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Novel series of acridone-1,2,3-triazole derivatives: microwave-assisted synthesis, DFT study and antibacterial activities

  • Mohammed Aarjane
  • Siham Slassi
  • Bouchra Tazi
  • Mohamed Maouloua
  • Amina AmineEmail author
Regular Article
  • 32 Downloads

Abstract

A series of novel acridones bearing a 1,2,3-triazole unit have been synthesized and characterized. The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) was performed using both a conventional method and a microwave-assisted synthetic method. The in vitro antibacterial potencies of all the synthesized compounds were determined against five clinically isolated strains: Escherichia coli, Klebsiella pneumonia, Pseudomonas putida, Serratia marcescens and Staphyloccocus aureus. Furthermore, DFT quantum chemical calculations were carried out to investigate geometry structures, frontier molecular orbital and gap energies, and molecular electrostatic potential maps (MEP). Lipophilicities of the studied compounds were also determined.

Graphic abstract

Novel acridone-1,2,3-triazole derivatives were synthesized using both a conventional and a microwave-assisted synthetic method. The antibacterial potencies of the compounds are reported. DFT quantum chemical calculations were carried out to investigate geometry structures, frontier molecular orbital and gap energies, and molecular electro static potential maps (MEP). Lipophilicities were also determined.

Keywords

Acridone 1, 2, 3-triazole microwave DFT study antibacterial activitiy 

Notes

Supplementary material

12039_2019_1653_MOESM1_ESM.pdf (1.5 mb)
Supplementary material 1 (pdf 1533 KB)

References

  1. 1.
    Dzierzbicka K 2017 Recent developments in the synthesis and biological activity of acridine/acridone analogues RSC Adv. 15776Google Scholar
  2. 2.
    Michel S and Tillequin F 1997 Bioactive natural and synthetic acronycine derivatives modified at the pyran ring Stud. Nat. Prod. Chem. 20 789CrossRefGoogle Scholar
  3. 3.
    Tillequin F and Koch M 2005 De l’acronycine aux dérivés de la benzo[b]acronycine:conception et développement d’une nouvelle série d’antitumoraux Ann. Pharm. Françaises 63 35CrossRefGoogle Scholar
  4. 4.
    Nguyen Q C, Nguyen T T, Yougnia R, Gaslonde T, Dufat H, Michel S and Tillequin F 2009 Acronycine derivatives: a promising series of anticancer agents, Anti-Cancer Agents Med. Chem. (Los. Angeles). 9 804Google Scholar
  5. 5.
    Belmont P and Dorange I 2008 Acridine/acridone: a simple scaffold with a wide range of application in oncology Expert Opin. Ther. Pat. 18 1211CrossRefGoogle Scholar
  6. 6.
    Lebegue N, Gallet S, Flouquet N, Carato P, Pfeiffer B, Renard P, Léonce S, Pierré A, Chavatte P and Berthelot P 2005 Novel Benzopyridothiadiazepines as Potential Active Antitumor Agents J. Med. Chem. 48 7363CrossRefGoogle Scholar
  7. 7.
    Cholewinski G, Dzierzbicka K and Kolodziejczyk A M 2011 Natural and synthetic acridines/acridones as antitumor agents: their biological activities and methods of synthesis Pharmacol. Rep. 63 305CrossRefGoogle Scholar
  8. 8.
    Denny W A 2002 Acridine Derivatives as Chemotherapeutic Agents Curr. Med. Chem. 9 1655CrossRefGoogle Scholar
  9. 9.
    Kukowska-Kaszuba M and Dzierzbicka K 2007 Synthesis and structure-activity studies of peptide-acridine/acridone conjugates Curr. Med. Chem. 14 3079CrossRefGoogle Scholar
  10. 10.
    Rewcastle G W, Atwell G J, Chambers D, Baguley B C and Denny W A 1986 Potential antitumor agents. 46. Structure-activity relationships for acridine monosubstituted derivatives of the antitumor agent N-[2-(dimethylamino)ethyl]-9-aminoacridine-4-carboxamide J. Med. Chem. 29 472CrossRefGoogle Scholar
  11. 11.
    Phanstiel O IV, Price H L, Wang L, Juusola J, Kline M and Majmundar Shah S 2000 The Effect of Polyamine Homologation on the Transport and Cytotoxicity Properties of Polyamine–(DNA-Intercalator) Conjugates J. Org. Chem. 65 5590CrossRefGoogle Scholar
  12. 12.
    Watterson S H, Chen P, Zhao Y, Gu H H, Dhar T G, Xiao Z, Ballentine S K, Shen Z, Fleener C A, Rouleau K A, Obermeier M, Yang Z, McIntyre K W, Shuster D J, Witmer M, Dambach D, Chao S, Mathur A, Chen B C, Barrish J C, Robl J A, Townsend R and Iwanowicz E J 2007 Acridone-Based Inhibitors of Inosine 5\(^{\prime }\)-Monophosphate Dehydrogenase: Discovery and SAR Leading to the Identification of N-(2-(6-(4-Ethylpiperazin-1-yl)pyridin-3-yl)propan-2-yl)-2- fluoro-9-oxo-9,10-dihydroacridine-3-carboxamide (BMS-566419) J. Med. Chem. 50 3730CrossRefGoogle Scholar
  13. 13.
    Stankiewicz-Drogon A, Palchykovska L G, Kostina V G, Alexeeva IV, Shved A D and Boguszewska-Chachulska A M 2008 New acridone-4-carboxylic acid derivatives as potential inhibitors of Hepatitis C virus infection Bioorg. Med. Chem. 16 8846CrossRefGoogle Scholar
  14. 14.
    Singh P, Kaur J, Yadav B and Komath S S 2009 Design, synthesis and evaluations of acridone derivatives using Candida albicans—search for MDR modulators led to the identification of an anti-candidiasis agent Bioorg. Med. Chem. 17 3973CrossRefGoogle Scholar
  15. 15.
    Antonini I, Polucci P, Magnano A, Gatto B, Palumbo M, Menta E, Pescalli N and Martelli S 2003 Design, synthesis, and biological properties of new bis(acridine-4-carboxamides) as anticancer agents J. Med. Chem. 46 3109CrossRefGoogle Scholar
  16. 16.
    Singh N, Pandey S K and Tripathi R P 2010 Regioselective [3+2] cycloaddition of chalcones with a sugar azide: easy access to 1-(5-deoxy-d-xylofuranos-5-yl)-4,5-disubstituted-1H-1,2,3-triazoles Carbohydr. Res. 345 1641CrossRefGoogle Scholar
  17. 17.
    Farajzadeh M A and Khoshmaram L 2013 Air-assisted liquid–liquid microextraction-gas chromatography-flame ionisation detection: a fast and simple method for the assessment of triazole pesticides residues in surface water, cucumber, tomato and grape juices samples Food Chem. 141 1881CrossRefGoogle Scholar
  18. 18.
    Lazrek H B, Taourirte M, Oulih T, Barascut J L, Imbach J L, Pannecouque C, Witrouw M and De Clercq E 2001 Synthesis and anti-HIV activity of new modified 1,2,3-triazole acyclonucleosides Nucleosides Nucleotides Nucleic Acids 20 1949CrossRefGoogle Scholar
  19. 19.
    Demaray J A, Thuener J E, Dawson M N and Sucheck S J 2008 Synthesis of triazole-oxazolidinones via a one-pot reaction and evaluation of their antimicrobial activity Bioorg. Med. Chem. Lett. 18 4868CrossRefGoogle Scholar
  20. 20.
    Khan I, Ali S, Hameed S, Rama N H, Hussain M T, Wadood A, Uddin R, Ul-Haq Z, Khan A, Ali S and Choudhary M I 2010 Synthesis, antioxidant activities and urease inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives Eur. J. Med. Chem. 455200CrossRefGoogle Scholar
  21. 21.
    Chen H, Zuo S, Wang X, Tang X, Zhao M, Lu Y, Chen L, Liu J, Liu Y, Liu D, Zhang S and Li T 2011 Synthesis of 4\(\upbeta \)-triazole-podophyllotoxin derivatives by azide–alkyne cycloaddition and biological evaluation as potential antitumor agents Eur. J. Med. Chem. 464709CrossRefGoogle Scholar
  22. 22.
    Sondhi S M, Singh J, Rani R, Gupta P P, Agrawal S K and Saxena A K 2010 Synthesis, anti-inflammatory and anticancer activity evaluation of some novel acridine derivatives Eur. J. Med. Chem. 45 555CrossRefGoogle Scholar
  23. 23.
    Mohammadi-Khanaposhtani M, Mahdavi M, Saeedi M, Sabourian R, Safavi M, Khanavi M, Foroumadi A, Shafiee A and Akbarzadeh T 2015 Design, synthesis, biological evaluation, and docking study of acetylcholinesterase inhibitors: new acridone-1,2,4- oxadiazole-1,2,3-triazole hybrids Chem. Biol. Drug Des. 86 1425CrossRefGoogle Scholar
  24. 24.
    Kolb H C, Finn M G and Sharpless K B 2001 Click chemistry: diverse chemical function from a few good reactions Angew. Chem. Int. Ed. Engl. 40 2004CrossRefGoogle Scholar
  25. 25.
    Rostovtsev V V, Green L G, Fokin V V and Sharpless K B 2002 A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective ‘ligation’ of azides and terminal alkynes Angew. Chem. Int. Ed. Engl. 41 2596CrossRefGoogle Scholar
  26. 26.
    Liang L and Astruc D 2011 The copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) “click” reaction and its applications. An overview Coord. Chem. Rev. 255 2933CrossRefGoogle Scholar
  27. 27.
    Kumar D, Reddy V B and Varma R S 2009 A facile and regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles using click chemistry Tetrahedron Lett. 502065CrossRefGoogle Scholar
  28. 28.
    Davies J and Davies D 2010 Origins and evolution of antibiotic resistance Microbiol. Mol. Biol. Rev. 74 417CrossRefGoogle Scholar
  29. 29.
    Ventola C L 2015 The antibiotic resistance crisis: part 1: causes and threats \(P \,T\) 40 277Google Scholar
  30. 30.
    Nouraie P, Moradi Dehaghi S and Foroumadi A 2019 Coumarin-1,2,3-triazole hybrid derivatives: green synthesis and DFT calculations Synth. Commun. 1Google Scholar
  31. 31.
    Liu, X-H 2007 Synthesis, bioactivity, theoretical and molecular docking study of 1-cyano-N-substituted-cyclopropanecarboxamide as ketol-acid reductoisomerase inhibitor Bioorg. Med. Chem. Lett. 17 3784CrossRefGoogle Scholar
  32. 32.
    Kosar B and Albayrak C 2011 Spectroscopic investigations and quantum chemical computational study of (E)-4-methoxy-2-[(p-tolylimino)methyl]phenol Spec-trochim. Acta Part A 78 160CrossRefGoogle Scholar
  33. 33.
    Sun Y-X, Hao Q-L, Yu Z-X, Wei W-X, Lu L-D and Wang X 2009 Experimental and density functional studies on 4-(4-cyanobenzylideneamino)antipyrine Mol. Phys. 107 223CrossRefGoogle Scholar
  34. 34.
    Reed A E, Weinstock R B and Weinhold F 1985 Natural population analysis J. Chem. Phys. 83 735CrossRefGoogle Scholar
  35. 35.
    Adant C, Dupuis M and Bredas J L 1995 Ab initio study of the nonlinear optical properties of urea: electron correlation and dispersion effects Int. J. Quantum Chem. 56 497CrossRefGoogle Scholar
  36. 36.
    Arivazhagan M and Meenakshi R 2011 Quantum chemical studies on structure of 1-3-dibromo-5-chlorobenzene Spectrochim. Acta Part A 82 316CrossRefGoogle Scholar
  37. 37.
    Reed J L 1997 Electronegativity: chemical hardness I J. Phys. Chem. 101 40Google Scholar
  38. 38.
    Mebi C 2011 DFT study on structure, electronic properties, and reactivity of cis-isomers of \([(\text{ NC }_{5}\text{ H }_{4}\text{- }\text{ S })_{2}\text{ Fe(CO) }_{2}]\) J. Chem. Sci. 123 727CrossRefGoogle Scholar
  39. 39.
    Parr R G and Yang W 1984 Density functional approach to the frontier-electron theory of chemical reactivity J. Am. Chem. Soc. 106 4049CrossRefGoogle Scholar
  40. 40.
    Kapustikova I, Bak A, Gonec T, Kos J, Kozik V and Jampilek J 2018 Investigation of Hydro-Lipophilic Properties of \(N\)-Alkoxyphenylhydroxynaphthalenecar-boxamides Molecules 23 1635CrossRefGoogle Scholar
  41. 41.
    Arnott J A, Kumar R and Planey S L 2013 Lipophilicity indices for drug development J. Appl. Biopharm. Pharmaco. 1 31Google Scholar
  42. 42.
    Scrocco E and Tomasi J 1978 Electronic molecular structure, reactivity and intermolecular forces: an Euristic interpretation by means of electrostatic molecular potentials Adv. Quantum Chem. 11 115CrossRefGoogle Scholar
  43. 43.
    Luque F J, López J M and Orozco M 2000 Perspective on “electrostatic interactions of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects” In Theoretical Chemistry Accounts C J Cramer and D G Truhlar (Eds.) (Berlin, Heidelberg: Springer)Google Scholar
  44. 44.
    Parthasarathi R, Padmanabhan J, Sarkar U, Maiti B, Subramanian V and Chattaraj P K 2003 Toxicity analysis of benzidine through chemical reactivity and selectivity profiles: a DFT approach Internet Electron. J. Mol. Des. 2 789Google Scholar
  45. 45.
    Avdović E H, Milenković D, Marković J M D, Đorović J, Vuković N, Vukić M D, Jevtić V V, Trifunović S R, Potočňák I and Marković Z 2018 Synthesis, spectroscopic characterization (FT-IR, FT-Raman, and NMR), quantum chemical studies and molecular docking of 3-(1-(phenylamino)ethylidene)-chroman-2,4-dione Spectrochim. Acta Part A 195 31CrossRefGoogle Scholar
  46. 46.
    CLSI. Performance Standards for Antimicrobial Disk Susceptibility Tests; Approved Standard – Twelfth Edition. CLSI document M02-A12. Wayne, PA: Clinical Laboratory Standard Institute; 2015. ISBN 1-56238-986-6Google Scholar

Copyright information

© Indian Academy of Sciences 2019

Authors and Affiliations

  1. 1.LCBAE, CMMBA, Faculty of ScienceUniversity Moulay IsmailZitoune, MeknesMorocco
  2. 2.Département des Sciences de BaseEcole Nationale d’AgricultureMeknesMorocco
  3. 3.Medical Microbiology LaboratoryMohamed V. HospitalMeknesMorocco

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