3-Cyanoazolo[5,1-c][1,2,4]triazines: synthesis and antiviral activity

Сапожникова, Ирина М.; Ulomsky, E. N.; Русинов, В. Л.; Чупахин, О. Н.; Степанов, А. В.; Savateeva-Lyubimova, T. N.; Сивак, К. В.

doi:10.1007/s10593-021-02925-3

Cited by 10 publications

(4 citation statements)

References 13 publications

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“…Triazavirin (riamilovir) is a non-nucleoside triazolotriazine-based analog that has been investigated for its antiviral activity against tick-borne encephalitis and influenza [ 180 , 181 ]. To assess if derivatives of triazavirin would be effective in VEEV and EEEV cell culture and in infected mice, analogs were generated as sodium salts that incorporated a nitrile group in place of the nitro group of the parent structure, and then modifications were made to the triazine thiomethyl substituent or in the triazine ring itself [ 181 ]. At a concentration of 100 µg/mL, a 1.9 and 2.6 log reduction in VEEV and EEEV titers, respectively, was observed for compound 4b ( Figure 12 , Table 4 ).…”

Section: Additional Small Molecule Inhibitors Of Encephalitic Alphavi...mentioning

confidence: 99%

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Advances in the Development of Small Molecule Antivirals against Equine Encephalitic Viruses

Ogorek

Golden

2023

Viruses

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Venezuelan, western, and eastern equine encephalitic alphaviruses (VEEV, WEEV, and EEEV, respectively) are arboviruses that are highly pathogenic to equines and cause significant harm to infected humans. Currently, human alphavirus infection and the resulting diseases caused by them are unmitigated due to the absence of approved vaccines or therapeutics for general use. These circumstances, combined with the unpredictability of outbreaks—as exemplified by a 2019 EEE surge in the United States that claimed 19 patient lives—emphasize the risks posed by these viruses, especially for aerosolized VEEV and EEEV which are potential biothreats. Herein, small molecule inhibitors of VEEV, WEEV, and EEEV are reviewed that have been identified or advanced in the last five years since a comprehensive review was last performed. We organize structures according to host- versus virus-targeted mechanisms, highlight cellular and animal data that are milestones in the development pipeline, and provide a perspective on key considerations for the progression of compounds at early and later stages of advancement.

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Section: Additional Small Molecule Inhibitors Of Encephalitic Alphavi...mentioning

confidence: 99%

“…For mice dosed at 24 h post infection, 40% and 70% survival were observed with 50 or 100 mg/kg/d of compound 4b, respectively. Mouse toxicology experiments did not reveal behavioral or morphological changes in mice up to 28 days with daily injections of 375 mg/kg [ 181 ].…”

Section: Additional Small Molecule Inhibitors Of Encephalitic Alphavi...mentioning

confidence: 99%

Advances in the Development of Small Molecule Antivirals against Equine Encephalitic Viruses

Ogorek

Golden

2023

Viruses

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“…Therefore, we tried to optimize the structure of moroxydine hydrochloride. As they are lead compounds, heterocyclic structures containing nitrogen atoms, such as triazines [14], indoles [15], and quinolines [16]-which are themselves active structures with superb biological activity levels-have been emphasized in drug development. Triazine is a common lead structure in pesticide development, and it has been recognized in previous studies because it possesses a broad spectrum of biological activities, such as herbicidal [17][18][19] and antibacterial [20][21][22] activities, in addition to being a pharmacophore with decent antiviral [23] activity.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Anti-PVY Biological Activity of 1,3,5-Triazine Derivatives Containing Piperazine Structure

Bai

Wei

Zhang

et al. 2023

IJMS

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In this study, a commercial agent with antivirus activity and moroxydine hydrochloride were employed to perform a lead optimization. A series of 1,3,5-triazine derivatives with piperazine structures were devised and synthesized, and an evaluation of their anti-potato virus Y (PVY) activity revealed that several of the target compounds possessed potent anti-PVY activity. The synthesis of compound C35 was directed by a 3D-quantitative structure–activity relationship that used the compound’s structural parameters. The assessment of the anti-PVY activity of compound C35 revealed that its curative, protective, and inactivation activities (53.3 ± 2.5%, 56.9 ± 1.5%, and 85.8 ± 4.4%, respectively) were comparable to the positive control of ningnanmycin (49.1 ± 2.4%, 50.7 ± 4.1%, and 82.3 ± 6.4%) and were superior to moroxydine hydrochloride (36.7 ± 2.7%, 31.4 ± 2.0%, and 57.1 ± 1.8%). In addition, molecular docking demonstrated that C35 can form hydrogen bonds with glutamic acid at position 150 (GLU 150) of PVY CP, providing a partial theoretical basis for the antiviral activity of the target compounds.

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“…7 This work also includes the preparation of azo compounds and Schiff bases, the latter of which are distinguished by the presence of a (N=N) group. Antibacterial, antifungal, antiviral, and anticancer properties [8][9][10] attest to its significance in biological processes. Hugo Schiff, a German chemist, discovered Schiff bases in 1864 when he observed that condensation of primary amines with carbonyl compounds produced compounds with an imine group.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Study the Biological Activity for Some New Heterocyclic Derivative from 4,5-dichloro Imidazole

Kamal¹,

Adnan²

2022

IJDDT

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Creating a multi-step method for synthesizing heterocyclic compounds is the goal of this research. The first step involves reacting 4,5-dichloro-2- phenylenediamine with 3- amino- 4-“hydroxybenzoic acid to produce an imidazole derivative (1), which then reacts with salicyldehyde to produce the azo compound (2). Two, a Schiff base derivative is produced via a reaction with p-chloro aniline (23). Final steps involve reactions (3) with chloroacetyl chloride, alanine, sodium azide, thioglycol acid, anthranilic acid, and maleic anhydride, yielding beta-lactam derivatives (4), imidazolidine (5), tetrazol(6), thiazolidine (7), hydroquinazoline”(8), and oxazepine (9), respectively. The spectroscopic techniques of fourier transform infrared (FTIR) and proton nuclear magnetic resonance (1HNMR) have been used to identify all of the compounds that have been prepared; next, the compounds’ biological effects on two types of cancer have been investigated.

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3-Cyanoazolo[5,1-c][1,2,4]triazines: synthesis and antiviral activity

Cited by 10 publications

References 13 publications

Advances in the Development of Small Molecule Antivirals against Equine Encephalitic Viruses

Advances in the Development of Small Molecule Antivirals against Equine Encephalitic Viruses

Design, Synthesis, and Anti-PVY Biological Activity of 1,3,5-Triazine Derivatives Containing Piperazine Structure

Synthesis, Characterization and Study the Biological Activity for Some New Heterocyclic Derivative from 4,5-dichloro Imidazole

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