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

Year 2018, Volume: 5 Issue: 1, 149 - 158, 01.09.2017
https://doi.org/10.18596/jotcsa.335894

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.


References

  • 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. Bayrak N. Novel Straight-chained Sulfanyl Members of Arylamino-1,4-naphthoquinones: Synthesis and Characterization. JOTCSA. 2017; 4(2):121
  • 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
Year 2018, Volume: 5 Issue: 1, 149 - 158, 01.09.2017
https://doi.org/10.18596/jotcsa.335894

Abstract

References

  • 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. Bayrak N. Novel Straight-chained Sulfanyl Members of Arylamino-1,4-naphthoquinones: Synthesis and Characterization. JOTCSA. 2017; 4(2):121
  • 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
There are 15 citations in total.

Details

Subjects Engineering, Chemical Engineering
Journal Section Articles
Authors

Hatice Yıldırım

Publication Date September 1, 2017
Submission Date August 24, 2017
Acceptance Date November 24, 2017
Published in Issue Year 2018 Volume: 5 Issue: 1

Cite

Vancouver Yıldırım H. Synthesis and Structural Analysis of Some New Sulfanyl Amino 1,4-Naphthoquinone Derivatives. JOTCSA. 2017;5(1):149-58.