2,4-二氨基-5,6,7,8-四氢蝶啶 | 15891-13-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 中文名称: 2,4-二氨基-5,6,7,8-四氢蝶啶
• 英文名称: 2,4-diamino-5,6,7,8-tetrahydropteridine
• 英文别名: 5,6,7,8-tetrahydro-pteridine-2,4-diamine；5,6,7,8-tetrahydro-pteridine-2,4-diyldiamine；5,6,7,8-Tetrahydro-pteridin-2,4-diyldiamin；2,4-Diamino-5,6,7,8-tetrahydro-pteridin；Pteridine, 2,4-diamino-5,6,7,8-tetrahydro-；5,6,7,8-tetrahydropteridine-2,4-diamine
• CAS: 15891-13-1
• 化学式: C₆H₁₀N₆
• 分子量: 166.186
• InChiKey: WUAKSYDPKFNCMY-UHFFFAOYSA-N

物化性质

• 沸点：
  531.4±60.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  102
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-二氨基-5,6,7,8-四氢蝶啶 在 potassium permanganate 作用下， 生成 蝶啶-2,4-二胺
  参考文献：
  名称：

  Pteridines. XVII. Reactions of 2,4,6,7-Tetrachloropteridine. The Synthesis of 5,6,7,8-Tetrahydropteridine¹

  摘要：

  DOI：

  10.1021/ja01519a046
• 作为产物：
  描述：

  2,4-二氯-5,6,7,8-四氢蝶啶 在 氨 作用下， 生成 2,4-二氨基-5,6,7,8-四氢蝶啶
  参考文献：
  名称：

  Pteridines. XVII. Reactions of 2,4,6,7-Tetrachloropteridine. The Synthesis of 5,6,7,8-Tetrahydropteridine¹

  摘要：

  DOI：

  10.1021/ja01519a046

文献信息

• Pteridines. Part C. Structure and nonenzymatic synthesis of aurodrosopterin
  作者：Jeongbin Yim、Sujeong Kim、Gunter Walcher、Wolfgang Pfleiderer

  DOI：10.1002/hlca.19930760516

  日期：1993.8.11

  The nonenzymatic synthesis of aurodrosopterin (5) from 6-acetyl-2-amino-3, 7, 8, 9-tetrahydro-4H-pyrimido-[4,5-b][1,4]diazepin-4-one (3) and 7,8-dihydrolumazine (4) at pH 3 (HCl) was performed. The identity of the synthesized compound with the natural eye pigment isolated from drosophila heads was confirmed by thin-layer chromatography on cellulose and by comparisons of the 1H-NMR and UV/VIS spectra

  aurodrosopterin（的非酶合成5）由6-乙酰基-2-氨基-3-，7，8，9四氢-4- ħ -pyrimido- [4,5- b ] [1,4]二氮杂-4-酮（3）和在pH 3（HCl）下进行7,8-二氢鲁嗪（4）。通过在纤维素上的薄层色谱法以及通过1 H-NMR和UV / VIS光谱的比较，证实了合成的化合物与从果蝇头部分离出的天然眼色素的身份。由3的非酶促合成新蝶呤类红色素也进行了2，4-二氨基-7，8-二氢蝶啶，但不能确定其身份。这种色素被称为氨基drosopterin，在489 nm处有一个吸收峰，与新drosopterin的吸收峰非常接近。
• Inhibition of Neuronal Nitric Oxide Synthase by 4-Amino Pteridine Derivatives:  Structure−Activity Relationship of Antagonists of (6<i>R</i>)-5,6,7,8-Tetrahydrobiopterin Cofactor
  作者：Lothar G. Fröhlich、Peter Kotsonis、Hermann Traub、Shahriyar Taghavi-Moghadam、Najim Al-Masoudi、Heinrich Hofmann、Hartmut Strobel、Hans Matter、Wolfgang Pfleiderer、Harald H. H. W. Schmidt

  DOI：10.1021/jm981129a

  日期：1999.10.1

  The family of nitric oxide synthases (NOS) catalyzes the conversion of L-arginine to L-citrulline and nitric oxide (NO), an important cellular messenger molecule which has been implicated in the pathophysiology of septic shock and inflammatory and neurodegenerative disease states. NOS can be maximally activated by the ubiquitous cofactor, (6R)-5,6,7,8-tetrahydrobiopterin (H(4)Bip), and antagonists of H(4)Bip may be of therapeutic importance to inhibit pathologically high NO formation. The 4-amino substituted analogue of H(4)Bip was reported to be a potent NOS inhibit-or. Therefore, we developed a series of novel 4-amino pteridine derivatives, antipterins, to pharmacologically target the neuronal isoform of nitric oxide synthase (NOS-I). To functionally characterize the pterin/anti-pterin interaction and establish a structure-activity relationship (SAR), we systematically altered the substituents in the 2-, 4-, 5-, 6-, and 7-position of the pteridine nucleus. Varying the substitution pattern in the 2-, 5-, and 7-position resulted in no significant inhibitory effect on enzyme activity. In contrast, bulky substituents in the B-position, such as phenyl, markedly increased the inhibitory potency of the reduced 4-amino-5,6,7,8-tetrahydropteridines, possibly as a consequence of hydrophobic interactions within NOS-I. However, this was not the case for the aromatic 4-amino pteridines. Interestingly, chemical modification of the 4-amino substituent by dialkyl/diaralkylation together with 6-arylation of the aromatic 2,4-diamino pteridine resulted in potent and efficacious inhibitors of NOS-I, suggesting possible hydrophilic and hydrophobic interactions within NOS-I. This SAR agrees with (a) the recently published crystal structure of the oxygenase domain of the inducible NOS isoform (NOS-II) and (b) the comparative molecular field analysis of selected NOS-I inhibitors, which resulted in a 3D-QSAR model of the pterin binding site interactions. Further optimization should be possible when the full length structure of NOS-I becomes available.
• Konrad; Pfleiderer, Chemische Berichte, 1970, vol. 103, p. 722,729
  作者：Konrad、Pfleiderer

  DOI：——

  日期：——
• Pteridines. XVII. Reactions of 2,4,6,7-Tetrachloropteridine. The Synthesis of 5,6,7,8-Tetrahydropteridine¹
  作者：Edward C. Taylor、William R. Sherman

  DOI：10.1021/ja01519a046

  日期：1959.5