New quinoxaline derivatives as VEGFR-2 inhibitors with anticancer and apoptotic activity: design, molecular modeling, and synthesis was written by Alsaif, Nawaf A.;Dahab, Mohammed A.;Alanazi, Mohammed M.;Obaidullah, Ahmad J.;Al-Mehizia, Abdulrahman A.;Alanazi, Manal M.;Aldawas, Saleh;Mahdy, Hazem A.;Elkady, Hazem. And the article was included in Bioorganic Chemistry in 2021.Computed Properties of C8H4Cl2N2 This article mentions the following:
New series of [1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one I [R = Et, Ph, 3-ClC6H4, etc.; X = CH2] and [1,2,4]triazolo[4,3-a]quinoxaline derivatives I [X = SCH2] were designed, synthesized, and biol. assessed for their anti-proliferative activities against two selected tumor cell lines MCF-7 and HepG2. Comparing to sorafenib (IC50 = 2.17 ± 0.13 and 3.51 ± 0.21μM against MCF-7 and HepG2, resp.), compounds I [R = 4-ClC6H4, 2,5-di-ClC6H3, 2-HO-5-MeC6H3; X = CH2, SCH2] exhibited the highest activities against the examined cell lines with IC50 values extending from 4.1 ± 0.4 to 11.7 ± 1.1μM. Furthermore, VEGFR-2 inhibitory activities were assessed for all the synthesized compounds as potential mechanisms for their anti-proliferative activities. Compounds I [R = 4-ClC6H4, 2,5-di-ClC6H3, 2-HO-5-MeC6H3; X = CH2, SCH2] displayed prominent inhibitory efficiency vs. VEGFR-2 kinase with IC50 value ranging from 3.4 ± 0.3 to 6.8 ± 0.5 nM. Fascinatingly, the results of VEGFR-2 inhibitory assays were matched with that of the cytotoxicity data, where the most potent anti-proliferative derivatives exhibited promising VEGFR-2 inhibitory activities. Further studies displayed the ability of compound I [R = 4-ClC6H4; X = CH2] to induce apoptosis in HepG2 cells and can arrest the growth of such cells at the G2/M phase. Also, compound I [R = 4-ClC6H4; X = CH2] produced a significant increase in the level of BAX/Bcl-2 ratio (3.8-fold), caspase- 3 (1.8-fold), and caspase-9 (1.9-fold) compared to the control cells. Mol. docking studies were carried out to investigate the possible binding interaction inside the active site of the VEGFR-2. In the experiment, the researchers used many compounds, for example, 2,3-Dichloroquinoxaline (cas: 2213-63-0Computed Properties of C8H4Cl2N2).
2,3-Dichloroquinoxaline (cas: 2213-63-0) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. Quinoxaline and its analogues may also be formed by reduction of amino acids substituted 1,5-difluoro-2,4-dinitrobenzene (DFDNB),One study used 2-iodoxybenzoic acid (IBX) as a catalyst in the reaction of benzil with 1,2-diaminobenzene.Computed Properties of C8H4Cl2N2
Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider