Design, Synthesis and Molecular Docking Studies of Novel Indole–Isoxazole–Triazole Conjugates as Potent Antibacterial Agents

Prashanthi, M.; Babu, H. Ramesh; Rani, J. Uma

doi:10.1134/s1068162021020217

Cited by 6 publications

(2 citation statements)

References 24 publications

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“…Isoxazoles are a type of azoles that contain adjacent oxygen and nitrogen heteroatoms. Compounds with isoxazole ring have numerous biological properties, [1] such as anti‐cancer, [2] anti‐bacterial, [3] anti‐fungal, [4] anti‐inflammatory, [5] anti‐proliferative [6] and disinfectant activities [7] . Reactions between hydroxylamine and β‐dicarbonyl compounds [8] or α,β‐enones [9] are the most frequently used routes to isoxazoles.…”

Section: Introductionmentioning

confidence: 99%

Regioselective Synthesis of Isoxazoles from Propargylic Alcohols via In‐situ‐formed α‐Iodo Enones/Enals

Yang.,

Chen,

et al. 2024

Asian J Org Chem

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A regioselective synthesis of isoxazoles with propargyl alcohols, N‐iodosuccinimide (NIS), and N‐tert‐butyl hydroxylamine hydrochloride (t‐BuNHOH•HCl) as the reaction substrates is reported. Reaction scope investigations indicated that primary and secondary propargyl alcohols underwent this transformation smoothly to afford 5‐, 3‐, and 3,5‐substituted isoxazoles in moderate to good yields. The reaction most likely involves an electrophilic‐intercepted Meyer–Schuster rearrangement of the propargyl alcohol, followed by intermolecular cyclocondensation of N‐tert‐butyl hydroxylamine and in‐situ‐formed α‐iodo enones/enals. This one‐pot method is regioselective and easy to perform, making it a valuable method for the construction of isoxazoles. Finally, its application was explored through the synthesis of valdecoxib.

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Section: Introductionmentioning

confidence: 99%

Regioselective Synthesis of Isoxazoles from Propargylic Alcohols via In‐situ‐formed α‐Iodo Enones/Enals

Yang.,

Chen,

et al. 2024

Asian J Org Chem

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“…Derivatives with antiviral, antimalarial, and anticancer activity are also known [26][27][28][29][30]. Thiosemicarbazides are often an initial compound for the synthesis of new active substances that include antibacterial and antifungal properties [31][32][33][34][35][36].…”

Section: Introductionmentioning

confidence: 99%

New Thiosemicarbazide Derivatives with Multidirectional Biological Action

Lasek,

Kosikowska,

Kołodziej

et al. 2024

Molecules

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Over the years, several new medicinal substances have been introduced for the treatment of diseases caused by bacteria and parasites. Unfortunately, due to the production of numerous defense mechanisms by microorganisms and parasites, they still pose a serious threat to humanity around the world. Therefore, laboratories all over the world are still working on finding new, effective methods of pharmacotherapy. This research work aimed to synthesize new compounds derived from 3-trifluoromethylbenzoic acid hydrazide and to determine their biological activity. The first stage of the research was to obtain seven new compounds, including six linear compounds and one derivative of 1,2,4-triazole. The PASS software was used to estimate the potential probabilities of biological activity of the newly obtained derivatives. Next, studies were carried out to determine the nematocidal potential of the compounds with the use of nematodes of the genus Rhabditis sp. and antibacterial activity using the ACCT standard strains. To determine the lack of cytotoxicity, tests were performed on two cell lines. Additionally, an antioxidant activity test was performed due to the importance of scavenging free radicals in infections with pathogenic microorganisms. The conducted research proved the anthelmintic and antibacterial potential of the newly obtained compounds. The most effective were two compounds with a 3-chlorophenyl substituent, both linear and cyclic derivatives. They demonstrated higher efficacy than the drugs used in treatment.

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Ethynyl‐B(dan) in [3+2] Cycloaddition and Larock Indole Synthesis: Synthesis of Stable Boron‐Containing Heteroaromatic Compounds

Li,

Tanaka,

Imagawa

et al. 2023

Chemistry A European J

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The cycloaddition of nitrile oxides with ethynyl‐B(dan) (dan=naphthalene‐1,8‐diaminato) allowed the facile preparation of diverse isoxazolyl‐B(dan) compounds, all of which displayed excellent protodeborylation‐resistant properties. The dan‐installation on the boron center proves vital to the high stability of the products as well as the perfect regioselectivity arising from hydrogen bond‐directed orientation in the cycloaddition. The diminished boron‐Lewis acidity of ethynyl‐B(dan) also renders it amenable to azide‐alkyne cycloaddition, Larock indole synthesis and related heteroannulations. The obtained boron‐containing triazole, indoles, benzofuran and indenone exhibit sufficient resistance toward protodeborylation. Despite the commonly accepted transmetalation‐inactive property derived from the diminished Lewis acidity, the synthesized heteroaryl‐B(dan) compound was still found to be convertible to the oligoarene via sequential Suzuki‐Miyaura coupling.

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Design, Synthesis and Molecular Docking Studies of Novel Indole–Isoxazole–Triazole Conjugates as Potent Antibacterial Agents

Cited by 6 publications

References 24 publications

Regioselective Synthesis of Isoxazoles from Propargylic Alcohols via In‐situ‐formed α‐Iodo Enones/Enals

Regioselective Synthesis of Isoxazoles from Propargylic Alcohols via In‐situ‐formed α‐Iodo Enones/Enals

New Thiosemicarbazide Derivatives with Multidirectional Biological Action

Ethynyl‐B(dan) in [3+2] Cycloaddition and Larock Indole Synthesis: Synthesis of Stable Boron‐Containing Heteroaromatic Compounds

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