Theophylline-7-acetic acid derivatives with amino acids as anti-tuberculosis agents

Voynikov, Yulian; Valcheva, Violeta; Momekov, Georgi; Peikov, Plamen; Stavrakov, Georgi

doi:10.1016/j.bmcl.2014.05.026

Cited by 34 publications

(21 citation statements)

References 11 publications

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“…Stimulated by the anti‐TB activities of purine analogues, Voynikov et al . in 2014 and Stavrakov et al . in 2016 extended the idea of purine‐based structural scaffold of theophylline and devised the synthesis of 7‐theophylline acetamides 174 (28–96%) from amino acids as potentially active anti‐mycobacterial candidates.…”

Section: Review Of Literaturementioning

confidence: 91%

“…Continuing their research on the exploration of theophylline‐based structural scaffold with diverse range biochemical profile, Voynikov et al . again in 2015 proposed the synthesis of acetamides of theophylline‐7‐acetic acid but in different mode. In their previous work , the synthesis of required product was achieved by coupling of theophylline‐7‐acetic acid 172 with various amino acid derivatives 173 under suitable reaction conditions.…”

Section: Review Of Literaturementioning

confidence: 99%

“…again in 2015 proposed the synthesis of acetamides of theophylline‐7‐acetic acid but in different mode. In their previous work , the synthesis of required product was achieved by coupling of theophylline‐7‐acetic acid 172 with various amino acid derivatives 173 under suitable reaction conditions. In this work, to accomplish the synthesis of theophylline‐7‐acetamides 199 , firstly, N ‐chloroacetyl amino acid methyl ester 197 was synthesized by carrying out the treatment of amino acid methyl ester hydrochloride 196 with chloroacetyl chloride in the presence of K 2 CO 3 that was then reacted with deprotonated theophylline 198 and furnished the required derivatives 199 in 76–82% yields (Scheme ).…”

Section: Review Of Literaturementioning

confidence: 99%

See 2 more Smart Citations

Recent Synthetic Approaches Towards Biologically Potent Derivatives/Analogues of Theophylline

Yousaf

Zahoor

Faiz

et al. 2018

Journal of Heterocyclic Chem

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Theophylline, also known as 1,3‐dimethylxanthine, belongs to class of purine‐based drugs, which are used in the treatment of air ways disorders such as asthma and chronic obstructive pulmonary disease. Its derivatives play a significant role in the variety of biological applications of medicinal interest as it exhibits numerous activities such as anticancer, anti‐inflammatory, bronchodilator activity, antibacterial, and antifungal activities. This review article summarizes the recent advances in the synthesis of theophylline derivatives, which were reported during 2008–2017, and also describes the detailed biological studies of synthesized analogues.

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Section: Review Of Literaturementioning

confidence: 91%

Section: Review Of Literaturementioning

confidence: 99%

Section: Review Of Literaturementioning

confidence: 99%

See 1 more Smart Citation

Recent Synthetic Approaches Towards Biologically Potent Derivatives/Analogues of Theophylline

Yousaf

Zahoor

Faiz

et al. 2018

Journal of Heterocyclic Chem

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“…THP reduces the replication of viral HIV-1 strain (Nunnari et al 2005). A study (Voynikov et al 2014) showed that theophylline-7-acetic acid derivatives along with amino acids inhibited the growth of Mycobacterium tuberculosis H 37 R v . Thus, despite wide range of studies on THP, a comprehensive study deciphering the anticandida potential of THP is still elusive.…”

Section: Introductionmentioning

confidence: 99%

Repurposing of respiratory drug theophylline againstCandida albicans: mechanistic insights unveil alterations in membrane properties and metabolic fitness

Singh

Fatima

Ahmad

et al. 2020

J. Appl. Microbiol.

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Aims Drug repurposing is an attractive chemotherapeutic strategy that serves to make up for the inadequacy of current antifungal drugs. The present study aims to repurpose theophylline (THP) against Candida albicans. THP is a methylxanthine derived from cocoa beans and tea extracts, generally used as the first‐line drug for asthma and other respiratory disorders. Methods and Results We investigated the antifungal activity of THP against C. albicans and non‐albicans species. Mechanistic insights revealed that THP induces membrane damage. Enhanced ionic disturbances and depleted ergosterol levels with the concomitant rise in membrane fluidity due to elevated flippase activity confirmed the membrane damaging effect. THP impeded the metabolic adaptability of C. albicans by inhibiting malate synthase and isocitrate lyase enzymes of the glyoxylate cycle. In vivo efficacy of THP was depicted by increased survival of C. albicans infected Caenorhabditis elegans model. Conclusions This study elucidates the antifungal potential of THP with mechanistic insights. Significance and Impact of the Study This study unveils the antifungal potential of THP, a known respiratory drug that can be further utilized for a wider range of applications such as combating fungal infections. The effect of THP with the known antifungal drugs can be exploited in the combinatorial drug approach for treating candidiasis.

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“…Despite their effectiveness, they cause a number of side effects, and thus the search for new antimicrobial and antifungal agents is currently one of the problems of pharmaceutical science of current interest. Literary data suggest that xanthine derivatives exhibit activity in relation to some strains of pathogenic microorganisms and fungi [1][2][3][4][5][6].…”

mentioning

confidence: 99%

Clinical and social aspects of dysmenorrhea development

Dolhikh

Романенко

Иванченко

et al. 2019

Current Issues in Pharmacy and Medicine: Science and Practice

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Modern antibiotics and synthetic antimicrobial agents play a leading role in the treatment of bacterial infections. Despite their effectiveness, they cause a number of side effects, and thus the search for new antimicrobial and antifungal agents is currently one of the problems of pharmaceutical science of current interest. Literary data suggest that xanthine derivatives exhibit activity in relation to some strains of pathogenic microorganisms and fungi. The aim of this work is to develop a method for the synthesis of new derivatives of xanthine-8-aminoalkanoic acids and to study their physical and chemical properties, as well as their antimicrobial and antifungal effects. Materials and methods. The melting point has been determined with the help of an open capillary method with PTP-M device. Elemental analysis has been performed with the help of the instrument Elementar Vario L cube, NMR-spectra have been taken on a spectrometer Bruker SF-400 (operating frequency of 400 MHz, solvent DMSO, internal standard-TMS). Study of antimicrobial and antifungal activity of synthesized compounds has been performed by a twofold serial dilution method. Standard test strains have been used for the study:

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Theophylline-7-acetic acid derivatives with amino acids as anti-tuberculosis agents

Cited by 34 publications

References 11 publications

Recent Synthetic Approaches Towards Biologically Potent Derivatives/Analogues of Theophylline

Recent Synthetic Approaches Towards Biologically Potent Derivatives/Analogues of Theophylline

Repurposing of respiratory drug theophylline againstCandida albicans: mechanistic insights unveil alterations in membrane properties and metabolic fitness

Clinical and social aspects of dysmenorrhea development

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