Synthesis, crystal structure, antioxidant activity and dft study of 2-aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-One

Rodríguez, Omar Alejandro Ramos; Magaña-Vergara, Nancy E.; Sánchez, Juan Pablo Mojica; Martínez, María Teresa Sumaya; Gómez‐Sandoval, Zeferino; Cruz, Alejandro; Organillo, Ángel Ramos

doi:10.1016/j.molstruc.2019.127036

Cited by 18 publications

(6 citation statements)

References 30 publications

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“…Впродовж останніх років особливою увагою дослідників користуються функціоналізовані похідні імідазо[2,1-b]тіазину, які характеризуються широким спектром біологічної дії. Серед представників цього типу сполук виявлено речовини з антиоксидантною І [1], противірусною ІІ [2], протитуберкульозною ІІІ [3], антитрипаноцидною ІV [4] дією, цитотоксичним ефектом до неракових F2408 і ракових 5RP7 клітин V [5]. Імідазотіазиновий цикл також є важливим фармакофорним фрагментом інгібіторів активованого канабіноїдами білка GPR18 VІ [6] та оборотних інгібіторів TbAdoMetDC африканського трипаносомозу VІІ [7] (див.…”

Section: публікація присвячена розробленню зручного та селективного м...unclassified

SYNTHESIS AND ANTIEXUDATIVE ACTIVITY OF N-ОXIDES 4-PYRIDINYLOXYSUBSTITUTED (BENZO)IMIDAZO[2,1-b][1,3]THIAZINES

SLYVKA¹,

Saliyeva²,

HOLOTA³

et al. 2022

Proc. Shevchenko Sci. Soc. Chem. Sci.

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The imidazo[2,1-b][1,3]thiazine nucleus, as well as the pyridine-N-oxide fragment, are pharmacophore groups that have received much attention from researchers. That is why the combination of these scaffolds in the structure of a single molecule seems to be quite attractive from chemical and biological point of view. Synthetically available 4-pyridinyloxy-substituted (benzo)imidazo[2,1-b]thiazines were used as precursors to obtain previously unknown (benzo)imidazo[2,1-b][1,3]thiazin-6-yloxypyridine 1-oxides. It was found that the oxidation of the latter with m-chlorobenzoic acid under mild reaction conditions using dichloromethane as a solvent at room temperature proceeds smoothly and selectively to obtain only the target products. The composition and structure of the synthesized pyridine-N-oxides are unambiguously confirmed by complex physicochemical analysis, particularly by 1H and 13C NMR spectroscopy, chromato-mass spectrometry, as well as elemental analysis data. The antiexudative activity of (benz)imidazo[2,1-b][1,3]thiazin-6-yloxypyridine 1-oxides was studied in vivo in a model of carrageenan-induced paw edema in white outbred male rats. The development of edema was considered from increasing the volume of the paw 4 hours after the introduction of carrageenan. Quantitative assessment of antiexudative activity was performed by the degree of reduction of rat paw edema, and the rate of suppression of the inflammatory process was calculated. Performed bioscreening showed that the synthesized pyridine-N-oxides are characterized by weak anti-inflammatory activity, and only 2-chloro-4-[(2,3-diphenyl-6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazin-6-yl)oxy]pyridine 1-oxide 2a has moderate antiexudative effect with of inflammatory inhibition rate of 31.9%. This compound is thus of interest for further structural modification in order to obtain potential non-steroidal anti-inflammatory agents. It is important to note that the presence in the structure of the synthesized derivatives 2a-e of N-oxide fragment is very promising for the design of anti-inflammatory agents, which are characterized by the absence of side effects caused by inhibition of cyclooxygenase-1.

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Section: публікація присвячена розробленню зручного та селективного м...unclassified

SYNTHESIS AND ANTIEXUDATIVE ACTIVITY OF N-ОXIDES 4-PYRIDINYLOXYSUBSTITUTED (BENZO)IMIDAZO[2,1-b][1,3]THIAZINES

SLYVKA¹,

Saliyeva²,

HOLOTA³

et al. 2022

Proc. Shevchenko Sci. Soc. Chem. Sci.

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“…Taha et al ( Taha et al, 2020 ) synthesized 20 benzimidazole derivates and found four potent antioxidant compounds 221–224 with IC 50 values (mean ± SEM: 22.42 ± 0.26 to 40.60 ± 0.80) comparable to standard propyl gallate (29.20 ± 1.25). Interestingly, compound 225 exhibited more inhibition (%) of DPPH-free radical than the standard antioxidant Trolox (73% ± 2.42 vs. 70% ± 0.35) ( Ramos Rodríguez et al, 2020 ). Furthermore, compounds 166, 168, 226 and 227 displayed prominent antioxidant property with lower IC 50 values than the standard BHT (8.834, 7.519, 0.038 and 0.959 μg/ml, respectively vs. 14.44 μg/ml) ( Brishty et al, 2020 ) .…”

Section: Biological Activitiesmentioning

confidence: 99%

A Comprehensive Account on Recent Progress in Pharmacological Activities of Benzimidazole Derivatives

et al. 2021

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Nowadays, nitrogenous heterocyclic molecules have attracted a great deal of interest among medicinal chemists. Among these potential heterocyclic drugs, benzimidazole scaffolds are considerably prevalent. Due to their isostructural pharmacophore of naturally occurring active biomolecules, benzimidazole derivatives have significant importance as chemotherapeutic agents in diverse clinical conditions. Researchers have synthesized plenty of benzimidazole derivatives in the last decades, amidst a large share of these compounds exerted excellent bioactivity against many ailments with outstanding bioavailability, safety, and stability profiles. In this comprehensive review, we have summarized the bioactivity of the benzimidazole derivatives reported in recent literature (2012–2021) with their available structure-activity relationship. Compounds bearing benzimidazole nucleus possess broad-spectrum pharmacological properties ranging from common antibacterial effects to the world’s most virulent diseases. Several promising therapeutic candidates are undergoing human trials, and some of these are going to be approved for clinical use. However, notable challenges, such as drug resistance, costly and tedious synthetic methods, little structural information of receptors, lack of advanced software, and so on, are still viable to be overcome for further research.

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“…[1][2][3][4][5][6] Among the latter, it is worth highlighting various derivatives of imidazo[2,1b] [1,3]thiazines, which are characterized by a wide spectrum of biological activity. In particular, compounds with antioxidant, 7 antibacterial, 8 antiviral, 9 antituberculosis, 10 and antitrypanocidal 11 effects and cytotoxic effects on non-cancerous F2408 and cancerous 5RP7 cells 12 were found among them. The imidazothiazine ring is an important pharmacophore fragment of inhibitors of the cannabi-noid-activated protein GPR18, 13 reversible inhibitors of TbAdoMetDC of African trypanosomiasis, 14 and also a potential agent in the therapy of Chagas disease.…”

Section: Introductionmentioning

confidence: 95%

Features of (Benzo)Imidazo[2,1-b][1,3]thiazine Mezylates Reaction with Nucleophilic Reagents

Slyvka,

Saliyeva,

Litvinchuk

et al. 2023

ChChT

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Peculiarities of the course of the methanesulfo-derivatives of (benzo)imidazo[2,1-b][1,3]thiazines reac-tions with a number of nucleophilic reagents were studied. It was determined that they react nonselectively with potassium thiocyanate to form a mixture of thio- and isothiocyanate derivatives. When interacting with sodium azide, nucleophilic substitution competes with an elimination reaction. The latter is dominant in the reaction with sodium cyanide. The spatial structure of one of the isomer elimination products, 4H-benzo[4,5]imidazo[2,1-b][1,3] thiazine, was established by X-ray structural analysis.

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Synthesis, crystal structure, antioxidant activity and dft study of 2-aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-One

Cited by 18 publications

References 30 publications

SYNTHESIS AND ANTIEXUDATIVE ACTIVITY OF N-ОXIDES 4-PYRIDINYLOXYSUBSTITUTED (BENZO)IMIDAZO[2,1-b][1,3]THIAZINES

SYNTHESIS AND ANTIEXUDATIVE ACTIVITY OF N-ОXIDES 4-PYRIDINYLOXYSUBSTITUTED (BENZO)IMIDAZO[2,1-b][1,3]THIAZINES

A Comprehensive Account on Recent Progress in Pharmacological Activities of Benzimidazole Derivatives

Features of (Benzo)Imidazo[2,1-b][1,3]thiazine Mezylates Reaction with Nucleophilic Reagents

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