616205-91-5Relevant academic research and scientific papers
Synthesis and antidiabetic activity of 5,7-dihydroxyflavonoids and analogs
Chang, Liu-Shuan,Li, Chun-Bao,Qin, Nan,Jin, Mei-Na,Duan, Hong-Quan
, p. 162 - 169 (2012)
In a study to evaluate the structural elements essential for the antidiabetic activity of flavonoids, we synthesized two series of flavonoids, 5,7-dihydroxyflavanones and 5,7-dihydroxyflavones. In a screening for potential antidiabetic activity, most of the flavonoids showed a remarkable in vitro activity, and compounds 1f, 2d, and 3c were significantly more effective than the positive control, metformin. The biological activity was mainly affected by structural modification at the ring B moiety of the flavonoid skeleton. The results suggest that 5,7-dihydroxyflavonoids can be considered as promising candidates in the development of new antidiabetic lead compounds. Copyright
Biological activity evaluation and molecular docking study of chromone derivatives as cyclooxygenase-2 inhibitors
Maicheen, Chirattikan,Phosrithong, Narumol,Ungwitayatorn, Jiraporn
, p. 662 - 671 (2017/02/15)
A series of chromone derivatives have been evaluated as potential cyclooxygenase-2 (COX-2) inhibitors. The four most potent compounds, 48, 41, 39, and 35 displayed IC50 values of 3.30, 6.86, 7.36 and 7.46 μM, respectively. Compounds 35 and 38 showed higher selectivity for COX-2 (selectivity index, SI = 7.48 and 5.46, respectively) than celecoxib (SI = 4.17 in the same test) whereas compound 39 showed comparable selectivity (SI = 4.19) to celecoxib. The molecular volumes of compounds 35 (312.84 ?3) and 38 (314.18 ?3) were similar to celecoxib (299.28 ?3) but larger than ibuprofen (211.83 ?3). Docking results were in good agreement with the experimental biological data in terms of evaluation of binding energy and binding mode. Compounds 35, 38, and 39 had higher binding affinity against COX-2 (binding energy between ?9.77 and ?11.42 kcal/mole) than COX-1 (binding energy between ?6.28 and ?7.88 kcal/mole). These three chromone compounds also displayed active conformation in the same orientation as that of celecoxib. Thus, compounds in this series has the potential to be a new class of selective COX-2 inhibitor.
Antimalarial activity of HIV-1 protease inhibitor in chromone series
Lerdsirisuk, Pradith,Maicheen, Chirattikan,Ungwitayatorn, Jiraporn
, p. 142 - 147 (2015/02/05)
Increasing parasite resistance to nearly all available antimalarial drugs becomes a serious problem to human health and necessitates the need to continue the search for new effective drugs. Recent studies have shown that clinically utilized HIV-1 protease (HIV-1 PR) inhibitors can inhibit the in vitro and in vivo growth of Plasmodium falciparum. In this study, a series of chromone derivatives possessing HIV-1 PR inhibitory activity has been tested for antimalarial activity against P. falciparum (K1 multi-drug resistant strain). Chromone 15, the potent HIV-1 PR inhibitor (IC50 = 0.65 μM), was found to be the most potent antimalarial compound with IC50 = 0.95 μM while primaquine and tafenoquine showed IC50 = 2.41 and 1.95 μM, respectively. Molecular docking study of chromone compounds against plasmepsin II, an aspartic protease enzyme important in hemoglobin degradation, revealed that chromone 15 exhibited the higher binding affinity (binding energy = -13.24 kcal/mol) than the known PM II inhibitors. Thus, HIV-1 PR inhibitor in chromone series has the potential to be a new class of antimalarial agent.
