1-phenyl-1H-imidazo[4,5-c]pyridine | 61532-35-2

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-phenyl-1H-imidazo[4,5-c]pyridine
• 英文别名: 1-phenyl-1H-imidazo[4,5-c]pyridine；1-Phenyl-1H-imidazo<4,5-c>pyridin；1-phenylimidazo[4,5-c]pyridine
• CAS: 61532-35-2
• 化学式: C₁₂H₉N₃
• mdl: MFCD03674877
• 分子量: 195.224
• InChiKey: CTOGPLXHZSSJBE-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• 沸点：
  393.0±34.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenyl-1H-imidazo[4,5-c]pyridine 在 sulfur 作用下， 反应 0.33h， 以83%的产率得到2H-Imidazo[4,5-c]pyridine-2-thione, 1,3-dihydro-1-phenyl-
  参考文献：
  名称：

  Thionation of imidazopyridines

  摘要：

  DOI：

  10.1007/bf00475602
• 作为产物：
  描述：

  4-(N-phenylamino)-3-nitropyridine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙二醇甲醚 为溶剂， 反应 6.0h， 生成 1-phenyl-1H-imidazo[4,5-c]pyridine
  参考文献：
  名称：

  Structure−Activity Relationships for 1-Phenylbenzimidazoles as Selective ATP Site Inhibitors of the Platelet-Derived Growth Factor Receptor

  摘要：

  1-Phenylbenzimidazoles are shown to be a new class of ATP-site inhibitors of the platelet-derived growth factor receptor (PDGFR). Structure-activity relationships (SARs) are narrow, with closely related heterocycles being inactive. A systematic study of substituted 1-phenyl-benzimidazoles showed clear SARs. Substituents at the 4'- and 3'-positions of the phenyl ring are tolerated but do not significantly improve activity, while substituents at the 2'-position abolish it. Substituents in the 2-, 4-, and 7-positions of the benzimidazole ring (with the exception of 4-OH) also abolish activity. Most substituents at the 5- and B-positions maintain or increase activity, with the 5-OH, 5-OMe, 5-COMe, and 5-CO2Me analogues being >10-fold more potent than the parent 1-phenylbenzimidazole. The 5-OMe analogue was both the most potent inhibitor, and showed the highest selectivity (50-fold) between PDGFR and FGFR isolated enzymes, and also a moderately effective inhibitor (IC50 = 1.9 mu M) of PDGF-stimulated PDGFR autophosphorylation in rat aorta smooth muscle cells.

  DOI：

  10.1021/jm9804681

文献信息

• HETEROCYCLIC COMPOUNDS AND METHODS OF USE
  申请人：Heald Robert

  公开号：US20120202785A1

  公开（公告）日：2012-08-09

  Formula I compounds, including stereoisomers, geometric isomers, tautomers, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting the delta isoform of PI3K, and for treating disorders mediated by lipid kinases such as inflammation, immunological disorders, and cancer. 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.

  化学式I类化合物，包括立体异构体、几何异构体、互变异构体、代谢物及其药学上可接受的盐，对抑制PI3K的δ异构体以及治疗由脂质激酶介导的疾病，如炎症、免疫性疾病和癌症，具有用途。公开了利用化合物I类进行体外、体内和体内诊断、预防或治疗哺乳动物细胞中的这类疾病，或相关的病理状况的方法。
• Identification of (<i>R</i>)-(2-Chloro-3-(trifluoromethyl)phenyl)(1-(5-fluoropyridin-2-yl)-4-methyl-6,7-dihydro-1<i>H</i>-imidazo[4,5-<i>c</i>]pyridin-5(4<i>H</i>)-yl)methanone (JNJ 54166060), a Small Molecule Antagonist of the P2X7 receptor
  作者：Devin M. Swanson、Brad M. Savall、Kevin J. Coe、Freddy Schoetens、Tatiana Koudriakova、Judith Skaptason、Jessica Wall、Jason Rech、Xiahou Deng、Meri De Angelis、Anita Everson、Brian Lord、Qi Wang、Hong Ao、Brian Scott、Kia Sepassi、Timothy W. Lovenberg、Nicholas I. Carruthers、Anindya Bhattacharya、Michael A. Letavic

  DOI：10.1021/acs.jmedchem.6b00989

  日期：2016.9.22

  The synthesis and SAR of a series of 4,5,6,7-tetrahydro-imidazo[4,5-c]pyridine P2X7 antagonists are described. Addressing P2X7 affinity and liver microsomal stability issues encountered with this template afforded methyl substituted 4,5,6,7-tetrahydro-imidazo[4,5-c]pyridines ultimately leading to the identification of 1 (JNJ 54166060). 1 is a potent P2X7 antagonist with an ED50 = 2.3 mg/kg in rats

  描述了一系列4,5,6,7-四氢咪唑并[4,5- c ]吡啶P2X7拮抗剂的合成和SAR 。解决此模板遇到的P2X7亲和力和肝微粒体稳定性问题，提供了甲基取代的4,5,6,7-四氢咪唑并[4,5- c ]吡啶，最终导致1的鉴定（JNJ 54166060）。1是一种有效的P2X7拮抗剂，在大鼠中的ED 50 = 2.3 mg / kg，在临床前物种中具有较高的口服生物利用度和低中度清除率，在大鼠中具有可接受的安全范围，并且预计的人类剂量为120 mg QD。此外，1具有独特的CYP谱，被发现是咪达唑仑CYP3A代谢的区域选择性抑制剂。
• P2X7 MODULATORS
  申请人：Janssen Pharmaceutica NV

  公开号：US20150322062A1

  公开（公告）日：2015-11-12

  The present invention is directed to compounds of Formulas (I, IIa and IIb): The invention also relates to pharmaceutical compositions comprising compounds of Formulas (I, IIa and IIb). Methods of making and using the compounds of Formulas (I, IIa and IIb) are also within the scope of the invention.

  本发明涉及公式（I，IIa和IIb）的化合物：本发明还涉及包括公式（I，IIa和IIb）的化合物的制药组合物。制备和使用公式（I，IIa和IIb）的方法也在本发明的范围内。
• Heterocyclic compounds and methods of use
  申请人：Heald Robert

  公开号：US08653089B2

  公开（公告）日：2014-02-18

  Formula I compounds, including stereoisomers, geometric isomers, tautomers, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting the delta isoform of PI3K, and for treating disorders mediated by lipid kinases such as inflammation, immunological disorders, and cancer. 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.

  包括立体异构体、几何异构体、互变异构体、代谢物和药学上可接受的盐在内的公式I化合物，可用于抑制PI3K的δ异构体，并用于治疗由脂质激酶介导的疾病，如炎症、免疫性疾病和癌症。本文揭示了使用公式I化合物进行哺乳动物细胞内、原位和体内诊断、预防或治疗此类疾病或相关病理状态的方法。
• P2X7 modulators
  申请人：Janssen Pharmaceutica NV

  公开号：US09066946B2

  公开（公告）日：2015-06-30

  The present invention is directed to compounds of Formulas (I, IIa and IIb): The invention also relates to pharmaceutical compositions comprising compounds of Formulas (I, IIa and IIb). Methods of making and using the compounds of Formulas (I, IIa and IIb) are also within the scope of the invention.

  本发明涉及公式（I、IIa和IIb）的化合物。本发明还涉及包含公式（I、IIa和IIb）的药物组成物。制备和使用公式（I、IIa和IIb）化合物的方法也在本发明的范围内。