3363-68-6Relevant academic research and scientific papers
Activation of Phenyl 4-(2-Oxo-3-Alkylimidazolidin-1-yl)benzenesulfonates Prodrugs by CYP1A1 as New Antimitotics Targeting Breast Cancer Cells
Fortin, Sébastien,Charest-Morin, Xavier,Turcotte, Vanessa,Lauvaux, Coraline,Lacroix, Jacques,C?té, Marie-France,Gobeil, Stéphane,Gaudreault, René C.
, p. 4963 - 4982 (2017/06/28)
Prodrug-mediated utilization of the cytochrome P450 (CYP) 1A1 to obtain the selective release of potent anticancer products within cancer tissues is a promising approach in chemotherapy. We herein report the rationale, preparation, biological evaluation, and mechanism of action of phenyl 4-(2-oxo-3-Alkylimidazolidin-1-yl)benzenesulfonates (PAIB-SOs) that are antimicrotubule prodrugs activated by CYP1A1. Although PAIB-SOs are inert in most cells tested, they are highly cytocidal toward several human breast cancer cells, including hormone-independent and chemoresistant types. PAIB-SOs are N-dealkylated into cytotoxic phenyl 4-(2-oxo-3-imidazolidin-1-yl)benzenesulfonates (PIB-SOs) in CYP1A1-positive cancer cells, both in vitro and in vivo. In conclusion, PAIB-SOs are novel chemotherapeutic prodrugs with no equivalent among current antineoplastics and whose selective action toward breast cancer is tailored to the characteristic pattern of CYP1A1 expression observed in a large percentage of human breast tumors.
SUBSTITUTED 2-IMIDAZOLIDONES AND ANALOGS
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, (2011/09/19)
Compounds of formula (I): wherein R1, R2, R3, R4, R7, R6, R7, R8, R9, A, X and Y as defined herein are provided as useful for the treatment of cancer or for
Lithiation of 1-arylimidazol-2(1H)-ones and 1-aryl-4,5-dihydroimidazol- 2(1H)-ones
Llopart, Carme Cantos,Ferrer, Conchita,Joule, John A.
, p. 1649 - 1661 (2007/10/03)
1-Arylimidazol-2(1H)-ones are shown to be readily lithiated, using 2 mol equiv. of n-butyllithium, on the benzene ring, ortho to the heterocycle. 1-Aryl-4,5-dihydroimidazol-2(1H)-ones also undergo metalation on the aromatic substitutuent ortho to the heterocycle, but less efficiently. 1-Aryl-3-methylimidazol-2(1H)-ones are lithiated on the heterocyclic ring and then on the benzene ring ortho to the heterocycle. No ortho-directing effect was found for 1-aryl-4,5-dihydro-3-methylimidazol-2(1H)-ones.
Investigation of the Mitsunobu reaction of N-(2-hydroxyethyl)-N'- phenyl-ureas
Kim, Taek Hyeon,Lee, Gue-Jae,Cha, Mi-Hyun
, p. 2753 - 2758 (2007/10/03)
The Mitsunobu reaction of N-(2-hydroxyethyl)-ureas 1 using PPh3 and EtO2CN=NCO2Et led to the mixture of N- and O-alkylation products or a single isomer depending on the substrates.
Human β3 adrenergic receptor agonists containing imidazolidinone and imidazolone benzenesulfonamides
Naylor, Elizabeth M.,Parmee, Emma R.,Colandrea, Vincent J.,Perkins, Leroy,Brockunier, Linda,Candelore, Mari R.,Cascieri, Margaret A.,Colwell Jr., Lawrence F.,Deng, Liping,Feeney, William P.,Forrest, Michael J.,Hom, Gary J.,MacIntyre, D. Euan,Strader, Catherine D.,Tota, Laurie,Wang, Pei-Ran,Wyvratt, Matthew J.,Fisher, Michael H.,Weber, Ann E.
, p. 755 - 758 (2007/10/03)
The cyclopentylpropylimidazolidinone L-766,892 is a potent β3 AR agonist (EC50 5.7 nM, 64% activation) with 420- and 130-fold selectivity over binding to the β1 and β2 ARs, respectively. In anesthetized rhesus monkeys, L-766,892 elicited dose-dependent hyperglycerolemia (ED50 0.1 mg/kg) with minimal effects on heart rate.
