Synthesis of Some Mono-, Bis- NH-substituted-1,4-Benzoquinones

Abstract

The preparation of new mono- and bis- NH-substituted-1,4-benzoquinones, namely 2,5-bis(5,6-dimethylbenzo[d]thiazol-2-ylamino)cyclohexa-2,5-diene-1,4-dione (3), 2,5-bis(3-(2-methylpiperidin-1-yl)propylamino)-3-chlorocyclohexa-2,5-diene-1,4-dione (6), 2-(4-tert-butylbenzylamino)-3,5,6-trichlorocyclohexa-2,5-diene-1,4-dione (9), 2-(4-fluorophenylamino)-6-tert-butylcyclohexa-2,5-diene-1,4-dione (12) is reported. The synthesis of new quinone derivatives (3, 6, 9, 12) have been carried out from the reactions between quinones (p-benzoquinone (1), 2,6-dichloro-1,4-benzoquinone (4), tetrachloro-1,4-benzoquinone (7), 2-tert-butyl-1,4-benzoquinone (10)) and different amines (2-Amino-5,6-dimethylbenzothiazole (2), N-(3-aminopropyl)-2-pipecoline (5), 4-tert-butylbenzylamine (8), 4-fluoroaniline (11)). The new compounds were characterized by elemental analysis, mass spectrometry, IR, ¹H-NMR, ¹³C-NMR spectroscopy.

Keywords

• Quinones
• NH-substituted-benzoquinones
• Amines

References

1. 1. Monks TJ, Hanzlık RP, Cohen GM, Ross D, Graham DG. Quinone Chemistry and Toxicity. Toxicol Appl Pharmacol. 1992; 112:2-16. https://doi.org/10.1016/0041-008X(92)90273-U
2. 2. Tandon VK, Maurya HK, Kumar S, Rashid A, Panda D.Synthesis and evaluation of 2-heteroaryl and 2,3-diheteroaryl-1,4-naphthoquinones that potently induce apoptosis in cancer cells. RSC Adv. 2014;4:12441-12447. DOI: 10.1039/c3ra47720g
3. 3. Satheshkumar A, Ganesh K, Elango KP. Charge transfer facilitated direct electrophilic substitution in phenylaminonaphthoquinones: experimental, theoretical and electrochemical studies. New J Chem. 2014;38:993-1003. DOI: 10.1039/c3nj01228j
4. 4. Brun M-P, Braud E, Angotti D, Mondesert O, Quaranta M, Montes M, Miteva M, Gresh N, Ducommun B, Garbay C, Design, synthesis, and biological evaluation of novel naphthoquinone derivatives with CDC25 phosphatase inhibitory activity. Bioorg Med Chem. 2005;13:4871–4879. DOI:10.1016/j.bmc.2005.05.005
5. 5. Szymczak AM, Podsiadly R, Podemska K, Sokolowska J. Dyes derived from 1,4-naphthoquinone as initiators for radical and cationic photopolymerisation. Color Technol. 2012;128:378–386. DOI: 10.1111/j.1478-4408.2012.00391.x
6. 6. Koroteev NI, Magnıtskii SA, Shubin VV, Sokolyuk NT. Photochemical and spectroscopic properties of naphthacenequinones as candidates for 3D optical data storage. Jpn J Appl Phys. Part 1, No. 1B, 1997;36:424-425.
7. 7. Ohkura K, Takeshima M, Omokawa S, Hasegawa Y, Kobayashi T. Quinone Compound, electrophotographic photoconductor and electrophotographic apparatus. US Patent 2006/0204874, Sep. 14, 2006.
8. 8. Won JH, Latifatu M, Jang M, Lee HS, Kim B-C, Hamenu L, Park JH, Kim KM, Ko JM. Supercapacitive properties of composite electrode consisting of activated carbon and a quinone-containing conducting additive. Synth Met. 2015;203:31–36. http://dx.doi.org/10.1016/j.synthmet.2015.02.010

9. 9. Hamenu L, Madzvamuse A, Mohammed L, Hu M, Park J, Ryou M-H, Lee YM, Ko JM. Highly stable 2,3,5,6-tetrachloro-1,4-benzoquinone electrodes for supercapacitors. Synth Met. 2017;231:25–33. http://dx.doi.org/10.1016/j.synthmet.2017.06.006
10. 10. Singh D, Kushwaha A, Banerjee A, Prasad RL. Synthesis and characterization of multifunctional coordination polymer of the type [CuxNi1-x(dedb).2H2O]n. Solid State Sciences. 2015;45:35-45. http://dx.doi.org/10.1016/j.solidstatesciences.2015.04.004
11. 11. Gafner S, Wolfender J-L, Nianga M, Stoeckli-Evans H, Hostettmann K. Antifungal and Antibacterial Naphthoquinones from Newbouldia laevis Roots. Phytochemistry. 1996;42(5):1315-1320.
12. 12. Delarmelina M, Daltoe RD, Cerri MF, Madeira KP, Rangel LBA, Junior VL, Romao W, Taranto AG, Greco SJ. Synthesis, Antitumor Activity and Docking of 2,3-(Substituted)-1,4-Naphthoquinone Derivatives Containing Nitrogen, Oxygen and Sulfur. J Braz Chem Soc. 2015;26(9):1804-1816. http://dx.doi.org/10.5935/0103-5053.20150157
13. 13. Huang LJ, Chang FC, Lee KH, Wang JP, Tengd CM, Kuo SC. Synthesis and antiplatelet, antiinflammatory, and antiallergic activities of substituted 3-Chloro-5,8-dimethoxy-1,4-naphthoquinone and related compounds. Bioorg Med Chem. 1998;6:2261-2269.
14. 14. Ma W,Zhou H, Ying Y-L, Li D-W, Chen G-R, Long Y-T, Chen H-Y. In situ spectroeletrochemistry and cytotoxic activities of natural ubiquinone analogues. Tetrahedron. 2011;67:5990-6000. DOI:10.1016/j.tet.2011.06.026
15. 15. Ganesh K, Balraj C, Satheshkumar A, Elango KP. Spectroscopic studies on the formation of molecular complexes of sulfamethoxazole with novel 2,3,5-trichloro-6-alkoxy-1,4-benzoquinones. J Mol Struct. 2013;1033:312–320. http://dx.doi.org/10.1016/j.molstruc.2012.09.062
16. 16. Kumagai Y, Shinkai Y, Miura T, Cho AK. The chemical biology of naphthoquinones and its environmental implications. Annu Rev Pharmacol Toxicol. 2012;52:221-247.
17. 17. Singh VK, Verma SK, Kadu R, Mobin SM. Identification of unusual C-Cl...л contacts in 2-(alkylamino)-3-chloro-1,4-naphthoquinones: effect of N-substituents on crystal packing, fluorescence, redox and anti-microbial properties. RSC Adv. 2015;5:43669-43686. DOI: 10.1039/c5ra02295a
18. 18. Tandon VK, Yadav DB, Singh RV, Vaish M, Chaturvedi AK, Shukla PK. Synthesis and biological evaluation of novel 1,4-naphthoquinone derivatives as antibacterial and antiviral agents. Bioorg Med Chem Lett. 2005;15:3463–3466.doi:10.1016/j.bmcl.2005.04.075
19. 19. Mori K, Takahashi K, Kishi T, Sayo H. Synthesis and biological activities of 2,3-Dimethyl-1,4-benzoquinones Having alkylthio and arylthio side chains. Chem Pharm Bull. 1987;35(3):1270-1274.
20. 20. Tandon VK, Chhor RB, Singh RV, Rai S, Yadav DB. Design, synthesis and evaluation of novel 1,4-naphthoquinone derivatives as antifungal and anticancer agents. Bioorg Med Chem Lett. 2004;14:1079–1083. DOI:10.1016/j.bmcl.2004.01.002
21. 21. Tandon VK, Maurya HK, Mishra NN, ShuklaPK. Design, synthesis and biological evaluation of novel nitrogen and sulfur containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents. Eur J Med Chem. 2009;44:3130–3137. DOI:10.1016/j.ejmech.2009.03.006
22. 22. Zee-Cheng K-Y, Cheng C-C, Preparation and the results of antitumor screening of some substituted amino-, azido-, halogeno- and hydroxy-p-benzoquinones. J Med Chem. 1970;13(2):264–268. DOI: 10.1021/jm00296a023
23. 23. Claes P, Jacobs J, Kesteleyn B, Van TN, De Kimpe N. Palladium(II)-Catalyzed Synthesis of 2H,3′H-Spiro[benzofuran-3,2′-naphthoquinones]. J Org Chem. 2013;78(17):8330-8339. DOI: 10.1021/jo400852z
24. 24. Jiao M, Ding C, Zhang A. Facile construction of 3-hydroxyphenanthrene-1,4-diones: key intermediates to tanshinone I and its A-ring-modified analogue. Tetrahedron 2014;70:2976-2981. http://dx.doi.org/10.1016/j.tet.2014.03.019
25. 25. Salunke-Gawali S, Pawar O, Nikalje M, Patil R, Weyhermüller T, Puranik VG, Konkimalla VB. Synthesis, characterization and molecular structures of homologated analogs of 2-bromo-3-(n-alkylamino)-1,4-napthoquinone. J Mol Struct. 2014;1056–1057:97–103. http://dx.doi.org/10.1016/j.molstruc.2013.10.016
26. 26. Leyva E, Lopez LI, Loredo-Carrillo SE, Rodrıguez-Kessler M, Montes-Rojas A. Synthesis, spectral and electrochemical characterization of novel 2-(fluoroanilino)-1,4-naphthoquinones. J Fluor Chem. 2011;132:94–101. DOI:10.1016/j.jfluchem.2010.12.001
27. 27. Yildirim H, Bayrak N, Tuyun AF, Kara Mataraci E, Celik Ozbek B, Gupta Kumar G. 2,3-Disubstituted-1,4-naphthoquinones containing an arylamine with trifluoromethyl group: synthesis, biological evaluation, and computational study. RSC Adv. 2017;7(41):25753-25764. DOI: 10.1039/c7ra00868f
28. 28. Deniz NG, Ozyurek M, Tufan AN, Apak R. One-pot synthesis, characterization, and antioxidant capacity of sulfur- and oxygen-substituted 1,4-naphthoquinones and a structural study. Monatsh Chem.2015;146:2117-2126.DOI 10.1007/s00706-015-1517-5
29. 29. Bayrak N, Yıldırım H, Tuyun AF, Kara Mataracı E, Çelik Ozbek B, Kumar Gupta G, Çiftçi IH, Fujita M, Otsuka M, Nasiri RH. Synthesis, Computational Study, and Evaluation of In Vitro Antimicrobial, Antibiofilm, and Anticancer Activities of New Sulfanyl Aminonaphthoquinone Derivatives. Lett Drug DesDiscov. 2017;14(6):647-661
30. 30. Ibis C, Sahinler Ayla S, Ozkok F, Bahar H. Synthesis of New Piperazinyl and Piperidinolyl Substituted p-Chloranil Derivatives and their Reactions with Thiols. Phosphorus, Sulfur Silicon Relat. Elem. 2015;190:2273–2282. DOI: 10.1080/10426507.2015.1071816
31. 31. Kutyrev AA. Nucleophilic reactions of quinones, Tetrahedron Report Number 298 Tetrahedron 1991;47(38):8043-8065.
32. 32. Yang J, Cohen Stuart MA, Kamperman M. Jack of all trades :versatile catechol crosslinking mechanisms, Chem Soc Rev. 2014;43:8271-8298.
33. 33. Barbosa LCA, Pereira UA, Maltha CRA, Teixeira RR, Valente VMM, Ferreira JRO, Costa-Lotufo LV, Moraes MO,Pessoa C. Synthesis and Biological Evaluation of 2,5-Bis(alkylamino)-1,4-benzoquinones. Molecules 2010;15:5629-5643. DOI:10.3390/molecules15085629
34. 34. Katritzky AR, Fedoseyenko D, Mohapatra PP, Steel PJ, Reactions of p-Benzoquinone with Sulfur Nucleophiles, Synthesis 2008;5:777-787. DOI: 10.1055/s-2008-1032186
35. 35. Bayen S, Barooah N, Sarma RJ, Kumar Sen T, Karmakar A, Baruah JB. Synthesis, structure and electrochemical properties of 2,5-bis(alkyl/arylamino)1,4-benzoquinones and 2-arylamino-1,4-naphthoquinones, Dyes Pigments. 2007;75:770-775. DOI:10.1016/j.dyepig.2006.07.033
36. 36. Smith RE, Davis WR. Spectrophotometric determination of amines with p-chloranil, Anal. Chem. 1984;56:2345-2349.
37. 37. Tandon VK, Maurya HK. ‘On water’: unprecedented nucleophilic substitution and addition reactions with 1,4-quinones in aqueous suspension. Tetrahedron Lett. 2009; 50:5896–5902. DOI:10.1016/j.tetlet.2009.07.149
38. 38. Martinez-Cifuentes M, Clavijo-Allancan G, Di Vaggio-Conejeros C, Weiss-Lopez B, Araya-Maturana R. On Water Reactivity and Regioselectivity of Quinones in C-N Coupling with Amines: Experimental and Theoretical Study. Aust. J. Chem. 2014; 67:217-224.
39. 39. Yogo M, Ito C, Furukawa H. Synthesis of Some Carbazolequinone Alkaloids and Their Analogues. Facile Palladium-Assisted Intramolecular Ring Closure of Arylamino-1,4-benzoquinones to Carbazole-1,4-quinones. Chem. Pharm. Bull. 1991;39(2); 328-334.
40. 40. Jeremic M, Pesic M, Dinic J, Bankovic J, Novakovic I, Simple avarone mimetics as selective agents against multidrug resistant cancer cells. Eur. J. Med. Chem. 2016; 118; 107-120.