Synthesis and properties of 1-[(3-fluoroadamantan-1-yl)methyl]-3-R-ureas and 1,1′-(alkan-1,n-diyl)bis{3-[(3-fluoroadamantan-1-yl)methyl]ureas} as promising soluble epoxide hydrolase inhibitors

被引：12
|
作者：
Danilov, D., V [1 ]
D'yachenko, V. S. [1 ,2 ]
Burmistrov, V. V. [1 ]
Butov, G. M. [1 ,2 ]
Novakov, I. A. [1 ]
机构：
[1] Volgograd State Tech Univ, 28 Prosp Lenina, Volgograd 400005, Russia
[2] Volgograd State Tech Univ, Volzhsky Polytech Inst Branch, 42a Ul Engelsa, Volzsky 404121, Volgograd Regio, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2022年 / 71卷 / 01期
基金：
俄罗斯科学基金会;
关键词：
Ishikawa's reagent; fluorinated adamantane derivatives; ureas; inhibitors; soluble epoxide hydrolase; IN-VIVO METABOLISM; 1,3-DISUBSTITUTED UREAS; ISOSTERIC ANALOGS; ADAMANTANES; FRAGMENTS; FLUORINATION; INFLUENZA; VITRO; ACIDS;
D O I：
10.1007/s11172-022-3383-8
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A two-step procedure to synthesize (3-fluoroadamantan-1-yl)methyl isocyanate from (3-hydroxyadamantane)acetic acid that involves fluorination with Ishikawa's reagent on the first step of the synthesis was developed. The reaction of (3-fluoroadamantan-1-yl)methyl isocyanate with aliphatic diamines gave 1,3-disubstituted bis-diureas in 60-97% yields. A strong decrease in the melting points of the obtained ureas (up to similar to 70-144 degrees C) was observed upon introduction of the fluorine atoms at the bridgehead positions of the adamantane unit.
引用
收藏
页码：107 / 113
页数：7
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