N-(naphthalen-1-yl)-3-nitropyridin-2-amine | 78750-64-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(naphthalen-1-yl)-3-nitropyridin-2-amine
• 英文别名: N-(1-Naphthyl)-3-nitro-2-pyridylamine；N-naphthalen-1-yl-3-nitropyridin-2-amine
• CAS: 78750-64-8
• 化学式: C₁₅H₁₁N₃O₂
• 分子量: 265.271
• InChiKey: JTULSYDADUJSQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(naphthalen-1-yl)-3-nitropyridin-2-amine 在 盐酸 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以54%的产率得到N₂-(naphthalen-1-yl)pyridine-2,3-diamine
  参考文献：
  名称：

  抗癌药，VI。一些苯并异α-咔啉的合成及抗肿瘤特性

  摘要：

  通过改进 Graebe-Ullmann 反应合成了一些苯并 - 异 - α - 咔啉，并检测了其抗肿瘤活性。与玫瑰树碱相关的线性四环 5,11-二甲基-5H-吲哚 [2,3-b] 喹啉 13b 对小鼠 P 388 和 L 1210 白血病以及黑色素瘤 B 16 显示出显着的抗肿瘤活性。

  DOI：

  10.1002/ardp.19883210807
• 作为产物：
  描述：

  2-氯-3-硝基吡啶 、 1-萘胺 以66%的产率得到N-(naphthalen-1-yl)-3-nitropyridin-2-amine
  参考文献：
  名称：

  抗癌药，VI。一些苯并异α-咔啉的合成及抗肿瘤特性

  摘要：

  通过改进 Graebe-Ullmann 反应合成了一些苯并 - 异 - α - 咔啉，并检测了其抗肿瘤活性。与玫瑰树碱相关的线性四环 5,11-二甲基-5H-吲哚 [2,3-b] 喹啉 13b 对小鼠 P 388 和 L 1210 白血病以及黑色素瘤 B 16 显示出显着的抗肿瘤活性。

  DOI：

  10.1002/ardp.19883210807

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。
• Heterobicyclic derivatives
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：US20020107251A1

  公开（公告）日：2002-08-08

  Heterobicyclic derivatives of the formula: 1 wherein R 1 is aryl which may have suitable substituent(s), ar(lower)alkyl which may have suitable substituent(s), halo(lower)alkyl, protected carboxy(lower)alkyl, acyl(lower)alkyl, heterocyclic group or heterocyclic(lower)alkyl which may have suitable substituent(s), R 2 is aryl which may have suitable substituent(s) or heterocyclic group, and R 3 is hydrogen, lower alkoxy or arylthio, and a pharmaceutically acceptable salt thereof which are useful as a medicament.

  公式为1的杂环双环衍生物，其中：R1是苯基，可以具有适当的取代基；芳基（较低）烷基，可以具有适当的取代基；卤代（较低）烷基；保护的羧基（较低）烷基；酰基（较低）烷基；杂环基或者可以具有适当的取代基的杂环（较低）烷基；R2是苯基，可以具有适当的取代基或者杂环基；R3是氢、较低烷氧基或者芳基硫醚。它们的药物可接受盐是有用的。
• Pyrido[2,3-a]pyrazine derivatives as PDE-IV and TNF inhibitors
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0920867A1

  公开（公告）日：1999-06-09

  Heterobicyclic derivatives of formula (I) wherein R1 is aryl which may have suitable substituent(s), ar(lower)alkyl which may have suitable substituent(s), halo(lower)alkyl, protected carboxy(lower)alkyl, acyl(lower)alkyl, heterocyclic group or heterocyclic(lower)alkyl which may have suitable substituent(s), R2 is aryl which may have suitable substituent(s) or heterocyclic group, and R3 is hydrogen, lower alkoxy or arylthio, and a pharmaceutically acceptable salt thereof which are useful as PDE IV and TNF inhibitors for the treatment of hepatitis in human beings and animals.

  式(I)的杂双环衍生物 其中 R1 是芳基，可具有合适的取代基；ar(低级)烷基，可具有合适的取代基；卤代(低级)烷基；受保护的羧基(低级)烷基；酰基(低级)烷基；杂环基团或杂环(低级)烷基，可具有合适的取代基、R2 是芳基（可有适当的取代基）或杂环基，R3 是氢、低级烷氧基或芳硫基，及其药学上可接受的盐，可作为 PDE IV 和 TNF 抑制剂用于治疗人类和动物的肝炎。
• 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.
• Fragmentation ofo-nitrodiarylamines on electron impact: Formation of carbazole radical cations
  作者：Ryszard Gawiuecki、Danuta Rasaia、Tomasz Bąk

  DOI：10.1002/oms.1210270110

  日期：1992.1

  AbstractThe HO· fragment eliminated on electron impact (EI) from the molecular ions of o‐nitrodiarylamines contains either the amine or the aryl hydrogen. Moreover, 2‐phenylamino‐3‐nitropyridine loses H· from the phenyl group. As confirmed by collision‐activated dissociation mass‐analysed ion kinetic energy spectra, the fragmentation of such compounds involves the formation of carbazole radical cations. Such a process was not observed for the corresponding o‐aminodiarylamines.