The purpose of this study was to synthesize (E)-2-benzylidene-7-chloro-9-phenyl-3,4-dihydroacridin-1(2H)-ones and investigate their larvicidal potential against Anopheles stephensi and Hippobosca maculata. Synthetic acridines are used in many commercial applications. The results obtained from FTIR, 1H and 13C NMR, and ESI-MS spectra confirm the synthesis of (E)-2-benzylidene-7-chloro-9-phenyl-3,4-dihydroacridin-1(2H)-ones, 3a-j. Larvae were exposed to different concentrations of compounds, 3a-j for 24 h. All the compounds had moderate activity; maximum efficacy was observed for 3e and 3j. © 2013 Springer Science+Business Media Dordrecht.

Mohana Roopan S

Department of Chemistry

School of Advanced Sciences

Vellore Campus

Bharathi A

Rahuman A.A

Rajakumar G.

Vellore Institute of Technology (VIT) is a private university located in&nbsp;Tamil Nadu, India. Founded in 1984, as Vellore Engineering College, the institution offers 20 undergraduate, 34 postgraduate, four integrated and four research programs. It has campuses in Vellore, Amravati, Bhopal and Chennai.

VIT is one of the top ranked private universities in India according to NIRF, THE and QS Rankings.&nbsp;Govt. of India has recognized&nbsp;VIT, Vellore as an&nbsp;Institution of Eminence. This has allowed VIT to take independent quality initiatives and move up in world ranking.

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VIT University

Research on Chemical Intermediates

A series of imidazo-pyrimido fused acridines were synthesized and identified using conventional spectroscopic techniques. All the synthesized title compounds were subjected to in vitro antibacterial and insecticidal screenings. For insecticidal activity, the synthesized fused compounds are testing against two pests namely, Sitophilus oryzae (S. oryzae) and Callosobruchus maculatus (C. maculatus). For antibacterial screening, the compounds are testing against four bacteria, Bacillus subtilis (B. subtilis), Proteus mirabilis (P. mirabilis), Staphylococcus aureus (S. aureus) and Vibrio parahaemolyticus (V. parahaemolyticus). Notably, compound 8-(4-isopropylphenyl)-16-phenyl-6,7-dihydrobenzo[4′,5′]imidazo[1′,2′:1,2]pyrimido[4,5-a]acridine and 8-(2,4-dimethoxyphenyl)-16-phenyl-6,7-dihydrobenzo[4′,5′]imidazo[1′,2′:1,2]pyrimido[4,5-a]acridine were identified as the most promising applicant for further studies. © 2017 Elsevier B.V.

Journal of Molecular Liquids

Conventional spectroscopic identification of biologically active imidazo-pyrimido fused acridines: In vitro anti-bacterial and anti-feedant activity

A new and highly efficient microwave promoted N-alkylation of triazolo-quinazolinones was developed by treating various phenyl-substituted heterocyclic amines with benzyl chloride using K2CO3 as a base in the presence of DMF. Also the heterocyclic amines were synthesized by condensing the 3-amino-1,2,4-triazole substituted benzaldehydes and 1,3-cyclohexanedione in the presence of microwave irradiation under solvent free condition. The synthesized heterocycles 4a–o and 6a–o were further confirmed by using different spectroscopic techniques such as NMR and HRMS. The compounds 6a–o was studied for their solvatochromic property with increasing polarity of solvents. The determinations of 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) scavenging effect of the scaffolds 6a–o were carried out by UV–Vis spectrometer. In terms of IC50 all the compounds have shown remarkable antioxidant property compared with Ascorbic acid. © 2016 Elsevier B.V.

Conventional spectroscopic identification of N-alkylated triazolo-quinazolinones and its antioxidant, solvatochromism studies

Dihydroquinazolinones is an important core structure reported with a wide variety of pharmacological activities. They are capable of undergoing various transformations because of its reactivity towards various reagents. The synthetic strategies for the functionalization and derivatization of the nucleus were explained. The diversified pharmacological actions of this moiety were illustrated through various biochemical pathways. The structural-activity relationship study of dihydroquinazolinones anticipated the relationship between the various substituents and its role in the pharmacological action. The main objective of this review is to summarize the importance of dihydroquinazolinones in the field of chemical biology.

European Journal of Medicinal Chemistry

Synthetic strategy with representation on mechanistic pathway for the therapeutic applications of dihydroquinazolinones

A non-conventional methodology has been utilized for the synthesis of a series of 1,2,4-triazolo-quinazoline-thiones (2a-l). Here the reaction was carried out between 1,2,4-triazolo-quinazolinones (1a-l), in the presence of 1,4-dioxane. The mixture was irradiated under microwave (100W) for 7min to obtain targeted molecules (2a-l). All the synthesized molecules were confirmed by (1)H, (13)C NMR and HRMS. The solvatochromic property (absorption spectra) of compounds (2a-l) in solvents of different polarities was studied. The compounds (2a-l) were further subjected for their in vitro free radical screening using 2,2-diphenyl-1-picrylhydrazyl (DPPH) method and also screened for their in vitro anti-fungal property against Aspergillus flavus (A. flavus) and Aspergillus niger (A. niger). The results from free radical scavenging assay showed promising activity for compounds 2a, e-i, whereas compound 2d showed significant antioxidant activity when compared to ascorbic acid. In vitro anti-fungal study showed that the 1,2,4-triazolo-quinazoline-thiones (2a-l) had significant activity against A. flavus and A. niger compared with widely used antifungal agent Fluconazole.

Journal of Photochemistry and Photobiology B: Biology

1,2,4-Triazolo-quinazoline-thiones: Non-conventional synthetic approach, study of solvatochromism and antioxidant assessment

The main aim of this study is to investigate the interaction of 7-fluoro-2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one with lysozyme through various spectrophotometric studies. The graph such as Stern-Volmer plot, modified Stern Volmer plot, double logarithmic plot and Van't Hoff plot were plotted to determine the various parameters essential for predicting the interaction. The interaction of the ligand with the protein was further confirmed by circular dichroism and NMR study. The molecular docking was performed and the results obtained were correlated with the other studies. The importance of fluorine was justified through the prediction of pKa values and the possible metabolic pathway using the in silico tools. In addition, the cytotoxicity of the compound was carried out using HeLa cancer cell.

Importance of fluorine in 2,3-dihydroquinazolinone and its interaction study with lysozyme

Acridin-1(2H)-one analogue of 7-chloro-3,4-dihydro-9-phenyl-2-[(pyridine-2yl) methylene] acridin-1(2H)-one, 5 was prepared by using 7-chloro-3,4-dihydro-9-phenylacridin-1(2H)-one, 3 and picolinaldehyde, 4 in the presence of KOH at room temperature. These compounds were characterized by analytical and spectral analyses. The purpose of the present study was to assess the efficacy of larvicidal and repellent activity of synthesized 7-chloro-3,4-dihydro-9-phenyl-acridin-1(2H)-one analogues such as compounds 3 and 5 against the early fourth instar larvae of filariasis vector, Culex quinquefasciatus and Japanese encephalitis vector, Culex gelidus (Diptera: Culicidae). The compound exhibited high larvicidal effects at 50mg/L against both the mosquitoes with LC(50) values of 25.02 mg/L (r(2)=0.998) and 26.40 mg/L (r(2)=0.988) against C. quinquefasciatus and C. gelidus, respectively. The 7-chloro-3,4-dihydro-9-phenyl-acridin-1(2H)-one analogues that are reported for the first time to our best of knowledge can be better explored for the control of mosquito population. This is an ideal ecofriendly approach for the control of Japanese encephalitis vectors, C. quinquefasciatus and C. gelidus.

Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy

Synthesis, spectral characterization and larvicidal activity of acridin-1(2H)-one analogues

Journal of Molecular Structure

Synthesis, spectral analysis and quantum chemical studies on molecular geometry, chemical reactivity of 7-chloro-9-(2′-chlorophenyl)-2,3-dihydroacridin-4(1H)-one and 7-chloro-9-(2′-fluorophenyl)-2,3-dihydroacridin-4(1H)-one

Journal	Data powered by TypesetResearch on Chemical Intermediates
Publisher	Data powered by TypesetSpringer Science and Business Media LLC
ISSN	0922-6168
Open Access	No