5-亚硝基-2-苯基嘧啶-4,6-二胺 | 56472-04-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-亚硝基-2-苯基嘧啶-4,6-二胺
• 英文名称: 4,6-diamino-5-nitroso-2-phenylpyrimidine
• 英文别名: 4,6-Diamino-5-nitroso-2-phenylpyrimidin；5-nitroso-2-phenyl-pyrimidine-4,6-diamine；5-nitroso-2-phenyl-pyrimidine-4,6-diyldiamine；5-Nitroso-2-phenyl-pyrimidin-4,6-diyldiamin；2-phenyl-4, 6-diamino-5-nitrosopyrimidine；2-Phenyl-4,6-diamino-5-nitroso-pyrimidin；5-Nitroso-2-phenyl-4,6-pyrimidinediamine；5-nitroso-2-phenylpyrimidine-4,6-diamine
• CAS: 56472-04-9
• 化学式: C₁₀H₉N₅O
• 分子量: 215.214
• InChiKey: BECPHSCHRNDJSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  5-亚硝基-2-苯基嘧啶-4,6-二胺 在 吡啶 、 lead(IV) acetate 作用下， 生成 N-(5-phenyl-[1,2,5]oxadiazolo[3,4-d]pyrimidin-7-yl)-acetamide
  参考文献：
  名称：

  Reduction of the amidine C=N bond of 7-aminofurazano(3,4-d)-pyrimidines with sodium borohydride.

  摘要：

  用硼氢化钠还原了 5-苯基-7-取代氨基呋喃并(3, 4-d)嘧啶。与氨基、烷基氨基和对甲苯磺酰胺衍生物形成鲜明对比的是，C7-氨基上乙酰基的存在导致脒的 C=N 键顺利还原，生成 7-乙酰胺基-6，7-二氢衍生物。苯甲酰基的存在导致 6，7-二氢衍生物的形成，同时失去苯甲酰胺。同样，还原 5-苯基-7-乙硫基呋喃并(3，4-d)嘧啶可得到 6，7-二氢衍生物。

  DOI：

  10.1248/cpb.24.235
• 作为产物：
  描述：

  isonitrosomalononitrile benzamidine salt 在 碳酸甲丙酯 作用下， 反应 3.0h， 以95%的产率得到5-亚硝基-2-苯基嘧啶-4,6-二胺
  参考文献：
  名称：

  核苷部分 LXVI I[1]：4-氨基-7(8H)蝶啶酮-N8-核苷的合成——腺苷的结构类似物

  摘要：

  各种 4-氨基-7(8H) 蝶啶酮 (6, 12, 14, 15, 20, 22) 已被 1-氯-2'-脱氧-D-呋喃核糖衍生物 (25, 26) 糖基化，应用新的 DBU-盐法形成 N8-2'-脱氧-D-呋喃核糖苷 (27-36)，可视为 2'-脱氧腺苷类似物。2-N,N-二甲基-氨基-亚甲基亚氨基-7（8H）蝶啶酮（43-48）类似地反应，优先得到相应的 N8-β-D-端基异构体（49-55）。1-溴-2,3,5-三-O-苯甲酰基-aD-呋喃核糖 (56) 的核糖基化也与 6、12、15、45 和 46 一起进行，得到 N8-β-D-呋喃核糖苷 57– 61. 糖脱保护分别导致游离的 N8-2'-deoxy-ß-D-ribofuranosides 37-42 和 N8-ß-D-ribofurano-sides 62-65。在 Vorbrüggen 条件下通过甲硅烷基方法进行的糖基化与 6、12

  DOI：

  10.1080/15257770903054241

文献信息

• Synthesis of New 2-Phenyladenines and 2-Phenylpteridines and Biological Evaluation as Adenosine Receptor Ligands
  作者：Irene Giorgi、Giuliana Biagi、Oreste Livi、Michele Leonardi、Valerio Scartoni、Daniele Pietra

  DOI：10.1002/ardp.200600168

  日期：2007.2

  maintain high activity towards adenosine receptors; in fact, pteridine derivatives did not show themselves to be good adenosine receptor ligands. On the contrary, N6‐cycloalkyl‐ or N6‐alkyl‐2‐phenyladenines showed a very high affinity and selectivity for A1 adenosine receptors. We demonstrate also that the 9‐benzyl substituent is crucial for conferring high affinity for A3 receptors to molecules having a

  描述了一系列 2-苯基蝶啶衍生物的合成和生物测定，以将它们对腺苷受体的亲和力与特意制备的相应腺嘌呤和先前描述的 8-氮杂腺嘌呤的亲和力进行比较。这项研究表明，腺嘌呤核的五元环扩大为六元环是一种修饰，不允许分子保持对腺苷受体的高活性；事实上，蝶啶衍生物本身并不是良好的腺苷受体配体。相反，N6-环烷基-或N6-烷基-2-苯基腺嘌呤对A1腺苷受体表现出非常高的亲和力和选择性。我们还证明了 9-苄基取代基对于将 A3 受体的高亲和力赋予具有 2-苯腺嘌呤样核的分子至关重要。
• Pteridinecarboxamide Diuretics. II. Reaction of 4,6-Diamino-5-nitrosopyrimidines with N-Substituted Cyanoacetamides
  作者：T. S. Osdene、Arthur A. Santilli、Lee E. McCardle、Marvin E. Rosenthale

  DOI：10.1021/jm00314a008

  日期：1967.3
• Harris, Roger; Pfleiderer, Wolfgang, Liebigs Annalen der Chemie, 1981, # 8, p. 1457 - 1468
  作者：Harris, Roger、Pfleiderer, Wolfgang

  DOI：——

  日期：——
• 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.
• Pteridinecarboxamide Diuretics. I. Reaction of 4,6-Diamino-5-nitrosopyrimidines with Substituted Malonamides¹
  作者：T. S. Osdene、Arthur A. Santilli、Lee E. McCardle、Marvin E. Rosenthale

  DOI：10.1021/jm00323a013

  日期：1966.9