Design, Identification and Anti-Bacterial activity of New Tropylated Heterocycles

Main Article Content

MuathJabbarTarfa Al-Abbasee
Taiseer Saleh
Ahmed Khalid Hussein
Suha Abdullah Hussein AlHaddad

Keywords

tropylateddihydropyridine, tropylatedpyrazole, 1,3,5-cycloheptatriene ring, anti-bacterial activity

Abstract

This work highlights design some modern tropylated five and six substituted pyrazole and dihydropyridine hetero cyclic derivatives. These derivatives obtained by efficient one pot reaction, this one involve direct N-tropylation of substituted pyrazole and dihydropyridine derivatives in conventional alcoholic solvent under reflux condition. The chemical structures of novel designed forms proved through FT-IR, 13C-NMR, CHNS elemental analysis and anti-bacterial activity.

Abstract 132 | pdf Downloads 139

References

1. Shafiee,M. R,Ghashang,M. and Fazlinia,A.Preparation of 1,4-dihydropyridine Derivatives Using Perchloric Acid Adsorbed on Magnetic
Fe3O4 Nanoparticles Coated with Silica. Current Nanoscience,9, 197-201. 2013
2. Ronald,C. Michael,F. McGlinchey, J. and Varadarajan,A. "Ring currents, NMR chemical shifts, and homoaromaticity: the homotropylium
ion revisited. Journal of the American Chemical Society, 106.20: 5974-5978. 1984
3. Dushenko, G. A., Mikhailova, O. I., Mikhailov, I. E., Minyaev, R. M., &Minkin, V. I., January). Structural nonrigidity of N (cycloheptatrienyl) phthalimide. Doklady Chemistry, 430 (1), 11- 17.2010
4. Profatilova, I. A., Bumber, A. A., Mikhailov, I. E., Dushenko, G. A., Bubnov, M. P., &Cherkasov, V. K. Electrochemical transformations of cycloheptatriene derivatives. Russian Journal of Electrochemistry, 44(7), 812-817.2008
5. Mashkovskii,M. D.Synthesis, Antiinflammatory and Analgesic Activity of 4-Antipyrine Derivatives. Drugs [in Russian], Vol. 2, Novaya
Volna, Moscow, pp. 432 – 433. 2002
6. Ffhlinger,M. Abraham, W. Calix [4] arenes bearing a tropylium substituent as hosts for organic cations. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 58.3-4: 263-274.2007
7. Yunnikova,L. Likhareva,P. Akent’eva, T. A. Electrophilic tropylation of 2- aminopyridine. Russian Journal of General Chemistry, 87.2: 347-349. 2017
8. Marian, S. Marcin,H. Sirichai, K. The Biological Activities of Troponoids and Their Use in Agriculture A Review. Journal of Horticultural
Research, 22.1: 5-19. 2014
9. Lidia,P.Yunnikova, Victoria,V. ESENBAEVA.Tropylium and tritylium salts in reactions with 2- amino-4, 6-disubstituted pyrimidines. 61.8: 47-52. 2018
10. Yunnikova,L. P. Likhareva, Yu. E. Islyaykin, M. K. and Danilova, E. A. Xanthylium, Thioxanthylium, and Tropylium Salts in
with Imidazole and Benzimidazole. Russian Journal of Organic Chemistry.Vol. 56,No. 5, pp. 828–832.2020
11. Khodamorady,M.Sohrabnezhadb, S.Bahrami,K. Dihydropyrimidinones and 1,4-Dihydropyridine Derivatives usingBNPs@SiO2(CH2)3 NHSO3H as a Ligand and Metal Free Acidic Heterogeneous Nano-catalyst. Polyhedron. 2020
12. Surendra,R., Jamal Abdul Nasser, A. J. Selvin.Synthesis
13. and anticoagulant activity of a new series of 1,4- dihydropyridine derivatives. European Journal of Medicinal Chemistry.Vol.46, 804-810. 2011
14. Michele De Luca, GiuseppinaIoele and Gaetano Ragno. 1,4-Dihydropyridine Antihypertensive Drugs: Recent Advances in Photostabilization Strategies. Pharmaceutics, Vol.11, 85.2019
15. Swarnalatha,G. Prasanthi,G. Sirisha,N. Chetty, C.M. 1,4-Dihydropyridines: A Multtifunctional Molecule- A Review. I. J. ChemTech Research. Vol.3, No.1, pp 75-89. 2011
16. Khedkar,A. Samrat, B. Auti, Pratibha.1,4-Dihydropyridines: A class of pharmacologically important molecules. Mini Rev. Med. Chem.
Vol.14, 282–290.2014
17. Orabi EA, Orabi MA, Mahross MH, AbdelHakim M. Computational investigation of the structure and antioxidant activity of some
pyrazole and pyrazolone derivatives. Journal of Saudi Chemical Society. Vol. 6:705-14. 2018
18. Gomha,S. M H. Abdel-Aziz, M. A. Facile Synthesis of Pyrazolo
19. [3,4-c ]Pyrazoles Bearing Coumarine Ring as Anticancer Agents. J. Heterocyclic Chem.Vol. 55, 1960-1965. 2018
20. Masoumi, A. Sadr,M.Soltani, H. B.Pyrazole ligands and their monometallic and bimetallic complexes: synthesis, characterization, and
application as novel corrosion inhibitors, Journal of Adhesion Science and Technology. 2020
21. Cheng,L.Zhao, W. Shen,Z. Synthesis, Nematicidal Activity and Docking Study of Novel Pyrazole-4-Carboxamide Derivatives
against Meloidogyne Incognita. Lett. Drug Des.Discov. Vol.16, 29–35.2019
22. Yoon,J-Y. Lee,S.-g. Shin,H.Recent Advances in the Regioselective Synthesis of Pyrazoles.Current Organic Chemistry, Vol.15, 657-
674.2011
23. Karakus, S.; Tok, F.; Turk, S.; Salva, E.; Tatar, G.; Taskin-Tok, T.; Kocyigit-Kaymakcioglu, B. Synthesis, Anticancer Activity and ADMET
Studies of N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-[(3-substituted)Ureido/Thioureido]Benzenesulfonamide Derivatives. Phosphorus Sulfur Silicon Relat. Elem, Vol. 193, 528–534.2018
24. Sun, N. B.; Shen, Z. H.; Zhai, Z. W.; Han, L.; Weng, J. Q.; Tan, C. X.; Liu, X. H. Design, Synthesis, Fungicidal Activity and Docking Study of Acyl Thiourea Derivatives Containing Pyrazole Moiety. Chin. J. Org. Chem. Vol. 37, 2705–2710.2017
25. Bielenica, A.; Stepien, K.; Sawczenko, A.; Lis, T.; Koziol, A. E.; Madeddu, S.; Collu, D.; Iuliano, F.; Kosmider, A.; Struga, M. Synthesis, Structural Studies and Biological Evaluation of Halogen Derivatives of 1,3-Disubstituted Thiourea. Lett. Drug Des. Discov.Vol. 14, 636–646. 2017
26. Larik, F. A.; Shah, M. S.; Saeed, A.; Shah, H. S.; Channar, P. A.; Bolte, M.; Iqbal, J. New Cholinesterase Inhibitors for Alzheimer’s
Disease: Structure Activity Relationship, Kinetics and Molecular Docking Studies of 1–Butanoyl–3–Arylthiourea Derivatives. Int. J.
Biol. Macromol, Vol. 116, 144–150.2018
27. Gundlewad, G. B.; Patil, B. R. Synthesis and Evaluation of Some Novel 2-Amino-4-Aryl Thiazoles for Antitubercular Activity. J.
Heterocyclic Chem. Vol. 55, 769–774.2018
28. CONNELLY,G. GEIGER,E. Chemical redox agents for organometallic chemistry. Chemical Reviews. Vol. 96.2, 877-910.1996
29. Yunnikova, L. P., Likhareva, Y. E., &Esenbaeva, V. V. Electrophilic Tropylation of Aminopyridines and 4-Aminoquinoline. Russian
Journal of General Chemistry. Vol. 89(9), 1927-1930.2019
30. Alderman, D. J., and Smith. P. "Development of draft protocols of standard reference methods for antimicrobial agent susceptibility testing of bacteria associated with fish diseases." J.Aquaculture. Vol. 196.3-4: 211-243. 2001
31. Al-Abbasee, M.J. et al. Synthesis and Characterization of Some New Tropylidene Derivatives and Studying their Biological
Activities. Iraqi Journal of Science, 2021, Vol.62, No. 9(Special Issue) pp: 3307-3322Vol.62.9(SI).2. 2021
32. Silverstein, R.M. Webester, F.X. Kiemle, D. Brycedl. 2005. Spectrometric identification of organic compounds. 7th ed. John Wiley and Sons. New York, US.
33. Mahdi, E. M., & Mustafa, M. A. (2022). Effect of different concentrations of extract of Urticadioica and Cladosporiumcladosporiodes on Triboliumcastaneum or: Coleoptera after 24-48 hours of exposure in Samarra City/Iraq. HIV Nursing, 22(2), 3207-3210.
34. Mustafa, M. A., Kadham, S. M., Abbass, N. K., Karupusamy, S., Jasim, H. Y., Alreda, B. A., ... & Ahmed, M. T. (2023). A novel fuzzy M-transform technique for sustainable ground water level prediction. Applied Geomatics, 1-7.
35. Kadham, S. M., Mustafa, M. A., Abbass, N. K.,&Karupusamy, S. (2022). IoT and artificial intelligence–based fuzzy-integral N-transform
for sustainable groundwater management. Applied Geomatics, 1-8.