2-amino-5-phenyl-1,4,5,6-tetrahydropyrimidine hemisulfate | 78534-19-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: 2-amino-5-phenyl-1,4,5,6-tetrahydropyrimidine hemisulfate
• 英文别名: 2-Amino-5-phenyl-1,4,5,6-tetrahydropyrimidine sulfate；5-phenyl-1,4,5,6-tetrahydropyrimidin-2-amine;sulfuric acid
• CAS: 78534-19-7
• 化学式: 2C₁₀H₁₃N₃*H₂O₄S
• 分子量: 448.546
• InChiKey: NWEWJZVPPFQVLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.04
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  133
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 海关编码：
  2933599090

反应信息

• 作为产物：
  描述：

  S-甲基异硫脲硫酸盐 、 2-苯基-1,3-丙烷二胺 以46%的产率得到2-amino-5-phenyl-1,4,5,6-tetrahydropyrimidine hemisulfate
  参考文献：
  名称：

  Synthesis and antidepressant profiles of phenyl-substituted 2-amino- and 2-[(alkoxycarbonyl)amino]-1,4,5,6-tetrahydropyrimidines

  摘要：

  A series of 4(6)- and 5-phenyl-substituted 2-amino- and 2-[(alkoxycarbonyl)amino]-1,4,5,6-tetrahydropyrimidines were prepared and evaluated for central nervous system (CNS) effects in animal models. Several 5-phenyl-substituted compounds possessed potent antidepressant activity and all compounds in this series were devoid of significant activity in any of the other CNS (anticonvulsant, muscle relaxant, and depressant) assays. The most active compound in the in vivo screen for antidepressant activity (reversal of reserpine-induced hypothermia), 2-[(methoxycarbonyl)amino]-5-phenyl-1,4,5,6-tetrahydropyrimidine was considerably more potent than tricyclic antidepressant (TCA) standards. The 2-amino parent compound on the other hand was greater than 100-fold as effective as TCA's in in vitro inhibition of norepinephrine and dopamine uptake.

  DOI：

  10.1021/jm00383a002

文献信息

• 4-Phenyl-and 5-phenyl-1,4,5,6-tetrahydropyrimidine derivatives
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04261995A1

  公开（公告）日：1981-04-14

  Certain 1,4,5,6-tetrahydropyrimidine compounds which are substituted with an amino, amido or carbamate at the 2-position, with an optionally substituted phenyl at the 5-position or at the 4-position when there is no alkyl at the 1-position and optionally a lower alkyl at the 1-position when the phenyl is at the 5-position are useful as CNS agents and as antihypertensives.

  某些在2-位上取代了氨基、酰胺基或氨基甲酸酯，5-位上或在1-位没有烷基时4-位上可选地取代了苯基，以及当苯基在5-位时在1-位可选地取代了低碳烷基的1,4,5,6-四氢嘧啶化合物可用作中枢神经系统药物和降压药。
• 4-Phenyl-and 5-phenyl-1,4,5,6-tetrahydro-pyrimidine derivatives
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04322421A1

  公开（公告）日：1982-03-30

  Certain 1,4,5,6-tetrahydropyrimidine compounds which are substituted with an amino, amido or carbamate at the 2-position, with an optionally substituted phenyl at the 5-position or at the 4-position when there is no alkyl at the 1-position and optionally a lower alkyl at the 1-position when the phenyl is at the 5-position are useful as CNS agents and as antihypertensives.

  特定的1,4,5,6-四氢嘧啶化合物，在2位被氨基，酰胺基或氨基甲酸酯取代，在5位或4位（当1位没有烷基时）被取代的苯基（可选取代）或当苯基在5位时，在1位可选取代为较低的烷基。这些化合物可用作中枢神经系统药物和降压药。
• 4-Phenyl and 5-phenyl-1,4,5,6-tetrahydropyrimidine derivatives, pharmaceutical compositions containing said derivatives, and process for preparing said derivatives
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0024776A1

  公开（公告）日：1981-03-11

  Compounds represented by the formula wherein A is H, where R is alkyl of one through six carbon atoms; X is hydrogen, fluoro, chloro, bromo, iodo, hydroxy, alkoxy of one through four carbon atoms, benzyloxy, alkyl of one through four carbon atoms, alkylthio of one through four carbon atoms, alkylsulfinyl of one through four carbon atoms, alkylsulfonyl of one through four carbon atoms or trifluoromethyl; and Y is hydrogen or is the same as X; and R' is hydrogen or alkyl of one through four carbon atoms; the phenyl substituent carrying the X and Y is at the 4- or 5-position of the tetrahydropyrimidine ring when R' is hydrogen or is at the 5-position when R' is alkyl; and the pharmaceutically acceptable salts thereof. These compounds are pharmaceutically useful for treating depression, anxiety, convulsions, centrally-induced' skeletal muscle spasm and spasticity.

  由式表示的化合物 式中 A 是 H 其中 R 是一至六个碳原子的烷基； X 是氢、氟、氯、溴、碘、羟基、一至四个碳原子的烷氧基、苄氧基、一至四个碳原子的烷基、一至四个碳原子的烷硫基、一至四个碳原子的烷基亚磺酰基、一至四个碳原子的烷基磺酰基或三氟甲基；和 Y 是氢或与 X 相同；以及 R'为氢或一至四个碳原子的烷基；当 R' 为氢时，携带 X 和 Y 的苯基取代基位于四氢嘧啶环的 4 位或 5 位，当 R' 为烷基时，位于 5 位；及其药学上可接受的盐类。 这些化合物可用于治疗抑郁症、焦虑症、抽搐、中枢诱发的骨骼肌痉挛和痉挛。
• Synthesis and antidepressant profiles of phenyl-substituted 2-amino- and 2-[(alkoxycarbonyl)amino]-1,4,5,6-tetrahydropyrimidines
  作者：Klaus Weinhardt、Marshall B. Wallach、Michael Marx

  DOI：10.1021/jm00383a002

  日期：1985.6

  A series of 4(6)- and 5-phenyl-substituted 2-amino- and 2-[(alkoxycarbonyl)amino]-1,4,5,6-tetrahydropyrimidines were prepared and evaluated for central nervous system (CNS) effects in animal models. Several 5-phenyl-substituted compounds possessed potent antidepressant activity and all compounds in this series were devoid of significant activity in any of the other CNS (anticonvulsant, muscle relaxant, and depressant) assays. The most active compound in the in vivo screen for antidepressant activity (reversal of reserpine-induced hypothermia), 2-[(methoxycarbonyl)amino]-5-phenyl-1,4,5,6-tetrahydropyrimidine was considerably more potent than tricyclic antidepressant (TCA) standards. The 2-amino parent compound on the other hand was greater than 100-fold as effective as TCA's in in vitro inhibition of norepinephrine and dopamine uptake.
• US4261995A
  申请人：——

  公开号：US4261995A

  公开（公告）日：1981-04-14