新型4-氨基-6-(1,3,4-恶二唑/1,3,4-噻二唑)-嘧啶衍生物的合成与抗菌活性评价
Synthesis and antimicrobial evaluation of novel 4-amino-6-(1,3,4-oxadiazolo/1,3,4-thiadiazolo)-pyrimidine derivatives.
作者信息
Shetty Poornima, Praveen B M, Raghavendra M, Manjunath K, Cheruku Srinivas
机构信息
Department of Chemistry, Srinivas School of Engineering, Mukka, Mangalore, 574146, India.
Department of Chemistry, Government Pre-University College, Kanasawadi, Doddaballapura taluk, Bangalore-Rural, Karnataka, India.
出版信息
Mol Divers. 2016 May;20(2):391-8. doi: 10.1007/s11030-015-9640-0. Epub 2015 Oct 26.
A series of novel 4-amino-6-(1,3,4-oxadiazolo/1,3,4-thiadiazolo)-pyrimidine derivatives of biological interest were prepared by sequential amination, hydrazide formation, and hydrazine carbothioamidination followed by cyclization. All the synthesized compounds (6a-6h and 7a-7f) were screened for antibacterial and antifungal activity. From this group, compound 7f (MIC (μg/mL μg/mL )/Inhibition (mm): 6.25/23-30) showed good antibacterial and antifungal activity. Reagents and conditions: (a) Ethyl acetoacetate, 60% NaH, 1,4-dioxane, 60°C, 6 h; (b) DIPEA, 1,4-dioxane, 100°C, 14 h; (c) NH2NH2 ⋅ H2O, EtOH, reflux, 14 h; (d) Tolyl isothiocyanatobenzene, DMF, RT, 2 h; (e) (if X = O) EDC⋅ HCl, TEA, DMF, RT, 14 h; (f) (if X = S) Conc. H2O4, RT, 14h.
通过连续胺化、酰肼形成、肼基硫代甲脒化然后环化，制备了一系列具有生物学意义的新型4-氨基-6-(1,3,4-恶二唑/1,3,4-噻二唑)-嘧啶衍生物。对所有合成化合物（6a - 6h和7a - 7f）进行了抗菌和抗真菌活性筛选。在该组化合物中，化合物7f（最低抑菌浓度（μg/mL μg/mL）/抑制圈（mm）：6.25/23 - 30）显示出良好的抗菌和抗真菌活性。试剂和条件：(a)乙酰乙酸乙酯、60%氢化钠、1,4 - 二氧六环、60°C、6小时；(b)二异丙基乙胺、1,4 - 二氧六环、100°C、14小时；(c)水合肼、乙醇、回流、14小时；(d)异硫氰酸苯酯、N,N - 二甲基甲酰胺、室温、2小时；(e)（如果X = O）1 - (3 - 二甲氨基丙基)-3 - 乙基碳二亚胺盐酸盐、三乙胺、N,N - 二甲基甲酰胺、室温、14小时；(f)（如果X = S）浓硫酸、室温、14小时。
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