Synthesis and biological evaluation of the new 1,3-dimethylxanthine derivatives with thiazolidine-4-one scaffold

Constantin, Sandra; Lupașcu, Florentina; Apotrosoaei, Maria; Vasincu, Ioana; Lupașcu, Dan; Buron, Frédéric; Routier, Sylvain; Profire, Lenuța

doi:10.1186/s13065-017-0241-0

Cited by 18 publications

(7 citation statements)

References 33 publications

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“…This has helped in exploring the significance of these derivatives in various therapeutics applications such as adenosine receptor antagonists, inducers of histone deacetylase activity, antitumor drugs, anti asthmatic drug, psycho-stimulant drug etc [ 10 , 11 , 12 , 13 , 14 ]. The wider pharmaceutical applications of natural xanthine derivatives has prompted medicinal chemist or pharmaceutical companies to go for certain changes over lead molecule to develop more specific compounds using synthesis methodologies [ 15 , 16 , 17 , 18 , 19 ]. In drug development process, one of the major challenges is deciding the lead molecule which would act as a scaffold to provide avenue for achieving molecular diversity.…”

Section: Introductionmentioning

confidence: 99%

Xanthine scaffold: scope and potential in drug development

Singh

Shreshtha

Thakur

et al. 2018

Heliyon

102

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Medicinal plants have been the basis for discovery of various important marketed drugs. Xanthine is one such lead molecule. Xanthines in various forms (caffeine, theophylline, theobromine, etc) are abode in tea, coffee, cocoa, chocolate etc. giving them popular recognition. These compounds are best known for their diverse pharmaceutical applications as cyclic nucleotide phosphodiesterase inhibition, antagonization of adenosine receptor, anti-inflammatory, anti-microbial, anti-oxidant and anti-tumor activities. These properties incentivize to use xanthine as scaffold to develop new derivatives. Chemical synthesis contributes greater diversity in xanthine based derivatisation. With highlighting the existing challenges in chemical synthesis, the present review focuses the probable solution to fill existing lacuna. The review summarizes the available knowledge of xanthine based drugs development along with exploring new xanthine led chemical synthesis path for bringing diversification in xanthine based research. The main objective of this review is to explore the immense potential of xanthine as scaffold in drug development.

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Section: Introductionmentioning

confidence: 99%

Xanthine scaffold: scope and potential in drug development

Singh

Shreshtha

Thakur

et al. 2018

Heliyon

102

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“…The synthesis of new xanthine derivatives with thiazolidine-4-one scaffold (6a–k) ( Figure 1 ) were presented in our previous paper [ 38 ]. Some of these compounds showed good antioxidant effects in terms of the antiradical scavenging effect (DPPH, ABTS) and phosphomolybdenum reducing antioxidant power [ 38 ].…”

Section: Resultsmentioning

confidence: 99%

“…ACS reagent), dimethyl sulfoxide (DMSO, p.a., ACS regent), Mueller–Hinton agar medium (Oxoid), Sabouraud agar medium were purchased from Sigma Aldrich. Xanthine derivatives with thiazolidine-4-one scaffold (XTDs: 6c, 6e, 6f, 6k) have been synthesized by our research group and were reported in a previous paper [ 38 ]. Bacterial strains ( Staphyloccoccus aureus ATCC 25923, Sarcina lutea ATCC 9341, Escherichia coli ATCC 25922) and yeast strains ( Candida albicans ATCC 10231, Candida glabrata ATCC MYA 2950, Candida parapsilosis ATCC 22019) were obtained from the Department of Microbiology, “Grigore T. Popa” University of Medicine and Pharmacy, Iasi, Romania.…”

Section: Methodsmentioning

confidence: 99%

Formulation and Characterization of New Polymeric Systems Based on Chitosan and Xanthine Derivatives with Thiazolidin-4-One Scaffold

et al. 2019

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In the past many research studies have focused on the thiazolidine-4-one scaffold, due to the important biological effects associated with its heterocycle. This scaffold is present in the structure of many synthetic compounds, which showed significant biological effects such as antimicrobial, antifungal, antioxidant, anti-inflammatory, analgesic, antidiabetic effects. It was also identified in natural compounds, such as actithiazic acid, isolated from Streptomyces strains. Starting from this scaffold new xanthine derivatives have been synthetized and evaluated for their antibacterial and antifungal effects. The antibacterial action was investigated against Gram positive (Staphyloccoccus aureus ATCC 25923, Sarcina lutea ATCC 9341) and Gram negative (Escherichia coli ATCC 25922) bacterial strains. The antifungal potential was investigated against Candida spp. (Candida albicans ATCC 10231, Candida glabrata ATCC MYA 2950, Candida parapsilosis ATCC 22019). In order to improve the antimicrobial activity, the most active xanthine derivatives with thiazolidine-4-one scaffold (XTDs: 6c, 6e, 6f, 6k) were included in a chitosan based polymeric matrix (CS). The developed polymeric systems (CS-XTDs) were characterized in terms of morphological (aspect, particle size), physic-chemical properties (swelling degree), antibacterial and antifungal activities, toxicity, and biological functions (bioactive compounds loading, entrapment efficiency). The presence of xanthine-thiazolidine-4-one derivatives into the chitosan matrix was confirmed using Fourier transform infrared (FT-IR) analysis. The size of developed polymeric systems, CS-XTDs, ranged between 614 µm and 855 µm, in a dry state. The XTDs were encapsulated into the chitosan matrix with very good loading efficiency, the highest entrapment efficiency being recorded for CS-6k, which ranged between 87.86 ± 1.25% and 93.91 ± 1.41%, depending of the concentration of 6k. The CS-XTDs systems showed an improved antimicrobial effect with respect to the corresponding XTDs. Good results were obtained for CS-6f, for which the effects on Staphylococcus aureus ATCC 25923 (21.2 ± 0.43 mm) and Sarcina lutea ATCC 9341 (25.1 ± 0.28 mm) were comparable with those of ciprofloxacin (25.1 ± 0.08 mm/25.0 ± 0.1 mm), which were used as the control. The CS-6f showed a notable antifungal effect, especially on Candida parapsilosis ATCC 22019 (18.4 ± 0.42 mm), the effect being comparable to those of nystatin (20.1 ± 0.09 mm), used as the control. Based on the obtained results these polymeric systems, consisting of thiazolidine-4-one derivatives loaded with chitosan microparticles, could have important applications in the food field as multifunctional (antimicrobial, antifungal, antioxidant) packaging materials.

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“…Constantin et al [147] developed a novel, selective, nontoxic synthesis of thiazolidine-4-one derivatives containing a xanthine structure and evaluated them for antioxidant and antidiabetic activity. Initially, theophylline (1,3-dimethylxanthine) reacted with sodium methoxide and furnished the salt, which combined with ethyl chloroacetate and gave theophylline ethyl acetate.…”

Section: Antioxidant Activitymentioning

confidence: 99%

Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications

Sahiba¹,

Sethiya²,

Soni³

et al. 2020

Top Curr Chem (Z)

100

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In past decades, interdisciplinary research has been of great interest for scholars. Thiazolidine motifs behave as a bridge between organic synthesis and medicinal chemistry and compel researchers to explore new drug candidates. Thiazolidine motifs are very intriguing heterocyclic five-membered moieties present in diverse natural and bioactive compounds having sulfur at the first position and nitrogen at the third position. The presence of sulfur enhances their pharmacological properties, and, therefore, they are used as vehicles in the synthesis of valuable organic combinations. They show varied biological properties viz. anticancer, anticonvulsant, antimicrobial, anti-inflammatory, neuroprotective, antioxidant activity and so on. This diversity in the biological response makes it a highly prized moiety. Based on literature studies, various synthetic approaches like multicomponent reaction, click reaction, nano-catalysis and green chemistry have been employed to improve their selectivity, purity, product yield and pharmacokinetic activity. In this review article, we have summarized systematic approaches for the synthesis of thiazolidine and its derivatives, along with their pharmacological activity, including advantages of green synthesis, atom economy, cleaner reaction profile and catalyst recovery which will help scientists to probe and stimulate the study of these scaffolds.

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Synthesis and biological evaluation of the new 1,3-dimethylxanthine derivatives with thiazolidine-4-one scaffold

Cited by 18 publications

References 33 publications

Xanthine scaffold: scope and potential in drug development

Xanthine scaffold: scope and potential in drug development

Formulation and Characterization of New Polymeric Systems Based on Chitosan and Xanthine Derivatives with Thiazolidin-4-One Scaffold

Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications

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