sodium 1-amino-4-(3-carboxy-4-hydroxyphenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate

• 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-(3-carboxy-4-hydroxyphenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate
• 英文别名: Sodium;4-[(4-amino-9,10-dioxo-3-sulfoanthracen-1-yl)amino]-2-carboxyphenolate；sodium;4-[(4-amino-9,10-dioxo-3-sulfoanthracen-1-yl)amino]-2-carboxyphenolate
• 化学式: C₂₁H₁₃N₂O₈S*Na
• 分子量: 476.399
• InChiKey: MCKJYYAMHDVPNB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  195
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  sodium 1-amino-4-(3-carboxy-4-hydroxyphenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate 在 盐酸 、 sodium nitrite 、 锌 作用下， 以 水 、 乙醇 为溶剂， 反应 0.09h， 生成
  参考文献：
  名称：

  Development of Anthraquinone Derivatives as Ectonucleoside Triphosphate Diphosphohydrolase (NTPDase) Inhibitors With Selectivity for NTPDase2 and NTPDase3

  摘要：

  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.

  DOI：

  10.3389/fphar.2020.01282
• 作为产物：
  描述：

  5-氨基水杨酸 、 sodium 1-amino-4-bromoanthraquinone-2-sulfonate 在 铜 作用下， 以 aq. phosphate buffer 为溶剂， 生成 sodium 1-amino-4-(3-carboxy-4-hydroxyphenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate
  参考文献：
  名称：

  Development of Anthraquinone Derivatives as Ectonucleoside Triphosphate Diphosphohydrolase (NTPDase) Inhibitors With Selectivity for NTPDase2 and NTPDase3

  摘要：

  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.

  DOI：

  10.3389/fphar.2020.01282

文献信息

• Rapid and Efficient Microwave-Assisted Copper(0)-Catalyzed Ullmann Coupling Reaction:  General Access to Anilinoanthraquinone Derivatives
  作者：Younis Baqi、Christa E. Müller

  DOI：10.1021/ol070102v

  日期：2007.3.1

  reaction of bromaminic acid (1) with aniline derivatives 2a-z in phosphate buffer. Good to excellent isolated yields were obtained within only 2-20 min at 80-120 degrees C and 40-100 W. The new procedure provides the first general access to anilinoanthraquinones, furnishing a number of previously inaccessible compounds. It is superior to classical methods in all aspects, including yields, reaction time

  [结构：见文字]。苯胺蒽醌3a-z的合成是通过新的Cu（0）催化的溴酸（1）与苯胺衍生物2a-z在磷酸盐缓冲液中的微波辅助的Ullmann偶联反应完成的。在80-120摄氏度和40-100 W下仅需2-20分钟即可获得良好至优异的分离收率。新方法首次提供了苯胺基蒽醌的通用途径，从而提供了许多以前无法获得的化合物。它在所有方面都比传统方法优越，包括产率，反应时间和多功能性。
• Novel P2Y12 receptor antagonists
  申请人：Rheinische Friedrich-Wilhelms-Universität Bonn

  公开号：EP1967513A1

  公开（公告）日：2008-09-10

  The present invention relates to compounds of Formula I, in which A and B are independently CH2, O, S, NH, C=O, C=NH, C=S or C=N-OH; X is NH, O, S, C=O or CH2 and R1-R5 are as defined in claim 1, which are P2Y12 receptor antagonists and useful for treating, alleviating and/or preventing diseases and disorders related to P2Y12 receptor function as well as pharmaceutical compositions comprising such compounds and methods for preparing such compounds. The present invention is further directed to the use of these compounds, alone or in combination with other therapeutic agents, for the alleviation, prevention and/or treatment of diseases and disorders, especially the use as antithrombotic agents for inhibiting platelet aggregation.

  本发明涉及化合物的I式，其中A和B分别为CH2、O、S、NH、C=O、C=NH、C=S或C=N-OH；X为NH、O、S、C=O或CH2，R1-R5如权利要求书中所定义，这些化合物是P2Y12受体拮抗剂，可用于治疗、缓解和/或预防与P2Y12受体功能相关的疾病和紊乱，以及包含这些化合物的药物组合物和制备这些化合物的方法。本发明进一步涉及使用这些化合物，单独或与其他治疗剂联合使用，用于缓解、预防和/或治疗疾病和紊乱，特别是作为抗血栓药物用于抑制血小板聚集。
• NOVEL P2Y12 RECEPTOR ANTAGONISTS
  申请人：Müller Christa E.

  公开号：US20100210654A1

  公开（公告）日：2010-08-19

  The present invention relates to novel P2Y 12 receptor antagonists useful for treating, alleviating and/or preventing diseases and disorders related to P2Y 12 receptor function as well as pharmaceutical compositions comprising such compounds and methods for preparing such compounds. The present invention is further directed to the use of these compounds, alone or in combination with other therapeutic agents, for the alleviation, prevention and/or treatment of diseases and disorders, especially the use as antithrombotic agents for inhibiting platelet aggregation.

  本发明涉及一种新的P2Y12受体拮抗剂，可用于治疗、缓解和/或预防与P2Y12受体功能相关的疾病和障碍，以及包含这些化合物的制药组合物和制备这些化合物的方法。本发明进一步涉及使用这些化合物，单独或与其他治疗剂联合使用，以缓解、预防和/或治疗疾病和障碍，特别是用作抗血栓药物来抑制血小板聚集。
• [EN] NOVEL P2Y12 RECEPTOR ANTAGONISTS<br/>[FR] NOUVEAUX ANTAGONISTES DU RÉCEPTEUR P2Y12
  申请人：UNIV BONN

  公开号：WO2008107211A2

  公开（公告）日：2008-09-12

  [EN] The present invention relates to novel P2Y₁₂ receptor antagonists useful for treating, alleviating and/or preventing diseases and disorders related to P2Y₁₂ receptor function as well as pharmaceutical compositions comprising such compounds and methods for preparing such compounds. The present invention is further directed to the use of these compounds, alone or in combination with other therapeutic agents, for the alleviation, prevention and/or treatment of diseases and disorders, especially the use as antithrombotic agents for inhibiting platelet aggregation.
  [FR] La présente invention concerne de nouveaux antagonistes du récepteur P2Y₁₂ utiles pour traiter, soulager et/ou prévenir des maladies et des états pathologiques liés à la fonction du récepteur P2Y₁₂ ainsi que des compositions pharmaceutiques comprenant ces composés et des procédés de préparation de ces composés. La présente invention concerne en outre l'utilisation de ces composés, seuls ou en combinaison avec d'autres agents thérapeutiques, pour soulager, prévenir et/ou traiter des maladies et états pathologiques, en particulier l'utilisation d'agents anti-thrombotiques pour inhiber l'agrégation plaquettaire.
• 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.