Synthesis, anti-inflammatory screening, molecular docking, and COX-1,2/-5-LOX inhibition profile of some novel quinoline derivatives

Development of pyrazole derivatives in the management of inflammation

“…The pyrazole derivative–enzyme interaction has been evaluated using molecular docking. The result of this assessment provides the affinity of designed compounds and contributes to the detection of acceptable inhibitors of COX‐2 ( 15 ; 17 ; 23–32 ; 34–37 ; 39 ; 51 ; 58 ; 60 ; 61 ; 69–72 ; 74 ; 85–87 ) [18,26,27–34,35–39] and 5‐LOX ( 46 ; 63 ; 82–84 ) [40–42] catalytic activity. The energy score of docked derivatives appears related to the degree of enzyme inhibition and selectivity.…”

“…Like COX‐2, the inhibition of LOX is important for the development of nonulcerogenic and cardiotoxic drugs [56–58]. The diaryl pyrazoles ( 10 ; 11 ) inhibited COX‐2 and 15‐LOX, while others ( 15 ; 16–19 ; 46 ; 82–84 ) inhibited COX‐2 and 5‐LOX [16,18,38,41,42] in an immunoassay. The pleural exudate ( 44 ) [46], cerebrospinal fluid ( 77 ) [44], blood samples ( 49 ; 63–66 ) [40,52], or cell culture of RAW 264.7 macrophages ( 56 ; 59 ) revealed that some compounds were able to reduce PGE 2 levels [51,59].…”

“…The anti‐inflammatory or antinociceptive potential of some derivatives ( 22 ; 38–40 ; 43 ; 44 ; 46 ; 68 ; 77 ; 82–96 ; 98 ; 99 ; 103–109 ) was demonstrated in a nonspecific abdominal writhing test [29,31,41,42,44,45,61,63–65,71–76]. The anti‐inflammatory activity of several compounds ( 10–14 ; 16–19 ; 22–24 ; 27–33 ; 38 ; 40–44 ; 46 ; 49 ; 51 ; 54 ; 55 ; 57 ; 58 ; 60–67 ; 73 ; 74 ; 76 ; 79–87 ; 89–91 ) was assessed in carrageenan‐induced paw edema [16,18,26,27–29,31,32,35,36,37–42,46–49,52–55,61,71,77–79]. Furthermore, the antiedematogenic effect of some derivatives ( 15 ; 34–37 ; 50 ; 109 ) has been evaluated with formalin [30,34,38,76,80] and histamine‐induced paw edema ( 52 ) [81], in addition to xylene ( 48 ) [66] and croton oil‐induced ear edema ( 77 ; 109 ) [44,76].…”

“…The anti‐inflammatory activity of several compounds ( 10–14 ; 16–19 ; 22–24 ; 27–33 ; 38 ; 40–44 ; 46 ; 49 ; 51 ; 54 ; 55 ; 57 ; 58 ; 60–67 ; 73 ; 74 ; 76 ; 79–87 ; 89–91 ) was assessed in carrageenan‐induced paw edema [16,18,26,27–29,31,32,35,36,37–42,46–49,52–55,61,71,77–79]. Furthermore, the antiedematogenic effect of some derivatives ( 15 ; 34–37 ; 50 ; 109 ) has been evaluated with formalin [30,34,38,76,80] and histamine‐induced paw edema ( 52 ) [81], in addition to xylene ( 48 ) [66] and croton oil‐induced ear edema ( 77 ; 109 ) [44,76]. The ability of other pyrazole derivatives ( 22 ; 38–40 ; 43 ; 44 ; 68 ; 73 ; 74 ) to decreased the cell migration to inflamed tissue was demonstrated by reduction in leukocytes count of pleural exudate using a carrageenan‐induced pleurisy model [31,39,46,47,62,72,78].…”

Discovery of 2-Substituted 3-Arylquinoline Derivatives as Potential Anti-Inflammatory Agents Through Inhibition of LPS-Induced Inflammatory Responses in Macrophages

“…More recently, Chaaban et al have revealed that the compound 4 , i.e. ( E )-{3-chloro-2-{2-[1-(4-chlorophenyl)-3-(4-methoxyphenyl)-1 H -pyrazol-4-yl]vinyl}- quinolin-4-yl} (morpholino)methanone [14] is a selective COX-2 inhibitor with an IC 50 value of 0.10 μM. 3-(4-Methyl-2-oxo-1,2-dihydroquinolin-7-yl)-2-(4-nitrophenyl)thiazolidin-4-one ( 5 ) [15] was discovered to show potent anti-inflammatory activity in a carrageenan-induced paw edema model while methyl 6-methoxy-1-(4-methylbenzyl)-4-oxo-1,4-dihydroquinoline-2-carboxylate ( 6 ) [16] showed potent anti-inflammatory activity with a potency approximately equal to that of indomethacin.…”