  作者：Enas M. Malik、Mahmoud Rashed、Lukas Wingen、Younis Baqi、Christa E. Müller

  DOI：10.1016/j.dyepig.2016.03.023

  日期：2016.8

  Novel 1-amino-4-(ar)alkylaminoanthraquinone derivatives bearing different substituents (Br, CH2OH, CN, or CH3) at the 2-position of the anthraquinone scaffold were synthesized by copper-catalyzed Ullmann condensation. The 2-substituted 1-amino-4-bromoanthraquinone derivatives (bromaminic acid analogues) were reacted with a variety of alkyl-, aryl-, and aralkylamines. Different reaction conditions were

  带有不同取代基（Br，CH 2 OH，CN或CH 3的新型1-氨基-4-（芳）烷基氨基蒽醌衍生物）通过铜催化的乌尔曼缩合反应合成了蒽醌骨架的2位。使2-取代的1-氨基-4-溴蒽醌衍生物（溴酸类似物）与各种烷基胺，芳基胺和芳烷基胺反应。根据胺的物理状态和蒽醌支架2-位的取代基的性质，采用不同的反应条件。开发了一种无溶剂的合成程序，用于与液体胺反应。与固体胺的缩合需要添加溶剂，并且必须为每种蒽醌衍生物优化反应条件。我们的结果强调，铜催化的反应高度可变，取决于存在于介质中的分子和阴离子，因为应用了不同的反应机理。
• Process for preparing substituted 9,10-dioxo-9,10-dihydroanthrecenes and 6H-anthra[1,9-cd]isoxazol-6-ones
  申请人：Purdue Pharma L.P.

  公开号：US10550090B2

  公开（公告）日：2020-02-04

  The disclosure provides processes of preparing compounds of Formula (I) and Formula (IV), their salts, and intermediates thereof, wherein R1, R2, R3, and R7 are defined as set forth in the specification.

  本公开提供了制备式（I）和式（IV）化合物、其盐类及其中间体的工艺，其中 R1、R2、R3 和 R7 的定义如说明书所述。
• Development of Anthraquinone Derivatives as Ectonucleoside Triphosphate Diphosphohydrolase (NTPDase) Inhibitors With Selectivity for NTPDase2 and NTPDase3
  作者：Younis Baqi、Mahmoud Rashed、Laura Schäkel、Enas M. Malik、Julie Pelletier、Jean Sévigny、Amelie Fiene、Christa E. Müller

  DOI：10.3389/fphar.2020.01282

  日期：——

  Ectonucleoside triphosphate diphosphohydrolases (NTPDases) catalyze the hydrolysis of nucleoside tri- and di-phosphates to mono-phosphates. The products are subsequently hydrolyzed by ecto-5 '-nucleotidase (ecto-5 '-NT) to nucleosides. NTPDase inhibitors have potential as novel drugs, e.g., for the treatment of inflammation, neurodegenerative diseases, and cancer. In this context, a series of anthraquinone derivatives structurally related to the anthraquinone dye reactive blue-2 (RB-2) was synthesized and evaluated as inhibitors of human NTPDases utilizing a malachite green assay. We identified several potent and selective inhibitors of human NTPDase2 and -3. Among the most potent NTPDase2 inhibitors were 1-amino-4-(9-phenanthrylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (20, PSB-16131, IC(50)of 539 nM) and 1-amino-4-(3-chloro-4-phenylsulfanyl)phenylamino-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (48, PSB-2020, IC(50)of 551 nM). The most potent NTPDase3 inhibitors were 1-amino-4-[3-(4,6-dichlorotriazin-2-ylamino)-4-sulfophenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (42, PSB-1011, IC(50)of 390 nM) and 1-amino-4-(3-carboxy-4-hydroxyphenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (33, PSB-2046, IC(50)of 723 nM). The best NTPDase2 inhibitor 20 showed a non-competitive inhibition type, while the NTPDase3 inhibitor 42 behaved as a mixed-type inhibitor. These potent compounds were found to be selective vs. other NTPDases. They will be useful tools for studying the roles of NTPDase2 and -3 in physiology and under pathological conditions.
• PROCESS FOR PREPARING SUBSTITUTED 9,10-DIOXO-9,10-DIHYDROANTHRECENES AND 6H-ANTHRA[1,9-CD]ISOXAZOL-6-ONES
  申请人：Purdue Pharma L.P.

  公开号：US20190084942A1

  公开（公告）日：2019-03-21

  The disclosure provides processes of preparing compounds of Formula (I) and Formula (IV), their salts, and intermediates thereof, wherein R 1′ R 2′ R 3 , and R 7 are defined as set forth in the specification.