An efficient synthesis and antimicrobial evaluation of 5-alkenyl- and 5-styryl-1,2,4-oxadiazoles

Tarasenko, M. V.; Sidneva, Vera V.; Belova, A. S.; Romanycheva, Anna; Sharonova, Tatyana; Baykov, Sergey V.; Shetnev, Аnton; Кофанов, Е. Р.; Кузнецов, М. А.

doi:10.24820/ark.5550190.p010.760

Cited by 22 publications

(10 citation statements)

References 37 publications

(48 reference statements)

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“…Among all the four oxadiazole types, 1,2,4- and 1,3,4-isomers are the most investigated for medicinal applications [ 23 ], and they are present in numerous marketed drugs, such as the Ataluren [ 25 ], Azilsartan [ 26 ], Opicapone [ 27 ], Naldemedine [ 28 ], and Raltegravir [ 29 ]. Moreover, many oxadiazole derivatives have been studied as antibiotics [ 30 , 31 , 32 , 33 , 34 ], fungicides [ 35 ], antivirals [ 36 ], anticancer [ 37 , 38 , 39 ], and anti-inflammatory [ 40 , 41 , 42 ] agents, neuroprotectors [ 43 , 44 , 45 ], as well as antidiabetic drugs [ 46 ] in recent years. This significantly stimulates further structural and theoretical studies on various noncovalent interactions involving oxadiazole-based compounds.…”

Section: Introductionmentioning

confidence: 99%

π–π Noncovalent Interaction Involving 1,2,4- and 1,3,4-Oxadiazole Systems: The Combined Experimental, Theoretical, and Database Study

et al. 2021

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A series of N-pyridyl ureas bearing 1,2,4- (1a, 2a, and 3a) and 1,3,4-oxadiazole moiety (1b, 2b, 3b) was prepared and characterized by HRMS, 1H and 13C NMR spectroscopy, as well as X-ray diffraction. The inspection of the crystal structures of (1–3)a,b and the Hirshfeld surface analysis made possible the recognition of the (oxadiazole)···(pyridine) and (oxadiazole)···(oxadiazole) interactions. The presence of these interactions was confirmed theoretically by DFT calculations, including NCI analysis for experimentally determined crystal structures as well as QTAIM analysis for optimized equilibrium structures. The preformed database survey allowed the verification of additional examples of relevant (oxadiazole)···π interactions both in Cambridge Structural Database and in Protein Data Bank, including the cocrystal of commercial anti-HIV drug Raltegravir.

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Section: Introductionmentioning

confidence: 99%

π–π Noncovalent Interaction Involving 1,2,4- and 1,3,4-Oxadiazole Systems: The Combined Experimental, Theoretical, and Database Study

et al. 2021

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“…Thus, we came up with an idea to examine 1,2,4-oxadiazole ring as an alternative core for the promising 2-imidazoline-containing periphery, as it could provide novel two-heterocycles-hybrid based series of compounds for further diverse biological evaluation. These expectations were supported by several successful series of variously biologically active oxadiazoles synthesized and evaluated in our group [7,8,9,10], as well as by recent example of anti-MRSA (Methicillin-Resistant Staphylococcus aureus ) and anti-VRE (Vancomycin-Resistant Enterococcus ) active antibiotics incorporating 3-phenoxyphenyl-substituted 1,2,4-oxadiazoles, that have been recently reported [11,12,13,14,15,16,17].…”

Section: Introductionmentioning

confidence: 71%

1,2,4-Oxadiazole/2-Imidazoline Hybrids: Multi-target-directed Compounds for the Treatment of Infectious Diseases and Cancer

Shetnev

Baykov

Kalinin

et al. 2019

IJMS

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Replacement of amide moiety with the 1,2,4-oxadiazole core in the scaffold of recently reported efflux pump inhibitors afforded a novel series of oxadiazole/2-imidazoline hybrids. The latter compounds exhibited promising antibacterial activity on both Gram-positive (Staphylococcus aureus, Bacillus subtilis) and Gram-negative (Escherichia coli, Pseudomonas fluorescens) strains. Furthermore, selected compounds markedly inhibited the growth of certain drug-resistant bacteria. Additionally, the study revealed the antiproliferative activity of several antibacterial frontrunners against pancreas ductal adenocarcinoma (PANC-1) cell line, as well as their type-selective monoamine oxidase (MAO) inhibitory profile.

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“…For instance, 1,2,4-oxadiazoles have lower water solubility than 1,3,4-oxadiazoles because of the reduced hydrogen bond acceptor character of the nitrogen in 1,2,4-oxadiazole ring [43]. Moreover, they have been extensively studied because of their peculiar reactivity [43,48] and possible applications in material chemistry [49,50,51,52,53,54,55] or as bioactive compounds [44,56,57,58].…”

Section: Classes Of Translational Readthrough-inducing Drugs (Trids)mentioning

confidence: 99%

Strategies against Nonsense: Oxadiazoles as Translational Readthrough-Inducing Drugs (TRIDs)

Campofelice

Lentini

Leonardo

et al. 2019

IJMS

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This review focuses on the use of oxadiazoles as translational readthrough-inducing drugs (TRIDs) to rescue the functional full-length protein expression in mendelian genetic diseases caused by nonsense mutations. These mutations in specific genes generate premature termination codons (PTCs) responsible for the translation of truncated proteins. After a brief introduction on nonsense mutations and their pathological effects, the features of various classes of TRIDs will be described discussing differences or similarities in their mechanisms of action. Strategies to correct the PTCs will be presented, particularly focusing on a new class of Ataluren-like oxadiazole derivatives in comparison to aminoglycosides. Additionally, recent results on the efficiency of new candidate TRIDs in restoring the production of the cystic fibrosis transmembrane regulator (CFTR) protein will be presented. Finally, a prospectus on complementary strategies to enhance the effect of TRIDs will be illustrated together with a conclusive paragraph about perspectives, opportunities, and caveats in developing small molecules as TRIDs.

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An efficient synthesis and antimicrobial evaluation of 5-alkenyl- and 5-styryl-1,2,4-oxadiazoles

Cited by 22 publications

References 37 publications

π–π Noncovalent Interaction Involving 1,2,4- and 1,3,4-Oxadiazole Systems: The Combined Experimental, Theoretical, and Database Study

π–π Noncovalent Interaction Involving 1,2,4- and 1,3,4-Oxadiazole Systems: The Combined Experimental, Theoretical, and Database Study

1,2,4-Oxadiazole/2-Imidazoline Hybrids: Multi-target-directed Compounds for the Treatment of Infectious Diseases and Cancer

Strategies against Nonsense: Oxadiazoles as Translational Readthrough-Inducing Drugs (TRIDs)

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