- Development of Imidazoline-2-one Derivatives as Potential Antifungal and Anthelminthic Agents: in silico and in vitro Evaluation
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Based on appropriate values of synthetic accessibility concerning from ADMET properties and docking scores by docking against proteins 3OZU and 1OJ0, a series of 4,5-diphenyl-1H-imidazol-2-ones (I1?15) were synthesized. The key intermediate, 2-hydroxy-1,2-disubstitutedethanones (E1?15) were prepared by benzoin condensation using 2:1 ratio of aromatic aldehydes and thiamine in the presence of alkali. Further, these cyclized ethanones (E1?15) were treated with urea to yield 4,5-diphenyl-1H-imidazol-2-one derivatives (I1?15) and were characterized by IR,1H NMR, Mass spectra, and CHNO analysis. The synthesized compounds were screened for their anthelmintic potential on Pheretima Posthuma along with standard albendazole, and antifungal activity (minimum inhibitory concentration method) on Candida albicans and Aspergillus niger along with standard miconazole. The results revealed that among all the tested compounds I3, I4, and I7 show considerable synthetic accessibility, docking scores, anthelminthic, and antifungal activity.
- Chilamakuru, Naresh Babu,Mallela, Vijaya Jyothi,Peraman, Ramalingam,Shaik, Shakir Basha,Simham, Venu,Singirisetty, Triveni
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p. 423 - 433
(2021/11/24)
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- Efficient Green Synthesis and Computational Chemical Study of Some Interesting Heterocyclic Derivatives as Insecticidal Agents
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A series of 5,5-diarylhydantoin (Dilantin) 3, 4, and 7, imidazole 1, 2, 5, 6, 8, and 9, thiazole 10–12, triazinthione 13, 15, 16, and 17, and thiadiazine 14 derivatives, containing diverse hydrophobic groups, were green synthesized through one-pot stepwise reaction of aromatic aldehydes, vitamin B1, and nitrogen nucleophiles, for example, urea, thiourea, and thiosemicarbazide using grinding technique as well as conventional thermal methods. Such synthesized compounds have potent insecticidal activities; for example, compounds 4, 6, and 17 exhibited the highest insecticidal activity against both Plutella xylostella and Helicoverpa armigera with minimum inhibitory concentration values at 500?μg/mL and LD50 activities at 50?μg/mL. The density functional theory was then applied to explore the structural and electronic characteristics of these compounds. All the synthesized compounds have been characterized based on their elemental analyses and spectral data.
- Fahmy,Rizk,Hemdan,El-Sayed,Hassaballah
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p. 2545 - 2555
(2018/09/27)
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- Condensation Reactions of Aryl Acyloins with Ureas in Ethylene Glycol
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4,5-Diaryl-4-imidazolin-2-ones were prepared in good yield by heating aryl acyloins with ureas in ethylene glycol for 0.5-2 hours. 4,4'-Dimethoxybenzoin and 2,2'-pyridoin gave 4-oxazolin-2-one derivatives in addition to 4-imidazolin-2-ones.
- Kim, Yong Boon,Kim, Chung Soo,Lee, Chang Kiu
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p. 1653 - 1656
(2007/10/02)
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- Interaction of calix(n)arenes with urea, dibenzoylurea and 4,5-diphenylimidazolin-2-one
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Interaction of urea, dibenzoylurea and 4,5-diphenylimidazolin-2-one with calix(n)arenes has been investigated by ultraviolet, infrared and NMR spectroscopy.It appears that urea can get incorporated into the cavity of 5,11,17,23-tetra-p-tert-butyl-25,26,27
- Chawla, H. Mohindra,Hooda, Usha
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p. 715 - 720
(2007/10/02)
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- Dye sensitized photooxygenation of imidazolin-2-ones
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Imidazolin-2-ones(13-18) on photooxygenation in the presence of methylene blue yielded the corresponding diacylureas as the only products isolated at room temperature. The rate of photooxygenation followed the order 16>17>18>13>14>15. The reaction was als
- Chawla, H. Mohindra,Pathak, Manisha
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p. 1331 - 1342
(2007/10/02)
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- Photoreactions of 4,5-diarylimidazoles: Singlet oxygenation and cyclodehydrogenation
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4,5-Diarylimidazoles (1) undergo singlet oxygenation and cleavage to give N,N'-diaroylureas (2) on irradiation in alcoholic solutions in the presence of methylene blue as sensitizer. 5-Methoxy-4,5-diphenylimidazolin-2-one (5) and 4,5-dimethoxy-4,5-diphenylimidazolidin-2-one (6) have been reported as the principal products in the dye-sensitized irradiation of 4,5-diphenylimidazole in methanol.The formation of diaroylureas appears to proceed through the intermediacy of the corresponding imidazolin-2-one.A mechanistic pathway for the photochemical dye-sensitized oxygenation of the imidazoles is suggested.The photochemical cyclodehydrogenation reaction of the stilbene system present in 4,5-diarylimidazoles has also been carried out.
- Purushothaman, E.,Pillai, V. N. Rajasekharan
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p. 290 - 293
(2007/10/02)
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- RECYCLIZATION OF 4,5-DIPHENYLOXAZOLIN-2-ONE AND -2-THIONE UNDER THE INFLUENCE OF AMINES
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4,5-Diphenyl-4-oxazolin-2-one and -2-thione undegro recyclization to 1-substituted 4,5-diphenyl-4-imidazolin-2-ones and -2-thiones, respectively, under the influence of primary amines.The action of hydrazine hydrate on the oxazolone leads to 5,6-diphenyl-1,2,3,4,-tetrahydro-1,2,4-triazin-3-one.The corresponding ureas were isolated from the reaction mixtures in a number of cases.
- Kalcheva, V. B.,Tsvetanska, L. I.
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p. 756 - 758
(2007/10/02)
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- Syntheses with α-Metalated Isocyanides, XLV. - Reactions of α-Metalated Isocyanides with Some 1,3-Dipoles
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Reaction of α-metalated isocyanides 1a-c, f with alkylideneamine oxides (nitrones) 4 affords the 2-imidazolidinones 8.The 6-metalated 2,3-dihydro-4H-1,2,5-oxadiazine of type 5 is postulated as decisive intermediate. - Benzonitrile oxide (17) reacts analogously with 1a and 1b to give 4-imidazolin-2-ones 18 and with 1e to give the 3-imidazolin-2-one 19. - Phenyl azide (20) reacts with two moles of 1b to give 5-(benzylidenamino)-4H,5H-1,2,3-triazoline 24.The reaction course is discussed.
- Schoellkopf, Ulrich,Lau, Hans-Hermann,Scheunemann, Karl-Heinz,Blume, Ernst,Madawinata, Kusuma
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p. 600 - 610
(2007/10/02)
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