Limits...
Design, Synthesis and antiHIV activity of Novel Isatine-Sulphonamides.

Selvam P, Murugesh N, Chandramohan M, Debyser Z, Witvrouw M - Indian J Pharm Sci (2008)

Bottom Line: A series of novel isatine-sulphonamide derivatives have been synthesized by combining isatin derivatives with sulphonamides.The structure of the synthesized compounds were elucidated by spectral analysis (IR, NMR and Mass).Investigation of anti-HIV activity was done against HIV-1(IIIB) in MT-4 cells and HIV integrase inhibitory activity. 4-(1-acetyl-5-methyl-2-oxoindolin-3-ylideneamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (SPIII-5ME-AC) inhibits the HIV Integrase enzymatic activity as both over all and strand transfer reaction and 4-(1-benzoyl-5-chloro-2-oxoindolin-3-ylideneamino)-N-(4,6-dimethylpyrimidin-2-yl)benzene sulfonamide (SPIII-5Cl-BZ) exhibits 36 percent maximum protection against HIV-1 at sub toxic concentration.

View Article: PubMed Central - PubMed

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

ABSTRACT
A series of novel isatine-sulphonamide derivatives have been synthesized by combining isatin derivatives with sulphonamides. The structure of the synthesized compounds were elucidated by spectral analysis (IR, NMR and Mass). Investigation of anti-HIV activity was done against HIV-1(IIIB) in MT-4 cells and HIV integrase inhibitory activity. 4-(1-acetyl-5-methyl-2-oxoindolin-3-ylideneamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (SPIII-5ME-AC) inhibits the HIV Integrase enzymatic activity as both over all and strand transfer reaction and 4-(1-benzoyl-5-chloro-2-oxoindolin-3-ylideneamino)-N-(4,6-dimethylpyrimidin-2-yl)benzene sulfonamide (SPIII-5Cl-BZ) exhibits 36 percent maximum protection against HIV-1 at sub toxic concentration.

No MeSH data available.


Related in: MedlinePlus

synthesis of isatinsulphonamide derivativesFor SPIII-S, R is H, R1 is H and R2 is H; for SPIII-SMe, R is CH3, R1 is H and R2 is H; for SPIII-SCl, R is Cl, R1 is H and R2 is H; for SPIII-SM, R is Cl, R1 is H and R2 is 4,5-dimethyl-2-isoxazolyl; for SPIII-5Br-AC, R is Br, R1 is COCH3 and R2 is 4,6-dimethyl-2-pyrimidinyl; for SPIII-5Br-BZ, R is Br, R1 is COC6H5 and R2 is 4,6-dimethyl-2-pyrimidinyl; for SPIII-5Me-AC, R is CH3, R1 is COCH3 and R2 is 4,6-dimethyl-2-pyrimidinyl and for SPIII-5Cl-BZ, R is Cl, R1 is COC6H5 and R2 is 4,6-dimethyl-2-pyrimidinyl
© Copyright Policy - open-access
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC3040873&req=5

Figure 0001: synthesis of isatinsulphonamide derivativesFor SPIII-S, R is H, R1 is H and R2 is H; for SPIII-SMe, R is CH3, R1 is H and R2 is H; for SPIII-SCl, R is Cl, R1 is H and R2 is H; for SPIII-SM, R is Cl, R1 is H and R2 is 4,5-dimethyl-2-isoxazolyl; for SPIII-5Br-AC, R is Br, R1 is COCH3 and R2 is 4,6-dimethyl-2-pyrimidinyl; for SPIII-5Br-BZ, R is Br, R1 is COC6H5 and R2 is 4,6-dimethyl-2-pyrimidinyl; for SPIII-5Me-AC, R is CH3, R1 is COCH3 and R2 is 4,6-dimethyl-2-pyrimidinyl and for SPIII-5Cl-BZ, R is Cl, R1 is COC6H5 and R2 is 4,6-dimethyl-2-pyrimidinyl

Mentions: Isatin (2,3-dioxoindole), a versatile lead molecule for potential bioactive agents and its derivatives were reported to possess wide spectrum of activity. Methisazone (N-methylisatin-ß-thiosemicarbazone) was one of the first clinically used synthetic antiviral agents1. N-Methyl isatin-β-4':4'-diethylthiosemicarbazone was found to inhibit Maloney leukemia virus replication2. N,N-disubstituted thiosemicarbazone derivatives of isatin were tested for inhibition of HIV-1 replication3. Schiff and Mannich bases of isatin derivatives were synthesized and evaluated for antiviral activity. Some of their derivatives showed significant inhibitory activity against the replication of HIV-14–10. In earlier studies, some novel isatin derivatives were synthesized and evaluated for antiviral, anticancer and antibacterial activities1112. These compounds showed significant inhibitory effects against HIV-1 replication. In this study we describe the antiviral activity of some novel of isatine-sulphonamide derivatives (Scheme 1) against HIV-1 in MT-4 cells. These studies prompted us to investigate their inhibitory effect against HIV integrase.


Design, Synthesis and antiHIV activity of Novel Isatine-Sulphonamides.

Selvam P, Murugesh N, Chandramohan M, Debyser Z, Witvrouw M - Indian J Pharm Sci (2008)

synthesis of isatinsulphonamide derivativesFor SPIII-S, R is H, R1 is H and R2 is H; for SPIII-SMe, R is CH3, R1 is H and R2 is H; for SPIII-SCl, R is Cl, R1 is H and R2 is H; for SPIII-SM, R is Cl, R1 is H and R2 is 4,5-dimethyl-2-isoxazolyl; for SPIII-5Br-AC, R is Br, R1 is COCH3 and R2 is 4,6-dimethyl-2-pyrimidinyl; for SPIII-5Br-BZ, R is Br, R1 is COC6H5 and R2 is 4,6-dimethyl-2-pyrimidinyl; for SPIII-5Me-AC, R is CH3, R1 is COCH3 and R2 is 4,6-dimethyl-2-pyrimidinyl and for SPIII-5Cl-BZ, R is Cl, R1 is COC6H5 and R2 is 4,6-dimethyl-2-pyrimidinyl
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3040873&req=5

Figure 0001: synthesis of isatinsulphonamide derivativesFor SPIII-S, R is H, R1 is H and R2 is H; for SPIII-SMe, R is CH3, R1 is H and R2 is H; for SPIII-SCl, R is Cl, R1 is H and R2 is H; for SPIII-SM, R is Cl, R1 is H and R2 is 4,5-dimethyl-2-isoxazolyl; for SPIII-5Br-AC, R is Br, R1 is COCH3 and R2 is 4,6-dimethyl-2-pyrimidinyl; for SPIII-5Br-BZ, R is Br, R1 is COC6H5 and R2 is 4,6-dimethyl-2-pyrimidinyl; for SPIII-5Me-AC, R is CH3, R1 is COCH3 and R2 is 4,6-dimethyl-2-pyrimidinyl and for SPIII-5Cl-BZ, R is Cl, R1 is COC6H5 and R2 is 4,6-dimethyl-2-pyrimidinyl
Mentions: Isatin (2,3-dioxoindole), a versatile lead molecule for potential bioactive agents and its derivatives were reported to possess wide spectrum of activity. Methisazone (N-methylisatin-ß-thiosemicarbazone) was one of the first clinically used synthetic antiviral agents1. N-Methyl isatin-β-4':4'-diethylthiosemicarbazone was found to inhibit Maloney leukemia virus replication2. N,N-disubstituted thiosemicarbazone derivatives of isatin were tested for inhibition of HIV-1 replication3. Schiff and Mannich bases of isatin derivatives were synthesized and evaluated for antiviral activity. Some of their derivatives showed significant inhibitory activity against the replication of HIV-14–10. In earlier studies, some novel isatin derivatives were synthesized and evaluated for antiviral, anticancer and antibacterial activities1112. These compounds showed significant inhibitory effects against HIV-1 replication. In this study we describe the antiviral activity of some novel of isatine-sulphonamide derivatives (Scheme 1) against HIV-1 in MT-4 cells. These studies prompted us to investigate their inhibitory effect against HIV integrase.

Bottom Line: A series of novel isatine-sulphonamide derivatives have been synthesized by combining isatin derivatives with sulphonamides.The structure of the synthesized compounds were elucidated by spectral analysis (IR, NMR and Mass).Investigation of anti-HIV activity was done against HIV-1(IIIB) in MT-4 cells and HIV integrase inhibitory activity. 4-(1-acetyl-5-methyl-2-oxoindolin-3-ylideneamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (SPIII-5ME-AC) inhibits the HIV Integrase enzymatic activity as both over all and strand transfer reaction and 4-(1-benzoyl-5-chloro-2-oxoindolin-3-ylideneamino)-N-(4,6-dimethylpyrimidin-2-yl)benzene sulfonamide (SPIII-5Cl-BZ) exhibits 36 percent maximum protection against HIV-1 at sub toxic concentration.

View Article: PubMed Central - PubMed

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

ABSTRACT
A series of novel isatine-sulphonamide derivatives have been synthesized by combining isatin derivatives with sulphonamides. The structure of the synthesized compounds were elucidated by spectral analysis (IR, NMR and Mass). Investigation of anti-HIV activity was done against HIV-1(IIIB) in MT-4 cells and HIV integrase inhibitory activity. 4-(1-acetyl-5-methyl-2-oxoindolin-3-ylideneamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (SPIII-5ME-AC) inhibits the HIV Integrase enzymatic activity as both over all and strand transfer reaction and 4-(1-benzoyl-5-chloro-2-oxoindolin-3-ylideneamino)-N-(4,6-dimethylpyrimidin-2-yl)benzene sulfonamide (SPIII-5Cl-BZ) exhibits 36 percent maximum protection against HIV-1 at sub toxic concentration.

No MeSH data available.


Related in: MedlinePlus