5207
Shimaa Ahmed Kamel Awad Gabal
Synthesis and Reactions of Some New Polynuclear Heterocyclic Compounds Containing Nitrogen, Sulfur and Some Related Acyclic Nucleosides with Expected Biological Activity
3-Amino-2-hydroxy-thiazolo[3,2-a]pyrimidin-5-one, Pyrimido-thiazolo[4,5-e][1,2,4]triazin-6-one derivative, Thiazolo[4,5-e][1,2,4]triazin-6-one, Pyrimido-thiazolo[4,5-e][1,2,3,4]tetrazin-9-one, Ethyl -3-(2-(3-amino-thiazolo[3,2-a]pyrimidin-2-yl) hydrazono) butanoate, N'-(3-amino-thiazolo[3,2-a]pyrimidin-2-yl)-2-cyanoacetohydrazide, Schiff‘s bases, 2-Pyrazolyl derivatives , Arylidene derivatives , 3-Amino-6-bromo-2-(2-(4-arylidene)hydrazinyl)-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one derivatives, 2-Thiazolidinone, N-glycoside In 3-thiazolidinyl derivatives .
This following synthetic work is classified into three main sections: In Section A: we discuss for one-pot synthesis to give the target a single regioisomer 3-amino-2-hydroxy-thiazolo[3,2-a]pyrimidin-5-one derivative (17) In Section B : Synthesis of 3-amino-2-hydrazinyl-thiazolo[3,2-a]pyrimidin-5-one derivative (26) by direct hydrazinolysis of compound 17 with hydrazine hydrate. The key compound 26 used for the preparation of pyrimido-thiazolo[4,5-e][1,2,4]triazin-6-one derivative (27) by reaction with (TEOF) or with formic acid. Thiazolo[4,5-e][1,2,4]triazin-6-one derivative (28) yielded by reaction of compound 26 with triethylorthoacetate. Pyrimido-thiazolo[4,5-e][1,2,3,4]tetrazin-9-one derivative (29) produced by reaction of compound 26 with nitrous acid. Ethyl -3-(2-(3-amino-thiazolo[3,2-a]pyrimidin-2-yl) hydrazono) butanoate (31) and N'-(3-amino-thiazolo[3,2-a]pyrimidin-2-yl)-2-cyanoacetohydrazide (35) resulted by condensation reaction of compound 26 with ethylacetoacetate or ethylcyanoacetate, respectively. 2-Pyrazolyl derivatives 30, 33 and 37 furnished by cyclo-condensation reaction of compound 26 with acetylacetone, ethyl acetoacetate or ethyl cyanoacetate, respectively. The arylidene derivatives (34a-f) are resulted due to reaction of compound 33 with various aldhyds. 2-Amino-2-hydrazino derivative (26) condensed with the appropriate aromatic or hetero aromatic aldehydes to yield the Schiff‘s bases 40a-f. Bromination reaction of the corresponding Schiff‘s bases 40a,b,f carried out to afford 3-amino-6-bromo-2-(2-(4-arylidene)hydrazinyl)-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one derivatives (41a,b,f). The azomethine moiety of the Schiff‘s bases (40a,c,f) underwent cyclo addition reaction upon treatment with thioglycolic to yield 2-thiazolidinone derivatives (44a,c,f) . The Schiff‘s bases 40c and their 2-thiazolidinone derivative 44c The corresponding N-glycoside (45a-e) were synthesized by condensing 2-amino-2-hydrazino derivative (26) with the appropriate linear sugar The corresponding N-glycosides (45a-e) and their acetylated acyclo analogs (46a-e) (Scheme D). The corresponding N-glycosides (45a,e). In Section C : the corresponding Schiff‘s bases 47a-f afforded by condensing the target compound 3-amino-2-hydroxy-thiazolo[3,2-a]pyrimidin-5-one (17) with aldehydes in presence a catalyst. The prepared Schiff bases 47a-f were used as key precursors for the synthesis of 3-thiazolidinyl derivatives (49a-f). This reaction including addition of thioglycolic acid on the azomethine moiety of the corresponding Schiff‘s bases 47a-f followed by cyclo-condensation reaction to afford 3-thiazolidinyl derivatives (49a-f). The Schiff‘s bases 47a, 47c and their 3-thiazolidinone derivatives 49a, 49c were synthesized as a trial to obtain anti-cancer agents with activity for treatment of breast cancer.
2016
Ph.d
Ain Shams
Science