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Synthesis and Antiviral Studies of Novel N-Sulphonamidomethyl piperazinyl Fluoroquinolones.

Selvam P, Rathore P, Karthikumar S, Velkumar K, Palanisamy P, Vijayalakhsmi S, Witvrouw M - Indian J Pharm Sci (2009)

Bottom Line: Cytotoxicity of the synthesized compounds was also tested in mock-infected MDCK and MT-4 cells.All compounds displayed cytostatic propertity in MT-4 cells.Among the compounds tested, GF-SDM (CC(50)=39.44 muM) most toxic compound in this series.

View Article: PubMed Central - PubMed

Affiliation: Arulmigu Kalasalingam College of Pharmacy, Anand Nagar, Krishnankoil-626 190, India.

ABSTRACT
A series of novel N-Sulphonamidomethyl piperzinyl fluoroquinolones were synthesized and screened antiviral activity. Eight compounds were synthesized through modifying the N(4)-hydrogen of piperazine in fluoroquinolones with formaldehyde and sulphanomides by Mannich reactions. The structures of the synthesized compounds were characterized by means of their IR and (1)H-NMR spectral data. Synthesized compounds were screened for antiviral activity against influenza A (H1N1, H3N2, H5N1) and influenza B viruses in MDCK cell culture. The antiHIV activities of the new compounds were screened for antiviral activity against replication of HIV-1(III(B)) in MT-4 cells. Cytotoxicity of the synthesized compounds was also tested in mock-infected MDCK and MT-4 cells. Compound CF-SD and CF-SDM inhibits the influenza A (H1N1) and compound GF-SDM inhibit the replication of influenza A (H5N1) and B in MDCK cells. All compounds displayed cytostatic propertity in MT-4 cells. Among the compounds tested, GF-SDM (CC(50)=39.44 muM) most toxic compound in this series.

No MeSH data available.


Related in: MedlinePlus

Synthesis of N-sulphonamidomethyl fluoroquinolones For NF-SA, R1 is ethyl, R2 is H and R3 is benzenesulphonamide; for NF-SD, R1 is ethyl, R2 is H and R3 is -(2-pyrimidinyl)-benzenesulphonamide; NF-SDM, R1 is ethyl, R2 is H and R3 is -(4,6-dimethyl-2-primidiniyl)-benzenesulphonamide; for GF-SA, R1 is cyclopropyl, R2 is methoxy and R3 is benzenesulphonamide; for GF-SD, R1 is cyclopropyl, R2 is methoxy and R3 is -(2-pyrimidinyl)-benzenesulphonamide; for GF-SDM, R1 is cyclopropyl, R2 is methoxy and R3 is -(4,6-dimethyl-2-primidiniyl)-benzenesulphonamide; for CF-SD, R1 cyclopropyl, R2 is H and R3 is -(2-pyrimidinyl)-benzenesulphonamide; for CF-SDM, R1 is cyclopropyl, R2 is H and R3 is -(4,6-dimethyl -2-primidiniyl)-benzenesulphonamide.
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Figure 0001: Synthesis of N-sulphonamidomethyl fluoroquinolones For NF-SA, R1 is ethyl, R2 is H and R3 is benzenesulphonamide; for NF-SD, R1 is ethyl, R2 is H and R3 is -(2-pyrimidinyl)-benzenesulphonamide; NF-SDM, R1 is ethyl, R2 is H and R3 is -(4,6-dimethyl-2-primidiniyl)-benzenesulphonamide; for GF-SA, R1 is cyclopropyl, R2 is methoxy and R3 is benzenesulphonamide; for GF-SD, R1 is cyclopropyl, R2 is methoxy and R3 is -(2-pyrimidinyl)-benzenesulphonamide; for GF-SDM, R1 is cyclopropyl, R2 is methoxy and R3 is -(4,6-dimethyl-2-primidiniyl)-benzenesulphonamide; for CF-SD, R1 cyclopropyl, R2 is H and R3 is -(2-pyrimidinyl)-benzenesulphonamide; for CF-SDM, R1 is cyclopropyl, R2 is H and R3 is -(4,6-dimethyl -2-primidiniyl)-benzenesulphonamide.

Mentions: Synthesis of N-sulphonamidomethyl fluoroquinolones derivatives was achieved by stirring on equimolar (0.01 mol) mixture of sulphonamides (sulphonamide, sulphadiazine and sulphadimidine), formaldehyde (37% v/v, ml) and fluoroquinolone (norfloxacin NF, ciprofloxacin CF and gatifloxacin GF) with ethanol using a magnetic stirrer for 3 h (Scheme 1). The mixture was allowed to cool over night in a refrigerator. The solid thus obtained was recrystallized from DMF with ethanol.


Synthesis and Antiviral Studies of Novel N-Sulphonamidomethyl piperazinyl Fluoroquinolones.

Selvam P, Rathore P, Karthikumar S, Velkumar K, Palanisamy P, Vijayalakhsmi S, Witvrouw M - Indian J Pharm Sci (2009)

Synthesis of N-sulphonamidomethyl fluoroquinolones For NF-SA, R1 is ethyl, R2 is H and R3 is benzenesulphonamide; for NF-SD, R1 is ethyl, R2 is H and R3 is -(2-pyrimidinyl)-benzenesulphonamide; NF-SDM, R1 is ethyl, R2 is H and R3 is -(4,6-dimethyl-2-primidiniyl)-benzenesulphonamide; for GF-SA, R1 is cyclopropyl, R2 is methoxy and R3 is benzenesulphonamide; for GF-SD, R1 is cyclopropyl, R2 is methoxy and R3 is -(2-pyrimidinyl)-benzenesulphonamide; for GF-SDM, R1 is cyclopropyl, R2 is methoxy and R3 is -(4,6-dimethyl-2-primidiniyl)-benzenesulphonamide; for CF-SD, R1 cyclopropyl, R2 is H and R3 is -(2-pyrimidinyl)-benzenesulphonamide; for CF-SDM, R1 is cyclopropyl, R2 is H and R3 is -(4,6-dimethyl -2-primidiniyl)-benzenesulphonamide.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC2865816&req=5

Figure 0001: Synthesis of N-sulphonamidomethyl fluoroquinolones For NF-SA, R1 is ethyl, R2 is H and R3 is benzenesulphonamide; for NF-SD, R1 is ethyl, R2 is H and R3 is -(2-pyrimidinyl)-benzenesulphonamide; NF-SDM, R1 is ethyl, R2 is H and R3 is -(4,6-dimethyl-2-primidiniyl)-benzenesulphonamide; for GF-SA, R1 is cyclopropyl, R2 is methoxy and R3 is benzenesulphonamide; for GF-SD, R1 is cyclopropyl, R2 is methoxy and R3 is -(2-pyrimidinyl)-benzenesulphonamide; for GF-SDM, R1 is cyclopropyl, R2 is methoxy and R3 is -(4,6-dimethyl-2-primidiniyl)-benzenesulphonamide; for CF-SD, R1 cyclopropyl, R2 is H and R3 is -(2-pyrimidinyl)-benzenesulphonamide; for CF-SDM, R1 is cyclopropyl, R2 is H and R3 is -(4,6-dimethyl -2-primidiniyl)-benzenesulphonamide.
Mentions: Synthesis of N-sulphonamidomethyl fluoroquinolones derivatives was achieved by stirring on equimolar (0.01 mol) mixture of sulphonamides (sulphonamide, sulphadiazine and sulphadimidine), formaldehyde (37% v/v, ml) and fluoroquinolone (norfloxacin NF, ciprofloxacin CF and gatifloxacin GF) with ethanol using a magnetic stirrer for 3 h (Scheme 1). The mixture was allowed to cool over night in a refrigerator. The solid thus obtained was recrystallized from DMF with ethanol.

Bottom Line: Cytotoxicity of the synthesized compounds was also tested in mock-infected MDCK and MT-4 cells.All compounds displayed cytostatic propertity in MT-4 cells.Among the compounds tested, GF-SDM (CC(50)=39.44 muM) most toxic compound in this series.

View Article: PubMed Central - PubMed

Affiliation: Arulmigu Kalasalingam College of Pharmacy, Anand Nagar, Krishnankoil-626 190, India.

ABSTRACT
A series of novel N-Sulphonamidomethyl piperzinyl fluoroquinolones were synthesized and screened antiviral activity. Eight compounds were synthesized through modifying the N(4)-hydrogen of piperazine in fluoroquinolones with formaldehyde and sulphanomides by Mannich reactions. The structures of the synthesized compounds were characterized by means of their IR and (1)H-NMR spectral data. Synthesized compounds were screened for antiviral activity against influenza A (H1N1, H3N2, H5N1) and influenza B viruses in MDCK cell culture. The antiHIV activities of the new compounds were screened for antiviral activity against replication of HIV-1(III(B)) in MT-4 cells. Cytotoxicity of the synthesized compounds was also tested in mock-infected MDCK and MT-4 cells. Compound CF-SD and CF-SDM inhibits the influenza A (H1N1) and compound GF-SDM inhibit the replication of influenza A (H5N1) and B in MDCK cells. All compounds displayed cytostatic propertity in MT-4 cells. Among the compounds tested, GF-SDM (CC(50)=39.44 muM) most toxic compound in this series.

No MeSH data available.


Related in: MedlinePlus