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2,4-二氨基-5-苄基嘧啶及其类似物作为抗菌剂。2. 嘧啶与曼尼希碱的C-烷基化反应及其在甲氧苄啶及其类似物合成中的应用。

2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 2. C-Alkylation of pyrimidines with Mannich bases and application to the synthesis of trimethoprim and analogues.

作者信息

Roth B, Strelitz J Z, Rauckman B S

出版信息

J Med Chem. 1980 Apr;23(4):379-84. doi: 10.1021/jm00178a007.

DOI:10.1021/jm00178a007
PMID:6991692
Abstract

A new route to 5-(p-hydroxybenzyl)pyrimidines has been developed which utilizes phenolic Mannich bases plus pyrimidines containing at least two activating groups. The products can be alkylated on the phenolic oxygen or on the pyrimidine N-1 atom, depending on conditions. This method has been used to prepare trimethoprim, a broad-spectrum antibacterial agent, starting from 2,4-diaminopyrimidine and 2,6-dimethoxyphenol.

摘要

已开发出一种合成5-（对羟基苄基）嘧啶的新路线，该路线利用酚醛曼尼希碱以及含有至少两个活化基团的嘧啶。根据反应条件，产物可以在酚氧原子上或嘧啶的N-1原子上进行烷基化。该方法已用于从2,4-二氨基嘧啶和2,6-二甲氧基苯酚出发制备广谱抗菌剂甲氧苄啶。

相似文献

1
2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 2. C-Alkylation of pyrimidines with Mannich bases and application to the synthesis of trimethoprim and analogues.2,4-二氨基-5-苄基嘧啶及其类似物作为抗菌剂。2. 嘧啶与曼尼希碱的C-烷基化反应及其在甲氧苄啶及其类似物合成中的应用。
J Med Chem. 1980 Apr;23(4):379-84. doi: 10.1021/jm00178a007.
2
2,4-Diamino-5-benzylpyrimidines as antibacterial agents. 4. 6-Substituted trimethoprim derivatives from phenolic Mannich intermediates. Application to the synthesis of trimethoprim and 3,5-dialkylbenzyl analogues.作为抗菌剂的2,4-二氨基-5-苄基嘧啶。4. 来自酚醛曼尼希中间体的6-取代甲氧苄啶衍生物。在甲氧苄啶和3,5-二烷基苄基类似物合成中的应用。
J Med Chem. 1980 May;23(5):535-41. doi: 10.1021/jm00179a012.
3
2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 3. C-Benzylation of aminopyridines with phenolic Mannich bases. Synthesis of 1- and 3-deaza analogues of trimethoprim.2,4-二氨基-5-苄基嘧啶及其类似物作为抗菌剂。3. 用酚醛曼尼希碱对氨基吡啶进行C-苄基化反应。甲氧苄啶1-去氮和3-去氮类似物的合成。
J Med Chem. 1980 Apr;23(4):384-91. doi: 10.1021/jm00178a008.
4
2,4-diamino-5-benzylpyrimidines and analogues as antibacterial agents. 6. A one-step synthesis of new trimethoprim derivatives and activity analysis by molecular modeling.作为抗菌剂的2,4-二氨基-5-苄基嘧啶及其类似物。6. 新型甲氧苄啶衍生物的一步合成及分子模拟活性分析。
J Med Chem. 1983 May;26(5):667-73. doi: 10.1021/jm00359a009.
5
2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 9. Lipophilic trimethoprim analogues as antigonococcal agents.2,4-二氨基-5-苄基嘧啶及其类似物作为抗菌剂。9. 亲脂性甲氧苄啶类似物作为抗淋球菌剂。
J Med Chem. 1988 Jan;31(1):122-9. doi: 10.1021/jm00396a018.
6
2,4-Diamino-5-benzylpyrimidines as antibacterial agents. 7. Analysis of the effect of 3,5-dialkyl substituent size and shape on binding to four different dihydrofolate reductase enzymes.
J Med Chem. 1987 Feb;30(2):348-56. doi: 10.1021/jm00385a017.
7
2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 10. 2,4-Diamino-5-(6-quinolylmethyl)- and -[(tetrahydro-6-quinolyl)methyl]pyrimidine derivatives. Further specificity studies.作为抗菌剂的2,4-二氨基-5-苄基嘧啶及其类似物。10. 2,4-二氨基-5-(6-喹啉基甲基)-和-[(四氢-6-喹啉基)甲基]嘧啶衍生物。进一步的特异性研究。
J Med Chem. 1989 Aug;32(8):1927-35. doi: 10.1021/jm00128a040.
8
2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 12. 1,2-Dihydroquinolylmethyl analogues with high activity and specificity for bacterial dihydrofolate reductase.2,4-二氨基-5-苄基嘧啶及其类似物作为抗菌剂。12. 对细菌二氢叶酸还原酶具有高活性和特异性的1,2-二氢喹啉基甲基类似物。
J Med Chem. 1989 Aug;32(8):1942-9. doi: 10.1021/jm00128a042.
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2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 5. 3',5'-Dimethoxy-4'-substituted-benzyl analogues of trimethoprim.
J Med Chem. 1981 Aug;24(8):933-41. doi: 10.1021/jm00140a005.
10
Pyrrolo[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines as conformationally restricted analogues of the antibacterial agent trimethoprim.吡咯并[2,3 - d]嘧啶和吡啶并[2,3 - d]嘧啶作为抗菌剂甲氧苄啶的构象受限类似物。
Bioorg Med Chem. 1996 Apr;4(4):593-602. doi: 10.1016/0968-0896(96)00045-4.

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