81154-11-2Relevant academic research and scientific papers
Synthesis of N-acetyl-S-(3-coumarinyl)-cysteine methyl ester and HPLC analysis of urinary coumarin metabolites
Eisenbrand, Gerhard,Otteneder, Michael,Tang, Weici
, p. 249 - 258 (2003)
N-Acetyl-S-(3-coumarinyl)cysteine, a metabolite of coumarin in rodents, has been synthesized as methyl ester. A new synthetic route to prepare N-acetyl-S-(3-coumarinyl)-D,L-cysteine methyl ester (1) comprises reaction of 3-mercaptocoumarin (3) with N-acetyl-3-chloro-D,L-alanine methyl ester (4). N-acetyl-S-(4-coumarinyl)-L-cysteine (10) was obtained by reaction of 3-bromocoumarin (12) and N-acetyl-L-cysteine (13). A method for the determination of N-acetyl-S-(3-coumarinyl)cysteine as its methyl ester in urine by HPLC has been developed.
E,Z-5-Arylmethylene-4-oxo-2-thioxo-1,3-thiazolidine and 3,3'-Dithiobis-2H-1-benzopyran-2-one Derivatives and their Reactions with Some Amines
Kandeel, Mamal A.
, p. 213 - 224 (2007/10/03)
The reaction of 4-oxo-2-thioxo-1,3-thiazolidine (1) with salicylaldehyde (2) or its 5-bromo derivative (2b) in acetic acid and sodium acetate gave a mixture of E,Z- or E-5-arylmethylene-4-oxo-2-thioxo-1,3-thiazolidines (3a or b) and 3,3'-dithiobis-2H-1-benzopyran-2-ones (4a and b), respectively. Treatment of E,Z-thiazolidinone (3a) with benzylamine or morpholine in dioxane at room temperature afforded 3-benzylamino-2H-1-benzopyran-2-one (6a) or E,Z-2-thiazolin-4-one derivative (7b) together with the amine salt (8), respectively. Similar treatment of E-(3b) with benzylamine yielded the E,Z-2-thiazolin-4-one derivative (7a) and the disulfide (4b) as the major product. The disulfide (4a) reacted with benzylamine in cold dioxane to yield the disulfide derivative (10) in addition to 6a whereas in boiling dioxane in gave 2H-1-benzopyran-2-one derivatives (6a and b). On the other hand, when E-(3b) or 4a was treated with dicyclohexylamine in dioxane, it gave 4b as well as the amine salt (9) in the former case and 3-mercapto-2H-1-benzopyran-2-one (5, X = H) in the latter one. Structures of all products were evidenced by microanalytical and spectra data.
