Synthesis of amide‐linked benzazolyl isoxazoles adopting green methods and evaluation as antimicrobials

Abstract

Some new benzoxazolyl isoxazoles, benzothiazolyl isoxazoles and benzimidazolyl isoxazoles connected by amide bonds (7‐9) were prepared from N‐benzazolylcarbamoylmethylcinnamamides (1‐3) adopting eco‐friendly synthetic methodologies. In fact, cycloaddition of nitrile oxide generated from araldoxime using iodosobenzene and cetyltrimethylammonium bromide to 1‐3 followed by treatment with iodine in dimethyl sulfoxide led to the formation of title compounds with good yields and in shorter reaction times. The structures of all the synthesized compounds were confirmed by spectral parameters, viz, IR, NMR, and mass spectra and were assayed for antimicrobial activity. Among all the tested compounds, 8a and 8c displayed excellent antibacterial activity, whereas 9a and 9c showed promising antifungal activity.

Diastereomerically pure (S)‐verbenone‐isoxazoline hybrids: Synthesis, molecular structure, Hirshfeld surface analysis, density functional theory, cytotoxic effect, and apoptosis induction

“…The six-membered ring (C3a/C4-C7/C7a) exhibits an conformation (QT = 0.786(2) Å, θ = 52.4(2) , φ = 176.8( 2) ). The dihedral angle between the chlorophenyl ring and isoxazole and cyclohexane plane (C3a/C4-C7/C7a) are 12.99(8) and 59.96 (8) , respectively. The molecular are stacked parallel to the axis through the action of intermolecular C8-H8AÁ Á ÁN1 and C5-H5Á Á Áπ.…”

“…They can be designed by cycloaddition reaction of nitrile oxides with alkenes or alkynes [1][2][3]. Isoxazoline derivatives have been reported to exhibit a broad spectrum of pharmacological activity, including anticancer [4,5], antifungal [6], antimicrobial [7,8], antidepressant [9], and antibacterial [10] activities.…”

An Efficient Synthesis, Antimicrobial Evaluation and In Silico Studies of 1,2,3‐Triazolyl‐isoxazolyl‐ethanol Derivatives

“…[24][25][26][27] 1,2,3-Triazole-containing compounds received more attention due to their varied biological activities such as antifungal, [28][29][30][31][32][33][34] antimicrobial, [35,36] antivirals, [37,38] antimalarial, [39,40] anticancer [41][42][43] and anti-inflammatory activities. [44,45] The isoxazole containing natural and synthetic compounds reported for a wide range of biological activities such as antimicrobial, [46,47] antibacterial, [48][49][50] antifungal, [51,52] antitubercular, [16,[53][54][55] antiviral, [56,57] anticancer, [58][59][60] and anti-inflammatory. [61][62][63] Some of the FDA-approved and commercialized drugs containing isoxazole and triazole pharmacophore are shown in Figure 1 1) The hybrids of 1,2,4-triazole drugs by clubbing with azole or structural modifications of the fluconazole, isavuconazole, ravuconazole and albaconazole were reported for potential antifungal activity.…”

“…1,2,3‐Triazole‐containing compounds received more attention due to their varied biological activities such as antifungal, [28–34] antimicrobial, [35,36] antivirals, [37,38] antimalarial, [39,40] anticancer [41–43] and anti‐inflammatory activities [44,45] . The isoxazole containing natural and synthetic compounds reported for a wide range of biological activities such as antimicrobial, [46,47] antibacterial, [48–50] antifungal, [51,52] antitubercular, [16,53–55] antiviral, [56,57] anticancer, [58–60] and anti‐inflammatory [61–63] …”

(3-(4-klorofenil)-4,5-dihidroizoksazol-4,5-diil)dimetanol Bileşiği: Antibakteriyel Aktivite, Antifungal Aktivite ve Hesaplanmış Yapısal Parametreler

“…The synthesis and antimicrobial activity results of some 4,5-dihydroisoxazole derivatives have been reported in the literature [15][16][17]. There is not any report about discussing 4,5-dihydroisoxazole-4,5diyldimethanol compounds antimicrobial activity backward.…”