title: Design and synthesis of novel iminothiazinylbutadienols and divinylpyrimidinethiones as ARE inducers.
abstract: Novel iminothiazinylbutadienols and divinylpyrimidinethiones were designed and synthesized as analogues of curcumin with its diketone moiety masked as a heterocyclic adduct with thiourea. The chemical stability of these novel heterocyclic compounds was improved as compared to curcumin. They exhibit longer half-lives and do not react with nucleophilic thiols under physiological conditions. In an ARE-luciferase reporter assay, some of these new curcumin analogues are more effective ARE activators than curcumin and isothiocyanates.
authors.affiliation: Department of Medicinal Chemistry, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey, 160 Frelinghuysen Road, Piscataway, NJ 08854, USA.
authors.forename: Lin
authors.initials: L
authors.lastname: Chen
authors.affiliation: Department of Medicinal Chemistry, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey, 160 Frelinghuysen Road, Piscataway, NJ 08854, USA.
authors.forename: Sadagopan
authors.initials: S
authors.lastname: Magesh
authors.affiliation: Department of Chemical Biology, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey, 160 Frelinghuysen Road, Piscataway, NJ 08854, USA.
authors.forename: Hong
authors.initials: H
authors.lastname: Wang
authors.affiliation: Department of Chemical Biology, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey, 160 Frelinghuysen Road, Piscataway, NJ 08854, USA; The Cancer Institute of New Jersey, New Brunswick, NJ 08901, USA; Center for Cancer Prevention Research, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey, Piscataway, NJ 08854, USA.
authors.forename: Chung S
authors.initials: CS
authors.lastname: Yang
authors.affiliation: Department of Pharmaceutics, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey, 160 Frelinghuysen Road, Piscataway, NJ 08854, USA; The Cancer Institute of New Jersey, New Brunswick, NJ 08901, USA; Center for Cancer Prevention Research, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey, Piscataway, NJ 08854, USA.
authors.forename: Ah-Ng Tony
authors.initials: AN
authors.lastname: Kong
authors.affiliation: Department of Medicinal Chemistry, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey, 160 Frelinghuysen Road, Piscataway, NJ 08854, USA; School of Pharmaceutical Sciences, Shanxi Medical University, Taiyuan 030001, PR China; The Cancer Institute of New Jersey, New Brunswick, NJ 08901, USA; Center for Cancer Prevention Research, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey, Piscataway, NJ 08854, USA. Electronic address: LongHu@rci.rutgers.edu.
authors.forename: Longqin
authors.initials: L
authors.lastname: Hu
mesh_terms: D061745:Antioxidant Response Elements / Q000187:drug effects*; D003474:Curcumin / Q000737:chemistry / Q000378:metabolism; D015195:Drug Design; D017879:Isothiocyanates / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013454:Sulfoxides; D013829:Thiadiazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013871:Thiones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013890:Thiourea / Q000737:chemistry / Q000378:metabolism
chemical_list: D017879:Isothiocyanates; D011743:Pyrimidines; D013454:Sulfoxides; D013829:Thiadiazines; D013871:Thiones; C016766:sulforaphane; D013890:Thiourea; D003474:Curcumin; C012864:dazomet
keywords: ARE induction; Anti-inflammatory agents; Curcumin; Divinylpyrimidinethiones; Iminothiazinylbutadienols