3-氧代-1,3,4,5,6,7-六氢-2H-吲唑-2-羧酰胺 | 210417-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: 3-氧代-1,3,4,5,6,7-六氢-2H-吲唑-2-羧酰胺
• 英文名称: 2-amidino-1,2,4,5,6,7-hexahydro-3H-indazol-3-one
• 英文别名: 3-oxo-1,3,4,5,6,7-hexahydro-2H-indazole-2-carboximidamide；3-oxo-4,5,6,7-tetrahydro-1H-indazole-2-carboximidamide
• CAS: 210417-14-4
• 化学式: C₈H₁₂N₄O
• mdl: MFCD03848521
• 分子量: 180.209
• InChiKey: JSUZAXZCHGYTBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-氧代-1,3,4,5,6,7-六氢-2H-吲唑-2-羧酰胺 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 6-Oxo-2-(3-oxo-1,3,4,5,6,7-hexahydro-indazol-2-yl)-1,6-dihydro-pyrimidine-5-carboxylic acid
  参考文献：
  名称：

  Nonsteroidal antiinflammatory agents - Part 1: Antiinflammatory, analgesic and antipyretic activity of some new 1-(pyrimidin-2-yl)-3-pyrazolin-5-ones and 2-(pyrimidin-2-yl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-ones

  摘要：

  In our reinvestigation of the cyclocondensation reaction of aminoguanidine bicarbonate 1 with 2-acetylbutyrolactone 2 and ethyl cyclohexanone-2-carboxylate 6, we have obtained the respective 1-amidino-3-pyrazolin-5-one derivative 3 and the 2-amidino-1,2,4,5,6,7-hexahydro-3H-indazol-3-one 7. These intermediates were utilized for the synthesis of two novel series of 1-(pyrimidin-2-yl)-3-pyrazolin-5-ones and 2-(pyrimidin-2-yl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-ones. Selected analogs from both series (15 compounds) were evaluated for their antiinflammatory activity in an acute and subacute model of inflammation. The analgesic and antipyretic activity of the target compounds were also evaluated. A structure-activity relationship (SAR) comparative study indicated that some compounds from both series exhibited excellent antiinflammatory activity, together with good analgesic and antipyretic activity and were found to be more potent than the reference drugs at a dose of 50 mg/kg, po. In consideration of the efficacy of the compounds in these assays, the 5-phenyl derivative 18 from the 1-(pyrimidin-2-yl)pyrazolinone series, the 5-butyl and 5-phenyl derivatives 26, 27 from the 2-(pyrimidin-2-yl)indazolone series were further studied at graded doses for their acute toxicity (ALD(50)) and ulcerogenic activity and were shown to have a large safety margin (ALD(50) > 4.0 g/kg, po) and devoid of ulcerogenic potentialities when administered orally at a dose of 300 mg/kg. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80002-0
• 作为产物：
  描述：

  氨基胍碳酸氢盐 、 2-环己酮甲酸乙酯 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 以41.6%的产率得到3-氧代-1,3,4,5,6,7-六氢-2H-吲唑-2-羧酰胺
  参考文献：
  名称：

  Nonsteroidal antiinflammatory agents - Part 1: Antiinflammatory, analgesic and antipyretic activity of some new 1-(pyrimidin-2-yl)-3-pyrazolin-5-ones and 2-(pyrimidin-2-yl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-ones

  摘要：

  In our reinvestigation of the cyclocondensation reaction of aminoguanidine bicarbonate 1 with 2-acetylbutyrolactone 2 and ethyl cyclohexanone-2-carboxylate 6, we have obtained the respective 1-amidino-3-pyrazolin-5-one derivative 3 and the 2-amidino-1,2,4,5,6,7-hexahydro-3H-indazol-3-one 7. These intermediates were utilized for the synthesis of two novel series of 1-(pyrimidin-2-yl)-3-pyrazolin-5-ones and 2-(pyrimidin-2-yl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-ones. Selected analogs from both series (15 compounds) were evaluated for their antiinflammatory activity in an acute and subacute model of inflammation. The analgesic and antipyretic activity of the target compounds were also evaluated. A structure-activity relationship (SAR) comparative study indicated that some compounds from both series exhibited excellent antiinflammatory activity, together with good analgesic and antipyretic activity and were found to be more potent than the reference drugs at a dose of 50 mg/kg, po. In consideration of the efficacy of the compounds in these assays, the 5-phenyl derivative 18 from the 1-(pyrimidin-2-yl)pyrazolinone series, the 5-butyl and 5-phenyl derivatives 26, 27 from the 2-(pyrimidin-2-yl)indazolone series were further studied at graded doses for their acute toxicity (ALD(50)) and ulcerogenic activity and were shown to have a large safety margin (ALD(50) > 4.0 g/kg, po) and devoid of ulcerogenic potentialities when administered orally at a dose of 300 mg/kg. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80002-0

文献信息

• Nonsteroidal antiinflammatory agents—part 2 antiinflammatory, analgesic and antipyretic activity of some substituted 3-pyrazolin-5-ones and 1,2,4,5,6,7-3H-hexahydroindazol-3-ones
  作者：Soad A.M. El-Hawash、El-Sayed A.M. Badawey、Ibrahim M. El-Ashmawey

  DOI：10.1016/j.ejmech.2005.09.006

  日期：2006.2

  2-(pyrimidin-2-yl)hexahydroindazol-3-ones and as a result of the interesting antiinflammatory, analgesic and antipyretic activities recorded for some of these compounds, some new 3-pyrazolin-5-ones and hexahydroindazol-3-ones linked to substituted imidazolyl, pyrimidyl and tetrahydroquinazolinyl moieties were prepared and evaluated for such activity (). A structure-activity relationship (SAR) comparative study indicated

  作为合成许多取代的1-（嘧啶-2-基）-3-吡唑啉-5-酮和2-（嘧啶-2-基）六氢吲唑-3-酮的研究项目的一部分，这些化合物中一些有趣的消炎，止痛和解热活性的结果，制备了一些与取代的咪唑基，嘧啶基和四氢喹唑啉基连接的新的3-吡唑啉-5-酮和六氢吲唑-3-酮，并对其活性进行了评估（） 。结构-活性关系（SAR）比较研究表明，3-吡唑啉-5-酮（2，6-8，10）和吲唑酮（18，20，24，27，29）系列的某些化合物表现出明显的抗炎，镇痛作用和消炎痛相关的解热活性。发现这些化合物中的大多数在抗炎筛选中几乎是等价的（ED（50）= 16.8-19）。9毫克/千克），而铅化合物2-吲唑基-4-嘧啶乙酸24（）被发现是该系列中最有效的化合物（ED（50）= 9.9毫克/千克）。此外，当以300 mg / kg的剂量口服时，活性最高的化合物显示出较大的安全系数（ALD（50）= 3.0 g / kg，po），并且没有致溃疡的潜力。
• Nonsteroidal antiinflammatory agents - Part 1: Antiinflammatory, analgesic and antipyretic activity of some new 1-(pyrimidin-2-yl)-3-pyrazolin-5-ones and 2-(pyrimidin-2-yl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-ones
  作者：El-Sayed A.M. Badawey、Ibrahim M. El-Ashmawey

  DOI：10.1016/s0223-5234(98)80002-0

  日期：1998.6

  In our reinvestigation of the cyclocondensation reaction of aminoguanidine bicarbonate 1 with 2-acetylbutyrolactone 2 and ethyl cyclohexanone-2-carboxylate 6, we have obtained the respective 1-amidino-3-pyrazolin-5-one derivative 3 and the 2-amidino-1,2,4,5,6,7-hexahydro-3H-indazol-3-one 7. These intermediates were utilized for the synthesis of two novel series of 1-(pyrimidin-2-yl)-3-pyrazolin-5-ones and 2-(pyrimidin-2-yl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-ones. Selected analogs from both series (15 compounds) were evaluated for their antiinflammatory activity in an acute and subacute model of inflammation. The analgesic and antipyretic activity of the target compounds were also evaluated. A structure-activity relationship (SAR) comparative study indicated that some compounds from both series exhibited excellent antiinflammatory activity, together with good analgesic and antipyretic activity and were found to be more potent than the reference drugs at a dose of 50 mg/kg, po. In consideration of the efficacy of the compounds in these assays, the 5-phenyl derivative 18 from the 1-(pyrimidin-2-yl)pyrazolinone series, the 5-butyl and 5-phenyl derivatives 26, 27 from the 2-(pyrimidin-2-yl)indazolone series were further studied at graded doses for their acute toxicity (ALD(50)) and ulcerogenic activity and were shown to have a large safety margin (ALD(50) > 4.0 g/kg, po) and devoid of ulcerogenic potentialities when administered orally at a dose of 300 mg/kg. (C) Elsevier, Paris.