Synthesis and Antidiabetic Activity of Thiazolo[2,3-f]Purine Derivatives and Their Analogs

Spasov, A. A.; Халиуллин, Ф. А.; Babkov, Denis A.; Тимирханова, Г. А.; Кузнецова, В. А.; Науменко, Л. В.; Muleeva, Diana R.; Maika, O. Yu.; Prokhorova, T. Yu.; Sturova, E. A.

doi:10.1007/s11094-017-1649-5

Cited by 8 publications

(3 citation statements)

References 9 publications

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“…олар адам ағзасына бөгде зат емес, ал олардың метаболизмі эволюция үдерісінен өткен [1,2]. Cонымен қатар ксантин туындыларын алу арзан әрі қолжетімді.…”

Section: оригинальные исследованияunclassified

Technique of thin-layer chromatography in the analysis of substance 8-bromo-3-methylxantine.

Kutymovna¹,

Bidaibek²,

Шарипов³

et al. 2019

Medicine

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Section: оригинальные исследованияunclassified

Technique of thin-layer chromatography in the analysis of substance 8-bromo-3-methylxantine.

Kutymovna¹,

Bidaibek²,

Шарипов³

et al. 2019

Medicine

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“…Its pyrimidine skeleton exists in many natural products such as vitamin B 1 (thiamine) and many synthetic compounds, that posses antibacterial, antifungal, antileishmanial, anticancer, anti‐inflammatory, and analgesic activities hence, they attract considerable attention in the design of biologically active molecules (Sharma, Rane, & Gurram, 2014; Agarwal, et al, 2002; Agarwal, et al, 2000; Ram, Haque, & Guru, 1992; Prachayasittikul, et al, 2017; Xie, Zhao, H., Zhao, L., Lou, & Hu, 2009; Amir, Javed, & Kumar, 2007; Sondhi, Jain, Dwivedi, Shukla, & Raghubir, 2008; Vega, Alonso, Diaz, & Junquera, 1990). Our research group investigate innovative thietan derivatives as they posses a broad spectrum of bioactivities: antimicrobial, broncholytic and wound healing (Kataev, Meshcheryakova, Lazarev, & Kuznetsov, 2013; Kataev, et al, 2018; Meshcheryakova, Kataev, Fattakhova, Nikolaeva, & Bulgakov, 2015; Meshcheryakova, Kataev, Munasipova, Shumadalova, & Bulgakov, 2017; Meshcheryakova, Kataev, & Galimova, 2013; Gabdrakhmanova, et al, 2019; Khaliullin, et al, 2021; Spasov, et al, 2017; Smirnova, et al, 2021). Structural modification of uracil by adding thietan fragment is an efficient way to get new antimicrobial compounds.…”

Section: Introductionmentioning

confidence: 99%

Innovative antimicrobial substances based on uracil S‐derivatives

et al. 2021

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The problem of antimicrobial resistance is an important global public health challenge.We propose that a development of new antibiotic compounds around known natural substances is a solution to this problem. We investigate reengineer natural products into potent antibiotics. Uracil fragment is abundant in nature and significant to treat infectious diseases due to its affection to the replication of the bacterial chromosome.12 new uracil S-derivatives were obtained and tested for their in vitro antimicrobial properties. N 3 -(thietan-3-yl)-and N 3 -(1,1-dioxothietan-3-yl)uracils derivatives were synthesized by thietanylation of 6-methyluracil with 2-chloromethylthiirane and subsequent oxidation of the thietan ring. A method of their alkylation with ethyl-2-chloroacetate was developed and acetohydrazides containing 3-(thietan-3-yl)-and 3-(1,1-dioxothietan-3-yl)uracilyls fragments in the acetyl group were obtained by hydrazinolysis of 2-(thietanyluracil-1-yl)acetic acid ethyl esters. Their interaction with β-dicarbonyl compounds, anhydride of mono-and dicarboxylic acids was studied.Antimicrobial activity was determined by the agar diffusion method on test organisms: S. aureus, E. coli, P. vulgaris, K. pneumoniae, C. diversus, E. aerogenes, P. aeruginosa, S. abosit. N-acyl-5-hydroxypyrazolines and N,N 0 -diacylhydrazines of 6-methyluracil thietanyl-and dioxothietanyl derivatives showed high antimicrobial activity, which is consistent with the results of structure activity relationship analysis (MIC 0.1-10 μg/ml).

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“…Учитывая, что лекарственные средства, созданные на основе комбинации веществ с известной фармакологической активностью и новых химических структур, могут приобретать более выраженную фармакологическую активность или проявлять совершенно иные биологические свойства, поиск в их ряду новых молекул-кандидатов в лекарства теоретически оправдан [29]. Это было подтверждено исследованиями, выполненными в БГМУ: установлено, что тиетан-содержащие гетероциклические соединения обладают гипотензивной [30], противовоспалительной [31], иммунотропной [32], гипогликемической [33], гемореологической [34], антиагрегационной [35], антиоксидантной [36], гепатопротективной активностью [37,38].…”

unclassified

Prospects for the creation of new drug candidates with antidepressant activity among thietanes

Nikitina,

Gaisina,

Klen

et al. 2023

Kazan Med J

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The article presents the results of systematic studies on the search for new biologically active molecules with antidepressant activity in the series of thietane-containing heterocyclic compounds and 3-substituted thietane dioxides. The used strategy for the search for antidepressant substances, based on in vivo pharmacological screening in combination with in silico methods of mathematical modeling and toxico-pharmacokinetic evaluation, is described. Studies of the biological activity of thietane-containing reaction products of azoles with thiiranes have been carried out in the series of thietanylimidazoles, titanixanthines, thietanyltriazoles, thietanyltriazolones, and 3-substituted thietane-1,1-dioxides (more than 300 compounds have been studied). The main results of the preclinical evaluation of promising drug candidates with antidepressant activity, 3-methoxythiethane-1,1-dioxide and 3-ethoxythiethane-1,1-dioxide, are presented. Both 3-substituted thietane-1,1-dioxides are characterized by low toxicity when administered intraperitoneally to mice (class IV low toxicity), the absence of toxic risks (mutagenic, carcinogenic, reproductive toxicity, local irritant action), high pharmaceutical potential (compliance with the rule of five Lipinsky), a wide range of action and pronounced antidepressant activity, not inferior to the reference drug amitriptyline (10 mg/kg), confirmed in highly valid in vivo models of depressive-like states (chronic mild stress and resident intruder). In tests of neuropharmacological interaction, it was found that the proposed mechanism of action of 3-substituted thietane-1,1-dioxides is associated with stimulation of 5-HT1A receptors, blockade of 5-HT2A/2C receptors and/or 2-adrenergic receptors. The need for further research is substantiated in order to create domestic first in class antidepressants on their basis.

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Synthesis and Antidiabetic Activity of Thiazolo[2,3-f]Purine Derivatives and Their Analogs

Cited by 8 publications

References 9 publications

Technique of thin-layer chromatography in the analysis of substance 8-bromo-3-methylxantine.

Technique of thin-layer chromatography in the analysis of substance 8-bromo-3-methylxantine.

Innovative antimicrobial substances based on uracil S‐derivatives

Prospects for the creation of new drug candidates with antidepressant activity among thietanes

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