Synthesis and Evaluation Antibacterial Activity of Some New Substituted 5-Bromoisatin Containing Five, Six Heterocyclic Ring

Abstract

This research includes the synthesis of some new different heterocyclic derivatives of 5-Bromoisatin. New sulfonylamide, diazine, oxazole, thiazole and 1,2,3-triazole derivatives of 5-Bromoisatin have been synthesized. The synthesis process started by the reaction of 5-Bromoisatin with different reagents to obtain schiff bases of 5-Bromoisatin intermediate compounds(1, 8, 19) by using glacial acetic acid as a catalyst in three routes. The first route, 5-Bromoisatin reacted with p-aminosulfonylchloride to product compound(1), then converted to sulfonyl amide derivatives(2-7) by the reaction of compound(1) with different substituted primary aromatic amine in absolute ethanol. The second route includes the reaction of 5-Bromoisatin reacted with ethyl glycinate to give 5-bromo-3-(Ethyl imino acetate)-2-oxo indole(8), which undergo react with hydrazine hydrate 80% to obtain hydrazine derivatives(9) that react with different acid anhydrides to obtain diazine derivatives(10-14). Also compound(8) reacts with urea and thiourea to give compounds(15,16) which undergo cyclization with p-bromophenacylbromide in absolute ethanol as a solvent to obtain oxazole (17) and thiazole (18), respectively. The third route included the reaction of 5-Bromoisatin with p-phenylenediamine in ethanol to obtain compound(19) which is converted to new substitutes 1,2,3-triazole derivatives(22,23) by diazotation of compound(19) and treating the resulted salt(20) with sodium azid, then acetylaceton or ethylacetoacetate, respectively. Newly synthesized compounds were identified by spectral methods. (FTIR, 1H-NMR, 13C-NMR) and measurements of some of its physical properties and also some specific reactions. Furthermore the effects of the synthesized compounds were studied on some strains of bacteria.

Synthesis, Characterization Of Thiazolidin-4-one, Oxazolidin-4-one And Imidazolidin-4-one Derivatives From 6-Amino-1, 3-dimethyluraciland Evaluation Of Their Antioxidant And Antimicrobial Agent

“…Compounds (9 and 19) have no inhibition against antifungal activity. While compound (15) have a strong and spesific inhibition zone against Candida parapsilosis but the rest of fungi had no inhibition as shown as Table (8).…”

“…The product was filtered and washed with water then further purification was done using recrystallized from ethanol. Some of the physical properties and yield of compounds (7)(8)(9)(10)(11)(12) are listed in Table (3.45).…”

“…1 H-NMR spectrum of compound (8) proved the disappearance of singlet signal of (N=CH-) of Schiff's base (2) and appearance a singlet signal at δ=(3.08)ppm of (-CH 3 ) protons, a singlet signal at δ=(3.28)ppm for ( ) protons, a singlet signal at δ=(3.75)ppm of (S-CH 2 ) thiazolidin-4-one ring protons (Kumar et al, 2019), a singlet signal at δ=(4.99)ppm for (N-C-H) thiazolidin-4-one ring proton, a singlet signal at δ=(5.03)ppm due to (=CH-) proton and multi signals at δ=(6.76-7.73)ppm belonged to aromatic ring protons. 1 H-NMR spectral data of compound (8) showed in Table ( 5) and 13 C-NMR spectral data are listed in Table (6).…”

Synthesis, identification of some new tetrazoline, thiazolidin-4-one and imidazolidin-4-one derivatives and evaluation anticancer of their molecular docking and anti-oxidant experimental

“…Sodium azide (0.05 g, 0.0009 mol.) dissolved in the same solvent was added and the solution was reflex for (18)(19)(20) house. The product was filtrated, water washed and recrystallized by ethanol Table-2 lists some of the physical properties of compounds (6)(7)(8)(9)(10) as well as FTIR spectral data.…”

“…as a result of their ease of synthesis, uracil derivatives are regarded as promising compounds in drug discovery. The pyrimidine core is an important pharmacophore moiety of biologically active natural and synthetic compounds that compete for the same binding sites [15] the most conmen biological activities of uracil derivatives in the last years application Antioxidan t [2], Anti-flamatory [16], Anticaner [17], Anti-leukemia [18], Antibacterial [19,20], anti-tumour [21], anti-angiogenesis [22] and Anti-diabetic [23].…”