Abstract
In a search of nitric oxide synthase inhibitors with prolonged vasoconstrictive activity, a series of lipophilic cyclohexafused 2-amino-2-thiazolines was obtained via cyclization of tert-butyl- or benzoyl-substituted N-(cyclohex-2-en-1-yl)thioureas. The crystal structure of intermediate N-[(3aRS,7aSR)-3a,4,5,6,7,7a-hexahydro-1,3-benzothiazol-2-yl]benzamide hydrobromide was determined by X-ray analysis. One compound was found to cause pronounced and prolonged vasoconstrictive effect after single injection to the Wystar rats with lipopolysaccharide induced acute endotoxic (vasodilatation) shock.
References
1.
Thomas D.D., Ridnour L.A., Isenberg J.S., Flores-Santana W., Switzer C.H., Donzelli S., Hussain P., Vecoli C., Paolocci N., Ambs S., Colton C.A., Harris C.C., Roberts D.D., Wink D.A.
Free Radical Biology and Medicine,
2008
2.
Titheradge M.A.
Biochimica et Biophysica Acta - Bioenergetics,
1999
3.
Ohta S., Matsuda S., Gunji M., Kamogawa A.
Biological and Pharmaceutical Bulletin,
2007
4.
S. K. Shah, S.K. Grant, M. Maccoss, K. Shankaran, H. Qi and R. Guthikonda, Patent WO 96/14842, 1996.
5.
Garvey E.P., Oplinger J.A., Tanoury G.J., Sherman P.A., Fowler M., Marshall S., Harmon M.F., Paith J.E., Furfine E.S.
Journal of Biological Chemistry,
1994
6.
Trofimova T.P., Zefirova O.N., Mandrugin A.A., Lys Y.I., Pushin A.N., Proshin A.N., Proskuryakov S.Y., Fedoseev V.M.
Moscow University Chemistry Bulletin,
2009
7.
Martinovich N.N., Abzianidze V.V., Kuznetsov V.A., Ramsh S.M.
Russian Journal of General Chemistry,
2016
8.
Zefirova O.N., Plotnikova E.D., Nurieva E.V., Peregud D.I., Onufriev M.V., Gulyaeva N.V.
Mendeleev Communications,
2013
9.
Plotnikova E.D., Nurieva E.V., Peregud D.I., Onufriev M.V., Gulyaeva N.V., Makarchuk V.M., Filimonova M.V., Zefirov N.S., Zefirova O.N.
Russian Journal of Organic Chemistry,
2013
10.
Zefirova O.N., Moisseeva N.N., Nurieva E.V., Trofimova T.P., Proshin A.N., Slovokhotov Y.L.
Mendeleev Communications,
2011
11.
Zefirova O.N., Nurieva E.V., Chupakhin V.I., Semenova I.S., Peregud D.I., Onufriev M.V., Gulyaeva N.V.
Mendeleev Communications,
2010
12.
Shankaran K., Donnelly K.L., Shah S.K., Guthikonda R.N., MacCoss M., Humes J.L., Pacholok S.G., Grant S.K., Kelly T.M., Wong K.K.
Bioorganic and Medicinal Chemistry Letters,
2004
13.
Levtsova A.A., Chupakhin V.I., Proshin A.N., Pushin A.N., Trofimova T.P., Zefirova O.N.
Moscow University Chemistry Bulletin,
2007
14.
Ueda S., Terauchi H., Yano A., Matsumoto M., Kubo T., Kyoya Y., Suzuki K., Ido M., Kawasaki M.
Bioorganic and Medicinal Chemistry,
2004
15.
Trofimova T.P., Zefirova O.N., Mandrugin A.A., Fedoseev V.M., Peregud D.I., Onufriev M.V., Gulyaeva N.V., Proskuryakov S.Y.
Moscow University Chemistry Bulletin,
2008
16.
Cambia R.C., Lee H.H., Rutledge P.S., Woodgate P.D.
Journal of the Chemical Society Perkin Transactions 1,
1979
17.
Trofimova T.P., Pushin A.N., Proshin A.N., Stash A.I., Mandrugin A.A., Fedoseev V.M., Proskuryakov S.Y.
Chemistry of Heterocyclic Compounds,
2007
18.
10.1016/j.mencom.2018.07.016_bib0090
Smolanka
Ukr. Khim. Zh.,
1968
19.
Buchanan J.G., Diggle R.A., Ruggiero G.D., Williams I.H.
Chemical Communications,
2006
20.
Proskuryakov S.Y., Filimonova M.V., Verkhovskii Y.G., Konoplyannikov A.G., Mandrugin A.A., Fedoseev V.M., Skvortsov V.G.
Bulletin of Experimental Biology and Medicine,
2004