Synthesis of 2,4,5-Trisubstituted Phenanthroimidazole Derivatives using SBA-Pr-SO3H as a Nanocatalyst

Ziarani, Ghodsi Mohammadi; Tavaf, Elham; Vavsari, Vaezeh Fathi; Badiei, Alireza

doi:10.17344/acsi.2016.3111

Cited by 7 publications

(5 citation statements)

References 26 publications

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“…The FT-IR spectrum (v, cm À 1 ) of compound 4 a was recorded as a KBr tablet, which contains the desired stretching and bending vibrations. In the FT-IR spectrum of this compound NÀ H stretching vibrations were observed at 3427, CÀ O stretching vibrations at 1272-1497, CÀ H stretching vibrations of the aromatic ring at 3070, C=C stretching vibrations of the aromatic ring at 1461-1651, aliphatic CÀ H stretching vibrations at 2930 [47] 4 b 90 298-301 347-349 [47] 4 c 85 248-250 -4 d 88 150-152 295-298 [48] 4 e 92 244-247 264-265 [49] 4 f 88 190-193 335-337 [47] [50] 4 h 80 160-163 176-179 [51] 4 i 80 181-183 -4 j 83 240-242 245-247 [50] 4k 86 198-200 - [52] 4 m 92 190-192 263-265 [50] 4 n 87 207-209 232-234 [53] 4 o 88 193-195 258-261 [54] 4 p 84 270-272 - [55] 4 s 90 225-228 233-235 [56] 4 t 87 216-218 232-233 [57] 4 u 86 280-282 270-272 [58] Messages related to 8 types of hydrogen were observed. NH amino protons appeared in the low field at 13.33 ppm as a small peak with the area under the peak equal to 1 hydrogen.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Synthesis, Characterization, Molecular Docking, and Investigation of Antibacterial Properties of New Derivatives of 1‐H‐Phenanthro [9,10‐d] Imidazole

Mahmoodi,

Rajabi,

Nyaki

et al. 2024

Chemistry & Biodiversity

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In this study, several imidazole derivatives in one pot multicomponent reaction from various aldehydes (1(a‐z)), 9,10‐phenanthrenequinone, or benzyl (2), and ammonium acetate (3) were synthesized in the presence of acetic acid (AcOH) under reflux conditions at 120°C. Also, the photochromic properties of synthesized compounds were investigated in AcOH as a solvent under laboratory conditions at a temperature of 120°C. Moreover, the antibacterial and antioxidant activity of the synthesized compounds was investigated. The structure of the products was confirmed using FT‐IR, UV‐Vis, 1HNMR, and 13CNMR spectroscopy. The antimicrobial activity of these compounds against gram‐positive bacteria including Bacillus subtilis (B.s) and gram‐negative bacteria including Escherichia coli (E. coli) bacteria was evaluated by the well diffusion (WD) method, and the compounds 4o showed significant results for both antibacterial activity. To gain insight into how these compounds interact with two types of targets, i.e., human topoisomerase II alpha (5GWK) and acetylcholinesterase (7AIX), binding calculations have been used that provide significant results for both targets and show that most ligands can effectively bind to cleft nucleotides. Interfere in the first one or be well placed in them. Hydrophobic pocket in the dimension, which can ultimately lead to high scores achieved.

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Section: Synthesis and Characterizationmentioning

confidence: 99%

Synthesis, Characterization, Molecular Docking, and Investigation of Antibacterial Properties of New Derivatives of 1‐H‐Phenanthro [9,10‐d] Imidazole

Mahmoodi,

Rajabi,

Nyaki

et al. 2024

Chemistry & Biodiversity

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“…In particular, alternative approaches have been widely investigated to facilitate the removal and reuse of heterogeneous catalysts as well as the purification of the product. Some tested heterogeneous catalysts include magnetic nanoparticles, heterogeneous silica-supported La 0.5 Pb 0.5 MnO 3 nanoparticles, solid acids based on mercaptopropyl silica, sulfamic acid (NH 2 SO 3 H), ionic liquid-like phase catalyst based on Merrifield resin, nanocatalysts, and SBAPr-SO 3 H incorporating propyl sulfonic acid groups . Although progress has been made in the synthesis of phenanthro[9,10- d ]imidazoles, the general approach of the condensation of phenanthrene-9,10-dione ( 13 ) with an aldehyde in the presence of ammonium acetate in acetic acid has been applied to prepare a set of fluorescent sensors for ionic and molecular recognition.…”

Section: Synthesis Of Phenanthro[910-d]imidazolesmentioning

confidence: 99%

Aryl-Phenanthro[9,10-d]imidazole: A Versatile Scaffold for the Design of Optical-Based Sensors

et al. 2022

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Fluorescent and colorimetric sensors are important tools for investigating the chemical compositions of different matrices, including foods, environmental samples, and water. The high sensitivity, low interference, and low detection limits of these sensors have inspired scientists to investigate this class of sensing molecules for ion and molecule detection. Several examples of fluorescent and colorimetric sensors have been described in the literature; this Review focuses particularly on phenanthro [9,10d]imidazoles. Different strategies have been developed for obtaining phenanthro [9,10d]imidazoles, which enable modification of their optical properties upon interaction with specific analytes. These sensing responses usually involve changes in the fluorescence intensity and/or color arising from processes like photoinduced electron transfer, intramolecular charge transfer, intramolecular proton transfer in the excited state, and Forster resonance energy transfer. In this Review, we categorized these sensors into two different groups: those bearing formyl groups and their derivatives and those based on other molecular groups. The different optical responses of phenanthro [9,10-d]imidazole-based sensors upon interaction with specific analytes are discussed.

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“…Over the last decade, 2, 4, 5-trisubstituted imidazoles have been synthesized using onepot three-component compression of an aldehyde and ammonium acetate with an αhydroxy ketone, or an α-keto-oxime, or a 1, 2dicarbonyl compound by using various catalyst such as ionic liquids [7,8], Lewis acids [9,10], protic acids [11][12][13], and other catalysts [14][15][16][17]. However, most of these methodologies are associated with low yields, high temperature requirement, longer reaction time, highly acidic conditions, use of expensive reagents and catalysts, requirement of large amount of catalysts, use of harmful solvents, formation of toxic wastes and tedious work-up [8].…”

Section: Introductionmentioning

confidence: 99%

Untitled

Mohammadi

cheldavi

2020

J. Med. Chem. Sci.

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Phenanthro[9, 10-d]imidazole derivatives were synthesized with the combinations of phenanthroquinone and benzealdehyde derivatives in the presence of ammonium acetate. The microwave-assisted protocol was investigated under solvent-free condition for 2 min (400 w). The structure of all products was studied by IR and 1 HNMR Spectroscopy. Excellent yields, short reaction times, simplicity of operation and easy separation are the advantages of this technique.

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Synthesis of 2,4,5-Trisubstituted Phenanthroimidazole Derivatives using SBA-Pr-SO3H as a Nanocatalyst

Cited by 7 publications

References 26 publications

Synthesis, Characterization, Molecular Docking, and Investigation of Antibacterial Properties of New Derivatives of 1‐H‐Phenanthro [9,10‐d] Imidazole

Synthesis, Characterization, Molecular Docking, and Investigation of Antibacterial Properties of New Derivatives of 1‐H‐Phenanthro [9,10‐d] Imidazole

Aryl-Phenanthro[9,10-d]imidazole: A Versatile Scaffold for the Design of Optical-Based Sensors

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