Synthesis and anti-HSV-1 activity of quinolonic acyclovir analogues

The synthesis of new 4-(phenylamino)-1-phenyl-1H-pyrazolo [3,4-b]pyridine-4-carboxylic acid (3a-l) derivatives and the new 4-[(methylpyridin-2-yl)amino]-1-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (5a-c) derivatives was achieved with an efficient synthetic route. Ethyl 4-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (1) on fusion with appropriate substituted anilines or aminopicolines gave the required new ethyl 4-(phenylamino)-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylates (2a-l) (52-82%) or new ethyl 4-[(methylpyridin-2-yl)amino]-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylates (4a-c) (50-60%), respectively. Subsequent hydrolysis of the esters afforded the corresponding carboxylic acids (3a-l) (86-93%) and (5a-c) in high yield (80-93%). Inhibitory effects of 4-(phenylamino)/4-[(methylpyridin-2-yl)amino]-1-phenyl-1H-pyrazolo [3,4-b]pyridine-4-carboxylic acids. Derivatives on Herpes simplex virus type 1 (HSV-1), Mayaro virus (MAY) and vesicular stomatitis virus (VSV) were investigated. Compounds 2d, 3f, 3a, and 3c exhibited antiviral activity against

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“…Plaque-reduction assay The assay followed procedures described previously (Lucero et al, 2006). Acyclovir was used as a positive control.…”

Section: Cytotoxicity Assaymentioning

confidence: 99%

Synthesis and antiviral activity of new 4-(phenylamino)/4-[(methylpyridin-2-yl)amino]-1-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acids derivatives

et al. 2007

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“…It is worth mentioning that 2-amino-substituted-4(3H)-quinazolinone moieties also have potent activity against Parkinson's and hypokinetic conditions, [6] such as nolatrexed (anticancer) [7] and acyclovir (antiviral) [8] (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

One-Pot Palladium-Catalyzed Ligand- and Metal-Oxidant-Free Aerobic Oxidative Isocyanide Insertion Leading to 2-Amino-substituted-4(3H)-quinazolinones

Vidyacharan

Chaitra

Sagar

et al. 2015

Synthetic Communications

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An efficient, ligand-and metal-oxidant-free, one-pot, cascade aerobic oxidative, palladium-catalyzed, multicomponent reaction has been developed through isocyanide insertion of less active secondary amide and aromatic amine, which leads to 2-aminosubstituted-4(3H)-quinazolinones. This approach proves to be one of the simplest methods for the synthesis of this class of valuable bioactive heterocyclic scaffolds.

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“…Compounds containing quinolones exhibiting variety of pharmacological and biological activities [13][14][15][16][17][18][19][20][21][22][23][24][25].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel heterocyclic Quinolone compound for anti -tubercular activity

Godge

Kunkulol²

2018

IJCBR

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In last few decades, though significant progress has been made in the treatment and control strategies of tubercular infections by introducing new diagnostic and monitoring tools and combination therapy, it still continues to be severe problem. The need of study was only because of there are many drugs in market to treat infection but most of the drugs are showing resistance because of the same it is difficult to treat the infection. In this study we chosen quinolone nucleus for study and over it. Thus with the aim of developing novel molecule with improved potency for treating Mycobacterium tuberculosis H37Rv strain infections and with decreased probability of developing drug resistance. Methodology: The synthesis of Quinolone derivatives, starting from substituted aniline and ethyl acetoacetate, by conventional organic reaction and results of investigations of their anti-mycobacterial activity. Results: MICs of the synthesized compounds are compared with existing drugs Cytotoxicity. The substituted quinolones are synthesized by taking mixture of 7-substituted-2-(3-chloro-2-oxopropyl) quinolin-4(1H)-one and different secondary amines. Many compounds have shown promising activity while some were inactive. Conclusion: It was found that Compound A1, A3, B1, B3, have shown promising anti tubercular activity whereas compound A2, A4,B2,B4 were showing moderate anti tubercular activity against std. Streptomycin.

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Synthesis and anti-HSV-1 activity of quinolonic acyclovir analogues

Cited by 70 publications

References 18 publications

Synthesis and antiviral activity of new 4-(phenylamino)/4-[(methylpyridin-2-yl)amino]-1-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acids derivatives

Synthesis and antiviral activity of new 4-(phenylamino)/4-[(methylpyridin-2-yl)amino]-1-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acids derivatives

One-Pot Palladium-Catalyzed Ligand- and Metal-Oxidant-Free Aerobic Oxidative Isocyanide Insertion Leading to 2-Amino-substituted-4(3H)-quinazolinones

Synthesis of novel heterocyclic Quinolone compound for anti -tubercular activity

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