Synthesis Of A Novel Series Of Indole Clubbed Oxazepine Derivatives Using Conventional And Microwave Action
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Abstract
A novel series of indole based oxazepine derivatives were synthesized using microwave irradiation and conventional method from commercially available isatin derivatives. Reaction of isain derivatives with hydrazine hydrate and undergo nucleophilic substitution reaction. In the presence of ethanol as a solvent, the compounds (2) will react with different aromatic aldehydes to generate Schiff's bases (3). Further, Schiff’s bases (3) undergo cyclization in the presence of phthalic anhydride will form the final proposed structure or compounds (5).
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Alvarez‐Builla, J., & Barluenga, J. (2011). Heterocyclic compounds: an introduction. Modern Heterocyclic Chemistry, 1-9.
Bassyouni, F. A., Saleh, T. S., ElHefnawi, M. M., El-Moez, S. I. A., El-Senousy, W. M., & Abdel-Rehim, M. E. (2012). Synthesis, pharmacological activity evaluation and molecular modeling of new polynuclear heterocyclic compounds containing benzimidazole derivatives. Archives of pharmacal research, 35, 2063-2075.
Wess, G., Urmann, M., & Sickenberger, B. (2001). Medicinal chemistry: challenges and opportunities. Angewandte Chemie International Edition, 40(18), 3341-3350.
Harvey, A. L. (2008). Natural products in drug discovery. Drug discovery today, 13(19-20), 894-901.
Thanikachalam, P. V., Maurya, R. K., Garg, V., & Monga, V. (2019). An insight into the medicinal perspective of synthetic analogs of indole: A review. European journal of medicinal chemistry, 180, 562-612.
Schneider, G. (2018). Automating drug discovery. Nature reviews drug discovery, 17(2), 97-113.
Sinha, S., & Vohora, D. (2018). Drug discovery and development: An overview. Pharmaceutical medicine and translational clinical research, 19-32.
Kumari, A., & Singh, R. K. (2019). Medicinal chemistry of indole derivatives: Current to future therapeutic prospectives. Bioorganic chemistry, 89, 103021.
Kumar, S., & Ritika. (2020). A brief review of the biological potential of indole derivatives. Future Journal of Pharmaceutical Sciences, 6, 1-19.
Rani, P., Srivastava, V. K., & Kumar, A. (2004). Synthesis and anti-inflammatory activity of heterocyclic indole derivatives. European journal of medicinal chemistry, 39(5), 449-452.
Zhu, Y., Zhao, J., Luo, L., Gao, Y., Bao, H., Li, P., & Zhang, H. (2021). Research progress of indole compounds with potential antidiabetic activity. European Journal of Medicinal Chemistry, 223, 113665.
Nazir, M., Abbasi, M. A., Siddiqui, S. Z., Khan, K. M., Salar, U., Shahid, M., ... & Khan, F. A. (2018). New indole-based hybrid oxadiazole scaffolds with N-substituted acetamides: As potent anti-diabetic agents. Bioorganic chemistry, 81, 253-263.
Solangi, M., Khan, K. M., Saleem, F., Hameed, S., Iqbal, J., Shafique, Z., ... & Perveen, S. (2020). Indole acrylonitriles as potential anti-hyperglycemic agents: Synthesis, α-glucosidase inhibitory activity and molecular docking studies. Bioorganic & medicinal chemistry, 28(21), 115605.
Goboza, M., Meyer, M., Aboua, Y. G., & Oguntibeju, O. O. (2020). In vitro antidiabetic and antioxidant effects of different extracts of Catharanthus roseus and its indole alkaloid, vindoline. Molecules, 25(23), 5546.
Sravanthi, T. V., Sajitha Lulu, S., Vino, S., Jayasri, M. A., Mohanapriya, A., & Manju, S. L. (2017). Synthesis, docking, and evaluation of novel thiazoles for potent antidiabetic activity. Medicinal Chemistry Research, 26, 1306-1315.
Rani, P., Srivastava, V. K., & Kumar, A. (2004). Synthesis and antiinflammatory activity of heterocyclic indole derivatives. European journal of medicinal chemistry, 39(5), 449-452.
Jacob, Í. T., Gomes, F. O., de Miranda, M. D., de Almeida, S. M., da Cruz-Filho, I. J., Peixoto, C. A., ... & de Lima, M. C. (2021). Anti-inflammatory activity of novel thiosemicarbazone compounds indole-based as COX inhibitors. Pharmacological Reports, 73, 907-925.
Özdemir, A., Altıntop, M. D., Turan-Zitouni, G., Çiftçi, G. A., Ertorun, I., Alataş, Ö., & Kaplancıklı, Z. A. (2015). Synthesis and evaluation of new indole-based chalcones as potential antiinflammatory agents. European journal of medicinal chemistry, 89, 304-309.
Hemalatha, K., Madhumitha, G., & Roopan, S. M. (2013). Indole as a core anti-inflammatory agent-A Mini Review. Chem. Sci. Rev. Lett, 2(1), 287-292.
Xu, D., & Xu, Z. (2020). Indole alkaloids with potential anticancer activity. Current topics in medicinal chemistry, 20(21), 1938-1949.
Kaur, K., & Jaitak, V. (2019). Recent development in indole derivatives as anticancer agents for breast cancer. Anti-Cancer Agents in Medicinal Chemistry (Formerly Current Medicinal Chemistry-Anti-Cancer Agents), 19(8), 962-983.
Prakash, B., Amuthavalli, A., Edison, D., Sivaramkumar, M. S., & Velmurugan, R. (2018). Novel indole derivatives as potential anticancer agents: Design, synthesis and biological screening. Medicinal Chemistry Research, 27, 321-331.
Biswal, S., Sahoo, U., Sethy, S., Kumar, H. K. S., & Banerjee, M. (2012). Indole: the molecule of diverse biological activities. Asian J. Pharm. Clin. Res, 5(1), 1-6.
Khan, K. M., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S., & Choudhary, M. I. (2009). Synthesis of bis-Schiff bases of isatins and their antiglycation activity. Bioorganic & medicinal chemistry, 17(22), 7795-7801.
Patel, T., Gaikwad, R., Jain, K., Ganesh, R., Bobde, Y., Ghosh, B., ... & Gayen, S. (2019). First Report on 3‐(3‐oxoaryl) Indole Derivatives as Anticancer Agents: Microwave Assisted Synthesis, In Vitro Screening and Molecular Docking Studies. ChemistrySelect, 4(15), 4478-4482.
Kerzare, D. R., Menghani, S. S., & Khedekar, P. B. (2018). Synthesis, characterization, antidepressant activity and docking studies of some novel indole bearing azetidinone derivatives. drugs, 52(1), 110-21.
Khorsheed, O. A., Al-Rubaye, I. M., & Samir, A. H. (2020). Synthesis and Characterization of Some New Heterocyclic Compounds and Their Antibacterial Study. International Journal of Pharmaceutical Research (09752366).