Substituted ureas and their analogues containing framework fragments. I. 1-(4-hydroxyadamanthane-1-yl)-3-(fluo, chlorophenyl)ureas

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Abstract

This work begins a new series of articles devoted to di-, tri- and tetra-substituted urea derivatives and is a continuation of research [1] on modification of the framework fragment in molecules of adamantyl-containing ureas. By the reaction of 1-(4-oxoadamant-1-yl)-3-(halophenyl)ureas with sodium borohydride, a series of 1,3-disubstituted ureas containing a 4-hydroxyadamantan-1-yl radical in their structure was synthesized, with a yield of target products of 55–87%. The synthesized ureas are potential metabolites and promising inhibitors of soluble human epoxide hydrolase (sEH).

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D. V. Danilov

Volgograd state technical university

Email: vburmistrov@vstu.ru
ORCID iD: 0000-0001-8734-2617
Russian Federation, prosp. Lenina, 28, Volgograd, 400005

V. S. D’yachenko

Volgograd state technical university

Email: vburmistrov@vstu.ru
ORCID iD: 0000-0002-6209-7106
Russian Federation, prosp. Lenina, 28, Volgograd, 400005

D. M. Zapravdina

Volgograd state technical university

Email: vburmistrov@vstu.ru
ORCID iD: 0000-0002-8654-2382
Russian Federation, prosp. Lenina, 28, Volgograd, 400005

E. S. Ilyina

Volgograd state technical university

Email: vburmistrov@vstu.ru
ORCID iD: 0009-0005-0475-1113
Russian Federation, prosp. Lenina, 28, Volgograd, 400005

E. K. Degtyarenko

Volgograd state technical university

Email: vburmistrov@vstu.ru
ORCID iD: 0000-0002-7337-4885
Russian Federation, prosp. Lenina, 28, Volgograd, 400005

V. V. Burmistrov

Volgograd state technical university

Author for correspondence.
Email: vburmistrov@vstu.ru
ORCID iD: 0000-0002-8547-9166
Russian Federation, prosp. Lenina, 28, Volgograd, 400005

References

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Supplementary files

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1. JATS XML
2. Fig. 1. The main pathways of modification (a) and metabolism (b) of 1,3-disubstituted urea molecules

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3. Scheme 1

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4. Scheme 2

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5. Table 4a

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6. Table 4b

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7. Table 4c

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8. Table 4d

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9. Table 4e

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10. Table 4f

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11. Table 4g

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12. Table 4h

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13. Table 4i

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14. Table 4j

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15. Table. 4k

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16. Fig. 2. Melting point of ureas 3a–k and 4a–k

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17. Fig. 3. Comparison of water solubility of 1-(4-R-adamantan-1-yl)-3-(4-fluorophenyl)ureas

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18. Content

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