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Vol. 34 No. 6 (2022): Vol 34 Issue 6

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Synthesis of Isoxazole, Pyrazole, Thiadiazole Cyclohexanol Analogues of 1,5-Benzodiazepines through Phenoxy/Phenylamino Linkage

https://doi.org/10.14233/ajchem.2022.23582
M. Amin Mir
Department of Mathematics & Natural Sciences, Prince Mohammad Bin Fahd University, AlKhobar, Saudi Arabia
M.M.S. Jassal
Department of Chemistry, DAV (PG) College, Dehradun, India
Kim Andrews
Department of Mathematics & Natural Sciences, Prince Mohammad Bin Fahd University, AlKhobar, Saudi Arabia

Corresponding Author(s) : M. Amin Mir

mmir@pmu.edu.sa; mohdaminmir@gmail.com

Asian Journal of Chemistry, Vol. 34 No. 6 (2022): Vol 34 Issue 6

Abstract

The modification in the structures of these compounds offers high degree of diversity and provides a gateway for the production and development of new therapeutic agents with enhanced potency and lesser toxicity. The present study involves the design and synthesis of some newer derivatives of isoxazole, pyrazole and thiadiazole by incorporating the phenoxyl/phenylamino linkage. The chemical structures of the synthesized compounds was confirmed by 1H NMR, 13C NMR, IR, UV-Vis spectroscopy, mass spectrometry and elemental analysis

Keywords

Isoxazole Pyrazole Thiadiazole Cyclohexane
Amin Mir, M., Jassal, M., & Andrews, K. (2022). Synthesis of Isoxazole, Pyrazole, Thiadiazole Cyclohexanol Analogues of 1,5-Benzodiazepines through Phenoxy/Phenylamino Linkage. Asian Journal of Chemistry, 34(6), 1531–1536. https://doi.org/10.14233/ajchem.2022.23582
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References
  1. N. Agrawal and P. Mishra, Med. Chem. Res., 27, 1309 (2018); https://doi.org/10.1007/s00044-018-2152-6
  2. G.M. Badrey and S.M. Gomha, Int. J. Pharm. Sci., 6, 236 (2014).
  3. H. Kaur, S. Kumar and A. Kumar, Int. J. Chemtech Res., 2, 1019 (2010).
  4. J.-P. Yong, C.-Z. Lu and X. Wu, Anticancer. Agents Med. Chem., 15, 131 (2014); https://doi.org/10.2174/1871520614666140812105445
  5. P. Mondal, S. Jana, A. Balaji, R. Ramakrishna and L.K. Kanthal, J. Young Pharm., 4, 38 (2012); https://doi.org/10.4103/0975-1483.93574
  6. S. El-Hawash, R. Soliman, A. Youssef, H. Ragab, P. Elzahhara, I. ElAshmawey, A. Abdel-Wahab and I. Shaat, Med. Chem., 10, 318 (2014); https://doi.org/10.2174/15734064113096660044
  7. K. Choi, C.K. Siegel, M. Piper, J.L. Yuan, L. Cho, E.P. Strnad, B. Omary, K.M. Rich and C. Khosla, Chem. Biol., 12, 469 (2005); https://doi.org/10.1016/j.chembiol.2005.02.007
  8. C.S. Reddy and A. Nagaraj, Heterocycl. Commun., 14, 289 (2008); https://doi.org/10.1515/HC.2008.14.4.289
  9. C.-Y. Zhang, B.-L. Wang, X.-H. Liu, Y.-H. Li, S.-H. Wang and Z.-M. Li, Heterocycl. Commun., 14, 397 (2008); https://doi.org/10.1515/HC.2008.14.6.397
  10. A. Kumar, R.A. Maurya, S. Sharma, P. Ahmad and A.B. Singh, Bioorg. Med. Chem., 17, 5285 (2009); https://doi.org/10.1016/j.bmc.2009.05.033
  11. T. Tatee, S. Kurashige, A. Shiozawa, K. Narita, M. Takei, S. Ito, H. Miyazaki, H. Yamanaka, M. Mizugaki, T. Sakamoto and H. Fukuda, Chem. Pharm. Bull. (Tokyo), 34, 1634 (1986); https://doi.org/10.1248/cpb.34.1634
  12. A. Srinivas, A. Nagaraj and C.S. Reddy, Eur. J. Med. Chem., 45, 2353 (2010); https://doi.org/10.1016/j.ejmech.2010.02.014
  13. A. Upadhyay, M. Gopal, C. Srivastava and N.D. Pandey, J. Pesticide Sci., 35, 464 (2010); https://doi.org/10.1584/jpestics.G10-40
  14. R. Sun, Y. Li, L. Xiong, Y. Liu and Q. Wang, J. Agric. Food Chem., 59, 4851 (2011); https://doi.org/10.1021/jf200395g
  15. S. Marri, R. Kakkerla, M.P.S.M. Krishna and M.V. Rajam, Heterocycl. Commun., 24, 285 (2018); https://doi.org/10.1515/hc-2018-0137
  16. M. Pieroni, A. Lilienkampf, B. Wan, Y. Wang, S.G. Franzblau and P.A. Kozikowski, J. Med. Chem., 52, 6287 (2009); https://doi.org/10.1021/jm900513a
  17. F. Abrigach and R. Touzani, Med. Chem., 6, 298 (2016); https://10.4172/2161-0444.1000359
  18. M.J. Alam, S. Alam, P. Alam and M.J. Naim, Int. J. Pharm. Sci. Res., 6, 1442 (2015).
  19. M.S. Abdel-Maksoud, M.I. El-Gamal, M.M.G. El-Din and C.H. Oh, J. Enzyme Inhib. Med. Chem., 34, 97 (2019); https://doi.org/10.1080/14756366.2018.1530225
  20. D.K. Achutha, V.H. Kameshwar, M.B. Ningappa and A.K. Kariyappa, Biointerface Res. Appl. Chem., 7, 2047 (2017).
  21. V. Prabhu, V. Kannan and N. Guruvayoorappan, Pharmacol. Rep., 65, 980 (2013); https://doi.org/10.1016/S1734-1140(13)71079-X
  22. V.L.M. Silva, J. Elguero and A.M.S. Silva, Eur. J. Med. Chem., 156, 394 (2018); https://doi.org/10.1016/j.ejmech.2018.07.007
  23. B.N. Chowdary, M. Umashankara, B. Dinesh, K. Girish and A.R. Baba, Asian J. Chem., 31, 45 (2019); https://doi.org/10.14233/ajchem.2019.21455
  24. A. Tanitame, Y. Oyamada, K. Ofuji, M. Fujimoto, N. Iwai, Y. Hiyama, K. Suzuki, H. Ito, H. Terauchi, M. Kawasaki, K. Nagai, M. Wachi and J. Yamagishi, J. Med. Chem., 47, 3693 (2004); https://doi.org/10.1021/jm030394f
  25. D. Secci, A. Bolasco, P. Chimenti and S. Carradori, Curr. Med. Chem., 18, 5114 (2011); https://doi.org/10.2174/092986711797636090
  26. E. Palaska, M. Aytemir, I. T. Uzbay and D. Erol, Eur. J. Med. Chem., 36, 539 (2001); https://doi.org/10.1016/s0223-5234(01)01243-0
  27. P.A. Datar and T.A. Deokule, Mini Rev. Med. Chem., 14, 136 (2014); https://doi.org/102174/1389557513666140103102447
  28. V.L.M. Silva, A.M.S. Silva, D.C.G.A. Pinto, N. Jagerovic, L.F. Callado, J.A.S. Cavaleiro and J. Elguero, Monatsh. Chem., 138, 797 (2007); https://doi.org/10.1007/s00706-007-0676-4
  29. V.L.M. Silva, A.M.S. Silva, D.C.G.A. Pinto, P. Rodríguez, M. Gomez and N. Jagerovic, ARKIVOC, 246 (2010); https://doi.org/10.3998/ark.5550190.0011.a19
  30. P.M.O. Gomes, A.M.S. Silva and V.L.M. Silva, Molecules, 25, 1722 (2020); https://doi.org/10.3390/molecules25071722
  31. A. Ansari, A. Ali, M. Asif and Shamsuzzaman, New J. Chem., 41, 16 (2017); https://doi.org/10.1039/C6NJ03181A
  32. S.G. Kucukguzel and S. Senkardes, Eur. J. Med. Chem., 97, 786 (2015); https://doi.org/10.1016/j.ejmech.2014.11.059
  33. C.M.M. Santos, V.L.M. Silva and A.M.S. Silva, Molecules, 22, 1665 (2017); https://doi.org/10.3390/molecules22101665
  34. J.V. Faria, P.F. Vegi, A.G.C. Miguita, M.S. Dos Santos, N. Boechat and A.M.R. Bernardino, Bioorg. Med. Chem., 25, 5891 (2017); https://doi.org/10.1016/j.bmc.2017.09.035
  35. R. Perez-Fernandez, P. Goya and J. Elguero, ARKIVOC, 233 (2014); https://doi.org/10.3998/ark.5550190.p008.131
  36. A. Marella, R. Ali, T. Alam, R. Saha, O. Tanwar, M. Shaquiquzzaman, M. Akhter and M.M. Alam, Mini Rev. Med. Chem., 13, 921 (2013).
  37. F. Giornal, S. Pazenok, L. Rodefeld, N. Lui, J. Vors and F.R. Leroux, J. Fluor. Chem., 152, 2 (2013); https://doi.org/10.1016/j.jfluchem.2012.11.008
  38. H. Garcia, S. Iborra, M.A. Miranda, I.M. Morera and J. Primo, Heterocycles, 32, 1748 (1991); https://doi.org/10.3987/COM-91-5773
  39. I. Ortmann, S. Werner, C. Krueger, S. Mohr and K. Schaffner, J. Am. Chem. Soc., 114, 5048 (1992); https://doi.org/10.1021/ja00039a015
  40. S. Trofimenko, Chem. Rev., 72, 497 (1972); https://doi.org/10.1021/cr60279a003
  41. A.I. Busev, V.K. Akimov and S.I. Gusev, Russ. Chem. Rev., 34, 237 (1965); https://doi.org/10.1070/RC1965v034n03ABEH001426
  42. H. Meier and A. Hormaza, Eur. J. Org. Chem., 3372 (2003); https://doi.org/10.1002/ejoc.200300221
  43. B. Willy and T.J.J. Muller, Org. Lett., 13, 2082 (2011); https://doi.org/10.1021/ol2004947
  44. A. Dorlars, C.W. Schellhammer and J. Schroeder, Angew. Chem. Int. Ed. Engl., 14, 665 (1975); https://doi.org/10.1002/anie.197506651
  45. Y. Li, J. Geng, Y. Liu, S. Yu and G. Zhao, ChemMedChem, 8, 27 (2013); https://doi.org/10.1002/cmdc.201200355
  46. A. Karaburun, U.A. Cevik, D. Osmaniye, B. Saglik, B.K. Cavusoglu, S. Levent, Y. Özkay, A. Koparal, M. Behçet and Z. Kaplancikli, Molecules, 23, 3129 (2018); https://doi.org/10.3390/molecules23123129
  47. M. Gür, N. Sener, Ç.A. Kastas, O.E. Özkan, H. Muglu and M.A.M. Elmaswari, J. Heterocycl. Chem., 54, 3578 (2017); https://doi.org/10.1002/jhet.2984
  48. H.N. Hafez, M.I. Hegab and I.S. Ahmed-Farag, Bioorg. Med. Chem. Lett., 18, 4543 (2008); https://doi.org/10.1016/j.bmcl.2008.07.042
  49. M.D. Altintop, B. Sever, A. Özdemir, S. Ilgin, Ö. Atli, G. Turan-Zitouni and Z.A. Kaplancikli, Anticancer. Agents Med. Chem., 18, 1606 (2019); https://doi.org/10.2174/1871520618666180509111351
  50. A. Arcoria, M.R. De Giorgi, F. Fatuzzo and M.L. Longo, Dyes Pigments, 21, 67 (1993); https://doi.org/10.1016/0143-7208(93)85005-K
  51. M.R. De Giorgi, R. Carpignano and A. Cerniani, Dyes Pigments, 37, 187 (1998); https://doi.org/10.1016/S0143-7208(97)00054-5
  52. H. Zollinger, Azo dyes and Pigments; In Color Chemistry: Syntheses, Properties, and Applications of Organic Dyes and Pigments, WileyVCH: Zurich, Switzerland, Ed. 3, p. 254 (2003).
  53. S.M. Tambe, R.G. Tasaganva, S.R. Inamdar and M.Y. Kariduraganavar, J. Appl. Polym. Sci., 125, 1049 (2012); https://doi.org/10.1002/app.34238
  54. I.H.R. Tomi, A.H.R. Al-Daraji, R.R.T. Al-Qaysi, M.M. Hasson and K.H.D. Al-Dulaimy, Arab. J. Chem., 7, 687 (2014); https://doi.org/10.1016/j.arabjc.2010.12.003
  55. C.T.K. Kumar, J. Keshavayya, T.N. Rajesk, S.K. Peethambar and A.R.S. Ali, Org. Chem. Int., 2013, 370626 (2013); https://doi.org/10.1155/2013/370626
  56. A. Kedzia, A. Kudelko, M. Swiatkowski and R. Kruszynski, Dyes Pigments, 172, 107865 (2020); https://doi.org/10.1016/j.dyepig.2019.107865
  57. M. Wroblowska, A. Kudelko, N. Kuznik, K. Laba and M. Lapkowski, J. Heterocycl. Chem., 54, 1550 (2017); https://doi.org/10.1002/jhet.2743
  58. M. Wroblowska, A. Kudelko and M. Lapkowski, Synlett, 26, 2130 (2015); https://doi.org/10.1055/s-0034-1378826
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