4-chloro-5-[4-hydroxy-imidazolidin-2-ylidenimino]-6-methoxy-2-methyl-pyrimidine | 272114-34-8

• 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: 4-chloro-5-[4-hydroxy-imidazolidin-2-ylidenimino]-6-methoxy-2-methyl-pyrimidine
• 英文别名: Hydroxy moxonidine；2-[(4-chloro-6-methoxy-2-methylpyrimidin-5-yl)amino]-4,5-dihydro-1H-imidazol-5-ol
• CAS: 272114-34-8
• 化学式: C₉H₁₂ClN₅O₂
• 分子量: 257.68
• InChiKey: PXMQSXSEMQEDHE-UHFFFAOYSA-N

物化性质

• 沸点：
  420.1±55.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  91.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-chloro-5-[4-hydroxy-imidazolidin-2-ylidenimino]-6-methoxy-2-methyl-pyrimidine 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 0.5h， 以0.43 g的产率得到Dehydrogenated Moxonidine
  参考文献：
  名称：

  Identification, synthesis and pharmacological activity of moxonidine metabolites

  摘要：

  The metabolism of moxonidine, 4-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxy-2-methyl-5-pyrimidinamine, LY326869, in rats, mice, dogs, and humans has been examined. At least 17 metabolites were identified or tentatively identified in the different species by HPLC, LC/MS and LC/MS/MS. The identities of seven of the major metabolites have been verified by independent synthesis. The metabolites are generally derived from oxidation and conjugation pathways. Oxidation occurred at the imidazolidine ring as well as the methyl at the 2 position of the pyrimidine ring. All seven metabolites were examined in the spontaneously hypertensive rats (3 mg kg(-1), i.v.) for pressure and heart rate. Only one, 2-hydroxymethyl-4-chloro-5-(imidazolidin-2-ylidenimino)-6-methoxypyrimidine, exerted a short-lasting decrease in blood pressure, albeit attenuated in magnitude compared to moxonidine. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(01)01293-4
• 作为产物：
  描述：

  2-甲基-4,6-二氯-5-氨基嘧啶 在 盐酸 、 氢氧化钾 、 potassium dihydrogenphosphate 、 lead acetate 作用下， 以 甲醇 、 水 、 丙酮 、 乙腈 为溶剂， 反应 12.67h， 生成 4-chloro-5-[4-hydroxy-imidazolidin-2-ylidenimino]-6-methoxy-2-methyl-pyrimidine
  参考文献：
  名称：

  Identification, synthesis and pharmacological activity of moxonidine metabolites

  摘要：

  The metabolism of moxonidine, 4-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxy-2-methyl-5-pyrimidinamine, LY326869, in rats, mice, dogs, and humans has been examined. At least 17 metabolites were identified or tentatively identified in the different species by HPLC, LC/MS and LC/MS/MS. The identities of seven of the major metabolites have been verified by independent synthesis. The metabolites are generally derived from oxidation and conjugation pathways. Oxidation occurred at the imidazolidine ring as well as the methyl at the 2 position of the pyrimidine ring. All seven metabolites were examined in the spontaneously hypertensive rats (3 mg kg(-1), i.v.) for pressure and heart rate. Only one, 2-hydroxymethyl-4-chloro-5-(imidazolidin-2-ylidenimino)-6-methoxypyrimidine, exerted a short-lasting decrease in blood pressure, albeit attenuated in magnitude compared to moxonidine. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(01)01293-4

文献信息

• VERWENDUNG VON MOXONIDIN ZUR BEHANDLUNG NACH HERZINFARKT
  申请人：Solvay Pharmaceuticals GmbH

  公开号：EP1150680A1

  公开（公告）日：2001-11-07
• [DE] VERWENDUNG VON MOXONIDIN ZUR BEHANDLUNG NACH HERZINFARKT<br/>[EN] USE OF MOXONIDINE FOR POSTMYOCARDIAL INFARCTION TREATMENT<br/>[FR] UTILISATION DE MOXONIDINE POUR LE TRAITEMENT POST-INFARCTUS DU MYOCARDE
  申请人：SOLVAY PHARM GMBH

  公开号：WO2000045820A1

  公开（公告）日：2000-08-10

  Es wird die Verwendung von Moxonidin und dessen physiologisch verträglichen Säureadditionssalzen zur Herstellung von pharmazeutischen Zubereitungen zur Behandlung von Herzinfarkt-bedingten Schädigungen des Myokards beschrieben. Moxonidin und dessen physiologisch verträgliche Säureadditionssalze enthaltende, pharmazeutische Zubereitungen eignen sich hierbei zur Anwendung im Rahmen der akuten Myokardinfarkt-Behandlung und/oder der Postmyokardinfarkt-Behandlung.
• Identification, synthesis and pharmacological activity of moxonidine metabolites
  作者：David D Wirth、Minxia M He、Boris A Czeskis、Karen M Zimmerman、Ulrike Roettig、Wolfgang Stenzel、Mitchell I Steinberg

  DOI：10.1016/s0223-5234(01)01293-4

  日期：2002.1

  The metabolism of moxonidine, 4-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxy-2-methyl-5-pyrimidinamine, LY326869, in rats, mice, dogs, and humans has been examined. At least 17 metabolites were identified or tentatively identified in the different species by HPLC, LC/MS and LC/MS/MS. The identities of seven of the major metabolites have been verified by independent synthesis. The metabolites are generally derived from oxidation and conjugation pathways. Oxidation occurred at the imidazolidine ring as well as the methyl at the 2 position of the pyrimidine ring. All seven metabolites were examined in the spontaneously hypertensive rats (3 mg kg(-1), i.v.) for pressure and heart rate. Only one, 2-hydroxymethyl-4-chloro-5-(imidazolidin-2-ylidenimino)-6-methoxypyrimidine, exerted a short-lasting decrease in blood pressure, albeit attenuated in magnitude compared to moxonidine. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.