title: Synthesis, antiviral activity and structure-activity relationship of 1-(1-aryl-4,5-dihydro-1H-imidazoline)-3-chlorosulfonylureas and products of their cyclization.
abstract: Novel 1-(1-aryl-4,5dihydro-1H-imidazoline)-3-chlorosulfonylourea derivatives 3a-3f were synthesized in the reaction of 1-aryl-4,5-dihydro-1H-imidazol-2-amines with chlorosulfonyl isocyanate. The second series of compounds 4a-4f was prepared from the respective 1-(1-aryl-4,5-dihydro-1H-imidazoline)-3-chlorsulfonylureas 3a-3f and 1,1'-carbonyldiimidazole (CDI). The selected compounds were tested for their activity against Herpes simplex virus and coxsackievirus B3 (CVB3). It was determined that three derivatives, i.e 3d, 4a and 4d are active against Herpes simplex virus (HSV-1). Compounds 3d and 4c are active against CVB3. Their favorable activity can be primarily attributed to their low lipophilicity values. Moreover, the lack of substituent in the phenyl moiety or 4-methoxy substitution can be considered as the most beneficial for the antiviral activity.
authors.affiliation: a Department of Synthesis and Chemical Technology of Pharmaceutical Substances with Computer Modeling Lab, Faculty of Pharmacy with Division of Medical Analytics , Medical University of Lublin , Lublin , Poland .
authors.forename: Marzena
authors.initials: M
authors.lastname: Rządkowska
authors.affiliation: a Department of Synthesis and Chemical Technology of Pharmaceutical Substances with Computer Modeling Lab, Faculty of Pharmacy with Division of Medical Analytics , Medical University of Lublin , Lublin , Poland .
authors.forename: Elżbieta
authors.initials: E
authors.lastname: Szacoń
authors.affiliation: a Department of Synthesis and Chemical Technology of Pharmaceutical Substances with Computer Modeling Lab, Faculty of Pharmacy with Division of Medical Analytics , Medical University of Lublin , Lublin , Poland .|b School of Pharmacy, University of Eastern Finland , Kuopio , Finland , and.
authors.forename: Agnieszka A
authors.initials: AA
authors.lastname: Kaczor
authors.affiliation: c Department of Virology , Medical University of Lublin, I Faculty of Medicine with Dentistry Division , Lublin , Poland.
authors.forename: Barbara
authors.initials: B
authors.lastname: Rajtar
authors.affiliation: c Department of Virology , Medical University of Lublin, I Faculty of Medicine with Dentistry Division , Lublin , Poland.
authors.forename: Łukasz
authors.initials: Ł
authors.lastname: Świątek
authors.affiliation: c Department of Virology , Medical University of Lublin, I Faculty of Medicine with Dentistry Division , Lublin , Poland.
authors.forename: Małgorzata
authors.initials: M
authors.lastname: Polz-Dacewicz
authors.affiliation: a Department of Synthesis and Chemical Technology of Pharmaceutical Substances with Computer Modeling Lab, Faculty of Pharmacy with Division of Medical Analytics , Medical University of Lublin , Lublin , Poland .
authors.forename: Dariusz
authors.initials: D
authors.lastname: Matosiuk
mesh_terms: D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002522:Chlorocebus aethiops; D003384:Coxsackievirus Infections / Q000188:drug therapy; D003500:Cyclization; D029822:Enterovirus B, Human / Q000187:drug effects*; D006561:Herpes Simplex / Q000188:drug therapy; D048288:Imidazolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D018139:Simplexvirus / Q000187:drug effects*; D013329:Structure-Activity Relationship; D013451:Sulfonic Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D014508:Urea / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D014709:Vero Cells
chemical_list: D000998:Antiviral Agents; D048288:Imidazolines; D013451:Sulfonic Acids; C013880:chlorosulfonic acid; D014508:Urea
keywords: 1-(1-Aryl-4,5dihydro-1H-imidazoline)-3-chlorosulfonylourea derivatives; Antiviral activity; Coxsackievirus B3,; Herpes simplex; structure–activity relationship