Microwave-assisted synthesis of (3,5-disubstituted isoxazole)-linked benzimidazolone derivatives: DFT calculations and biological activities

Ibrahim, Sana; Ghabi, Ameni; Amiri, Nesrine; Mtiraoui, Hasan; Hajji, Melek; Bel-Hadj-Tahar, Radhouane; Msaddek, Moncef

doi:10.1007/s00706-021-02764-0

Cited by 12 publications

(3 citation statements)

References 44 publications

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“…Benzimidazolone derivatives display diverse pharmacological and biological properties including antiviral (Ferro et al, 2017), antibacterial (Saber et al, 2020;Mentes ¸e et al, 2021), anticancer (Guillon et al, 2022), anti-Alzheimer's (Mo et al, 2020), antifungal (Ibrahim et al, 2021), and antioxidant (Ibrahim et al, 2021) activities. In our ongoing research in this area, we are synthesizing compounds that combine the 1,2,3triazole motif with benzimidazol-2-one derivatives.…”

Section: Chemical Contextmentioning

confidence: 99%

Synthesis, structure and Hirshfeld surface analysis of 1,3-bis[(1-octyl-1H-1,2,3-triazol-4-yl)methyl]-1H-benzo[d]imidazol-2(3H)-one

Zouhair,

El Ghayati,

El Monfalouti

et al. 2023

Acta Cryst E

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The title molecule, C29H44N8O, adopts a conformation resembling a two-bladed fan with the octyl chains largely in fully extended conformations. In the crystal, C—H...O hydrogen bonds form chains of molecules extending along the b-axis direction, which are linked by weak C—H...N hydrogen bonds and C—H...π interactions to generate a three-dimensional network. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (68.3%), H...N/N...H (15.7%) and H...C/C...H (10.4%) interactions.

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Section: Chemical Contextmentioning

confidence: 99%

Synthesis, structure and Hirshfeld surface analysis of 1,3-bis[(1-octyl-1H-1,2,3-triazol-4-yl)methyl]-1H-benzo[d]imidazol-2(3H)-one

Zouhair,

El Ghayati,

El Monfalouti

et al. 2023

Acta Cryst E

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“…Compounds 90d and 90e showed best antibacterial activity specifically against E. coli , P. aeruginosa , and S. aureus and showed the highest antifungal activity against C. albicans , A. fumigatus , and A. brasiliensis ( Scheme 24 ). 29 …”

Section: Synthesis Of Cu-catalyzed Heterocyclic Moieties Via Microwav...mentioning

confidence: 99%

Copper Catalyzed Synthesis of Heterocyclic Molecules via C–N and C–O Bond Formation under Microwaves: A Mini-Review

Jena

Chanda

2023

ACS Omega

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Heterocyclic moieties play a significant role in the field of drug discovery. C−N and C−O bond formation reactions are the primary synthetic sequence for the generation of heterocyclic molecules. The generation of C−N and C−O bonds involves the use of mostly Pd or Cu catalysts although other transition metal catalyst's are also involved. However, in C−N and C−O bond formation reactions, several problems were faced such as catalytic systems containing costly ligands, lack of substrate scope, lots of waste generation, and high temperature conditions. So it is imperative to uncover new eco-friendly synthetic strategies. In view of enormous drawbacks, it is important to develop an alternate microwave-assisted synthesis of heterocycles via C−N and C−O bond formation, which provides a short reaction time, tolerance for functional groups, and less waste production. Numerous chemical reactions have been accelerated using microwave irradiation which provides a cleaner reaction profile, lower energy consumption, and higher yields. This review article highlights a comprehensive overview on the potential application of microwave assisted synthetic routes for the synthesis of diverse heterocycles via mechanistic pathways covering the year ranges from 2014 to 2023, along with possible biological interests.

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“…Herein, in this study, we attempt to replace the triketone pharmacophore of mesotrione with the tetrazolamide fragment to improve chelation and introduce a benzo-heterocyclic unit to enhance the π–π interaction between the molecule and the amino acid residues. Benzimidazol-2-one is a privileged structure widely discovered in many drugs and pesticides, and its derivatives show anticancer, antiviral, and antibacterial activity. − Therefore, we hybridized tetrazolamide and benzimidazol-2-one fragments, affording tetrazolamide-benzimidazol-2-ones 8 – 34 (Figure ). The structural characterization, At HPPD inhibitory activity, and greenhouse herbicidal activity of the synthesized compounds were systematically investigated.…”

Section: Introductionmentioning

confidence: 99%

Discovery of Tetrazolamide-benzimidazol-2-ones as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

Cai,

Huang,

Dong

et al. 2024

J. Agric. Food Chem.

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4-Hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) is one of the most valuable herbicide targets due to its unique biological functions. In search of HPPD inhibitors with promising biological performance, we designed and synthesized a series of novel tetrazolamide-benzimidazol-2-ones using a structure-based drug design strategy. Among the synthesized compounds,imidazole-4-carboxamide, 25, IC 50 = 10 nM, was identified to be the most outstanding HPPD inhibitor, which showed more than 36-fold increased Arabidopsis thaliana HPPD (AtHPPD) inhibition potency than mesotrione (IC 50 = 363 nM). Our AtHPPD−25 complex indicated that one nitrogen atom on the tetrazole ring and the oxygen atom on the amide group formed a classical bidentate chelation interaction with the metal ion, the benzimidazol-2-one ring created a tight π−π stacking interaction with Phe381 and Phe424, and some hydrophobic interactions were also found between the ortho-Cl-benzyl group and surrounding residues. Compound 32 showed more than 80% inhibition against all four tested weeds at 150 g ai/ha by the postemergence application. Our results indicated that the tetrazolamidebenzimidazol-2-one scaffold may be a new lead structure for herbicide discovery.

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Microwave-assisted synthesis of (3,5-disubstituted isoxazole)-linked benzimidazolone derivatives: DFT calculations and biological activities

Cited by 12 publications

References 44 publications

Synthesis, structure and Hirshfeld surface analysis of 1,3-bis[(1-octyl-1H-1,2,3-triazol-4-yl)methyl]-1H-benzo[d]imidazol-2(3H)-one

Synthesis, structure and Hirshfeld surface analysis of 1,3-bis[(1-octyl-1H-1,2,3-triazol-4-yl)methyl]-1H-benzo[d]imidazol-2(3H)-one

Copper Catalyzed Synthesis of Heterocyclic Molecules via C–N and C–O Bond Formation under Microwaves: A Mini-Review

Discovery of Tetrazolamide-benzimidazol-2-ones as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

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