2,6-二氨基-5-氯-吡啶-3-羧酸 | 465513-33-1

• 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: 2,6-二氨基-5-氯-吡啶-3-羧酸
• 英文名称: 2,6-diamino-5-chloro-pyridine-3-carboxylic acid
• 英文别名: 2,6-diamino-5-chloronicotinic acid；2,6-Diamino-5-chloronicotinic acid；2,6-diamino-5-chloropyridine-3-carboxylic acid
• CAS: 465513-33-1
• 化学式: C₆H₆ClN₃O₂
• 分子量: 187.586
• InChiKey: PLQMKIQPPSHFPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-(4-((1,1,1-trifluoropropan-2-yl)oxy)phenyl)methanamine 、 2,6-二氨基-5-氯-吡啶-3-羧酸 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 palladium diacetate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 83.0h， 生成 (R)-2,6-diamino-5-(1-(difluoromethyl)-1H-pyrazol-4-yl)-N-(4-((1,1,1-trifluoropropan-2-yl)oxy)benzyl)nicotinamide
  参考文献：
  名称：

  [EN] NOVEL ANTIMALARIAL AGENT CONTAINING HETEROCYCLIC COMPOUND
  [FR] NOUVEL AGENT ANTIPALUDIQUE CONTENANT UN COMPOSÉ HÉTÉROCYCLIQUE

  摘要：

  本文披露了具有抗疟激活作用的二氨基吡啶化合物或其药用盐。

  公开号：

  WO2021149692A1
• 作为产物：
  描述：

  S-烯丙基-N-甲酰基-DL-半胱氨酸 在 ammonium hydroxide 、 sodium hydroxide 、 氯化亚砜 、 mercurous nitrate 、 氨 、 硝酸 、 copper(II) sulfate 作用下， 以 1,4-二氧六环 、 硫酸 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 11.5h， 生成 2,6-二氨基-5-氯-吡啶-3-羧酸
  参考文献：
  名称：

  Synthesis and biological evaluation of aroylguanidines related to amiloride as inhibitors of the human platelet Na+/H+ exchanger

  摘要：

  Pyridine and benzene bioisosteres of amiloride were synthesized and evaluated for their inhibitory Potency against the sodium-hydrogen exchanger (NHE) involved in intracellular pH regulation. The inhibition of NHE was determined by using the platelet swelling assay (PSA) in which the swelling of human platelets was induced by their incubation in an acid buffer (pH 6.7). Additionally, the inhibitory potency of the most active compounds was assessed by measuring the inhibition of the EIPA-sensitive Na-22 (+) uptake (UIA) by human platelets after intracellular acidosis. The results indicated that several benzene derivatives and compounds bearing an carbonylguanidine moiety in the meta position of the pyridine nitrogen were much more potent than amiloride (PSA:IC50 = 43.5 muM, UIA:IC50 = 100.1 muM), but less than EIPA, a pyrazine NHE inhibitor (PSA:IC50=0.08 muM, UIA: IC50 - 0.5 muM). In both biological assays (2-amino-5-bromo-pyridine-3-carbonyl)guanidine (32) was the most active molecule (PSA: IC50 = 0.8 muM, UIA : IC50 = 0.8 muM). Our investigations demonstrated that the replacement of the pyrazine ring of amiloride e by a pyridine ora phenyl ring improved the NHE inhibitory potency (phenyl >pyridine >pyrazine). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00022-6

文献信息

• Synthesis and biological evaluation of aroylguanidines related to amiloride as inhibitors of the human platelet Na+/H+ exchanger
  作者：D Laeckmann

  DOI：10.1016/s0968-0896(02)00022-6

  日期：2002.6

  Pyridine and benzene bioisosteres of amiloride were synthesized and evaluated for their inhibitory Potency against the sodium-hydrogen exchanger (NHE) involved in intracellular pH regulation. The inhibition of NHE was determined by using the platelet swelling assay (PSA) in which the swelling of human platelets was induced by their incubation in an acid buffer (pH 6.7). Additionally, the inhibitory potency of the most active compounds was assessed by measuring the inhibition of the EIPA-sensitive Na-22 (+) uptake (UIA) by human platelets after intracellular acidosis. The results indicated that several benzene derivatives and compounds bearing an carbonylguanidine moiety in the meta position of the pyridine nitrogen were much more potent than amiloride (PSA:IC50 = 43.5 muM, UIA:IC50 = 100.1 muM), but less than EIPA, a pyrazine NHE inhibitor (PSA:IC50=0.08 muM, UIA: IC50 - 0.5 muM). In both biological assays (2-amino-5-bromo-pyridine-3-carbonyl)guanidine (32) was the most active molecule (PSA: IC50 = 0.8 muM, UIA : IC50 = 0.8 muM). Our investigations demonstrated that the replacement of the pyrazine ring of amiloride e by a pyridine ora phenyl ring improved the NHE inhibitory potency (phenyl >pyridine >pyrazine). (C) 2002 Elsevier Science Ltd. All rights reserved.
• [EN] NOVEL ANTIMALARIAL AGENT CONTAINING HETEROCYCLIC COMPOUND<br/>[FR] NOUVEL AGENT ANTIPALUDIQUE CONTENANT UN COMPOSÉ HÉTÉROCYCLIQUE
  申请人：EISAI R&D MAN CO LTD

  公开号：WO2021149692A1

  公开（公告）日：2021-07-29

  Disclosed herein are diaminopyridine compounds or pharmaceutically acceptable salts thereof having antimalarial activation effect.

  本文披露了具有抗疟激活作用的二氨基吡啶化合物或其药用盐。