2-苄硫基-4,6-二氨基嘧啶 | 84890-62-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2-苄硫基-4,6-二氨基嘧啶
• 英文名称: 2-(benzylthio)pyrimidine-4,6-diamine
• 英文别名: 2-(Benzylthio)-4,6-pyrimidinediamine；2-benzylsulfanylpyrimidine-4,6-diamine
• CAS: 84890-62-0
• 化学式: C₁₁H₁₂N₄S
• mdl: MFCD00449213
• 分子量: 232.309
• InChiKey: DAZJCNWHHPUGCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 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：
  103
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-苄硫基-4,6-二氨基嘧啶 在 platinum(IV) oxide 、 氢气 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.5h， 生成 2-(benzylthio)pyrimidine-4,5,6-triamine
  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：

  溴甲苯 、 4,6-二氨基-2-巰基嘧啶 在 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-苄硫基-4,6-二氨基嘧啶
  参考文献：
  名称：

  Exploring 8-benzyl pteridine-6,7-diones as inhibitors of glutamate racemase (MurI) in Gram-positive bacteria

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.10.022

文献信息

• Disperse azopyrimidine dyestuffs
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0065811A1

  公开（公告）日：1982-12-01

  Disperse azo pyrimidine dyes of the formula: wherein A is the residue of a diazo component from a number of defined classes; R' and R4 are each independently hydrogen, optionally substituted alkyl, optionally substituted aralkyl or optionally substituted aryl, and R is optionally substituted alkyl, optionally substituted aralkyl or optionally substituted aryl. Provides valuable dyes for colouring aromatic polyesters.

  分散型偶氮嘧啶染料，其式如下：其中 A 是若干定义类别中重氮组分的残基；R'和 R4 各自独立地是氢、任选取代的烷基、任选取代的芳基或任选取代的芳基，R 是任选取代的烷基、任选取代的芳基或任选取代的芳基。 提供用于芳香族聚酯着色的有价值染料。
• 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.
• Investigations into the Origin of the Molecular Recognition of Several Adenosine Deaminase Inhibitors
  作者：Irina Gillerman、Bilha Fischer

  DOI：10.1021/jm101286g

  日期：2011.1.13

  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