2,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)-6-methyl-pyrimidine | 28831-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)-6-methyl-pyrimidine
• 英文别名: 2,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)-6-methylpyrimidine；2,4-bis-(3,5-dimethyl-pyrazol-1-yl)-6-methyl-pyrimidine；2,4-Di-(3',5'-dimethyl-pyrazol)-6-methyl-pyrimidin；2,4-Bis(3,5-dimethylpyrazol-1-yl)-6-methylpyrimidine
• CAS: 28831-59-6
• 化学式: C₁₅H₁₈N₆
• 分子量: 282.348
• InChiKey: SFFXSVQMOKZZGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  iron(II) chloride tetrahydrate 、 2,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)-6-methyl-pyrimidine 以 乙醇 为溶剂， 以82%的产率得到dichlorido(2,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)-6-methyl-pyrimidine)iron(II) hemihydrate
  参考文献：
  名称：

  Spin crossover complex [](ClO4)2·H2O (L1 = 4-methyl-2,6-bis(1H-pyrazol-1-yl)pyrimidine): Synthesis and properties

  摘要：

  The complex [FeL21](ClO4)(2)center dot H2O (1a) (L-1 = 4-methyl-2,6-bis(1H-pyrazol-1-yl)pyrimidine) was synthesized by the reaction of Fe(ClO4)(2)center dot 6H(2)O with new NNN-tridentate pyrazolylpyrimidine ligand L-1 in MeOH/EtOH mixture. It is the first example of iron(II) spin crossover complexes with 2,4(6)-di(1H-pyrazol-1-yl)pyrimidines and manifests gradual spin transition centered around 150 K on the chi T-M versus T curve without hysteresis. A broad heat capacity anomaly with the maximum at 150 K was observed on the C-p(T) dependence, Delta H-trs = 5.50 kJ/mol and Delta S-trs = 42.0 J/(mol K). Surprisingly, the syntheses of iron(II) perchlorate compound with L-1 performed in EtOH and iPrOH afford another modification of the complex, [FeL21](ClO4)(2)center dot H2O (1b), being high spin in the 78-300 K temperature range. The complexes with 2,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)-6-methylpyrimidine (L-2). [FeL22](ClO4)(2)center dot EtOH (2), [FeL22](CF3SO3)(2) (3), [(FeLCl2)-Cl-2] 0.5H(2)O (9) and [FeL2(NCS)(2)] (5) were synthesized in EtOH solutions. They are in the high spin state within 78-300 K temperature range. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.05.039

文献信息

• Pyrazolyl-Pyrimidines as Potassium Channel Modulating Agents and Their Medical Use
  申请人：Eriksen Birgitte L.

  公开号：US20090036475A1

  公开（公告）日：2009-02-05

  This invention relates to novel potassium channel modulating agents, and their use in the preparation of pharmaceutical compositions. Moreover the invention is directed to pharmaceutical compositions useful for the treatment or alleviation of diseases or disorders associated with the activity of potassium channels, in particular respiratory diseases, epilepsy, convulsions, vascular spasms, coronary artery spasms, renal disorders, polycystic kidney disease, bladder spasms, urinary incontinence, bladder outflow obstruction, irritable bowel syndrome, gastrointestinal dysfunction, secretory diarrhoea, ischaemia, cerebral ischaemia, ischaemic heart disease, angina pectoris, coronary heart disease, traumatic brain injury, psychosis, schizophrenia, anxiety, depression, dementia, memory and attention deficits, Alzheimer's disease, dysmenorrhea, narcolepsy, Reynaud's disease, intermittent claudication, Sjorgren's syndrome, migraine, arrhythmia, hypertension, absence seizures, myotonic muscle dystrophia, xerostomi, diabetes type II, hyperinsulinemia, premature labour, baldness, cancer, immune suppression or pain.

  这项发明涉及新型钾通道调节剂，以及它们在制备药物组合物中的应用。此外，该发明针对用于治疗或缓解与钾通道活性相关的疾病或障碍的药物组合物，特别是呼吸道疾病、癫痫、抽搐、血管痉挛、冠状动脉痉挛、肾功能紊乱、多囊肾病、膀胱痉挛、尿失禁、膀胱排出道梗阻、肠易激综合征、胃肠功能紊乱、分泌性腹泻、缺血、脑缺血、缺血性心脏病、心绞痛、冠心病、创伤性脑损伤、精神病、精神分裂症、焦虑、抑郁症、痴呆、记忆和注意力缺陷、阿尔茨海默病、痛经、嗜睡症、雷诺氏病、间歇性跛行、干燥综合征、偏头痛、心律失常、高血压、缺席性癫痫发作、肌肉肌无力症、干燥综合症、2型糖尿病、胰岛素高血症、早产、秃头、癌症、免疫抑制或疼痛。
• PYRAZOLYL-PYRIMIDINES AS POTASSIUM CHANNEL MODULATING AGENTS AND THEIR MEDICAL USE
  申请人：NeuroSearch A/S

  公开号：EP1863796A1

  公开（公告）日：2007-12-12
• [EN] PYRAZOLYL-PYRIMIDINES AS POTASSIUM CHANNEL MODULATING AGENTS AND THEIR MEDICAL USE<br/>[FR] PYRAZOLYL-PYRIMIDINES COMME AGENTS DE MODULATION DE LA VOIE DU POTASSIUM ET LEUR UTILISATION MEDICALE
  申请人：NEUROSEARCH AS

  公开号：WO2006100212A1

  公开（公告）日：2006-09-28

  [EN] This invention relates to novel potassium channel modulating agents of formul (I) with the definitions of R1-R4, X, Y and n according to claiml, and their use in the preparation of pharmaceutical compositions. Moreover the invention is directed to pharmaceutical compositions useful for the treatment or alleviation of diseases or disorders associated with the activity of potassiu channels, in particular respiratory diseases, epilepsy, convulsions, vascular spasms, coronary artery spasms, renal disorders, polycystic kidney disease, bladder spasms, urinary incontinence, bladder outflow obstruction, irritable bowel syndrome, gastrointestinal dysfunction, secretory diarrhoea, ischaemia, cerebral ischaemia, ischaemic heart disease, angina pectoris, coronary heart disease, traumatic brain injury, psychosis, schizophrenia, anxiety, depression, dementia, memory and attention deficits, Alzheimer's disease, dysmenorrhea, narcolepsy, Reynaud's disease, intermittent claudication, Sjorgren's syndrome, migraine, arrhythmia, hypertension, absence seizures, myotonic muscle dystrophia, xerostomi, diabetes type II, hyperinsulinemia, premature labour, baldness, cancer, immune suppression or pain.
  [FR] Cette invention se rapporte à de nouveaux agents de modulation de la voie du potassium de formule (I) avec les définitions de R1 à R4, X, Y et n en accord avec la revendication I, et leur utilisation dans la préparation de compositions pharmaceutiques. En outre, l'invention porte sur des compositions pharmaceutiques pour le traitement ou l'atténuation de maladies ou de troubles associés avec l'activité des voies du potassium, en particulier les maladies respiratoires, l'épilepsie, les convulsions, les spasmes vasculaires, les spasmes coronaires, les troubles rénaux, la maladie du rein polycystique, les spasmes de la vessie, l'incontinence urinaire, les obstacles sur les voies excrétrices, le syndrome d'irritation à la défécation, le dysfonctionnement gastro-intestinal, la diarrhée sécrétoire, l'ischémie, l'ischémie cérébrale, la cardiopathie ischémique, l'angine de poitrine, la maladie coronarienne, la lésion traumatique du cerveau, la psychose, la schizophrénie, l'anxiété, la dépression, la démence, les troubles de la mémoire et de l'attention, la maladie d'Alzheimer, l'algoménorrhée, la narcolepsie, la maladie de Reynaud, la claudication intermittente, le syndrome de Sjorgren, la migraine, l'arythmie, l'hypertension, les absences, la dystrophie myotonique du muscle, la xérostomie, les diabètes de type II, l'hyperinsulinémie, l'accouchement prématuré, la calvitie, le cancer, l'immuno-suppression ou la douleur.
• Spin crossover complex [](ClO4)2·H2O (L1 = 4-methyl-2,6-bis(1H-pyrazol-1-yl)pyrimidine): Synthesis and properties
  作者：Mark B. Bushuev、Viktor P. Krivopalov、Elena B. Nikolaenkova、Vasiliy A. Daletsky、Gleb A. Berezovskii、Lilia A. Sheludyakova、Vladimir A. Varnek

  DOI：10.1016/j.poly.2012.05.039

  日期：2012.8

  The complex [FeL21](ClO4)(2)center dot H2O (1a) (L-1 = 4-methyl-2,6-bis(1H-pyrazol-1-yl)pyrimidine) was synthesized by the reaction of Fe(ClO4)(2)center dot 6H(2)O with new NNN-tridentate pyrazolylpyrimidine ligand L-1 in MeOH/EtOH mixture. It is the first example of iron(II) spin crossover complexes with 2,4(6)-di(1H-pyrazol-1-yl)pyrimidines and manifests gradual spin transition centered around 150 K on the chi T-M versus T curve without hysteresis. A broad heat capacity anomaly with the maximum at 150 K was observed on the C-p(T) dependence, Delta H-trs = 5.50 kJ/mol and Delta S-trs = 42.0 J/(mol K). Surprisingly, the syntheses of iron(II) perchlorate compound with L-1 performed in EtOH and iPrOH afford another modification of the complex, [FeL21](ClO4)(2)center dot H2O (1b), being high spin in the 78-300 K temperature range. The complexes with 2,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)-6-methylpyrimidine (L-2). [FeL22](ClO4)(2)center dot EtOH (2), [FeL22](CF3SO3)(2) (3), [(FeLCl2)-Cl-2] 0.5H(2)O (9) and [FeL2(NCS)(2)] (5) were synthesized in EtOH solutions. They are in the high spin state within 78-300 K temperature range. (C) 2012 Elsevier Ltd. All rights reserved.