952-10-3Relevant articles and documents
Design, synthesis, antimicrobial activity and molecular docking studies of some novel di-substituted sulfonylquinoxaline derivatives
Ali, Abeer M.,Ammar, Yousry A.,Askar, Ahmed A.,Belal, Amany,Elsisi, Doaa M.,Farag, Awatef A.,Ragab, Ahmed
, (2020)
2,3-Dioxo-1,2,3,4-tetrahydroquinoxaline-6-sulfonyl chloride 1 was prepared via reaction of o-phenylene diamine with oxalic acid followed by chlorosulfonation with excess chlorosulfonic acid. A series of new sulfonylquinoxaline derivatives 2–6 were obtained upon reacting compound 1 with different types of amines. 2,3-Dichloro-6-morpholinosulfonylquinoxaline derivative 6 was subjected to further chemical reactions to afford many derivatives of 6-morpholino 2,3-disubstitutedquinoxalines, thus reaction of compound 6 with different secondary amines yielded mono and di secondary aminoquinoxaline derivatives 7–10 depending on the reactivity difference of the two chlorine atoms. Hydrazinolysis of compound 7 furnished hydrazino quinoxaline derivatives 11a-c. Additionally triazolo and pyrazolyl quinoxaline derivatives 12–14 were obtained through the reaction of compound 11a with phenyl isothiocyanate, formylpyrazole and ethyl acetoacetate. All the synthesized compounds were screened for their antibacterial and antifungal activities. Compounds 7a, 9b, 10a, 10c, 10f and 11c showed good to moderate antimicrobial activity against the tested Gram-positive, Gram-negative bacteria and fungi with MIC values ranging from 2.44 to 180.14 μM. Their MBC values were also evaluated using the same tested microorganisms. Moreover, screening against multi-drug resistant strains revealed the promiscuity of these new derivatives, especially compound 7a that showed comparable antibacterial activity (MIC 4.91–9.82 μM) with Norfloxacin (MIC 2.44–9.80 μM). Furthermore, these compounds were evaluated as DNA Gyrase inhibitors and the obtained results were in the range of 15.69–23.72 μM. Immunomodulatory effect was also investigated and compounds 7a, 11c, 10f, 10c, 10a and 9b showed high immunostimulatory action with ratio (142.6 ± 0.4, 135.7 ± 0.5, 117.8 ± 0. 39, 112.5 ± 0. 83, 86.4 ± 0. 47, 72.8 ± 0. 77) respectively. Molecular docking studies of the promising derivatives into DNA Gyrase binding site proved the usefulness of hybridizing quinoxaline scaffold with SO2 and morpholine moieties as a hopeful strategy in designing new DNA Gyrase binding molecules.
Synthesis and characterization of some novel quinoxaline-2, 3-dione derivatives: A preliminary investigation on their activity against a human epithelial carcinoma cell line
Jubie, Selvaraj,Gayathri, Rajamanickam,Srividya, Ammayappan Byung,Kalirajan, Rajagopal,Prabitha, Prabakaran,Sankar, Sundaram,Elango, Kannan
experimental part, p. 317 - 320 (2012/05/20)
Quinoxaline-2, 3-dione obtained from cyclocondensation reaction of o-phenylene diamine with oxalic acid, was reacted with chlorosulphonic acid under cold condition followed by a reaction with various benzimidazoles to give 2, 3- dioxo-1, 2, 3, 4-tetrahydroquinoxaline-6-sulphonyl benzimidazoles in satisfactory yield. Their structures were confirmed using 1H NMR, IR and mass analysis. Cytotoxicity of these derivatives were evaluated by growth inhibition of HEp-2 cells in vitro. The preliminary bioassay indicated that these compounds showed moderate cytotoxicity.
Synthesis of some sulfonamide derivatives with potential antibacterial activity
El-Din, Nabaweya Sharaf
, p. 449 - 454 (2007/10/03)
Some new quinoxaline-6-sulfonamide and phthalazine-6-sulfonamide derivatives were synthesized. The majority of the prepared compounds showed antibacterial activity.
