5582
Ahmed Sabt Ibrahim Mohamed
Synthesis Of Some New Coumarin Derivatives And Study Their Antitumor Activity
Synthesis, Coumarin derivatives, Phosphitylation, apopotosis, anti-proliferative activity and k-ras.
Coumarin was subjected to chlorosulfonation via chlorosulfonic aicd to yield coumarin-6-sulfonylchloride 1 which was utilized as a key intermediate to prepare new series from coumarin-6-sulfonamides derivatives. Therefore, compound 1 was refluxed in ethanol with sulfanilamide, pyridine sulfanilamide and/or 4-aminoacetophenone to afford the corresponding coumarin-6-sulfonamides 2 - 4, repectively. N- (4-acetylphenyl)-2-oxo-2H-chromene-6-sulfonamide 4 reacted with phenyhydrazine derivatives in absolute ethanol and triethylamineto afford 5a-c. On the other hand, when compound 4 reacted with p-toluene sulfonylhydrazide, compound 6 was isolated. When compound 4 was refluxed with thiosemicarbazide in the presence of ethanol and acetic aicd, the thiosemacarbaone 7 was obtained. The reaction of thiosemacarbazone 7 with chloroacetone, ethyl-2- chloroacetoacetate, hydrozonylchlorides-p-Cl and p-CH3, phencylbromide and/or 3-(2-bromoacetyl)-2H-chromen-2-one under reflux condition in dioxane and triethylamine gave the corresponding coumarinthiazole derivative 8-12, repectively. Also, thiazolidinone derivatives were obtained via reaction of thiosemicarbazone 7 with bromoacetic acid and/or 2-bromopropanoic to afford the thiazolidinone derivatives 13 and 14, repectively. 2-((6-hydroxyhexyl)oxy)isoindoline-1,3-dione 15 reacted with 4,4dimethoxy tritryl chloride (DMTrCl) in dry pyridine to give 16.
2018
Ph.d
Ain Shams
Science