Synthesis, Characterization, Spectroscopic Studies and Biological Evaluation of Schiff Bases Derived from 1-hydroxy-2-acetonapthanone

Overview

Journal Heliyon

Specialty Social Sciences

Date 2019 Nov 26

PMID 31763472

Citations 3

Authors

B T Vhanale

N J Deshmukh

A T Shinde

Affiliations

Soon will be listed here.

Abstract

The four Schiff bases were synthesized by the condensation reaction of 1(1-hydroxynaphthalen-2-yl)ethanone, 1-(4-chloro-1hydroxynaphthalen-2-yl)ethanone and 1-(4-bromo-1-hydroxynaphthalen-2-yl)ethanone with propane-1,3-diamine and pentane-1,3-diamine. The structural analysis is done by UVvis., FT-IR, H NMR, C NMR, LCMS and elemental analyses. These compounds were assayed for antibacterial ( and activity and antioxidant ( and ) activity. The antibacterial and antioxidant activities of synthesized Schiff bases exhibited better degrees of inhibitory effects. Among these, Schiff base 2,2'-((propane-1,3-diylbis(azanylylidene))bis(ethan-1-yl-1-ylidene))bis(4-chloronaphthalen-1-ol) exhibited excellent antibacterial activity with MICs of 0.12, 0.25, 0.5 and 1 mg/ml against and . Furthermore, two Schiff bases such as, 2,2'-((propane-1,3-diylbis(azanylylidene))bis(ethan-1-yl-1-ylidene))bis(naphthalen-1-ol) and 2,2'-((pentane-1,3-diylbis(azanylylidene))bis(ethan-1-yl-1-ylidene))bis(4-bromonaphthalen-1-ol) exhibited promising antioxidant activity.

Citing Articles

Synthesis, spectral studies, antioxidant and antibacterial evaluation of aromatic nitro and halogenated tetradentate Schiff bases.

Vhanale B, Kadam D, Shinde A Heliyon. 2022; 8(6):e09650.

PMID: 35711981 PMC: 9192811. DOI: 10.1016/j.heliyon.2022.e09650.

Docking and molecular biology studies of -anisidine-appended 1-hydroxy-2-acetonapthanone Schiff base lanthanum(iii) complexes.

Sathiyanarayanan V, Prasath P, Sekhar P, Ravichandran K, Easwaramoorthy D, Mohammad F RSC Adv. 2022; 10(28):16457-16472.

PMID: 35692617 PMC: 9122577. DOI: 10.1039/d0ra01936d.

Palladium(0) Catalyzed Synthesis of ()-4-Bromo--((3-bromothiophen-2-yl)methylene)-2-methylaniline Derivatives via Suzuki Cross-Coupling Reaction: An Exploration of Their Non-Linear Optical Properties, Reactivity and Structural Features.

Rizwan K, Rasool N, Hashmi M, Noreen S, Zubair M, Arshad M Molecules. 2021; 26(18).

PMID: 34577076 PMC: 8465532. DOI: 10.3390/molecules26185605.

References

Chen J, Gu B, LeBoeuf E, Pan H, Dai S . Spectroscopic characterization of the structural and functional properties of natural organic matter fractions. Chemosphere. 2002; 48(1):59-68. DOI: 10.1016/s0045-6535(02)00041-3. View

Pandeya S, Sriram D, Nath G, Declercq E . Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4'-chlorophenyl)thiazol-2-yl] thiosemicarbazide. Eur J Pharm Sci. 1999; 9(1):25-31. DOI: 10.1016/s0928-0987(99)00038-x. View

Saravanan G, Pannerselvam P, Prakash C . Synthesis and anti-microbial screening of novel schiff bases of 3-amino-2-methyl quinazolin 4-(3H)-one. J Adv Pharm Technol Res. 2012; 1(3):320-5. PMC: 3255421. DOI: 10.4103/0110-5558.72426. View

Panneerselvam P, Nair R, Vijayalakshmi G, Subramanian E, Sridhar S . Synthesis of Schiff bases of 4-(4-aminophenyl)-morpholine as potential antimicrobial agents. Eur J Med Chem. 2005; 40(2):225-9. DOI: 10.1016/j.ejmech.2004.09.003. View

Largeron M, Fleury M . Chemistry. Bioinspired oxidation catalysts. Science. 2013; 339(6115):43-4. DOI: 10.1126/science.1232220. View

Jiang L, Jin L, Tian H, Yuan X, Yu X, Xu Q . Direct and mild palladium-catalyzed aerobic oxidative synthesis of imines from alcohols and amines under ambient conditions. Chem Commun (Camb). 2011; 47(38):10833-5. DOI: 10.1039/c1cc14242a. View

Barluenga J, Aznar F, Valdes C . N-trialkylsilylimines as coupling partners for pd-catalyzed C[bond]N-forming reactions: one-step synthesis of imines and azadienes from aryl and alkenyl bromides. Angew Chem Int Ed Engl. 2004; 43(3):343-5. DOI: 10.1002/anie.200352808. View

Pontiki E, Hadjipavlou-Litina D, Chaviara A . Evaluation of anti-inflammatory and antioxidant activities of copper (II) Schiff mono-base and copper(II) Schiff base coordination compounds of dien with heterocyclic aldehydes and 2-amino-5-methyl-thiazole. J Enzyme Inhib Med Chem. 2008; 23(6):1011-7. DOI: 10.1080/14756360701841251. View

Pandeya S, Sriram D, Nath G, De Clercq E . Synthesis, antibacterial, antifungal and anti-HIV evaluation of Schiff and Mannich bases of isatin derivatives with 3-amino-2-methylmercapto quinazolin-4(3H)-one. Pharm Acta Helv. 2000; 74(1):11-7. DOI: 10.1016/s0031-6865(99)00010-2. View

10.

Azam F, Singh S, Khokhra S, Prakash O . Synthesis of Schiff bases of naphtha[1,2-d]thiazol-2-amine and metal complexes of 2-(2'-hydroxy)benzylideneaminonaphthothiazole as potential antimicrobial agents. J Zhejiang Univ Sci B. 2007; 8(6):446-52. PMC: 1879160. DOI: 10.1631/jzus.2007.B0446. View

11.

Zhang B, Luo H, Xu Q, Lin L, Zhang B . Antitumor activity of a Trans-thiosemicarbazone schiff base palladium (II) complex on human gastric adenocarcinoma cells. Oncotarget. 2017; 8(8):13620-13631. PMC: 5355125. DOI: 10.18632/oncotarget.14620. View

12.

Demirbas N, Ugurluoglu R, Demirbas A . Synthesis of 3-alkyl(aryl)-4-alkylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones and 3-alkyl-4-alkylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones as antitumor agents. Bioorg Med Chem. 2002; 10(12):3717-23. DOI: 10.1016/s0968-0896(02)00420-0. View

13.

Sriram D, Yogeeswari P, Myneedu N, Saraswat V . Abacavir prodrugs: microwave-assisted synthesis and their evaluation of anti-HIV activities. Bioorg Med Chem Lett. 2006; 16(8):2127-9. DOI: 10.1016/j.bmcl.2006.01.050. View

14.

Kumar K, Ganguly S, Veerasamy R, De Clercq E . Synthesis, antiviral activity and cytotoxicity evaluation of Schiff bases of some 2-phenyl quinazoline-4(3)H-ones. Eur J Med Chem. 2010; 45(11):5474-9. PMC: 7115544. DOI: 10.1016/j.ejmech.2010.07.058. View

15.

El-Wakiel N, El-keiy M, Gaber M . Synthesis, spectral, antitumor, antioxidant and antimicrobial studies on Cu(II), Ni(II) and Co(II) complexes of 4-[(1H-Benzoimidazol-2-ylimino)-methyl]-benzene-1,3-diol. Spectrochim Acta A Mol Biomol Spectrosc. 2015; 147:117-23. DOI: 10.1016/j.saa.2015.03.020. View

16.

Shiraishi Y, Ikeda M, Tsukamoto D, Tanaka S, Hirai T . One-pot synthesis of imines from alcohols and amines with TiO2 loading Pt nanoparticles under UV irradiation. Chem Commun (Camb). 2011; 47(16):4811-3. DOI: 10.1039/c0cc05615d. View

17.

Shanty A, Philip J, Sneha E, Prathapachandra Kurup M, Balachandran S, Mohanan P . Synthesis, characterization and biological studies of Schiff bases derived from heterocyclic moiety. Bioorg Chem. 2016; 70:67-73. DOI: 10.1016/j.bioorg.2016.11.009. View

18.

Liu M, Lin T, Sartorelli A . Synthesis and antitumor activity of amino derivatives of pyridine-2-carboxaldehyde thiosemicarbazone. J Med Chem. 1992; 35(20):3672-7. DOI: 10.1021/jm00098a012. View

19.

Shi L, Ge H, Tan S, Li H, Song Y, Zhu H . Synthesis and antimicrobial activities of Schiff bases derived from 5-chloro-salicylaldehyde. Eur J Med Chem. 2006; 42(4):558-64. DOI: 10.1016/j.ejmech.2006.11.010. View