6-氨基-5-(硝基)-1-甲基嘧啶-2,4(1h,3h)-二酮 | 50996-12-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 6-氨基-5-(硝基)-1-甲基嘧啶-2,4(1h,3h)-二酮
• 英文名称: 6-amino-1-methyl-5-nitro-1H-pyrimidine-2,4-dione
• 英文别名: 6-amino-1-methyl-5-nitro-1H-pyrimidine-2,4-dione；4-Amino-3-methyl-5-nitrouracil；6-amino-5-(nitro)-1-methylpyrimidine-2,4(1H,3H)-dione；6-amino-1-methyl-5-nitropyrimidine-2,4-dione
• CAS: 50996-12-8
• 化学式: C₅H₆N₄O₄
• 分子量: 186.127
• InChiKey: MIWHTOMZYBTGCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  6-氨基-5-(硝基)-1-甲基嘧啶-2,4(1h,3h)-二酮 在 ammonium hydroxide 、 sodium dithionite 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 5,6-二氨基-1-甲基尿嘧啶
  参考文献：
  名称：

  Synthesis and lipid-lowering evaluation of 3-methyl-1H-purine-2,6-dione derivatives as potent and orally available anti-obesity agents

  摘要：

  Obesity accompanied with metabolic disorder is often complicated with a strong link of dyslipidemia and insulin resistance, whose indicator is the excess accumulation of triglycerides (TG) in cells. Consideration the idea of lipid-lowering and improving insulin resistance, 34 novel compounds by combination the xanthine scaffold with the chain of Rosiglitazone have been synthesized. Among them, several compounds showed efficiency on reducing TG in 3T3-L1 adipoctyes, and 11c exhibited the most optimal capacity in lipid-lowering and improving obese clinical symptoms in DIO mice. Furthermore, the hydrochloride of 11c (11c center dot HCl) showed excellent bioavailability, 58.94%, over 2 folds than that (28.03%) of 11c, and the anti-obesity effect of 11c center dot HCl at 50 mg/kg dose was better than that of Metjormin at 150 mg/kg dose in DIO mice, almost reversed HFD to a normal level. Thus, 11c center dot HCl might be a potent and orally available anti-obesity agent via alleviating the obese clinical symptoms, body fat, improving serum parameters and insulin resistance and TG clearance in liver. (c) 2014 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2014.09.094
• 作为产物：
  描述：

  6-氨基-1-甲基尿嘧啶 在 溶剂黄146 、 sodium nitrite 作用下， 反应 5.0h， 生成 6-氨基-5-(硝基)-1-甲基嘧啶-2,4(1h,3h)-二酮
  参考文献：
  名称：

  Synthesis and lipid-lowering evaluation of 3-methyl-1H-purine-2,6-dione derivatives as potent and orally available anti-obesity agents

  摘要：

  Obesity accompanied with metabolic disorder is often complicated with a strong link of dyslipidemia and insulin resistance, whose indicator is the excess accumulation of triglycerides (TG) in cells. Consideration the idea of lipid-lowering and improving insulin resistance, 34 novel compounds by combination the xanthine scaffold with the chain of Rosiglitazone have been synthesized. Among them, several compounds showed efficiency on reducing TG in 3T3-L1 adipoctyes, and 11c exhibited the most optimal capacity in lipid-lowering and improving obese clinical symptoms in DIO mice. Furthermore, the hydrochloride of 11c (11c center dot HCl) showed excellent bioavailability, 58.94%, over 2 folds than that (28.03%) of 11c, and the anti-obesity effect of 11c center dot HCl at 50 mg/kg dose was better than that of Metjormin at 150 mg/kg dose in DIO mice, almost reversed HFD to a normal level. Thus, 11c center dot HCl might be a potent and orally available anti-obesity agent via alleviating the obese clinical symptoms, body fat, improving serum parameters and insulin resistance and TG clearance in liver. (c) 2014 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2014.09.094

文献信息

• Facile Synthesis and NO-Generating Property of 4<i>H</i>-[1,2,5]Oxadiazolo[3,4-<i>d</i>]pyrimidine-5,7-dione 1-Oxides
  作者：Magoichi Sako、Souichi Oda、Seiji Ohara、Kosaku Hirota、Yoshifumi Maki

  DOI：10.1021/jo980732y

  日期：1998.10.1

  4H-[1,2,5]Oxadiazolo[3,4-d]pyrimidine-5,7-dione 1-oxides (2) are conveniently prepared in high yields by the oxidative intramolecular cyclization of 6-amino-5-nitro-1H-pyrimidine-2,4-diones (1) employing iodosylbenzene diacetate as an oxidant in the presence of lithium hydride. The generation of nitric oxide (NO) and NO-related species from 2 occurs in the presence of thiols such as N-acetylcysteamine

  通过6-氨基-5-硝基-的氧化分子内环化，可方便地以高收率制备4H- [1,2,5]氧杂二唑[3,4-d]嘧啶-5,7-二酮1-氧化物（2） 1H-嘧啶-2,4-二酮（1），在氢化锂存在下，使用碘乙酸二苯酯作为氧化剂。在生理条件下，当硫醇（例如N-乙酰半胱胺，半胱氨酸和谷胱甘肽）存在时，会从2中生成一氧化氮（NO）和与NO相关的物种。NO生成的证据来自2与硫醇反应的机械解释和其他化学观察结果。
• ——
  作者：A. A. Yavolovsky、E. I. Ivanov、R. Yu. Ivanova

  DOI：10.1023/a:1017504525260

  日期：——
• Synthesis and lipid-lowering evaluation of 3-methyl-1H-purine-2,6-dione derivatives as potent and orally available anti-obesity agents
  作者：Linhong He、Heying Pei、Liang Ma、Yuzhi Pu、Jinying Chen、Zhuowei Liu、Yan Ran、Lei Lei、Suhong Fu、Minghai Tang、Aihua Peng、Chaofeng Long、Lijuan Chen

  DOI：10.1016/j.ejmech.2014.09.094

  日期：2014.11

  Obesity accompanied with metabolic disorder is often complicated with a strong link of dyslipidemia and insulin resistance, whose indicator is the excess accumulation of triglycerides (TG) in cells. Consideration the idea of lipid-lowering and improving insulin resistance, 34 novel compounds by combination the xanthine scaffold with the chain of Rosiglitazone have been synthesized. Among them, several compounds showed efficiency on reducing TG in 3T3-L1 adipoctyes, and 11c exhibited the most optimal capacity in lipid-lowering and improving obese clinical symptoms in DIO mice. Furthermore, the hydrochloride of 11c (11c center dot HCl) showed excellent bioavailability, 58.94%, over 2 folds than that (28.03%) of 11c, and the anti-obesity effect of 11c center dot HCl at 50 mg/kg dose was better than that of Metjormin at 150 mg/kg dose in DIO mice, almost reversed HFD to a normal level. Thus, 11c center dot HCl might be a potent and orally available anti-obesity agent via alleviating the obese clinical symptoms, body fat, improving serum parameters and insulin resistance and TG clearance in liver. (c) 2014 Published by Elsevier Masson SAS.