Synthesis and Structural Analysis of Some New Sulfanyl Amino 1,4-Naphthoquinone Derivatives

Abstract

In this study, some new sulfanyl substituted amino 1,4-naphthoquinone derivatives which possess two electron donating groups in the amino fragment were synthesized and their structures were analyzed by spectroscopic techniques. First, 2-chloro-3-[(2,4-dimethoxy phenyl)amino]naphthalene-1,4-dione (3a) and 2-chloro-3-[(3,5-dimethoxy phenyl)amino]naphthalene-1,4-dione (3b) were obtained from the reactions of dichloro 1,4-naphthoquinone (1) with 2,4-dimethoxy phenyl amine and 3,5-dimethoxy phenyl amine. Then the compounds 3a,b were reacted with aliphatic nucleophiles; ethyl-, propyl- and pentyl mercaptan. S-Nucleophiles attacked to the carbon atom of 1,4-naphthoquinone core and displaced with the chlorine atom to create target molecules; 2-aryl amino-3-(ethyl thio)naphthalene-1,4-dione (5a,b), 2-aryl amino-3-(propyl thio)naphthalene-1,4-dione (5c,d), 2-aryl amino-3-(pentyl thio)naphthalene-1,4-dione (5e,f) derivatives. The structures of synthesized compounds were proved by utilizing 1D and 2D NMR techniques and also mass spectra and FTIR data.

Keywords

• Sulfanyl and/or arylamine substituted quinones,1,4-naphthoquinone,spectroscopic analysis,HMQC/HMBC analysis

References

1. 1. Sieveking I, Thomas P, Estevez JC, Quinones N, Cuellar MA, Villena J, et al. 2-Phenylaminonaphthoquinones and related compounds: Synthesis, trypanocidal and cytotoxic activities. Bioorgan Med Chem. 2014;22(17):4609-20
2. 2. Senoh H, Yao M, Sakaebe H, Yasuda K, Siroma Z. A two-compartment cell for using soluble benzoquinone derivatives as active materials in lithium secondary batteries. Electrochim Acta. 2011;56(27):10145-50
3. 3. Ding Y, Yu GH. A Bio-Inspired, Heavy-Metal-Free, Dual-Electrolyte Liquid Battery towards Sustainable Energy Storage. Angew Chem Int Edit. 2016;55(15):4772-6
4. 4. Huskinson B, Marshak MP, Suh C, Er S, Gerhardt MR, Galvin CJ, et al. A metal-free organic-inorganic aqueous flow battery. Nature. 2014;505(7482):195-211
5. 5. Ding Y, Li YF, Yu GH. Exploring Bio-inspired Quinone-Based Organic Redox Flow Batteries: A Combined Experimental and Computational Study. Chem. 2016;1(5):790-801
6. 6. Matsuda S, Adachi K, Matsuo Y, Nukina M, Shizuri Y. Salinisporamycin, a novel metabolite from Salinispora arenicora. J Antibiot. 2009;62(9):519-26
7. 7. Cai P, Kong FM, Ruppen ME, Glasier G, Carter GT. Hygrocins A and B, naphthoquinone macrolides from Streptomyces hygroscopicus. J Nat Prod. 2005;68(12):1736-42
8. 8. Yildirim H, Bayrak N, Tuyun AF, Kara EM, Celik BO, Gupta GK. 2,3-Disubstituted-1,4-naphthoquinones containing an arylamine with trifluoromethyl group: synthesis, biological evaluation, and computational study. RSC Adv. 2017;7(41):25753-64

9. 9. Bayrak N, Yildirim H, Tuyun AF, Kara EM, Celik BO, Gupta GK, et al. Synthesis, Computational Study, and Evaluation of In Vitro Antimicrobial, Antibiofilm, and Anticancer Activities of New Sulfanyl Aminonaphthoquinone Derivatives. Lett Drug Des Discov. 2017;14(6):647-61
10. 10. Bayrak N, Yildirim H, Tuyun AF, Kara EM, Celik BO, Gupta GK. Synthesis, Biological, and Computational Study of Naphthoquinone Derivatives Containing Heteroatoms. J Chem Soc Pakistan. 2016;38(6):1211-21
11. 11. Tandon VK, Maurya HK, Mishra NN, Shukla PK. 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(8):3130-7
12. 12. Rau G, Cretu FM, Andrei AM, Pisoschi CG, Mogosanu GD, Boroghina A, et al. Synthesis and Evaluation of Antimicrobial Activity of New 2-Mercapto-3-Substituted-1,4-Naphthoquinones (I). Farmacia. 2015;63(5):665-9
13. 13. Tuyun AF, Bayrak N, Yildirim H, Onul N, Kara EM, Celik BO. Synthesis and In Vitro Biological Evaluation of Aminonaphthoquinones and Benzo[b]phenazine-6,11-dione Derivatives as Potential Antibacterial and Antifungal Compounds. J Chem. 2015: Artn 645902
14. 14. Bayrak N. Novel Straight-chained Sulfanyl Members of Arylamino-1,4-naphthoquinones: Synthesis and Characterization. JOTCSA. 2017; 4(2):121
15. 15. Luo YL, Chou TC, Cheng CC. Design of antineoplastic agents on the basis of the ''2-phenyl-naphthalene-type'' structural pattern .3. Synthesis and biological activity evaluation of 5H-benzo[b]naphtho[2,3-d]pyrrole-6,11-dione derivatives. J Heterocyclic Chem. 1996;33(1):113-7