Synthesis and Properties of 1,3-Disubstituted Ureas and Their Isosteric Analogues Containing Polycyclic Fragments. XVII. 1-[(3-Bromadamantan-1-yl)]-3-R-Ureas and Symmetric Diureas

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Resumo

A series of 1,3-disubstituted ureas and diureas was synthesized by the reaction of (3-bromoadamantan-1-yl)isocyanate with aliphatic diamines, fluorine-containing anilines, and trans-4-amino-(cyclohexyloxy)benzoic acid in 36–85% yields. Hydrolysis of (3-bromoadamantan-1-yl)isocyanate in the presence of catalytic amounts of DBU afforded symmetrical 1,3-bis-((3-bromadamantan-1-yl)urea in 60% yield. are promising inhibitors of human soluble epoxide hydrolase hsEH.

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Sobre autores

B. Gladkikh

Volgograd state technical university (VSTU)

Autor responsável pela correspondência
Email: butov@post.volpi.ru
ORCID ID: 0000-0001-6271-0479
Rússia, Volgograd

V. D’yachenko

Volgograd state technical university (VSTU)

Email: butov@post.volpi.ru
Rússia, Volgograd

D. Danilov

Volgograd state technical university (VSTU)

Email: butov@post.volpi.ru
ORCID ID: 0000-0001-8734-2617
Rússia, Volgograd

A. Matyukhina

Institute of General and Inorganic Chemistry. N.S. Kurnakov RAS

Email: butov@post.volpi.ru
ORCID ID: 0000-0002-2831-6838
Rússia, Moscow

V. Burmistrov

Volgograd state technical university (VSTU)

Email: butov@post.volpi.ru
ORCID ID: 0000-0002-8547-9166
Rússia, Volgograd

G. Butov

Volgograd state technical university (VSTU); Volzhsky polytechnic institute (branch) VSTU

Email: butov@post.volpi.ru
Rússia, Volgograd; Volzhsky

Bibliografia

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2. Fig. 1. Compounds containing 3-bromoadamantyl fragment possessing biological activity

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3. Fig. 2. ORTEP diagram showing the anisotropic displacement ellipsoids of non-hydrogen atoms with a probability of 50% for compound 4k according to the X-ray diffraction data of a single crystal collected at 100 K.

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4. Fig. 3. Dependence of the melting point of halogenated diureas 4a–i on the number of methylene groups n: 1 – F-Ad-(diurea) [14]; 2 – Br-Ad-(diurea); 3 – Cl-Ad-(diurea) [9]

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5. Scheme 1

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6. Scheme 2

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7. Scheme 3

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