TY - JOUR
T1 - Synthesis and biological activity of novel amidrazones incorporating 5-nitroimidazole, ciprofloxacin, and 7-chloro-4-piperazinylquinoline
AU - Saadeh, Haythem A.
AU - Al-Qaoud, Khaled M.
AU - Abu-Qatouseh, Luay F.
AU - Shihab, Penelope A.
AU - Kaur, Hargobinder
AU - Goyal, Kapil
AU - Sehgal, Rakesh
AU - Mubarak, Mohammad S.
N1 - Publisher Copyright:
© 2014 Springer Science+Business Media New York.
PY - 2015/5/1
Y1 - 2015/5/1
N2 - Abstract Series of new amidrazones Ia-c, IIa-c, and IIIc, incorporating 5-nitroimidazole (a), ciprofloxacin (b), and 7-chloro-4-piperazinylquinoline (c) moieties, were synthesized by reacting hydrazonoyl chlorides I-III, derived from 4-fluoroaniline and 4-chloroaniline with the proper amine, in the presence of triethylamine. Structures of the prepared compounds were confirmed by 1H NMR, 13C NMR, and ESI-HRMS spectral data. The antitumor, antibacterial, and antiparasitic activities of the newly synthesized compounds were evaluated. Compounds Ic and IIc exhibited strong anticancer activity against all tested cancer cell lines. In addition, compounds Ia and IIa displayed stronger antimicrobial potency than metronidazole against microaerophilic bacteria. Compounds IIa, IIIc, and IIc, exhibited remarkable antigiardial activity and were found to be more active than metronidazole with IC50 of 5.6, 5.9, and 6.8 μg/mL, respectively. Compounds Ia, Ib, and Ic also exhibited antigiardial activity with similar IC50 values compared to the reference drug metronidazole (IC50 = 6.9 μg/mL). On the other hand, compounds Ia, Ib, and IIa exhibited significant antitrichomonal activity and found to be more active than metronidazole with IC50 of 3.79, 4.6, and 5.1 μg/mL, respectively, compared to the reference drug metronidazole (8.79 μg/mL).
AB - Abstract Series of new amidrazones Ia-c, IIa-c, and IIIc, incorporating 5-nitroimidazole (a), ciprofloxacin (b), and 7-chloro-4-piperazinylquinoline (c) moieties, were synthesized by reacting hydrazonoyl chlorides I-III, derived from 4-fluoroaniline and 4-chloroaniline with the proper amine, in the presence of triethylamine. Structures of the prepared compounds were confirmed by 1H NMR, 13C NMR, and ESI-HRMS spectral data. The antitumor, antibacterial, and antiparasitic activities of the newly synthesized compounds were evaluated. Compounds Ic and IIc exhibited strong anticancer activity against all tested cancer cell lines. In addition, compounds Ia and IIa displayed stronger antimicrobial potency than metronidazole against microaerophilic bacteria. Compounds IIa, IIIc, and IIc, exhibited remarkable antigiardial activity and were found to be more active than metronidazole with IC50 of 5.6, 5.9, and 6.8 μg/mL, respectively. Compounds Ia, Ib, and Ic also exhibited antigiardial activity with similar IC50 values compared to the reference drug metronidazole (IC50 = 6.9 μg/mL). On the other hand, compounds Ia, Ib, and IIa exhibited significant antitrichomonal activity and found to be more active than metronidazole with IC50 of 3.79, 4.6, and 5.1 μg/mL, respectively, compared to the reference drug metronidazole (8.79 μg/mL).
KW - Amidrazones
KW - Anticancer
KW - Antigiardial and antitrichomonal activities
KW - Antimicrobial activity
KW - Ciprofloxacin
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U2 - 10.1007/s00044-014-1288-2
DO - 10.1007/s00044-014-1288-2
M3 - Article
AN - SCOPUS:84939961945
SN - 1054-2523
VL - 24
SP - 2247
EP - 2256
JO - Medicinal Chemistry Research
JF - Medicinal Chemistry Research
IS - 5
M1 - 1288
ER -