A new series of thiazolyl pyrazoline derivatives linked to benzo[1,3]dioxole moiety: Synthesis and evaluation of antimicrobial and anti-proliferative activities
Safaa.I.elewa; Eman Mansour, Asmaa Aboelnaga, Ekhlass M. Nassar;
Abstract
2-(5-(Benzo[d][1,3]dioxol-5-yl)-3-(naphthalen-1-yl)-4,5-dihydro-1H-pyra zol-1-yl)-4-(4-substituted phenyl)thiazole (7) and thiazole derivatives
(9) were synthesized via reaction of 4,5-dihydro-1H-pyrazoles (5a,b)
with substituted phenacyl bromide and a number of a-halo-com pounds respectively. Also, (E)-2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(naph thalen-1-yl)-4,5 dihydro-1H-pyrazol-1-yl)-4-methyl-5-(substituted
phenyldiazenyl)thiazole (11) were prepared through reactions of car bothioamide (5a,b) with hydrazonoyl halides. In addition, thioamides
(5a–b) were used as starting materials for preparation of thiazoles
(12a–b) and benzylidene thiazoles (13a–b). Most of synthesized
compounds show interesting biological properties as antimicrobial
and antiproliferative activities, the results of minimum inhibitory con centration showed that pyrazole derivative 7c (MIC: 0.23 mg/mL)
showed better results when compared with 11c and 12a (MIC:
0.1–0.125 mg/mL) as obtained from their MIC values. On the other
hand, 2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(naphthalen-2-yl)-4,5-dihydro 1H-pyrazol-1-yl)-4-(4-chlorophenyl) thiazole (7c) can be considered as
the most promising anti-proliferative agent against HCT-116 cancer
cells owing to its notable inhibitory effect on HCT-116 cells with an
IC50 value of 6.19 mM.
(9) were synthesized via reaction of 4,5-dihydro-1H-pyrazoles (5a,b)
with substituted phenacyl bromide and a number of a-halo-com pounds respectively. Also, (E)-2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(naph thalen-1-yl)-4,5 dihydro-1H-pyrazol-1-yl)-4-methyl-5-(substituted
phenyldiazenyl)thiazole (11) were prepared through reactions of car bothioamide (5a,b) with hydrazonoyl halides. In addition, thioamides
(5a–b) were used as starting materials for preparation of thiazoles
(12a–b) and benzylidene thiazoles (13a–b). Most of synthesized
compounds show interesting biological properties as antimicrobial
and antiproliferative activities, the results of minimum inhibitory con centration showed that pyrazole derivative 7c (MIC: 0.23 mg/mL)
showed better results when compared with 11c and 12a (MIC:
0.1–0.125 mg/mL) as obtained from their MIC values. On the other
hand, 2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(naphthalen-2-yl)-4,5-dihydro 1H-pyrazol-1-yl)-4-(4-chlorophenyl) thiazole (7c) can be considered as
the most promising anti-proliferative agent against HCT-116 cancer
cells owing to its notable inhibitory effect on HCT-116 cells with an
IC50 value of 6.19 mM.
Other data
Title | A new series of thiazolyl pyrazoline derivatives linked to benzo[1,3]dioxole moiety: Synthesis and evaluation of antimicrobial and anti-proliferative activities | Authors | Safaa.I.elewa ; Eman Mansour, Asmaa Aboelnaga, Ekhlass M. Nassar | Keywords | Acetylnaphthalene;anti microbial and anti proliferative;carbothioa mide;chalcone; piperonal;thiazole;pyrazolin | Issue Date | 2020 | Publisher | Taylor & francis | Journal | SYNTHETIC COMMUNICATIONS | Volume | 50 | Issue | 3 | Start page | 368 | End page | 379 |
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