Synthesis of adamantyl-containing 1,3-disubstituted diureas and thioureas, efficient targeted inhibitors of human soluble epoxide hydrolase

Бутов, Г. М.; Burmistrov, V. V.; Данилов, Д. В.; Pitushkin, D. A.; Morisseau, Christophe; Hammock, Bruce D.

doi:10.1007/s11172-015-1043-y

Cited by 15 publications

(4 citation statements)

References 25 publications

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“…To a stirred solution of 2-(4-R-phenoxymethyl)benzoic acid chloride (4) (0.01 mol) in acetone (15 mL) was added a solution of ammonium thiocyanate (0.01 mol) in acetone (5 mL). The reaction mixture was heated for 1 h, to obtain the benzoyl isothiocyanates (5). The mixture was cooled at room temperature and a solution of 1-adamantylamine (0.01 mol) in acetone (2 mL) was added and heated under reflux for 8 h. The reaction mixture was poured into cold water, the solid was isolated by filtration.…”

Section: The Synthesis Of N-(1-adamantylcarbamothioyl)benzamides (6a-e)mentioning

confidence: 99%

“…The structure of the synthesized compound was inspired from the second line of antituberculosis pro-drugs thioacetazone, thiocarlide, ethionamide and prothionamide [11]. 1-(Adamantane-2-yl)-3-phenyl/benzyl/phenethylthiourea and 1-(1-(adamantan-1-yl)ethyl)-3-phenyl/ benzyl/phenethyl-thiourea have been synthesized and their inhibitory activity against mammalian and human soluble epoxide hydrolase have been examined [5]. Our research group has been involved in the synthesis and biological assay of different thiourea derivatives [16,17,[19][20][21]24].…”

Section: Introductionmentioning

confidence: 99%

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N-(1-Adamantylcarbamothioyl)benzamides: Synthesis, Biological Evaluation and Adme Predictions

Gurgu¹

2018

FARMACIA

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This paper presents the synthesis of five novel benzamide derivatives containing adamantane moiety. The compounds structure was proven through elemental analysis, FT-IR, 1 H-NMR and 13 C-NMR spectroscopy. Their therapeutic potential was evaluated by the in vitro testing of the antimicrobial activity. Two different parameters of the antimicrobial activity were determined: minimum inhibitory concentration (MIC) and minimal biofilm eradication concentration (MBEC). Also, an in vitro cytotoxicity study was carried out on Hep-2 cell line. An in silico study of the compounds determined their ADME profile. The study reports the preliminary biological screening of five novel benzamides with adamantane scaffold, that evidenced a good toxicological and ADME profile, thus representing favourable candidates for further studies. RezumatÎn această lucrare este prezentată sinteza a cinci noi derivați ai benzamidei care conțin fragmentul adamantan. Structura compușilor a fost dovedită prin analiză elementală, spectroscopie FT-IR, 1 H-RMN și 13 C-RMN. Potențialul lor terapeutic a fost evaluat prin testarea in vitro a activității antimicrobiene. S-au determinat doi parametri diferiți ai activității antimicrobiene, respectiv: concentrația minimă inhibitorie (MIC) și concentrația minimă de eradicare a biofilmului (MBEC). De asemenea, a fost efectuat un studiu de citotoxicitate in vitro, pe linia celulară HEp-2. Un studiu in silico al compușilor a determinat profilul lor ADME. Studiul raportează screening-ul biologic preliminar a cinci noi benzamide cu fragment de adamantan, care prezintă profil toxicologic și ADME favorabil, prezentând astfel un potențial promițător pentru studii ulterioare.

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Section: The Synthesis Of N-(1-adamantylcarbamothioyl)benzamides (6a-e)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

N-(1-Adamantylcarbamothioyl)benzamides: Synthesis, Biological Evaluation and Adme Predictions

Gurgu¹

2018

FARMACIA

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“…With the goal of obtaining new sEH-P inhibitors, we have developed approaches to the design of inhibitor molecules via isosteric replacement of chalcogen atom and synthesized a series of sulfur-containing urea analogs [11][12][13][14]. In this connection, isosteric replacement of chalcogen atom in the ureido group by selenium is of significant scientific and practical interest.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XI. 1-[(Adamantan-1 yl)alkyl]-3-arylselenoureas

et al. 2021

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A series of N,N′-disubstituted selenoureas containing an adamantane fragment have been synthesized in 23-75% yields. Procedures for the isolation and purification of aromatic isoselenocyanates have been improved. The chemical shift of the C=Se carbon nucleus in the 13 C NMR spectra of selenoureas has been refined. The synthesized selenoureas have been found to be promising as inhibitors of not only epoxide hydrolase (sEH-H) but also phosphatase domains (sEH-P) of human soluble epoxide hydrolase.

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“…Thioureas formed from adamantyl isothiocyanates are promising as soluble epoxide hydrolase (sEH, E.C. 3.3.2.10) inhibitors, 1 and as urokinase-type plasminogen activator (uPA, 3.4.21.73) inhibitors. 2 Moreover, thioureas can be readily transformed 3 into ureas, which find wide applications in medicinal chemistry.…”

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confidence: 99%

New Facile Synthesis of Adamantyl Isothiocyanates

Burmistrov¹,

Pitushkin²,

Бутов³

2017

SynOpen

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Synthesis of adamantyl-containing 1,3-disubstituted diureas and thioureas, efficient targeted inhibitors of human soluble epoxide hydrolase

Cited by 15 publications

References 25 publications

N-(1-Adamantylcarbamothioyl)benzamides: Synthesis, Biological Evaluation and Adme Predictions

N-(1-Adamantylcarbamothioyl)benzamides: Synthesis, Biological Evaluation and Adme Predictions

Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XI. 1-[(Adamantan-1 yl)alkyl]-3-arylselenoureas

New Facile Synthesis of Adamantyl Isothiocyanates

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