New potent antibacterials against Gram-positive multiresistant pathogens: Effects of side chain modification and chirality in linezolid-like 1,2,4-oxadiazoles

Fortuna, Cosimo G.; Berardozzi, Roberto; Bonaccorso, Carmela; Caltabiano, Gianluigi; Bari, Lorenzo Di; Goracci, Laura; Guarcello, Annalisa; Pace, Andrea; Piccionello, Antonio Palumbo; Pescitelli, Gennaro; Pierro, Paola; Lonati, Elena; Bulbarelli, Alessandra; Cocuzza, Clementina; Musumarra, Giuseppe; Musumeci, Rosario

doi:10.1016/j.bmc.2014.10.037

Cited by 23 publications

(20 citation statements)

References 44 publications

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“…In turn, the ligand bipyOXA was synthesized through a solvent-free reaction between 2-cyanopyridine and 2-picolinamidoxime, by following the amidoxime-route (Fig. 1B) [27,28].…”

Section: Synthesismentioning

confidence: 99%

The dissociation of the Hsp60/pro-Caspase-3 complex by bis(pyridyl)oxadiazole copper complex ( CubipyOXA ) leads to cell death in NCI-H292 cancer cells

Bavisotto

Nikolić

Gammazza

et al. 2017

Journal of Inorganic Biochemistry

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“…In turn, the ligand bipyOXA was synthesized through a solvent-free reaction between 2-cyanopyridine and 2-picolinamidoxime, by following the amidoxime-route (Fig. 1B) [27,28].…”

Section: Synthesismentioning

confidence: 99%

The dissociation of the Hsp60/pro-Caspase-3 complex by bis(pyridyl)oxadiazole copper complex ( CubipyOXA ) leads to cell death in NCI-H292 cancer cells

Bavisotto

Nikolić

Gammazza

et al. 2017

Journal of Inorganic Biochemistry

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“…As shown in Table 1, the corresponding acylamidine 2a was obtained only in the presence of polar protic solvents (entries 8-11); however, the desired product was obtained in good yield and in a shorter time by heating the reaction in methanol (entry 12). Interestingly, formic acid could also be used as a reducing agent (entry [10][11]. The use of zinc dust or the absence of catalyst did not produce the desired product (entry 6-7).…”

Section: Reduction Reactionsmentioning

confidence: 99%

“…1,2,4-Oxadiazoles are five-membered heterocycles that have been widely studied for their valuable applications ranging from the pharmaceutical field to material science [1]. The use of a 1,2,4-oxadiazole ring as an isosteric replacement of esters and amides increased their presence in medicinal chemistry projects [2] with biological applications ranging from the treatment of nonsense mutations [3,4] and Alzheimer's disease (AD) [5][6][7] to antibiotics [8][9][10] and antitumorals [11,12]. Applications in the field of materials chemistry, such as liquid crystals [13] metal sensors [14], OLED [15], energetic materials [16] and gas sorbing/releasing systems [17][18][19], have been reported.…”

Section: Introductionmentioning

confidence: 99%

Ammonium Formate-Pd/C as a New Reducing System for 1,2,4-Oxadiazoles. Synthesis of Guanidine Derivatives and Reductive Rearrangement to Quinazolin-4-Ones with Potential Anti-Diabetic Activity

Marzullo

Vasto

Buscemi

et al. 2021

IJMS

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1,2,4-Oxadiazole is a heterocycle with wide reactivity and many useful applications. The reactive O-N bond is usually reduced using molecular hydrogen to obtain amidine derivatives. NH4CO2H-Pd/C is here demonstrated as a new system for the O-N reduction, allowing us to obtain differently substituted acylamidine, acylguanidine and diacylguanidine derivatives. The proposed system is also effective for the achievement of a reductive rearrangement of 5-(2′-aminophenyl)-1,2,4-oxadiazoles into 1-alkylquinazolin-4(1H)-ones. The alkaloid glycosine was also obtained with this method. The obtained compounds were preliminarily tested for their biological activity in terms of their cytotoxicity, induced oxidative stress, α-glucosidase and DPP4 inhibition, showing potential application as anti-diabetics.

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“…It is crucial to remember the importance of antibiotics research for modern medicine to counter the growing threat posed by AMR. With the continuous rise of difficult-to-treat pathogens and related infectious diseases, the development of new strategies [ 2 , 3 , 4 ] and improved effective therapeutics, including antibiotics and their combinations, are urgently needed [ 5 , 6 , 7 , 8 ].…”

Section: Introductionmentioning

confidence: 99%

Heteroaryl-Ethylenes as New Lead Compounds in the Fight against High Priority Bacterial Strains

et al. 2021

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The widespread use of antibiotics has led to a gradual increase in drug-resistant bacterial infections, which severely weakens the clinical efficacy of antibacterial therapies. In recent decades, stilbenes aroused great interest because of their high bioavailability, as well as their manifold biological activity. Our research efforts are focused on synthetic heteroaromatic stilbene derivatives as they represent a potentially new type of antibiotic with a wide antibacterial spectrum. Herein, a preliminary molecular modeling study and a versatile synthetic scheme allowed us to define eight heteroaromatic stilbene derivatives with potential antimicrobial activity. In order to evaluate our compound’s activity spectrum and antibacterial ability, minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) tests have been performed on Gram-positive and Gram-negative ATCC strains. Compounds PB4, PB5, PB7, and PB8 showed the best values in terms of MIC and were also evaluated for MBC, which was found to be greater than MIC, confirming a bacteriostatic activity. For all compounds, we evaluated toxicity on colon-rectal adenocarcinoma cells tumor cells (CaCo2), once it was established that the whole selected set was more active than 5-Fluorouracil in reducing CaCo-2 cells viability. To the best of our knowledge, the biological assays have shown for these derivatives an excellent bacteriostatic activity, compared to similar molecular structures previously reported, thus paving the way for a new class of antibiotic compounds.

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New potent antibacterials against Gram-positive multiresistant pathogens: Effects of side chain modification and chirality in linezolid-like 1,2,4-oxadiazoles

Cited by 23 publications

References 44 publications

The dissociation of the Hsp60/pro-Caspase-3 complex by bis(pyridyl)oxadiazole copper complex ( CubipyOXA ) leads to cell death in NCI-H292 cancer cells

The dissociation of the Hsp60/pro-Caspase-3 complex by bis(pyridyl)oxadiazole copper complex ( CubipyOXA ) leads to cell death in NCI-H292 cancer cells

Ammonium Formate-Pd/C as a New Reducing System for 1,2,4-Oxadiazoles. Synthesis of Guanidine Derivatives and Reductive Rearrangement to Quinazolin-4-Ones with Potential Anti-Diabetic Activity

Heteroaryl-Ethylenes as New Lead Compounds in the Fight against High Priority Bacterial Strains

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