5-Nitroso-4,6-diamino-2-benzylmercapto-pyrimidin | 52222-45-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-Nitroso-4,6-diamino-2-benzylmercapto-pyrimidin
• 英文别名: 2-(benzylthio)-5-nitrosopyrimidine-4,6-diamine；2-benzylsulfanyl-5-nitroso-pyrimidine-4,6-diamine；5-nitroso-2-[(phenylmethyl)thio]-4,6-pyrimidinediamine；6-Amino-2-(benzylsulfanyl)-5-nitrosopyrimidin-4-ylamine；2-benzylsulfanyl-5-nitrosopyrimidine-4,6-diamine
• CAS: 52222-45-4
• 化学式: C₁₁H₁₁N₅OS
• 分子量: 261.307
• InChiKey: BAMMZILBCUFCAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-Nitroso-4,6-diamino-2-benzylmercapto-pyrimidin 在 盐酸 、 platinum(IV) oxide 、 氢气 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 5-(benzylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine
  参考文献：
  名称：

  Investigations into the Origin of the Molecular Recognition of Several Adenosine Deaminase Inhibitors

  摘要：

  Inhibitors of adenosine deaminase (ADA, EC 3 5 4 4) are potential therapeutic agents for the treatment of various health disorders Several highly potent inhibitors were previously identified, yet they exhibit unacceptable toxicities We performed a SAR study involving a series of C2 or C8 substituted purine-riboside analogues with a view to discover less potent inhibitors with a lesser toxicity We found that any substitution at C8 position of nebularine resulted in total loss of activity toward calf intestinal ADA However several 2-substituted-adenosine, 8-aza-adenosine, and nebularine analogues exhibited inhibitory activity Specifically, 2-Cl-purine riboside, 8-aza-2-thiohexyl adenosine, 2-thiohexyl adenosine, and 2-MeS-purine riboside were found to be competitive inhibitors of ADA with K-i values of 25, 22, 6, and 3 mu M, respectively We concluded that electronic parameters are not major recognition determinants of ADA but rather steric parameters A C2 substituent which fits ADA hydrophobic pocket and improves H-bonding with the enzyme makes a good inhibitor In addition, a gg rotamer about C4'-C5' bond is apparently an important recognition determinant

  DOI：

  10.1021/jm101286g
• 作为产物：
  描述：

  2-苄硫基-4,6-二氨基嘧啶 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.5h， 以86%的产率得到5-Nitroso-4,6-diamino-2-benzylmercapto-pyrimidin
  参考文献：
  名称：

  Investigations into the Origin of the Molecular Recognition of Several Adenosine Deaminase Inhibitors

  摘要：

  Inhibitors of adenosine deaminase (ADA, EC 3 5 4 4) are potential therapeutic agents for the treatment of various health disorders Several highly potent inhibitors were previously identified, yet they exhibit unacceptable toxicities We performed a SAR study involving a series of C2 or C8 substituted purine-riboside analogues with a view to discover less potent inhibitors with a lesser toxicity We found that any substitution at C8 position of nebularine resulted in total loss of activity toward calf intestinal ADA However several 2-substituted-adenosine, 8-aza-adenosine, and nebularine analogues exhibited inhibitory activity Specifically, 2-Cl-purine riboside, 8-aza-2-thiohexyl adenosine, 2-thiohexyl adenosine, and 2-MeS-purine riboside were found to be competitive inhibitors of ADA with K-i values of 25, 22, 6, and 3 mu M, respectively We concluded that electronic parameters are not major recognition determinants of ADA but rather steric parameters A C2 substituent which fits ADA hydrophobic pocket and improves H-bonding with the enzyme makes a good inhibitor In addition, a gg rotamer about C4'-C5' bond is apparently an important recognition determinant

  DOI：

  10.1021/jm101286g

文献信息

• Pteridine compounds for the treatment of psoriasis
  申请人：——

  公开号：US20030055250A1

  公开（公告）日：2003-03-20

  The invention provides pteridine compounds of formula (I), processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy. Formula (I) in which A is a group of formula (a) or (b).

  本发明提供了式(I)的蝶啶化合物，制备这些化合物的方法和中间体，含有这些化合物的药物组合物，以及它们在治疗中的用途。式(I)中，A为式(a)或式(b)的基团。
• Exploring 8-benzyl pteridine-6,7-diones as inhibitors of glutamate racemase (MurI) in Gram-positive bacteria
  作者：Gloria A. Breault、Janelle Comita-Prevoir、Charles J. Eyermann、Bolin Geng、Randy Petrichko、Peter Doig、Elise Gorseth、Brian Noonan

  DOI：10.1016/j.bmcl.2008.10.022

  日期：2008.12

  A successful scaffold-hopping approach gave a novel series of inhibitors of bacterial glutamate racemase (MurI). Early SAR studies of the 8-benzyl pteridine-6,7-diones led to compounds with micromolar enzyme potency and antibacterial activity. (C) 2008 Elsevier Ltd. All rights reserved.
• PTERIDINE COMPOUNDS FOR THE TREATMENT OF PSORIASIS
  申请人：AstraZeneca AB

  公开号：EP1259512A1

  公开（公告）日：2002-11-27
• US6875868B2
  申请人：——

  公开号：US6875868B2

  公开（公告）日：2005-04-05
• US7579342B2
  申请人：——

  公开号：US7579342B2

  公开（公告）日：2009-08-25