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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

Structure of SPIII lead molecule
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Figure 0002: Structure of SPIII lead molecule

Mentions: 4-(1-acetyl-5-methyl-2-oxoindolin-3-ylideneamino)-N-(4,6-dimethylpyrimidin-2-yl)benzene sulfonamide (SPIII-5ME-AC) inhibits the HIV Integrase enzymatic activity and 4-(1-benzoyl-5-chloro-2-oxoindolin-3-ylideneamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (SPIII-5Cl-BZ) exhibits 36 percent maximum protection against HIV-1 at subtoxic concentration. None of the compounds exhibited antiHIV effect and all the compounds displayed cytotoxic properties in the lymphocyte cell line (MT-4 cells). The 50% effective concentration (EC50) values of the synthesized compounds against the replication of HIV-1(IIIB) in acutely infected MT-4 cells were higher than the cytotoxic concentration (CC50). Lead molecules isatins (isatin, 5-chloroisatin, 5-bromoisatin, and 5-methylisatin) and sulphadimidine not active against HIV-1(IIIB) in MT-4 cells, but the combined product isatinesulphadimidine (SPIII, fig. 1 and Table 1) were active against HIV-1 and 2 in MT-4 cells13. Presence of 4,6-dimethylpyrimidinyl group in SO2NH2 of Isatine-sulphadimidine (SPIII) lead molecule is essential for antiHIV activity. Substitution in NH group of isatin (N-acylation) abolishes the antiHIV activity of the lead molecule SPIII (Table 1).


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

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

Structure of SPIII lead molecule
© Copyright Policy - open-access
Related In: Results  -  Collection

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

Figure 0002: Structure of SPIII lead molecule
Mentions: 4-(1-acetyl-5-methyl-2-oxoindolin-3-ylideneamino)-N-(4,6-dimethylpyrimidin-2-yl)benzene sulfonamide (SPIII-5ME-AC) inhibits the HIV Integrase enzymatic activity and 4-(1-benzoyl-5-chloro-2-oxoindolin-3-ylideneamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (SPIII-5Cl-BZ) exhibits 36 percent maximum protection against HIV-1 at subtoxic concentration. None of the compounds exhibited antiHIV effect and all the compounds displayed cytotoxic properties in the lymphocyte cell line (MT-4 cells). The 50% effective concentration (EC50) values of the synthesized compounds against the replication of HIV-1(IIIB) in acutely infected MT-4 cells were higher than the cytotoxic concentration (CC50). Lead molecules isatins (isatin, 5-chloroisatin, 5-bromoisatin, and 5-methylisatin) and sulphadimidine not active against HIV-1(IIIB) in MT-4 cells, but the combined product isatinesulphadimidine (SPIII, fig. 1 and Table 1) were active against HIV-1 and 2 in MT-4 cells13. Presence of 4,6-dimethylpyrimidinyl group in SO2NH2 of Isatine-sulphadimidine (SPIII) lead molecule is essential for antiHIV activity. Substitution in NH group of isatin (N-acylation) abolishes the antiHIV activity of the lead molecule SPIII (Table 1).

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