Synthesis, Characterization and Biological Evaluation Of 2-Chloroquinoline-Tetramethyl-Hexahydro- 1H-xanthene-1,8-(2H) Dione Derivatives

Authors

  • Arun Vaghasiya  Department of Chemistry, M.V.M. Science and Home Science College, Rajkot, Gujarat, India
  • Chetana Rajyaguru  Department of Chemistry, M.V.M. Science and Home Science College, Rajkot, Gujarat, India
  • Kaushik Joshi  Department of Chemistry, D.K.V. Arts and Science College, Jamnagar, Gujarat, India
  • Govind Kher  Department of Chemistry, Tolani College of Arts and Science, Adipur, Gujarat, India
  • Jatin Upadhiyay  Department of Chemistry, M.V.M. Science and Home Science College, Rajkot, Gujarat, India

Keywords:

2-chloro-5,8-dimethylquinoline-3-carbaldehyde, 5,5-dimethylcyclohexane-1,3-dione, HCl.

Abstract

9-(2-chloro-substitutedquinolin-3-yl)-3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-2H-xanthene-1,8(5H,9H)-diones (DMDMO-1 to 12) were prepared with good yield by very effective method using the basic idea with quite novel approach 2-chloro-5,8-dimethylquinoline-3-carbaldehyde and 5,5-dimethylcyclohexane-1,3-dione was refluxed for 12 to 18 hrs. in presence of HCl. Completion of reaction was checked by thin layer chromatographic (TLC) technique. All the new synthesized compounds authorized with better functional group and derivatizations were characterized by IR, 1HNMR and elemental analyses. All the synthesized compounds were assessed for their antimicrobial activity.

References

  1. (a) M. R. Taghartapeh, N. N. Pesyan, H. Rashidnejad, H. R. Khavasi and A. Soltani, J. Mol. Struct., 2017, 1149, 862; (b) L. Jeyaseeli, A. D. Gupta, K. A. Kumar, K. Mazumdar, N. K. Dutta and S. G. Dastidar, Int. J. Antimicrob. Agents, 2006, 27, 58; (c) T. Y?ld?z and H. B. Kuc¨ uk, ¨ RSC Adv., 2017, 7, 16644.
  2. S. Y. Wu, Y. H. Fu, G. Y. Chen, X. B. Li, Q. Zhou, C. R. Han, X. P. Song, X. J. Du, M. L. Xie and G. G. Yao, Phytochem. Lett., 2015, 11, 236.
  3. (a) S. Naseem, M. Khalid, M. N. Tahir, M. A. Halim, A. A. C. Braga, M. M. Naseer and Z. Shaa, J. Mol. Struct., 2017, 1143, 235; (b) A. Barmak, K. Niknam, G. Mohebbi and H. Pournabi, Microb. Pathog., 2019, 130, 95; (c) A. Akbari and A. Hosseini-Nia, J. Saudi Chem. Soc., 2017, 21, S7.
  4. (a) J. M. Khurana, D. Magoo, K. Aggarwal, N. Aggarwal, R. Kumar and C. Srivastava, Eur. J. Med. Chem., 2012, 58, 470; (b) U. Kusampally, R. Pagadala and C. R. Kamatala, Tetrahedron Lett., 2017, 58, 3316.
  5. (a) H. N. Hafez, M. I. Hegab, I. S. Ahmed-Farag and A. B. A. ElGazzar, Bioorg. Med. Chem. Lett., 2008, 18, 4538; (b) A. G. Banerjee, L. P. Kothapalli, P. A. Sharma, A. B. Thomas, R. K. Nanda, S. K. Shrivastava and V. V. Khatanglekar, Arabian J. Chem., 2016, 9, S480.
  6. (a) C. G. Piscopo, S. Buhler, G. Sartori and R. Maggi, ¨ Catal. Sci. Technol., 2012, 2, 2449; (b) H. Jian, K. Liu, W. H. Wang, Z. J. Li, B. Dai and L. He, Tetrahedron Lett., 2017, 58, 1137; (c) Q. Chen, G. D. Yu, X. F. Wang, Y. C. Ou and Y. P. Huo, Green Chem., 2019, 21, 798; (d) Subodh, N. K. Mogha, K. Chaudhary, G. Kumar and D. T. Masram, ACS Omega, 2018, 3, 16377; (e) Q. Chen, X. F. Wang, G. D. Yu, C. X. Wen and Y. P. Huo, Org. Chem. Front., 2018, 5, 2652.
  7. (a) F. Peng, S. Y. Hou, T. Y. Zhang, Y. Y. Wu, M. Y. Zhang, X. M. Yan, M. Y. Xia and Y. X. Zhang, RSC Adv., 2019, 9, 28754; (b) A. Kumari and R. K. Singh, Bioorg. Chem., 2019, 89, 103021; (c) P. V. Thanikachalam, R. K. Maurya, V. Garg and V. Monga, Eur. J. Med. Chem., 2019, 180, 562; (d) S. Nomiyama, T. Hondo and T. Tsuchimoto, Adv. Synth. Catal., 2016, 358, 1136.
  8. Hideu T. Jpn Tokkyo Koho JP, 56005480; 1981, Chem Abstr 1981, 95, 80922b.
  9. Lambert RW, Martin JA, Merrett JH, Parkes KEB, Thomas GJ. PCT Int. Appl. WO 9706178; 1997. Chem Abstr 1997,126, P212377y.
  10. Poupelin JP, Saint-Rut G, Foussard-Blanpin O, Narcisse G, Uchida-Ernouf G, Lacroix R. Synthesis and anti-inflammatory properties of bis(2-hydroxy-1- naphthyl)methane derivatives. I. Monosubstituted derivatives. Eur J Med Chem 1978 13, 67-71.
  11. Ion RM, Frackowiak D, Wiktorowicz K. The incorporation of various porphyrins into blood cells measured via flow cytometry, absorption and emission spectroscopy. Acta Biochim Polonica 1998, 45, 833-45.
  12. Saint-Ruf G, Hieu HT, Poupelin JP. The effect of dibenzoxanthenes on the paralyzing action of zoxazolamine. Naturwissenschaften 1975, 62(12), 584.
  13. Menchen SM, Benson SC, Lam JYL, Zhen W, Sun D, Rosenblum BB, et al. U.S. Patent, 6,583,168; 2003. Chem Abstr 2003, 139, 54287.
  14. Ahmad, M., King, T. A., Ko, D. K., Cha, B. H., & Lee, J. (2002). Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases. Journal of Physics D: Applied Physics, 35(13), 1473-1476.
  15. Knight CG, Stephens T. Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH. Biochem J. 1989, 258, 683.
  16. Bekaert A, Andrieux J, Plat M. New total synthesis of bikaverin. Tetrahedron Lett 1992, 33, 2805.
  17. Knight DW, Little PB. The first high-yielding benzyne cyclisation using a phenolic nucleophile: a new route to xanthenes. Synlett 1998, 10, 1141.
  18. Jha A, Beal J. Convenient synthesis of 12H-benzo[a]xanthenes from 2-tetralone. Tetrahedron Lett 2004, 45(49), 8999-9001.
  19. Chih-Wei Kuo & Jim-Min Fang (2001) synthesis of xanthenes, indanes, and tetrahydronaphthalenes via intramolecular phenyl–carbonyl coupling reactions, Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry, 31, 877-892

Downloads

Published

2019-05-30

Issue

Section

Research Articles

How to Cite

[1]
Arun Vaghasiya, Chetana Rajyaguru, Kaushik Joshi, Govind Kher, Jatin Upadhiyay, " Synthesis, Characterization and Biological Evaluation Of 2-Chloroquinoline-Tetramethyl-Hexahydro- 1H-xanthene-1,8-(2H) Dione Derivatives, International Journal of Scientific Research in Science, Engineering and Technology(IJSRSET), Print ISSN : 2395-1990, Online ISSN : 2394-4099, Volume 6, Issue 3, pp.420-426, May-June-2019.