3-(naphthalen-1-yl)-3H-imidazo[4,5-b]pyridine-2-thiol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(naphthalen-1-yl)-3H-imidazo[4,5-b]pyridine-2-thiol
• 英文别名: 3-(1-naphthyl)-2-mercapto-3H-imidazo[4,5-b]pyridine；3-naphthalen-1-yl-1H-imidazo[4,5-b]pyridine-2-thione
• 化学式: C₁₆H₁₁N₃S
• 分子量: 277.349
• InChiKey: OWNTVQDVUMICLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(naphthalen-1-yl)-3-nitropyridin-2-amine 在 palladium on activated charcoal 、 氢气 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 3-(naphthalen-1-yl)-3H-imidazo[4,5-b]pyridine-2-thiol
  参考文献：
  名称：

  一种咪唑并吡啶巯乙酸类衍生物及其制备方 法与应用

  摘要：

  本发明涉及一种咪唑并吡啶巯乙酸类衍生物及其制备方法和应用。所述化合物具有式I、II、III所示的结构。本发明还涉及含有式I、II、III结构化合物的制备方法以及药物组合物。本发明还提供上述化合物在制备抗痛风的药物中的应用。

  公开号：

  CN106083847B

文献信息

• 一种咪唑并吡啶巯乙酸类衍生物及其制备方 法与应用
  申请人：山东大学

  公开号：CN106083847B

  公开（公告）日：2018-10-30

  本发明涉及一种咪唑并吡啶巯乙酸类衍生物及其制备方法和应用。所述化合物具有式I、II、III所示的结构。本发明还涉及含有式I、II、III结构化合物的制备方法以及药物组合物。本发明还提供上述化合物在制备抗痛风的药物中的应用。
• IMIDAZOPYRIDINE THIOGLYCOLIC ACID DERIVATIVE, PREPARATION METHOD THEREFOR AND APPLICATION THEREOF
  申请人：Shandong University

  公开号：EP3495362A1

  公开（公告）日：2019-06-12

  Provided are an imidazopyridine thioglycolic acid derivative, a preparation method therefor and an application thereof. Said compound has the structure as shown in formula I, II and III. Also provided are a preparation method for the compound having the structure as shown in formula I, II and III, and a pharmaceutical composition thereof. Also provided is an application of the above compound in the preparation of anti-gout drugs.

  本发明提供了一种咪唑吡啶硫代乙醇酸衍生物、其制备方法及其应用。所述化合物具有如式 I、II 和 III 所示的结构。还提供了具有式 I、II 和 III 所示结构的化合物的制备方法及其药物组合物。还提供了上述化合物在制备抗痛风药物中的应用。
• Imidazopyridine thioglycolic acid derivatives as potent inhibitors of human urate transporter 1
  申请人：SHANDONG UNIVERSITY

  公开号：US10399978B2

  公开（公告）日：2019-09-03

  It relates to the imidazopyridine thioglycolic acid derivatives, the preparation, and use thereof. The invention contained imidazopyridine thioglycolic acid derivatives with the formula I or II or III. Also described here are preparation of imidazopyridine thioglycolic acid derivatives, pharmaceutical compositions comprising these compounds as therapy and prevention for gout.

  本发明涉及咪唑吡啶硫代乙醇酸衍生物、其制备方法和用途。本发明包含式 I 或 II 或 III 的咪唑吡啶硫代乙醇酸衍生物。这里还描述了咪唑吡啶硫代乙醇酸衍生物的制备、包含这些化合物的药物组合物作为痛风的治疗和预防。
• Novel Imidazopyridine Thioglycolic Acid Derivatives as Potent Inhibitors of Human Urate Transporter 1
  申请人：SHANDONG UNIVERSITY

  公开号：US20190225606A1

  公开（公告）日：2019-07-25

  It relates to the imidazopyridine thioglycolic acid derivatives, the preparation, and use thereof. The invention contained imidazopyridine thioglycolic acid derivatives with the formula I or II or III. Also described here are preparation of imidazopyridine thioglycolic acid derivatives, pharmaceutical compositions comprising these compounds as therapy and prevention for gout.
• Novel Human Urate Transporter 1 Inhibitors as Hypouricemic Drug Candidates with Favorable Druggability
  作者：Tong Zhao、Qing Meng、Zhuosen Sun、Yanyu Chen、Wei Ai、Zean Zhao、Dongwei Kang、Yue Dong、Ruipeng Liang、Ting Wu、Jianxin Pang、Xinyong Liu、Peng Zhan

  DOI：10.1021/acs.jmedchem.0c00223

  日期：2020.10.8

  Lesinurad, a human urate transporter 1 (URAT1) inhibitor approved as a medication for the treatment of hyperuricemia associated with gout in 2015, can cause liver and renal toxicity. Here, we modified all three structural components of lesinurad by applying scaffold hopping, bioisosterism, and substituent-decorating strategies. In a mouse model of acute hyperuricemia, 21 of the synthesized compounds showed increased serum uric acid (SUA)-reducing activity; SUA was about 4-fold lower in animals treated with 44, 54, and 83 compared with lesinurad or benzbromarone. In the URAT1 inhibition assay, 44 was over 8-fold more potent than lesinurad (IC50: 1.57 mu M vs 13.21 mu M). Notably, 83 also displayed potent inhibitory activity (IC50 = 31.73 mu M) against GLUT9. Furthermore, we also preliminarily explored the effect of chirality on the potency of the promising derivatives 44 and 54. Compounds 44, 54, and 83 showed favorable drug-like pharmacokinetics and appear to be promising candidates for the treatment of hyperuricemia and gout.