334829-66-2Relevant academic research and scientific papers
Discovery of a crystalline sulforaphane analog with good solid-state stability and engagement of the Nrf2 pathway in vitro and in vivo
Boehm, Jeffrey,Davis, Roderick,Murar, Claudia E.,Li, Tindy,McCleland, Brent,Dong, Shuping,Yan, Hongxing,Kerns, Jeffrey,Moody, Christopher J.,Wilson, Anthony J.,Graves, Alan P.,Mentzer, Mary,Qi, Hongwei,Yonchuk, John,Kou, Jen-Pyng,Foley, Joseph,Sanchez, Yolanda,Podolin, Patricia L.,Bolognese, Brian,Booth-Genthe, Catherine,Galop, Marc,Wolfe, Lawrence,Carr, Robin,Callahan, James F.
supporting information, p. 579 - 588 (2019/01/08)
The antioxidant natural product sulforaphane (SFN) is an oil with poor aqueous and thermal stability. Recent work with SFN has sought to optimize methods of formulation for oral and topical administration. Herein we report the design of new analogs of SFN with the goal of improving stability and drug-like properties. Lead compounds were selected based on potency in a cellular screen and physicochemical properties. Among these, 12 had good aqueous solubility, permeability and long-term solid-state stability at 23 °C. Compound 12 also displayed comparable or better efficacy in cellular assays relative to SFN and had in vivo activity in a mouse cigarette smoke challenge model of acute oxidative stress.
Synthesis of isothiocyanate-derived mercapturic acids
Vermeulen, Martijn,Zwanenburg, Binne,Chittenden, Gordon J.F.,Verhagen, Hans
, p. 729 - 737 (2007/10/03)
Twelve mercapturic acids derived from saturated and unsaturated aliphatic and aromatic isothiocyanates were synthesised, by adding isothiocyanate to a solution of N-acetyl-L-cysteine and sodium bicarbonate, in a typical yield of 77%. Isothiocyanates were synthesised first by adding the corresponding alkyl bromide to phthalimide potassium salt. The obtained N-alkyl-phthalimide was hydrazinolysed yielding the alkyl amine, which subsequently was reacted with thiophosgene yielding the isothiocyanate with an overall yield of 16%. Mercapturic acids in urine can serve as a biomarker of intake to determine the health promoting potential of isothiocyanates present in cruciferous vegetables.
