2-(1-苯基-1H-吡唑-4-基)-乙胺 | 369652-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(1-苯基-1H-吡唑-4-基)-乙胺
• 英文名称: 2-(1-phenyl-1H-pyrazol-4-yl)-ethylamine
• 英文别名: 2-(1-phenyl-1H-pyrazol-4-yl)ethanamine；2-(1-phenylpyrazol-4-yl)ethanamine
• CAS: 369652-04-0
• 化学式: C₁₁H₁₃N₃
• mdl: MFCD07186397
• 分子量: 187.244
• InChiKey: XCVXHLSNYSXXEO-UHFFFAOYSA-N

物化性质

• 沸点：
  326.7±17.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  4,9-Dihydropyrano<3,4-b>indol-1(3H)-on 、 2-(1-苯基-1H-吡唑-4-基)-乙胺 以 甲苯 为溶剂， 反应 48.0h， 以55%的产率得到3-(2-hydroxy-ethyl)-1H-indole-2-carboxylic acid [2-(1-phenyl-1H-pyrazol-4-yl)-ethyl]-amide
  参考文献：
  名称：

  Synthesis and 5-HT2A Antagonist Activity of Derivatives of the Novel Heterocycles Indolo[3,2-d]pyrrolo[3,2-g]azecine and Benzo[d]pyrrolo[3,2-g]azecine compared to the Benz[d]indolo[2,3-g]azecine Derivative LE 300

  摘要：

  An indolo[3,2-d]pyrrolo[3,2-g]azecine and a benzo[d]pyrrolo[3,2-glazecine analogue of the potent dopamine receptor antagonist LE 300 {7-methyl-6,7,8,9,14,15-hexahydro-5H-benz[d]indolo[2,3-g]azecine) have been prepared in mufti-step reactions via C-N bond cleavage of corresponding quaternary N-methylquinolizinium iodides. LE 300, the target compounds and two precursor quinolizines have been tested in vitro for antagonist activity at 5-HT2A receptors (rat tail artery) and Hl receptors {guinea-pig ileum), respectively. LE 300 and compound 19 {3,6-dimethyl-4,5,6,7,8,13-hexahydro-3H-benzo[d]pyrrolo[3,2-glazecine) competitively inhibited S-HT-induced contractions with similar nanomolar potency (pA(2) = 8.32 and 8.01, respectively) but were less active than the reference antagonist ketanserin (pA(2) = 9.55). Compound 19 displayed moderate H-1-antihistaminic activity in the guinea-pig ileum assay (pA(2) = 7.37).

  DOI：

  10.1002/1521-4184(200107)334:7<241::aid-ardp241>3.0.co;2-b
• 作为产物：
  描述：

  1-苯基-1H-吡唑-4-甲醛 在 哌啶 、 lithium aluminium tetrahydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 48.0h， 生成 2-(1-苯基-1H-吡唑-4-基)-乙胺
  参考文献：
  名称：

  Synthesis and 5-HT2A Antagonist Activity of Derivatives of the Novel Heterocycles Indolo[3,2-d]pyrrolo[3,2-g]azecine and Benzo[d]pyrrolo[3,2-g]azecine compared to the Benz[d]indolo[2,3-g]azecine Derivative LE 300

  摘要：

  An indolo[3,2-d]pyrrolo[3,2-g]azecine and a benzo[d]pyrrolo[3,2-glazecine analogue of the potent dopamine receptor antagonist LE 300 {7-methyl-6,7,8,9,14,15-hexahydro-5H-benz[d]indolo[2,3-g]azecine) have been prepared in mufti-step reactions via C-N bond cleavage of corresponding quaternary N-methylquinolizinium iodides. LE 300, the target compounds and two precursor quinolizines have been tested in vitro for antagonist activity at 5-HT2A receptors (rat tail artery) and Hl receptors {guinea-pig ileum), respectively. LE 300 and compound 19 {3,6-dimethyl-4,5,6,7,8,13-hexahydro-3H-benzo[d]pyrrolo[3,2-glazecine) competitively inhibited S-HT-induced contractions with similar nanomolar potency (pA(2) = 8.32 and 8.01, respectively) but were less active than the reference antagonist ketanserin (pA(2) = 9.55). Compound 19 displayed moderate H-1-antihistaminic activity in the guinea-pig ileum assay (pA(2) = 7.37).

  DOI：

  10.1002/1521-4184(200107)334:7<241::aid-ardp241>3.0.co;2-b

文献信息

• [EN] NOVEL COMPOUNDS USEFUL FOR THE TREATMENT OF DEGENERATIVE AND INFLAMMATORY DISEASES<br/>[FR] NOUVEAUX COMPOSÉS UTILES POUR LE TRAITEMENT DE MALADIES DÉGÉNÉRATIVES ET INFLAMMATOIRES
  申请人：GALAPAGOS NV

  公开号：WO2010010186A1

  公开（公告）日：2010-01-28

  [1,2,4]Triazolo[1,5-a]pyridine compounds are disclosed that have a formula represented by the following: (I) These compound may be prepared as a pharmaceutical composition, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, diseases involving cartilage degradation, bone and/or joint degradation, for example osteoarthritis; and/or conditions involving inflammation or immune responses, such as Crohn's disease, rheumatoid arthritis, psoriasis, allergic airways disease (e.g. asthma, rhinitis), juvenile idiopathic arthritis, colitis, inflammatory bowel diseases, endotoxin-driven disease states (e.g. complications after bypass surgery or chronic endotoxin states contributing to e.g. chronic cardiac failure), diseases involving impairment of cartilage turnover (e.g. diseases involving the anabolic stimulation of chondrocytes), congenital cartilage malformations, diseases associated with hypersecretion of IL6 and transplantation rejection (e.g. organ transplant rejection) and proliferative diseases.

  [1,2,4]三唑并[1,5-a]吡啶化合物被披露，其具有以下公式(I)表示的化合物。这些化合物可以制备成药物组合物，并且可以用于预防和治疗包括人类在内的哺乳动物的多种病症，包括但不限于涉及软骨降解、骨骼和/或关节退化的疾病，例如骨关节炎；以及/或涉及炎症或免疫反应的状况，如克罗恩病、类风湿性关节炎、银屑病、过敏性呼吸道疾病（例如哮喘、鼻炎）、幼年特发性关节炎、结肠炎、炎症性肠病、内毒素驱动的疾病状态（例如搭桥手术后的并发症或慢性内毒素状态导致慢性心力衰竭）、涉及软骨转换受损的疾病（例如涉及软骨细胞合成代谢刺激的疾病）、先天性软骨畸形、与IL6过度分泌和移植排斥反应相关的疾病（例如器官移植排斥）以及增殖性疾病。
• NOVEL COMPOUNDS USEFUL FOR THE TREATMENT OF DEGENERATIVE AND INFLAMMATORY DISEASES
  申请人：Menet Christel Jeanne Marie

  公开号：US20110190260A1

  公开（公告）日：2011-08-04

  [1,2,4]Triazolo[1,5-a]pyridine compounds are disclosed that have a formula represented by the formula (I). The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, diseases involving cartilage degradation, bone and/or joint degradation, for example osteoarthritis; and/or conditions involving inflammation or immune responses, such as Crohn's disease, rheumatoid arthritis, psoriasis, allergic airways disease (e.g. asthma, rhinitis), juvenile idiopathic arthritis, colitis, inflammatory bowel diseases, endotoxin-driven disease states (e.g. complications after bypass surgery or chronic endotoxin states contributing to e.g. chronic cardiac failure), diseases involving impairment of cartilage turnover (e.g diseases involving the anabolic stimulation of chondrocytes), congenital cartilage malformations, diseases associated with hypersecretion of IL6, transplantation rejection (e.g. organ transplant rejection) and proliferative diseases.

  本文披露了一种具有公式（I）所表示的化学式的[1,2,4]三唑并[1,5-a]吡啶化合物。这些化合物可以制备为药物组合物，并可用于预防和治疗哺乳动物（包括人类）的各种疾病，包括但不限于涉及软骨降解、骨骼和/或关节降解的疾病，例如骨关节炎；以及涉及炎症或免疫反应的疾病，如克隆病、类风湿性关节炎、牛皮癣、过敏性呼吸道疾病（例如哮喘、鼻炎）、少年特发性关节炎、结肠炎、炎性肠病、内毒素驱动的疾病状态（例如旁路手术后的并发症或慢性内毒素状态导致的慢性心力衰竭等）、涉及软骨周转障碍的疾病（例如涉及软骨细胞的合成刺激的疾病）、先天性软骨畸形、与IL6高分泌相关的疾病、移植排斥（例如器官移植排斥）和增生性疾病。
• Late-Stage Isotopic Exchange of Primary Amines
  作者：Julia R. Dorsheimer、Tomislav Rovis

  DOI：10.1021/jacs.3c09442

  日期：2023.11.8

  isotopes via isotopic exchange allows for the direct conversion of complex molecules into their valuable isotopologues without requiring a de novo synthesis. While synthetic methods exist for the conversion of hydrogen and carbon atoms into their less abundant isotopes, a corresponding method for accessing 15N-primary amines from their naturally occurring 14N-analogues has not yet been disclosed. We

  2 H、13C 和 15N 等稳定同位素在化学和药物发现中具有重要应用。通过同位素交换掺入不常见同位素的后期可以将复杂分子直接转化为有价值的同位素，而无需从头合成。虽然存在将氢和碳原子转化为丰度较低的同位素的合成方法，但尚未披露从其天然存在的 14N 类似物中获得 15N 仲胺的相应方法。我们报道了一种使用简单的二苯甲酮亚胺作为 15N 源，通过后期同位素交换获得 15N 标记伯胺的方法。通过将 α-1 和 α-2° 胺活化为 Katritzky 吡啶盐，将 α-3° 胺活化为氧化还原活性亚胺，我们可以在脱氨基化过程中与伯烷基胺结合。氧化还原活性亚胺通过自由基-极叉机制进行，而 Katritzky 盐通过电子供体-受体复合物参与铜催化。该方法适用于多种胺类，包括多种药物化合物，并产生完整的选择性同位素标记。
• Compounds useful for the treatment of degenerative and inflammatory diseases
  申请人：GALAPAGOS NV

  公开号：US10206907B2

  公开（公告）日：2019-02-19

  [1,2,4]triazolo[1,5-a]pyridine compounds are disclosed that have a formula represented by the following: The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, diseases involving cartilage degradation, bone and/or joint degradation, for example osteoarthritis; and/or conditions involving inflammation or immune responses, such as Crohn's disease, rheumatoid arthritis, psoriasis, allergic airways disease (e.g. asthma, rhinitis), juvenile idiopathic arthritis, colitis, inflammatory bowel diseases, endotoxin-driven disease states (e.g. complications after bypass surgery or chronic endotoxin states contributing to e.g. chronic cardiac failure), diseases involving impairment of cartilage turnover (e.g. diseases involving the anabolic stimulation of chondrocytes), congenital cartilage malformations, diseases associated with hypersecretion of IL6 and transplantation rejection (e.g. organ transplant rejection) and proliferative diseases.

  所公开的[1,2,4]三唑并[1,5-a]吡啶化合物具有下式： 这些化合物可制备成药物组合物，并可用于预防和治疗包括人类在内的哺乳动物的各种疾病，包括非限制性实例，涉及软骨退化、骨和/或关节退化的疾病，例如骨关节炎；和/或涉及炎症或免疫反应的疾病，例如克罗恩病、类风湿性关节炎、银屑病、过敏性气道疾病（如哮喘、鼻炎、幼年特发性关节炎、荨麻疹等）。哮喘、鼻炎）、幼年特发性关节炎、结肠炎、肠道炎症性疾病、内毒素驱动的疾病状态（如搭桥手术后的并发症或导致慢性心力衰竭等的慢性内毒素状态）、涉及软骨代谢损伤的疾病（如涉及合成代谢疾病的疾病）、涉及骨质疏松症的疾病（如骨质疏松症）、涉及骨质疏松症的疾病（如骨质疏松症）、涉及骨质疏松症的疾病（如骨质疏松症）。先天性软骨畸形、与 IL6 分泌过多和移植排斥有关的疾病（如器官移植排斥）以及增殖性疾病。
• Triazolopyridines as Selective JAK1 Inhibitors: From Hit Identification to GLPG0634
  作者：Christel J. Menet、Stephen R Fletcher、Guy Van Lommen、Raphael Geney、Javier Blanc、Koen Smits、Nolwenn Jouannigot、Pierre Deprez、Ellen M. van der Aar、Philippe Clement-Lacroix、Liên Lepescheux、René Galien、Béatrice Vayssiere、Luc Nelles、Thierry Christophe、Reginald Brys、Muriel Uhring、Fabrice Ciesielski、Luc Van Rompaey

  DOI：10.1021/jm501262q

  日期：2014.11.26

  Janus kinases (JAK1, JAK2, JAK3, and TYK2) are involved in the signaling of multiple cytokines important in cellular function. Blockade of the JAK-STAT pathway with a small molecule has been shown to provide therapeutic immunomodulation. Having identified JAK1 as a possible new target for arthritis at Galapagos, the compound library was screened against JAK1, resulting in the identification of a triazolopyridine-based series of inhibitors represented by 3. Optimization within this chemical series led to identification of GLPG0634 (65, filgotinib), a selective JAK1 inhibitor currently in phase 2B development for RA and phase 2A development for Crohns disease (CD).