sulfuric acid mono-(2,4-diamino-pyrimidin-5-yl ester) | 99171-27-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: sulfuric acid mono-(2,4-diamino-pyrimidin-5-yl ester)
• 英文别名: Schwefelsaeure-mono-(2,4-diamino-pyrimidin-5-ylester)；2,4-diamino-5-pyrimidinyl hydrogen sulfate；(2,4-diaminopyrimidin-5-yl) sulfate;hydron
• CAS: 99171-27-4
• 化学式: C₄H₆N₄O₄S
• 分子量: 206.182
• InChiKey: RGYVDOAMWQKART-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  sulfuric acid mono-(2,4-diamino-pyrimidin-5-yl ester) 在 硫酸 作用下， 以 水 为溶剂， 生成 2,4-diamino-5-hydroxy-pyrimidine hydrosulfate salt
  参考文献：
  名称：

  Insecticidal 5-substituted-2,4-diaminopyrimidine derivatives

  摘要：

  一种杀虫组合物，与农业可接受的载体混合，包括化学式为：##STR1## 的化合物的杀虫有效量，其中R、R.sup.1、R.sup.2、R.sup.3、R.sup.7、R.sup.8、m、n和p如本文所定义，以及其农业可接受的盐，以及使用方法。

  公开号：

  US05521192A1
• 作为产物：
  描述：

  2,4-二氨基嘧啶 在 sodium hydroxide 、 ammonium persulfate 作用下， 生成 sulfuric acid mono-(2,4-diamino-pyrimidin-5-yl ester)
  参考文献：
  名称：

  Folate-Synthesizing Enzyme System as Target for Development of Inhibitors and Inhibitor Combinations against Candida albicansSynthesis and Biological Activity of New 2,4-Diaminopyrimidines and 4‘-Substituted 4-Aminodiphenyl Sulfones

  摘要：

  The paper describes the design, synthesis, and testing of inhibitors of folate-synthesizing enzymes and of whole cell cultures of Candida albicans. The target enzymes used were dihydropteroic acid synthase (SYN) and dihydrofolate reductase (DHFR). Several series of new 2,4-diaminopyrimidines were synthesized and tested as inhibitors of DHFR and compared with their activity against DHFR derived from mycobacteria and Escherichia coli. To test for selectivity, also rat DHFR was used. A series of substituted 4-aminodiphenyl sulfones was tested for inhibitory activity against SYN and the I-50 values compared to those obtained previously against Plasmodium berghei- and E. coli-derived SYN. Surprisingly, QSAR equations show very similar structural dependencies. To find an explanation for the large difference in the I-50 values observed for enzyme inhibition (SYN, DHFR) and for inhibition of cell cultures of Candida, mutant strains with overexpressed efflux pumps and strains in which such pumps are deleted were included in the study and the MICs compared. Efflux pumps were responsible for the low activity of some of the tested derivatives, others showed no increase in activity after pumps were knocked out. In this case it may be speculated that these derivatives are not able to enter the cells.

  DOI：

  10.1021/jm030931w

文献信息

• Hurst, Derek T., Australian Journal of Chemistry, 1983, vol. 36, # 6, p. 1285 - 1289
  作者：Hurst, Derek T.

  DOI：——

  日期：——
• 399. Pyrimidines. Part I. The synthesis of some 5-hydroxypyrimidines
  作者：R. Hull

  DOI：10.1039/jr9560002033

  日期：——
• Insecticidal 5-substituted-2,4-diaminopyrimidine derivatives
  申请人：FMC Corporation

  公开号：US05521192A1

  公开（公告）日：1996-05-28

  An insecticidal composition comprising, in admixture with an agriculturally acceptable carrier, an insecticidally effective amount of a compound of the formula: ##STR1## wherein R, R.sup.1, R.sup.2, R.sup.3, R.sup.7, R.sup.8, m, n, and p are as defined herein, and agriculturally acceptable salts thereof, and methods of using the same.

  一种杀虫组合物，与农业可接受的载体混合，包括化学式为：##STR1## 的化合物的杀虫有效量，其中R、R.sup.1、R.sup.2、R.sup.3、R.sup.7、R.sup.8、m、n和p如本文所定义，以及其农业可接受的盐，以及使用方法。
• Folate-Synthesizing Enzyme System as Target for Development of Inhibitors and Inhibitor Combinations against <i>Candida </i><i>a</i><i>lbicans</i>Synthesis and Biological Activity of New 2,4-Diaminopyrimidines and 4‘-Substituted 4-Aminodiphenyl Sulfones
  作者：Thomas Otzen、Ellen G. Wempe、Brigitte Kunz、Rainer Bartels、Gudrun Lehwark-Yvetot、Wolfram Hänsel、Klaus-Jürgen Schaper、Joachim K. Seydel

  DOI：10.1021/jm030931w

  日期：2004.1.1

  The paper describes the design, synthesis, and testing of inhibitors of folate-synthesizing enzymes and of whole cell cultures of Candida albicans. The target enzymes used were dihydropteroic acid synthase (SYN) and dihydrofolate reductase (DHFR). Several series of new 2,4-diaminopyrimidines were synthesized and tested as inhibitors of DHFR and compared with their activity against DHFR derived from mycobacteria and Escherichia coli. To test for selectivity, also rat DHFR was used. A series of substituted 4-aminodiphenyl sulfones was tested for inhibitory activity against SYN and the I-50 values compared to those obtained previously against Plasmodium berghei- and E. coli-derived SYN. Surprisingly, QSAR equations show very similar structural dependencies. To find an explanation for the large difference in the I-50 values observed for enzyme inhibition (SYN, DHFR) and for inhibition of cell cultures of Candida, mutant strains with overexpressed efflux pumps and strains in which such pumps are deleted were included in the study and the MICs compared. Efflux pumps were responsible for the low activity of some of the tested derivatives, others showed no increase in activity after pumps were knocked out. In this case it may be speculated that these derivatives are not able to enter the cells.