4-氨基-5-硝基-2-吡啶羧酸甲酯 | 850544-21-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4-氨基-5-硝基-2-吡啶羧酸甲酯
• 中文别名: 4-氨基-5-硝基-2-吡啶甲酸甲酯
• 英文名称: methyl 4-amino-5-nitropyridine-2-carboxylate
• CAS: 850544-21-7
• 化学式: C₇H₇N₃O₄
• mdl: MFCD11113383
• 分子量: 197.15
• InChiKey: UNPOGSAFUSHRDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-氨基-5-硝基-2-吡啶羧酸甲酯 在 platinum(IV) oxide 盐酸 、 sodium hydroxide 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.02h， 生成 5-acetylamino-4-aminopicolinic acid
  参考文献：
  名称：

  Synthesis and inhibitory activity of benzoic acid and pyridine derivatives on influenza neuraminidase

  摘要：

  Based upon the activity and X-ray crystallographic studies of tri-substituted benzene derivatives containing carboxylic acid, acetamido and guanidine groups, we investigated the effect of the fourth substituent to fulfill the fourth pocket of neuraminidase enzyme. The groups selected as fourth substituents were hydroxymethyl, hydroxyethyl, oxime and amino. These tetra-substituted benzene derivatives were synthesized and evaluated for neuraminidase inhibitory activity. All these compounds were found to have poorer IC50 values than the tri-substituted compounds. Further, benzene ring was replaced by pyridine ring and di, tri and tetra-substituted pyridine derivatives were synthesized. The activity of the pyridine derivatives was comparable to benzene derivatives. The fourth substituent seems to disturb the binding of the other three substituents, so the activity is reduced as compared to trisubstituted benzene and pyridine derivatives. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.042
• 作为产物：
  描述：

  ammonium 4-amino-5-nitropyridine-2-carboxylate 、 甲醇 在 硫酸 作用下， 反应 96.0h， 以58%的产率得到4-氨基-5-硝基-2-吡啶羧酸甲酯
  参考文献：
  名称：

  Synthesis and inhibitory activity of benzoic acid and pyridine derivatives on influenza neuraminidase

  摘要：

  Based upon the activity and X-ray crystallographic studies of tri-substituted benzene derivatives containing carboxylic acid, acetamido and guanidine groups, we investigated the effect of the fourth substituent to fulfill the fourth pocket of neuraminidase enzyme. The groups selected as fourth substituents were hydroxymethyl, hydroxyethyl, oxime and amino. These tetra-substituted benzene derivatives were synthesized and evaluated for neuraminidase inhibitory activity. All these compounds were found to have poorer IC50 values than the tri-substituted compounds. Further, benzene ring was replaced by pyridine ring and di, tri and tetra-substituted pyridine derivatives were synthesized. The activity of the pyridine derivatives was comparable to benzene derivatives. The fourth substituent seems to disturb the binding of the other three substituents, so the activity is reduced as compared to trisubstituted benzene and pyridine derivatives. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.042

文献信息

• [EN] QUINOXALINES AND AZA-QUINOXALINES AS CRTH2 RECEPTOR MODULATORS<br/>[FR] QUINOXALINES ET AZA-QUINOXALINES COMME MODULATEURS DU RÉCEPTEUR CRTH2
  申请人：MERCK SHARP & DOHME

  公开号：WO2012087861A1

  公开（公告）日：2012-06-28

  The invention provides certain quinoxalines and aza-quinoxalines of the Formula (I), and their pharmaceutically acceptable salts, wherein J1, J2, R1, R2, R3, R22, Ra, Rb, Rc, Rd, X, Y, b, n, and q are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds, and methods of using the compounds for treating diseases or conditions associated with with uncontrolled or inappropriate stimulation of CRTH2 function.

  该发明提供了式（I）中的某些喹喔啉和氮杂喹喔啉，以及它们的药用盐，其中J1、J2、R1、R2、R3、R22、Ra、Rb、Rc、Rd、X、Y、b、n和q如本文所定义。该发明还提供包含这些化合物的药物组合物，以及使用这些化合物治疗与CRTH2功能的不受控制或不适当刺激相关的疾病或症状的方法。
• 3H-Imidazo [4, 5-C] Pyridine- 6 -Carboxamides As Anti-Inflammatory Agents
  申请人：Pfau Roland

  公开号：US20110275656A1

  公开（公告）日：2011-11-10

  There are provided compounds of formula (I), wherein R 1 , R 6 , R 8 , Q 2 , Q 3 , Q 3a , Q 4 , L and A have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful in the treatment of diseases in which inhibition of the activity of a member of the MAPEG family is desired and/or required, and particularly in the treatment of inflammation and/or cancer.

  提供了化合物的公式(I)，其中R1、R6、R8、Q2、Q3、Q3a、Q4、L和A的含义如描述中所示，以及其药学上可接受的盐，这些化合物在治疗需要抑制MAPEG家族成员活性的疾病，特别是在治疗炎症和/或癌症方面非常有用。
• QUINOXALINES AND AZA-QUINOXALINES AS CRTH2 RECEPTOR MODULATORS
  申请人：Boyce Christopher W.

  公开号：US20130303517A1

  公开（公告）日：2013-11-14

  The invention provides certain quinoxalines and aza-quinoxalines of the Formula (I), and their pharmaceutically acceptable salts, wherein J 1 , J 2 , R 1 , R 2 , R 3 , R 22 , R a , R b , R c , R d , X, Y, b, n, and q are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds, and methods of using the compounds for treating diseases or conditions associated with uncontrolled or inappropriate stimulation of CRTH 2 function.

  本发明提供了式（I）的某些喹喔啉和氮杂喹喔啉，以及其药学上可接受的盐，其中J1、J2、R1、R2、R3、R22、Ra、Rb、Rc、Rd、X、Y、b、n和q如本文所定义。本发明还提供了包含这些化合物的制药组合物，并使用这些化合物治疗与CRTH2功能不受控制或不适当刺激相关的疾病或病症的方法。
• 3H-imidazo [4, 5-C] pyridine-6-carboxamides as anti-inflammatory agents
  申请人：Pfau Roland

  公开号：US08598190B2

  公开（公告）日：2013-12-03

  There are provided compounds of formula (I), wherein R1, R6, R8, Q2, Q3, Q3a, Q4, L and A have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful in the treatment of diseases in which inhibition of the activity of a member of the MAPEG family is desired and/or required, and particularly in the treatment of inflammation and/or cancer.

  提供了公式(I)的化合物，其中R1、R6、R8、Q2、Q3、Q3a、Q4、L和A的含义见说明书，并且其药学上可接受的盐，这些化合物在治疗需要抑制MAPEG家族成员活性的疾病中非常有用，特别是在治疗炎症和/或癌症方面。
• 3H-IMIDAZO [4, 5-C]PYRIDINE-6-CARBOXAMIDES AS ANTI -INFLAMMATORY AGENTS
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2361252A1

  公开（公告）日：2011-08-31