6-amino-1-benzyl-5-(propylamino)pyrimidine-2,4(1H,3H)-dione | 343346-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-amino-1-benzyl-5-(propylamino)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 6-amino-1-benzyl-5-(propylamino)uracil；6-Amino-1-benzyl-5-(propylamino)-1,2,3,4-tetrahydropyrimidine-2,4-dione；6-amino-1-benzyl-5-(propylamino)pyrimidine-2,4-dione
• CAS: 343346-91-8
• 化学式: C₁₄H₁₈N₄O₂
• mdl: MFCD02167430
• 分子量: 274.323
• InChiKey: GNRVAJOIWMSZEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  87.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-amino-1-benzyl-5-(propylamino)pyrimidine-2,4(1H,3H)-dione 、 苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以54%的产率得到N-(6-amino-1-benzyl-2,4-dioxopyrimidin-5-yl)-N-propylbenzenesulfonamide
  参考文献：
  名称：

  Allosteric Competitive Inhibitors of the Glucose-1-phosphate Thymidylyltransferase (RmlA) from Pseudomonas aeruginosa

  摘要：

  Glucose-1-phosphate thymidylyltransferase (RmlA) catalyzes the condensation of glucose-1-phosphate (G1P) with deoxy-thymidine triphosphate (dTTP) to yield dTDP-D-glucose and pyrophosphate. This is the first step in the L-rhamnose biosynthetic pathway. L-Rhamnose is an important component of the cell wall of many microorganisms, including Mycobacterium tuberculosis and Pseudomonas aeruginosa. Here we describe the first nanomolar inhibitors of P. aeruginosa RmlA. These thymine analogues were identified by high-throughput screening and subsequently optimized by a combination of protein crystallography, in silico screening, and synthetic chemistry. Some of the inhibitors show inhibitory activity against M. tuberculosis, The inhibitors do not bind at the active site of RmlA but bind at a second site active site. Despite this, the compounds act as competitive inhibitors of G1P but with high cooperativity. This novel behavior was probed by structural analysis, which suggests that the inhibitors work by preventing RmlA from undergoing the conformational change key to its ordered bi-bi mechanism.

  DOI：

  10.1021/cb300426u
• 作为产物：
  描述：

  正丙胺 、 6-氨基-1-苄基-5-溴尿嘧啶 以 水 为溶剂， 反应 5.0h， 以55%的产率得到6-amino-1-benzyl-5-(propylamino)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  嘌呤。第十六部分

  摘要：

  一系列Ñ取代8- aminoxanthines（= 8-氨基-3,7-（或3,9） -二氢- 1 ħ嘌呤-2,6-二酮）8 - 16和34 - 37，从相应的合成8 nitroxanthines 17 ，30 - 33，和8-（苯偶氮基）黄嘌呤17和18通过催化还原。另一种方法是从6-氨基-5-（氰基氨基）尿嘧啶（= N-（6-氨基-1,2,3,4-四氢-2,4-二氧代嘧啶5-5基）氰胺）23，24，和27通过碱催化环化产生25 – 28。所有8 aminoxanthines 8 - 29和34 - 37被乙酰化为相应的8-（乙酰氨基）黄嘌呤40 - 57，和长时间加热导致8-（二乙酰基）黄嘌呤58和59。几个8 aminoxanthines 8 - 13进行重氮化形成8 diazoxanthines 60 - 64。分离出的62和64与中间体形成的8-重氮黄嘌呤与1,3-二甲基巴比妥酸（=

  DOI：

  10.1002/hlca.201000254