ethyl 4-hydroxy-1-methyl-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridin-5-carboxylate | 66857-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: ethyl 4-hydroxy-1-methyl-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridin-5-carboxylate
• 英文别名: ethyl 4-hydroxy-1-methyl-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate；ethyl 4-hydroxy-1-methyl-6-oxo-7H-pyrazolo[3,4-b]pyridine-5-carboxylate
• CAS: 66857-96-3
• 化学式: C₁₀H₁₁N₃O₄
• 分子量: 237.215
• InChiKey: RLHJWTHFWCHXAN-UHFFFAOYSA-N

物化性质

• 沸点：
  502.0±50.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  93.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-hydroxy-1-methyl-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridin-5-carboxylate 在 2,6-二叔丁基-4-甲基吡啶 、 苄基三甲基氯化铵 、 三氯氧磷 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 38.5h， 生成 4-[N'-(3-Fluoro-phenyl)-hydrazino]-1-methyl-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Structure–activity studies of a series of dipyrazolo[3,4- b :3′,4′- d ]pyridin-3-ones binding to the immune regulatory protein B7.1

  摘要：

  The interaction of co-stimulatory molecules on T cells with 137 molecules on antigen presenting cells plays an important role in the activation of naive T cells. Consequently, agents that disrupt these interactions should have applications in treatment of transplant rejection as well as autoimmune diseases. To this end, specific small molecule inhibitors of human B7.1 were identified and characterized. Herein, we report the identification of potent small molecule inhibitors of the B7.1-CD28 interaction. In a high-throughput screen we identified several leads that prevented the interaction of B7.1 with CD28 with activities in the nanomolar to low micromolar range. One of these, the dihydrodipyrazolopyridinone 1, was subsequently shown to bind the V-like domain of human B7.1 at equimolar stoichiometry. With this as a starting point, we report here the synthesis and initial in vitro structure-activity relationships of a series of these compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00183-4
• 作为产物：
  描述：

  5-氨基-1-甲基吡唑-4-甲酸乙酯 、 丙二酸二乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以64%的产率得到ethyl 4-hydroxy-1-methyl-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridin-5-carboxylate
  参考文献：
  名称：

  [EN] PYRAZOLOPYRIDINE PI3K INHIBITOR COMPOUNDS AND METHODS OF USE
  [FR] COMPOSÉS INHIBITEURS DE PI3K DE TYPE PYRAZOLOPYRIDINE ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  公式(I)的化合物，包括立体异构体、几何异构体、互变异构体、溶剂合物、代谢产物及其药用盐，用于抑制脂质激酶包括p110α和PI3K的其他同系物，并用于治疗由脂质激酶介导的癌症或炎症等疾病。公开了使用公式(I)的化合物在哺乳动物细胞中进行体外、体内和体内诊断、预防或治疗此类疾病，或相关病理状况的方法。

  公开号：

  WO2010059788A1

文献信息

• [EN] ECTONUCLEOTIDE PYROPHOSPHATASE/PHOSPHODIESTERASE 1 (ENPP1) MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS D'ECTONUCLÉOTIDES PYROPHOSPHATASES/PHOSPHODIESTÉRASES 1 (ENPP1) ET LEURS UTILISATIONS
  申请人：SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INST

  公开号：WO2021133915A1

  公开（公告）日：2021-07-01

  Provided herein are small molecule modulators of ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1), compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.

  本文提供了外胞核苷酸焦磷酸酶/磷酸二酯酶1（ENPP1）的小分子调节剂，包括这些化合物的组合物，以及使用这些化合物和包含这些化合物的组合物的方法。
• Dihydrodipyrazolopyridinone inhibitors of B7-1
  申请人：Wyeth

  公开号：US20040044024A1

  公开（公告）日：2004-03-04

  The present invention provides a compound of formula I and the use thereof for the immunotherapeutic treatment of transplant rejection, autoimmune disease or graft vs. host disease. 1

  本发明提供了一种I式化合物及其用于免疫治疗移植排斥、自身免疫疾病或移植物抗宿主病的用途。
• PYRAZOLOPYRIDINE PI3K INHIBITOR COMPOUNDS AND METHODS OF USE
  申请人：Dotson Jennafer

  公开号：US20120035208A1

  公开（公告）日：2012-02-09

  Compounds of Formula (I), and including stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting lipid kinases including p110 alpha and other isoforms of PI3K, and for treating disorders such as cancer or inflammation mediated by lipid kinases. Methods of using compounds of Formula (I) for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  具有化学式（I）的化合物，包括立体异构体、几何异构体、互变异构体、溶剂化物、代谢物和药学上可接受的盐，对于抑制脂质激酶包括p110α和其他PI3K同源物的活性非常有用，用于治疗由脂质激酶介导的癌症或炎症等疾病。本文披露了使用化合物（I）进行体外、原位和体内诊断、预防或治疗哺乳动物细胞中的这些疾病，或相关病理条件的方法。
• Pyrazolopyridine PI3K inhibitor compounds and methods of use
  申请人：Dotson Jennafer

  公开号：US08653098B2

  公开（公告）日：2014-02-18

  Compounds of Formula (I), and including stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting lipid kinases including p110 alpha and other isoforms of PI3K, and for treating disorders such as cancer or inflammation mediated by lipid kinases. Methods of using compounds of Formula (I) for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  公式（I）的化合物，包括立体异构体，几何异构体，互变异构体，溶剂化物，代谢产物和其药学上可接受的盐，用于抑制脂质激酶，包括p110α和其他PI3K的亚型，并用于治疗由脂质激酶介导的癌症或炎症等疾病。公开了使用公式（I）的化合物在哺乳动物细胞中进行体外，原位和体内诊断，预防或治疗此类疾病或相关病理条件的方法。
• US6900223B2
  申请人：——

  公开号：US6900223B2

  公开（公告）日：2005-05-31