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

页码：107 / 113

页数：7

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