Synthesis and Antifungal Activity of 2-Carbalkoxyalkyl/(n-butyl)-4-aryl-1,5-benzothiazepines

Abstract

A series of novel 2-substituted-1,5-benzothiazepines were synthesized successfully and their structures were determined by elemental analysis, IR, MS/HRMS and 1 H NMR. The synthetic conditions of 2-substituted-4-aryl-1,5-benzothiazepines were investigated. The antifungal activities of these 2-substituted-1,5-benzothiazepine derivatives were tested and the results confirmed that the 2-ethyl carboxylate was necessary for antifungal activity in 1,5-benzothiazepine compounds 1.

Discovery of Oxime Ethers as Hepatitis B Virus (HBV) Inhibitors by Docking, Screening and In Vitro Investigation

“…Treatment of 3-aroylpropionic acids ( 2a , 2b and 2c ) with ethanol in the presence of p -toluenesulfonic acid provided ethyl 4-(4-substituted benzoyl)-4-oxobutanoate ( 3a , 3b and 3c ) in 94~96% yield. Compounds 4a , 4b , 4c , 5a , 5b and 5c were formed by the reaction of 3-aroylpropionic acids ( 2a , 2b and 2c ) with furfuryl alcohol or aniline in the presence of N , N -dicyclohexylcarbodiimide and 4-dimethylamioprdine in THF with yields of 88~96% [ 38 , 39 , 40 , 41 , 42 , 43 ]. The intermediate compounds ( 3a , 3b , 3c , 4a , 4b , 4c , 5a , 5b and 5c ) finally reacted with methoxylamine or hydroxylamine hydrochloride in pyridine and DCM to afford oxime ethers derivatives ( 3a-1 , 3a-2 , 3a-3 ; 3b-1 , 3b-2 , 3b-3 ; 3c-1 , 3c-2 , 3c-3 ; 4a-1 , 4a-2 , 4a-3 ; 4b-1 , 4b-2 , 4b-3 ; 4c-1 , 4b-2 , 4b-3 ; 5a-1 , 5a-2 , 5a-3 ; 5b-1 , 5b-2 , 5b-3 ; and 5c-1 , 5c-2 , 5c-3 ) as mixture of isomers.…”

“…The mixture was stirred and cooled to 0 °C and then N , N -dicyclohexylcarbodiimide (DCC) (1.1 equiv, 11 mmol) was added over a 5-min period and the reaction was stirred under anhydrous conditions for 6–8 h at room temperature. The mixture was filtered and the filtrate was evaporated to yield a crude product which was finally purified by recrystallization to give 4a , 4b , 4c , 5a , 5b and 5c as crystals [ 38 , 39 , 40 , 41 , 42 , 43 ].…”