4-(6-hydrazino-pyridazin-3-yl)-thiomorpholine | 56420-25-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(6-hydrazino-pyridazin-3-yl)-thiomorpholine
• 英文别名: (6-Thiomorpholin-4-ylpyridazin-3-yl)hydrazine
• CAS: 56420-25-8
• 化学式: C₈H₁₃N₅S
• 分子量: 211.291
• InChiKey: HINFMRUYPYAZDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  92.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(6-hydrazino-pyridazin-3-yl)-thiomorpholine 、 2,5-己二酮 以 溶剂黄146 为溶剂， 反应 3.0h， 以50%的产率得到N-(2,5-Dimethyl-1H-pyrrol-1-yl)-6-(4-thiomorpholinyl)-3-pyridazineamine
  参考文献：
  名称：

  Antihypertensives. N-1H-Pyrrol-1-yl-3-pyridazinamines

  摘要：

  The hypothesis that the side effects of hydralazine, such as mutagenicity and lupus erythematosus like syndrome, might be due to the NHNH2 group prompted us to incorporate part of this moiety into a pyrrole ring. Therefore, we prepared a series of N-1H-pyrrol-1-yl-3-pyridazinamines and a limited number of N-1H-pyrrol-1-yl-1-phthalazinamines by reaction of 3-hydrazinopyridazines and 1-hydrazinophthalazines with gamma-diketones. Most of these compounds, especially in the pyridazine series, showed moderate to strong antihypertensive activity in spontaneously hypertensive rats. The decrease in blood pressure generally had a slow onset after either oral or intravenous administration. N-(2,5-Dimethyl-1H-pyrrol-1-yl)-6-(4-morpholinyl)-3-pyridazinamine hydrochloride (30) (MDL 899) showed no mutagenic activity in several tests and is now in clinical trials in patients.

  DOI：

  10.1021/jm00374a024
• 作为产物：
  描述：

  4-(6-氯哒嗪-3-基)硫代吗啉 在 一水合肼 作用下， 反应 4.0h， 生成 4-(6-hydrazino-pyridazin-3-yl)-thiomorpholine
  参考文献：
  名称：

  Synthesis and antihypertensive properties of new 3-hydrazinopyridazine derivatives

  摘要：

  3-Hydrazinopyridazines substituted in position 6 with a primary amine, secondary amine, or an alkoxy group were synthesized and screened for antihypertensive activity. In general, the 6-dialklamino derivatives are the most active; the (2-hydroxypropyl)methylamino chain provides the best combination of high antihypertensive activity and toxicity.

  DOI：

  10.1021/jm00241a020

文献信息

• PIFFERI G.; PARRAVICINI F.; CARPI C.; DORIGOTTI L., J. MED. CHEM. <JMCM-AR>, 1975, 18, NO 7, 741-746
  作者：PIFFERI G.、 PARRAVICINI F.、 CARPI C.、 DORIGOTTI L.

  DOI：——

  日期：——
• Antihypertensives. N-1H-Pyrrol-1-yl-3-pyridazinamines
  作者：Elvio Bellasio、Ambrogio Campi、Nunzio Di Mola、Emiliana Baldoli

  DOI：10.1021/jm00374a024

  日期：1984.8

  The hypothesis that the side effects of hydralazine, such as mutagenicity and lupus erythematosus like syndrome, might be due to the NHNH2 group prompted us to incorporate part of this moiety into a pyrrole ring. Therefore, we prepared a series of N-1H-pyrrol-1-yl-3-pyridazinamines and a limited number of N-1H-pyrrol-1-yl-1-phthalazinamines by reaction of 3-hydrazinopyridazines and 1-hydrazinophthalazines with gamma-diketones. Most of these compounds, especially in the pyridazine series, showed moderate to strong antihypertensive activity in spontaneously hypertensive rats. The decrease in blood pressure generally had a slow onset after either oral or intravenous administration. N-(2,5-Dimethyl-1H-pyrrol-1-yl)-6-(4-morpholinyl)-3-pyridazinamine hydrochloride (30) (MDL 899) showed no mutagenic activity in several tests and is now in clinical trials in patients.
• Synthesis and antihypertensive properties of new 3-hydrazinopyridazine derivatives
  作者：Giorgio Pifferi、Francesco Parravicini、Carlo Carpi、Luciano Dorigotti

  DOI：10.1021/jm00241a020

  日期：1975.7

  3-Hydrazinopyridazines substituted in position 6 with a primary amine, secondary amine, or an alkoxy group were synthesized and screened for antihypertensive activity. In general, the 6-dialklamino derivatives are the most active; the (2-hydroxypropyl)methylamino chain provides the best combination of high antihypertensive activity and toxicity.