Synthesis, isomerism, and hypotensive activity of thiethane-containing hydrazones of uracilylacetic acid

Synthesis and biological activity of 2-[6-methyl-4-(thietan-3-yloxy)pyrimidin-2-ylthio]acetohydrazide derivatives

“…Infrared spectra were recorded in KBr pellets on an Infralum FT-02 (Russia) spectrophotometer. 1 H and 13 C NMR spectra were recorded on Bruker AMX-300 300 MHz and Bruker Avance III 500 MHz in CDCl 3 and DMSO-d 6 using tetramethylsilane as internal standard (chemical shifts were expressed as δ-values, J in hertz). CHNS elemental analyses were performed on a Hekatech Euro-EA (Germany) elemental analyzer.…”

“…The pyrimidine fragment has been gaining special interest as it is part of many biological active compounds: vitamins, nucleotides and nucleosides. Our research group has published much research in the field of the synthesis of thietan derivatives [ 8 , 9 ] as they possess a broad spectrum of bioactivities: antimicrobial [ 10 , 11 ], hypotensive [ 12 , 13 ], broncholytic [ 14 ] and wound healing [ 15 , 16 ]. Compounds containing thietan and pyrimidine in their molecules are suitable candidates for further chemical modifications and may be pharmacologically active.…”

“…The solid obtained by concentration was collected, and then purified by recrystallization. The new compounds were characterized by 1 H, 13 C NMR, IR spectroscopy and elemental analysis. The antibacterial and antifungal activities of the new compounds were analysed using agar diffusion and tenfold broth (pH 7.2 -7.4) dilution methods, in comparison with the clinical used drugs, ceftriaxone and Pimafucin.…”

“…H NMR (300 MHz, DMSO-d 6 , δ, ppm): 2.29 (E), 2.50 (Z) (3Н, s,6 C-CH 3 ,), 3.35-3.49 (Z, E) (4H, m, S(CH 2 ) 2 ), 5.68-5.77 (E, Z) (1H, m, OCH), 6.45 (E),6.48 (Z) (1H, s,5 C-H), 3.92 (Z), 4.26 (E) (1H, s, SCH 2 CO),10.29 (Z), 10.39 (E) (1H, wid s, CONH), 1.90 (E), 1.91 (Z) s (3Н, =С(СН 3 )); 1.92 (Z), 1.94 (E) s (3Н, =С(СН 3 )) 1. H NMR (300 MHz, CDCl 3 , δ, ppm): 2.35 (Z), 2.41 (E) (3Н, s,6 C-CH 3 ,), 3.33-3.37, 3.41-3.45(E), 3.49-3.54 (Z) (4H, m, S(CH 2 ) 2 ), 5.78-5.86 (E, Z) (1H, m, OCH),6.19 (E), 6.30 (Z) (1H, s,5 C-H),3.87 (Z), 4.29 (E) (1H, s, SCH 2 CO), 8.56 (Z), 9.57 (E) (1H, wid s, CONH), 1.78 (E), 1.91 (Z) s (3Н, =С(СН 3 )); 2.05 (Z), 2.07 (E) s (3Н, =С(СН 3 )) 13. C NMR (125,5 MHz, CDCl 3 , δ, ppm): 165.07 (E, Z) (C 6 ); 25.41 (E); 25.48 (Z) ( 6 C-CH 3 ); 102.13 (Z); 103.30 (E) ( 5 CH); 167.45 (Z); 167.65(E) ( 4 C); 69.51 (Z); 70.29 (E) (OC 3 ); 35.10 (E); 35.56 (Z) (SC 2,4 ); 168.30 (E); 168.49 (Z) ( 2 C); 33.35 (Z); 33.58 (E) (2-SCH 2 CO); 169.44 (Z); 170.02 (E) (2-SCH 2 CO); 16.10 (Z), 16.91 (E) (N=C(CH 3 )); 23.72 (Z), 23.93 (E) (N=C(CH 3 )); 150.21 (Z), 155.49 (E) (N=C).…”

Innovative antimicrobial substances based on uracil S‐derivatives

“…2-[6-methyl-2,4-dioxo-3-(thietan-3-yl)-1,2,3,4-tetrahydropyrimidin-1-yl]acetohydrazide (1) was synthesized as previously described (Meshcheryakova, et al, 2014a).…”