5-amino-4-<(2-hydroxyethyl)amino>uracil hydrochloride | 17801-78-4

• 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: 5-amino-4-<(2-hydroxyethyl)amino>uracil hydrochloride
• 英文别名: 5-amino-6-(2-hydroxyethylamino)-1H-pyrimidine-2,4-dione;hydrochloride
• CAS: 17801-78-4
• 化学式: C₆H₁₀N₄O₃*ClH
• 分子量: 222.631
• InChiKey: KTRYODAMXAKPHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.53
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  117
• 氢给体数：
  6
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,1,1,4,4,4-六氟-2,3-丁二酮 、 5-amino-4-<(2-hydroxyethyl)amino>uracil hydrochloride 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以44%的产率得到8-(2-hydroxyethyl)-6,7-bis(trifluoromethyl)-7,8-dihydropteridine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Cushman, Mark; Wong, Wai Cheong; Bacher, Adelbert, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1051 - 1054

  摘要：

  DOI：
• 作为产物：
  描述：

  5-nitro-6-((2-hydroxyethyl)amino)uracil 在 sodium dithionite 、 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 2.0h， 以68%的产率得到5-amino-4-<(2-hydroxyethyl)amino>uracil hydrochloride
  参考文献：
  名称：

  Agonistic or antagonistic mucosal-associated invariant T (MAIT) cell activity is determined by the 6-alkylamino substituent on uracil MR1 ligands

  摘要：

  6-烷基氨基尿嘧啶MR1配体的侧链控制MAIT细胞的激动或拮抗活性。

  DOI：

  10.1039/d0cc00247j

文献信息

• The biosynthesis of pteridines. Part VI. Studies of the mechanism of riboflavin biosynthesis
  作者：Thomas Paterson、H. C. S. Wood

  DOI：10.1039/p19720001051

  日期：——

  1 H N.m.r. spectroscopy has been used to study the deuterium exchange of the methyl protons in the lumazine precursor (6,7-dimethyl-8-D-ribitylpteridine-2,4-dione) of riboflavin, and in related compounds. The protons of the 7-methyl group exchange with the solvent, whereas those of the 6-methyl group do not. An explanation which involves a highly delocalized anionic species is suggested.

  1 H Nmr光谱已用于研究核黄素的lumazine前体（6,7-二甲基-8- D -ribitylpteridine-2,4-dione）和相关化合物中甲基质子的氘交换。7-甲基的质子与溶剂交换，而6-甲基的质子不交换。建议一种涉及高度离域的阴离子物质的解释。
• Fluorine-19 NMR studies on the mechanism of riboflavin synthase. Synthesis of 6-(trifluoromethyl)-7-oxo-8-(D-ribityl)lumazine and 6-(trifluoromethyl)-7-methyl-8-(D-ribityl)lumazine
  作者：Mark Cushman、Hemantkumar H. Patel、Johannes Scheuring、Adelbert Bacher

  DOI：10.1021/jo00047a015

  日期：1992.10

  The reactions of hexafluoropropene oxide (19), methyl trifluoropyruvate (21), and 1,1,1-trifluorobutane-2,3-dione (45) with a series of ortho diamines were investigated as an approach to the synthesis of trifluoromethyl-substituted quinoxalinones and lumazines. 6-(Trifluoromethyl)-7-oxo-8-(D-ribityl)lumazine (11) was synthesized by reaction of methyl trifluoropyruvate (21) with 5-amino-6-(D-ribitylamino)-2,4(1H,3H)-pyrimidinedione (3) hydrochloride and utilized as a F-19 NMR probe of the light riboflavin synthase of Bacillus subtilis. The fluorolumazine 11 was found to be an inhibitor of the enzyme with an inhibition constant K(I) = 55 muM. Equilibrium dialysis experiments indicated the binding of six molecules of 11 per enzyme molecule, corresponding to one molecule bound at each of the three donor and three acceptor sites of the enzyme. The apparent dissociation constants K(D) were approximately 4 and 112 muM. The enzyme-bound ligand gave rise to several broad F-19 NMR signals which were shifted to low field. The bound ligand 11 could be displaced from the enzyme by the enzyme product, riboflavin (2), and the product analog, 5-nitroso-6-(ribitylamino)-2,4(1H,3H)-pyrimidinedione (56). 6-(Trifluoromethyl)-7-methyl-8-(D-ribityl)lumazine (13) was synthesized by reaction of the hydrochloride salt of 3 with 1,1,1-trifluorobutane-2,3-dione (45). Three molecules of 13 can be bound relatively tightly per mole of riboflavin synthase, i.e., one ligand molecule per protein subunit. The inhibition constant K(I) was determined to be 75 muM, while dissociation constants of 17 and 70 muM were determined by equilibrium dialysis and F-19 NMR, respectively. The bound ligand 13 could also be displaced by riboflavin and product analog 56. A scheme for the catalytic cycle of riboflavin synthase is proposed.
• Synthesis of trifluoromethylated pyrazine-containing nitrogen heterocycles from trifluoropyruvaldehyde and ortho-diamines: scope and regiochemistry
  作者：Mark Cushman、Hemantkumar Patel、Ann McKenzie

  DOI：10.1021/jo00256a034

  日期：1988.10
• CUSHMAN, MARK;PATEL, HEMANTKUMAR;MCKENZIE, ANN, J. ORG. CHEM., 53,(1988) N 21, C. 5088-5092
  作者：CUSHMAN, MARK、PATEL, HEMANTKUMAR、MCKENZIE, ANN

  DOI：——

  日期：——
• US3946012A
  申请人：——

  公开号：US3946012A

  公开（公告）日：1976-03-23