Recent Synthetic Approaches Towards Biologically Potent Derivatives/Analogues of Theophylline

Yousaf, Muhammad; Zahoor, Ameer Fawad; Faiz, Sadia; Javed, Sadia; Irfan, Muhammad

doi:10.1002/jhet.3311

Cited by 13 publications

(5 citation statements)

References 37 publications

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“…24 Theophylline has gained considerable interest among the widely distributed methylxanthines, as it has been the commonly used dimethylxanthine for treating respiratory diseases such as asthma for over 80 years. 25 Theophylline comprises an important scaffold for modifications in the structure to develop CNS stimulant, 26 analgesic and antiinflammatory, 27,28 anti-bacterial, 29 hypotensive, 30 hypoglycemic, 31 anti-HIV, 32 and anti-cancer 33 derivatives. Theophylline is an appropriate drug used in cardiology for the treatment of bradyarrhythmias and disorder of atrioventricular conduction.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Hemolytic Studies, and In Silico Modeling of Novel Acefylline–1,2,4-Triazole Hybrids as Potential Anti-cancer Agents against MCF-7 and A549

et al. 2021

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A series of novel theophylline-7-acetic acid (acefylline)-derived 1,2,4-triazole hybrids with N -phenyl acetamide moieties ( 11a – j ) have been synthesized and tested for their inhibitory ( in vitro ) potential against two cancer cell lines, A549 (lung) and MCF-7 (breast), using MTT assay. Among these derivatives, 11a , 11c , 11d , 11g , and 11h displayed remarkable activity against both cancer cell lines having cell viability values in the 21.74 ± 1.60–55.37 ± 4.60% range compared to acefylline (86.32 ± 1.75%) using 100 μg/μL concentration of compounds. These compounds were further screened against the A549 cancer cell line (lung) to find their half-maximal inhibitory concentration (IC 50 ) by applying various concentrations of these compounds. Compound 11g (2-(5-((1,3-dimethyl-2,6-dioxo-2,3-dihydro-1 H -purin-7(6 H )-yl)methyl)-4-phenyl-4 H -1,2,4-triazol-3-ylthio)- N - p -tolylacetamide) with the least IC 50 value (1.25 ± 1.36 μM) was discerned as a strong inhibitor of cancer cell multiplication in both cell lines (A549 and MCF-7). Their hemolytic studies revealed that all of them had very low cytotoxicity. Finally, in silico modeling was carried out to find the mode of binding of the highly active compound ( 11g ), which was according to the results of anti-cancer activity.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Hemolytic Studies, and In Silico Modeling of Novel Acefylline–1,2,4-Triazole Hybrids as Potential Anti-cancer Agents against MCF-7 and A549

et al. 2021

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“…These agents normally, can be obtained by the reaction of theophylline with different alkyl halides. [15] It was also noted that the N 7derivatives show more selectivity towards adenosine receptors. [16] Recently, the field of structure-based drug design is a rapidly growing area in which many successes have occurred in recent years.…”

Section: Introductionmentioning

confidence: 99%

“…Among of xanthine derivatives, N 7 ‐alkyltheophyllines are appropriate bioactive compounds with low toxicity and side effects. These agents normally, can be obtained by the reaction of theophylline with different alkyl halides [15] . It was also noted that the N 7 ‐derivatives show more selectivity towards adenosine receptors [16] …”

Section: Introductionmentioning

confidence: 99%

Aryloxy Alkyl Theophylline Derivatives as Antifungal Agents: Design, Synthesis, Biological Evaluation and Computational Studies

et al. 2022

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Infectious diseases are still one of the leading causes of death and disability in human society. Synthetic antimicrobial agents have recently emerged as promising candidates against drugresistant pathogens. Here we described an efficient procedure for synthesis of aryloxyalkyl theophylline analouges as novel antimicrobial agents. Fourtheen new compounds were synthesized (5 a-5 n) and their chemical structures were approved by different spectroscopic methods. The synthesized compounds were screened for their antimicrobial activities by broth micro dilution method as recommended by Clinical and Laboratory Standards Institute (CLSI). Molecular docking studies were also performed to forecast their binding modes against cytochrome P 450 lanosterol 14α-demethylase as a main target. The results represented appropriate correlation between molecular docking and antimicrobial activity of the compounds. Based on biological results and in silico ADMET (absorption, distribution, metabolism, excretion, and toxicity) predictions, compound 5 g can be considered as an ideal antimicrobial agent for the future studies.

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“…NHCs, also named imidazol-2-ylidene carbenes, can be synthetized by the deprotonation of N , N ′-disubstituted imidazolium salts; moreover, they can be obtained, as well, from caffeine (1,3,7-trimethylxanthine), one of the xanthine derivatives, which presents the methylimidazole moiety in its structure [ 18 ]. Xanthine and its derivatives were also studied for their unique structural scaffold and attractive medicinal effects [ 19 , 20 , 21 , 22 ] and a silver complex having a caffeine-derived NHC ligand, which has been patented as Silvamist, was proved to possess antibacterial activity against tobramycin-resistant bacteria [ 23 , 24 , 25 ].…”

Section: Introductionmentioning

confidence: 99%

Silver and Gold Complexes with NHC-Ligands Derived from Caffeine: Catalytic and Pharmacological Activity

Mariconda,

Iacopetta,

Sirignano

et al. 2024

IJMS

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N-heterocyclic carbene (NHC) silver(I) and gold(I) complexes have found different applications in various research fields, as in medicinal chemistry for their antiproliferative, anticancer, and antibacterial activity, and in chemistry as innovative and effective catalysts. The possibility of modulating the physicochemical properties, by acting on their ligands and substituents, makes them versatile tools for the development of novel metal-based compounds, mostly as anticancer compounds. As it is known, chemotherapy is commonly adopted for the clinical treatment of different cancers, even though its efficacy is hampered by several factors. Thus, the development of more effective and less toxic drugs is still an urgent need. Herein, we reported the synthesis and characterization of new silver(I) and gold(I) complexes stabilized by caffeine-derived NHC ligands, together with their biological and catalytic activities. Our data highlight the interesting properties of this series as effective catalysts in A3-coupling and hydroamination reactions and as promising anticancer, anti-inflammatory, and antioxidant agents. The ability of these complexes in regulating different pathological aspects, and often co-promoting causes, of cancer makes them ideal leads to be further structurally functionalized and investigated.

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Recent Synthetic Approaches Towards Biologically Potent Derivatives/Analogues of Theophylline

Cited by 13 publications

References 37 publications

Synthesis, Hemolytic Studies, and In Silico Modeling of Novel Acefylline–1,2,4-Triazole Hybrids as Potential Anti-cancer Agents against MCF-7 and A549

Synthesis, Hemolytic Studies, and In Silico Modeling of Novel Acefylline–1,2,4-Triazole Hybrids as Potential Anti-cancer Agents against MCF-7 and A549

Aryloxy Alkyl Theophylline Derivatives as Antifungal Agents: Design, Synthesis, Biological Evaluation and Computational Studies

Silver and Gold Complexes with NHC-Ligands Derived from Caffeine: Catalytic and Pharmacological Activity

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