Substituted oxadiazoles: a patent review (2010 – 2012)

Zarghi, Afshin; Hajimahdi, Zahra

doi:10.1517/13543776.2013.797409

Cited by 23 publications

(6 citation statements)

References 105 publications

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“…The oxadiazoles are a class of five-membered heterocycles that are of considerable interest in organic and medicinal chemistry [20]. In some bioactive compounds, they act as bioisosteres of ester and amide, with improved pharmacokinetic and pharmacodynamic profiles and enhanced selectivity; in other cases, the rigid heterocyclic ring acts as a flat aromatic spacer, assuring the appropriate substituent geometry.…”

Section: Discussionmentioning

confidence: 99%

Synergism of a Novel 1,2,4-oxadiazole-containing Derivative with Oxacillin against Methicillin-Resistant Staphylococcus aureus

et al. 2021

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Staphylococcusaureus is an important opportunistic pathogen that causes many infections in humans and animals. The inappropriate use of antibiotics has favored the diffusion of methicillin-resistant S. aureus (MRSA), nullifying the efforts undertaken in the discovery of antimicrobial agents. Oxadiazole heterocycles represent privileged scaffolds for the development of new drugs because of their unique bioisosteric properties, easy synthesis, and therapeutic potential. A vast number of oxadiazole-containing derivatives have been discovered as potent antibacterial agents against multidrug-resistant MRSA strains. Here, we investigate the ability of a new library of oxadiazoles to contrast the growth of Gram-positive and Gram-negative strains. The strongest antimicrobial activity was obtained with compounds 3 (4 µM) and 12 (2 µM). Compound 12, selected for further evaluation, was found to be noncytotoxic on the HaCaT cell line up to 25 µM, bactericidal, and was able to improve the activity of oxacillin against the MRSA. The highest synergistic interaction was obtained with the combination values of 0.78 μM for compound 12, and 0.06 μg/mL for oxacillin. The FIC index value of 0.396 confirms the synergistic effect of compound 12 and oxacillin. MRSA treatment with compound 12 reduced the expression of genes included in the mec operon. In conclusion, 12 inhibited the growth of the MRSA and restored the activity of oxacillin, thus resulting in a promising compound in the treatment of MRSA infection.

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Section: Discussionmentioning

confidence: 99%

Synergism of a Novel 1,2,4-oxadiazole-containing Derivative with Oxacillin against Methicillin-Resistant Staphylococcus aureus

et al. 2021

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“…The 1,3,4‐derivatives acting as bioisosteres for the carbonyl group with compounds like amides, carbamates, or esters are known to show better water solubility, lower lipophilicity, and higher metabolic stability compared with different isomeric oxadiazoles. Used as an essential part of the pharmacophore capable of interacting with the ligand, the oxadizole ring acts in some cases as a straight aromatic linker to ensure the correct orientation of the molecule [11,12]. In view of the continuously growing incidence of various types of cancer, the study on the anticancer residences of 1,3,4‐oxadiazole derivatives seems to be of targeted interest [13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of novel 1,3,4‐oxadiazole derivatives as anticancer agents and potential EGFR inhibitors

Osmaniye

Görgülü

Sağlık

et al. 2021

Journal of Heterocyclic Chem

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EGFR (epidermal growth factor receptor) tyrosine kinases are frequently used in recent years, especially in small cell lung cancer. As with all other anticancer drugs, problems such as high side‐effect profiles and resistance to anticancer drugs call for new antiproliferative compounds. In the light of the above information, novel quinoxalin‐oxadiazole derivatives were synthesized as EGFR inhibitors in this study. Synthesis of compounds (3a–3j) was performed according to the literature methods. Their structures were elucidated by 1H‐NMR, 13C‐NMR, and HRMS spectroscopic methods. Structure elucidation was performed for compound 3e using 2D NMR technique. MTT test was performed to assess the cell proliferation effects of the different compounds on lung and mammary cell lines (A549, MCF7). In addition, obtained compounds (3a–3j) were screened against healthy CCD19‐Lu cell line (human lung fibroblast normal cells) to determine selectivity of the cytotoxic activities. Among the tested compounds, 3e and 3j showed significant cytotoxic activity against A549 cancer cell. Moreover, compound 3g and 3h displayed good activity. And the compounds 3e and 3j performed significant EGFR inhibition. Interaction modes of the compounds 3e, 3j were investigated against EGFR tyrosine kinase by means of docking studies. As a result of the studies, the importance of the quinoxaline ring and the NO2 substituent has been understood. In future studies, it is planned to make modifications by keeping these two structures constant. The activity can be contributed by using other heterocyclic rings instead of the oxadizaole ring.

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“…They are frequently found in marine organisms [ 26 ]. These are more attractable heterocyclic structural framework to medicinal chemist [ 27 ], due to their broad spectrum of biological properties including (2S)cannabinoid receptor 2 (CB2) [ 28 ], immunosuppressive [ 29 ], muscarinic [ 30 ], α,β 3 -receptor antagonist [ 31 ], antimicrobial [ 32 ], insecticides [ 33 ], histamine-H3 [ 34 ], anti-inflammatory [ 35 ], analgesic [ 36 ], diabetic, anticancer, antiparasitic and anti-helminthic properties. The US FDA approved drug such as ataluren ( 2 ), contains 1,2,4-oxadiazole framework as a part of the structure and is used for the treatment of muscular dystrophy [ 37 – 39 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, biological evaluation and docking studies of 1,2,4-oxadiazole linked 5-fluorouracil derivatives as anticancer agents

Bommera¹,

Kethireddy²,

Govindapur

et al. 2021

BMC Chemistry

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Background 1,2,4-oxadiazole derivatives exhibited significant anti-cancer activity when they were evaluated, against human cancer cell lines. They also showed anti-inflammatory, analgesic, diabetic, immunosuppressive, α,β3-receptor antagonist, antimicrobial, anti-helminthic, histamine-H3 and antiparasitic properties. A pyrimidine analog, 5 fluoro-uracil is a chemotherapeutic drug used for treating multiple solid malignant tumors. But its application is limited, as it has side effects like low bioavailability and high toxicity. Molecular docking is an exemplary tool, helps in identifying target and designing a drug containing high bio-availability and minimum toxicity. Results A set of 1,2,4-oxadiazole linked 5-fluoruracil derivatives (7a–j) were synthesized and their structures were confirmed by 1HNMR, 13CNMR and Mass spectral analysis. Further, these compounds were investigated for their anticancer activity towards a panel of four human cancer cell lines such as (MCF-7, MDA MB-231), lung cancer (A549) and prostate cancer (DU-145) by using MTT method. Among them, compounds 7a, 7b, 7c, 7d and 7i demonstrated more promising anticancer activity than standard. Conclusion Synthesized derivatives (7a–j) of 1,2,4-oxadiazole linked 5-fluorouracil and investigated for their anticancer activity towards a panel of four human cancer cell lines.

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Substituted oxadiazoles: a patent review (2010 – 2012)

Cited by 23 publications

References 105 publications

Synergism of a Novel 1,2,4-oxadiazole-containing Derivative with Oxacillin against Methicillin-Resistant Staphylococcus aureus

Synergism of a Novel 1,2,4-oxadiazole-containing Derivative with Oxacillin against Methicillin-Resistant Staphylococcus aureus

Synthesis and biological evaluation of novel 1,3,4‐oxadiazole derivatives as anticancer agents and potential EGFR inhibitors

Synthesis, biological evaluation and docking studies of 1,2,4-oxadiazole linked 5-fluorouracil derivatives as anticancer agents

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