Synthesis and anti-HIV activity of 4-[(1,2-dihydro-2-oxo-3H-indol-3-ylidene) amino]-N(4,6-dimethyl-2-pyrimidinyl)-benzene sulfonamide and its derivatives

Selvam, Periyasamy; Chandramohan, M.; Clercq, Erik De; Witvrouw, Myriam; Pannecouque, Christophe

doi:10.1016/s0928-0987(01)00197-x

Cited by 58 publications

(43 citation statements)

References 12 publications

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“…Recently, benzophenones of type 95 [119] incorporating primary sulfonamide moieties and 4-[(1,2-dihydro-2-oxo-3H-indol-3-ylidene)amino]-N-(4,6-dimethyl-2-pyrimidinyl) benzenesulfonamides of type 96 [120] were reported to possess strong anti-HIV properties, their mechanism of action being that of the NNRTIs. Probably by using efavirenz 91 as lead molecule, the thienothiadiazines 97 and the benzothiadiazines 98 were recently reported as new classes of NNRTIs [121,122] Both these types of derivatives incorporate the sulfamoyl functionalities in a fused bicyclic ring system, and possess strong anti-HIV-1 properties, with IC 50 in the range of 0.18 -60 µM [121,122].…”

Section: Non Nucleoside Hiv Reverse Transcriptase Inhibitorsmentioning

confidence: 99%

Anticancer and Antiviral Sulfonamides

Scozzafava

Owa²,

Mastrolorenzo³

et al. 2003

CMC

690

334

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The sulfonamides constitute an important class of drugs, with several types of pharmacological agents possessing antibacterial, anti- carbonic anhydrase, diuretic, hypoglycemic and antithyroid activity among others. A large number of structurally novel sulfonamide derivatives have ultimately been reported to show substantial antitumor activity in vitro and in vivo. Although they have a common chemical motif of aromatic/heterocyclic or amino acid sulfonamide, there are a variety of mechanisms of their antitumor action, such as carbonic anhydrase inhibition, cell cycle perturbation in the G1 phase, disruption of microtubule assembly, functional suppression of the transcriptional activator NF-Y, and angiogenesis (matrix metalloproteinase, MMP) inhibition among others. Some of these compounds selected via elaborate preclinical screenings or obtained through computer-based drug design, are currently being evaluated in clinical trials. The review summarizes recent classes of sulfonamides and related sulfonyl derivatives disclosed as effective tumor cell growth inhibitors, or for the treatment of different types of cancer. Another research line that progressed much in the last time regards different sulfonamides with remarkable antiviral activity. Thus, at least two clinically used HIV protease inhibitors possess sulfonamide moieties in their molecules, whereas a very large number of other derivatives are constantly being synthesized and evaluated in order to obtain compounds with less toxicity or activity against drug-resistant viruses. Several non nucleoside HIV reverse transcriptase or HIV integrase inhibitors containing sulfonamido groups were also reported. Another approach to inhibit the growth of retroviruses, including HIV, targets the ejection of zinc ions from critical zinc finger viral proteins, which has as a consequence the inhibition of viral replication in the absence of mutations leading to drug resistance phenotypes. Most compounds with antiviral activity possessing this mechanism of action incorporate in their molecules primary sulfonamide groups. Some small molecule chemokine antagonists acting as HIV entry inhibitors also possess sulfonamide functionalities in their scaffold.

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Section: Non Nucleoside Hiv Reverse Transcriptase Inhibitorsmentioning

confidence: 99%

Anticancer and Antiviral Sulfonamides

Scozzafava

Owa²,

Mastrolorenzo³

et al. 2003

CMC

690

334

View full text Add to dashboard Cite

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“…Methisazone (Nmethylisatin-β-thiosemicarbazone) was one of the first clinically used synthetic antiviral agents (Bauer et al, 1960), and N,N′−disubstitutedthiosemicarbazone derivatives of isatin were tested for inhibition of HIV-1 replication (Teitz et al, 1994). In earlier studies, we synthesized some novel isatin derivatives and evaluated them for antiviral activity (Selvam et al, 2001;Selvam et al, 2005). Our results demonstrated these compounds possessed significant inhibitory effects against HIV-1 replication.…”

Section: Introductionmentioning

confidence: 93%

Inhibitory Activity of 4-[(1,2-dihydro-2-oxo-3H-indol-3-ylidene)amino]-N-(4,6-dimethylpyrimidin-2-yl) Benzenesulphonamide and its Derivatives against Orthopoxvirus Replication in vitro

Selvam

Murugesh

Chandramohan³

et al. 2006

Antivir Chem Chemother

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“…Sulfonamides demonstrated bacteriostatic activity by inhibiting the bio-synthesis of folic acid (Brown, 1962). Its derivatives possess versatile activity, e.g., carbonic anhydrase inhibitors (Supuran et al, 1998), anticancer (Reddy et al, 2004), anti-inflammatory (Li et al, 1995), anti-HIV (Selvam et al, 2001), COX-2 inhibitors (Dannhardt et al, 2002), selective 5-HT receptor antagonist (Bromidge et al, 2002), antitubercular (Kamal et al, 2007) and antifungal (Briganti et al, 1997) etc. Pyridoquinolones were synthesized and evaluated for antimicrobial activity (Lee et al, 1992;Chang, 1994, 1996), in which pyridine ring was fused with quinazoline ring, and generally known as phenanthroline.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and in vitro microbial activities of amides of pyridoquinolone

Patel

Chauhan

2010

Med Chem Res

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In this study, we report the antimicrobial evaluation of newly synthesized amides of pyridoquinolones from substituted aniline, substituted phenyl thioureas and 4-amino-N-(substitutedphenyl)benzenesulfonamide. Structures of selected compounds have been established by IR and 1 H NMR spectra and elemental analysis. The structureactivity releationships have been studied by screening of antimicrobial activity over S. aureus, B. subtilis, E. coli, P. aeruginosa, and C. albicans using cup-plate method.

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Synthesis and anti-HIV activity of 4-[(1,2-dihydro-2-oxo-3H-indol-3-ylidene) amino]-N(4,6-dimethyl-2-pyrimidinyl)-benzene sulfonamide and its derivatives

Cited by 58 publications

References 12 publications

Anticancer and Antiviral Sulfonamides

Anticancer and Antiviral Sulfonamides

Inhibitory Activity of 4-[(1,2-dihydro-2-oxo-3H-indol-3-ylidene)amino]-N-(4,6-dimethylpyrimidin-2-yl) Benzenesulphonamide and its Derivatives against Orthopoxvirus Replication in vitro

Synthesis and in vitro microbial activities of amides of pyridoquinolone

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