Many naturally occurring and synthetic compounds containing dihydrocyanopyridine and cyanopyran moiety show pharmacological properties. The aim of this study is to investigate the larvicidal and antioxidant potential of dihydrophenanthroline-3-carbonitrile derivatives4a–f. A novel series of 2-amino-10-chloro-4,12-diphenyl-1,4,5,6-tetrahydrobenzo[j ][1,7]phenanthroline-3-carbonitrile derivatives were synthesized by reacting different substituted acridine chalcones through Michel addition. The compounds were synthesized in excellent yields and the structures were corroborated on the basis of FT-IR,1H NMR,13C NMR, and ESI Mass analysis data. All the synthesized compounds were evaluated for larvicidal activity againstAedes aegypti andCulex quinquefasciatuslarvae. Furthermore, the antioxidant activity was studied by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay method. From the antioxidant assay, the compound4cwas reported with profound antioxidant potential.

Mohana Roopan S

Department of Chemistry

School of Advanced Sciences

Vellore Campus

Bharathi A

Rahuman A.A

Rajakumar G.

Fulltext

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

In Vitro Larvicidal and Antioxidant Activity of Dihydrophenanthroline-3-carbonitriles

BioMed Research International

The photochemical preparation of benzo[4,5]imidazo[2,1-b]quinazoline was assessed under the illumination of UV wavelength (&gt;360 nm). The compound 3,4-dihydronaphthalen-1(2H)-one 1 with 1H-benzo[d]imidazol-2-amine 2 in the existence of KOH/DMF which lead to the aromatized compound 3. The notable remark of this reaction is that the UV irradiation (312 nm) plays a vital part in the formation of compound, 3 in shorter duration (2 h) which resulted in higher yield of 96%. Compound 3 was analyzed by H1, C13 NMR, and HRMS. Solvatochromism impacts of the compound 3 was computed with different solvents (DCM

Journal of Photochemistry and Photobiology B: Biology

UV-light intervened synthesis of imidazo fused quinazoline and its solvatochromism, antioxidant, antifungal and luminescence properties

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.

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

The photochemical synthesis of a series of 2,3-dihydroquinazolin-4(1H)-ones were evaluated under the irradiation of visible light ({\textgreater}390 nm). The effect of the visible light mediated synthesis was carried out in the presence/absence of solvent. The effect of solvent plays a key role in the synthesis was evidenced through the formation of product in short duration. The solvatochromic effects of the fluorescent compounds (3a-k) were studied with respect to the solvents of increasing polarity (DCM {\textless} methanol {\textless} DMF {\textless} DMSO). The determination of in vitro anti-inflammatory activity of the compounds (3a-k) by the inhibition of bovine serum albumin (BSA) denaturation and 2,2-di(4-t-octylphenyl)-1-picrylhydrazyl (DOPPH•) radical scavenging consequence of the compounds (3a-k) were determined by spectroscopic technique. The compound 3j in DMSO exhibited extreme high quantum yield. The compound 3i was found to be superior both in the efficiency of the anti-inflammatory activity and radical scavenging ability.

2,3-Dihydroquinazolin-4(1H)-ones: Visible light mediated synthesis, solvatochromism and biological activity

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.

Research on Chemical Intermediates

(E)-2-Benzylidene-7-chloro-9-phenyl-3,4-dihydroacridin-1(2H)-ones: synthesis and larvicidal activity

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

Solvent-free syntheses of quinazolin-4(3H)-ones were performed by reaction of anthranillic acid with different amides, such as nicotinamide, benzamide, formamide, etc., on montmorillonite K-10. Products were confirmed by FTIR, 1HNMR, and 13CNMR spectroscopic techniques. All synthesized compounds exhibited antioxidant properties and have been compared with standard antioxidant BHT.Key words: quinazolinone, montmorillonite K-10, solvent-free conditions, antioxidant properties.

Journal	BioMed Research International
Publisher	Hindawi Limited
ISSN	2314-6133
Open Access	Yes