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Recent investigation on heterocycles with one nitrogen [piperidine, pyridine and quinoline], two nitrogen [1,3,4-thiadiazole and pyrazole] and three nitrogen [1,2,4-triazole]: a review

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Abstract

Heterocycles form by far the largest of classical divisions of organic chemistry and are of immense importance biologically and industrially, and about one half of over six million compounds recorded in chemical abstracts are heterocyclic. The majority of pharmaceuticals and biologically active agrochemicals are heterocyclic while countless additives and modifiers used in industrial applications ranging from cosmetics, reprography, information storage and plastics are heterocyclic in nature. One striking structural feature inherent to heterocycles, which continue to be exploited to great advantage by the drug industry, lies in their ability to manifest substituents around a core scaffold in defined three-dimensional representations. Among the approximately 20 million chemical compounds identified by the end of the second millennium, more than two-thirds are fully or partially aromatic and approximately half are heterocyclic. The presence of heterocycles in all kinds of organic compounds of interest in electronics, biology, optics, pharmacology, material sciences and so on is very well known. Between them, nitrogen-containing heterocyclic compounds have maintained the interest of researchers through decades of historical development of organic synthesis. In the present work, focus on the literature survey of chemical diversity (piperidine 1, pyridine 2, quinoline 3, [1,3,4]-thiadiazole 4, pyrazole 5 and [1,2,4]-triazole 6) in the molecular framework in order to get a complete information regarding pharmacologically interesting compounds of widely different composition.

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References

  1. K.R. Campos, P.J. Coleman, J.C. Alvarez, S.D. Dreher, R.M. Garbaccio, N.K. Terrett, R.D. Tillyer, M.D. Truppo, E.R. Parmee, Science 363, 6424 (2019)

    Article  Google Scholar 

  2. A. Kashyap, N. Adhikari, A. Das, A. Shakya, S.K. Ghosh, U.P. Singh, H.R. Bhat, Curr. Drug Discov. Technol. 15, 1 (2018)

    Article  Google Scholar 

  3. M. Baumann, I.R. Baxendale, J. Organ. Chem. 9, 2265 (2013)

    Google Scholar 

  4. E.M. Carreira, E.T.H. Zurich, Chem. Rev. 115, 8945 (2015)

    Article  CAS  PubMed  Google Scholar 

  5. J.W. Scannell, A. Blanckley, H. Boldon, B. Warrington, Nat. Rev. Drug Discov. 11, 191 (2012)

    Article  CAS  PubMed  Google Scholar 

  6. I.R. Baxendale, J.J. Hayward, S.V. Ley, G.K. Tranmer, ChemMedChem 2, 768 (2007)

    Article  CAS  PubMed  Google Scholar 

  7. M. Hossain, A.K. Nanda, Sci. J. Chem. 6, 83 (2018)

    Article  CAS  Google Scholar 

  8. P. Arora, V. Arora, H.S. Lamba, D. Wadhwa, Int. J. Pharm. Sci. Res. 3, 2947 (2012)

    Google Scholar 

  9. T. Omara, B. Musau, S. Kagoya, Am. J. Heterocycl. Chem. 4, 49 (2018)

    Google Scholar 

  10. S.A. Khanum, S. Shashikanth, S.G. Sathyanarayana, S. Lokesh, S.A. Deepak, Pest Manag. Sci. Former. Pest. Sci. 65, 776 (2009)

    Article  CAS  Google Scholar 

  11. Zabiulla, A.R. Gulnaz, Y.H.E. Mohammed, S.A. Khanum, Bioorgan. Chem. 92, 103220 (2019)

    Article  Google Scholar 

  12. Zabiulla, M.J.N. Khadri, B.A. Begum, M.K. Sunil, S.A. Khanum, Results Chem. 2, 100045 (2020)

    Article  Google Scholar 

  13. M. Danac, Eur. J. Med. Chem. 74, 664 (2014)

    Article  CAS  PubMed  Google Scholar 

  14. S.G. Kini, A. Bhat, Z. Pan, F.E. Dayan, J. Enzyme Inhib. Med. Chem. 25, 730 (2010)

    Article  CAS  PubMed  Google Scholar 

  15. V.R. Solomon, W. Haq, K. Srivastava, S.K. Puri, S.B. Katti, J. Med. Chem. 50, 394 (2007)

    Article  CAS  PubMed  Google Scholar 

  16. S.I. Pathan, N.S. Chundawat, N.P.S. Chauhan, G.P. Singh, Synth. Commun. 50, 1251 (2020)

    Article  CAS  Google Scholar 

  17. M. Zhu, H. Zhou, L. Ma, B. Dong, J. Zhou, G. Zhang, M. Wang, J. Wang, S. Cen, Y. Wang, Eur. J. Med. Chem. 1, 113450 (2021)

    Article  Google Scholar 

  18. R. Paruszewski, M. Strupińska, G. Rostafińska-Suchar, J.P. Stables, Protein Pept. Lett. 10, 475 (2003)

    Article  CAS  PubMed  Google Scholar 

  19. T. Legigan, E. Migianu-Griffoni, M.A. Redouane, A. Descamps, J. Deschamp, O. Gager, M. Monteil, F. Barbault, M. Lecouvey, Eur. J. Med. Chem. 214, 11324 (2021)

    Article  Google Scholar 

  20. M.A.S. Abdelwahid, T. Elsaman, M.S. Mohamed, S.A. Latif, M.M. Mukhtar, M.A. Mohamed, J. Chem. 2019, 1 (2019)

    Article  Google Scholar 

  21. C.M. Zhua, L.R. Konga, Q.L. Shenb, M. Zhanga, J.W. Chena, Q.G. Huanga, L.S. Wanga, Toxicol. Environ. Chem. 65, 145 (1998)

    Article  Google Scholar 

  22. L. He, R. Zhuo, Wuhan Univ. J. Nat. Sci. 3, 126 (1998)

    Article  CAS  Google Scholar 

  23. H.D. Gurupadaswamy, P. Thirusangu, B.R.V. Avin, V. Vigneshwaran, M.V.P. Kumar, T.S. Abhishek, V.L. Ranganatha, S.A. Khanum, B.T. Prabhakar, Biomed. Pharmacother. 68, 791 (2014)

    Article  CAS  PubMed  Google Scholar 

  24. C. Labriere, J.H. Andersen, M. Albrigtsen, J.H. Hansen, J. Svenson, Bioorgan. Chem. 84, 106 (2019)

    Article  CAS  Google Scholar 

  25. K. Swathi, M. Sarangapani, World J. Pharm. Pharm. Sci. 3, 2720 (2014)

    Google Scholar 

  26. A. Nehad, Abdel-Latif, Sci. Pharm. 74, 193 (2005)

  27. A.S. Lunkad, S.N. Kothawade, K.K. Darkunde, B. Priya, U.R. Bagmar, D.S. Bhandari, Int. J. Chem. Sci. 11, 1146 (2013)

    CAS  Google Scholar 

  28. B.L. Wang, H.W. Zhu, Y. Ma, L.X. Xiong, Y.Q. Li, Y. Zhao, J.F. Zhang, Y.W. Chen, S. Zhou, Z.M. Li, J. Agric. Food Chem. 61, 5483 (2013)

    Article  CAS  PubMed  Google Scholar 

  29. M.K. Hosseinnezhad, S. Gharanjig, S. Moradian, Tafaghodi, Arab. J. Chem. 1, 1 (2015)

    Google Scholar 

  30. T. Mori, Chem. Rev. 104, 4947 (2004)

    Article  CAS  PubMed  Google Scholar 

  31. W. Haiss, H.V. Zalinge, H.H. Benreich, D. Bethell, D.J. Schiffrin, S.J. Higgins, R.J. Nichols, Langmuir 20, 7694 (2004)

    Article  CAS  PubMed  Google Scholar 

  32. A.E.A. Wahab, A.A.K. Wasaf, J. Phys. 1032, 1 (2018)

    Google Scholar 

  33. B.A. Begum, N.D. Rekha, B.C.V. Kumar, V.L. Ranganatha, S.A. Khanum, Bioorgan. Med. Chem. Lett. 24, 3559 (2014)

    Article  Google Scholar 

  34. G.W. Nyce, J.A. Lamboy, E.F. Connor, R.M. Waymouth, J.L. Hedrick, Organ. Lett. 4, 3587 (2002)

    Article  CAS  Google Scholar 

  35. C. Ramalingan, Y.T. Park, S. Kabilan, Eur. J. Med. Chem. 41, 683 (2006)

    Article  CAS  PubMed  Google Scholar 

  36. K. Lv, Z. Tao, Q. Liu, L. Yang, B. Wang, S. Wu, A. Wang, M. Huang, M. Liu, Y. Lu, Eur. J. Med. Chem. 10, 151 (2018)

    Google Scholar 

  37. M. Al-Ghorbani, N.D. Rekha, V.L. Ranganatha, T. Prashanth, T. Veerabasappagowda, S.A. Khanum, Russ. J. Bioorgan. Chem. 41, 554 (2015)

    Article  CAS  Google Scholar 

  38. Hu. De-Jin, S.-F. Liu, T.-H. Huang, Tu. Hai-Yang, A.-D. Zhang, Molecules 14, 1288 (2009)

    Article  Google Scholar 

  39. C. Ding, Y. Pan, X. Yin, C. Tan, Z. Guofu, J. Organ. Chem. 39, 836 (2019)

    CAS  Google Scholar 

  40. X. Zhang, P. Lei, T. Sun, X. Jin, X. Yang, Y. Ling, Molecules 22, 2085 (2017)

    Article  PubMed Central  Google Scholar 

  41. R.K. Manjusha, S. Begum, A. Begum, K. Bharathi, Asian J. Pharm. Clin. Res. 66, 73 (2018)

    Google Scholar 

  42. D. Ole, Wolthers, Biomed. Res. Int. 1, 6 (2013)

    Google Scholar 

  43. C.R. Ganellin, R.G.W. Spickett, J. Med. Chem. 8, 619 (1965)

    Article  CAS  PubMed  Google Scholar 

  44. P.S. Watson, B. Jiang, B. Scott, Organ. Lett. 2, 3679 (2000)

    Article  CAS  Google Scholar 

  45. Zabiulla, V.H. Malojirao, Y.H.E. Mohammed, P. Thirusangu, B.T. Prabhakar, S.A. Khanum, Med. Chem. Res. 28, 1132 (2019)

    Article  Google Scholar 

  46. M.T. Gulluoglu, Y. Erdogdu, S. Yurdakul, J. Mol. Struct. 834, 540 (2007)

    Article  Google Scholar 

  47. Y. Zhou, E. Vlad, K.G. Benjamin, C.A. Geoffrey, Z.W. Sun, D. Murphy, G. Haley, D. Bailey, M. Jamie, F.S. Fish, E. Stephen, T.W. Hermann, D. Wall, Bioorg. Med. Chem. Lett. 17, 1206 (2007)

    Article  CAS  PubMed  Google Scholar 

  48. Q. Zhou, L. Zhang, M. Meng, X. Feng, J. Yang, H. Du, Org. Lett. 18, 5189 (2016)

    Article  CAS  PubMed  Google Scholar 

  49. Z.Y. Liu, Z.H. Wen, X.C. Wang, AngewandteChemie 56, 5817 (2017)

    CAS  Google Scholar 

  50. H.P. Singh, S.D. Gupta, N.S.H.N. Moorthy, Int. J. Pharm. Tech. Res. 1, 282 (2009)

    CAS  Google Scholar 

  51. Y.Y. Zheng, L. Guo, X.C. Zhen, J.Q. Li, Eur. J. Med. Chem. 54, 123 (2012)

    Article  CAS  PubMed  Google Scholar 

  52. I. Sato, K. Morihira, H. Inami, H. Kubota, T. Morokata, K. Suzuki, N. Hamada, Y. Iura, A. Nitta, T. Imaoka, T. Takahashi, M. Takeuchi, M. Ohtaa, S. Tsukamotoa, Bioorg. Med. Chem. 16, 144 (2008)

    Article  CAS  PubMed  Google Scholar 

  53. Y. Zeng, R. Cao, T. Zhang, S. Li, W. Zhong, Eur. J. Med. Chem. 97, 19 (2015)

    Article  CAS  PubMed  Google Scholar 

  54. S.A. Khanum, V. Girish, S.S. Suparshwa, N.F. Khanum, Bioorgan. Med. Chem. Lett. 19, 1887 (2009)

    Article  CAS  Google Scholar 

  55. S. Yang, D. Lu, P. Ouyang, Bioorgan. Med. Chem. Lett. 28, 1731 (2018)

    Article  CAS  Google Scholar 

  56. R. Sharma, S. ShubhangiSoman, Eur. J. Med. Chem. 90, 342 (2015)

    Article  CAS  PubMed  Google Scholar 

  57. L. James, V.N.W. Marcus, de Souza, M.S.V. Solange, C.S.W. Maria, Lourenço, J. Mol. Struct. 990, 67 (2011) 

  58. L. Kai, Z. Tao, Q. Liu, L. Yang, B. Wang, S. Wu, A. Wang, M. Huang, M. Liu, Y. Lu, Eur. J. Med. Chem. 151, 1 (2018)

    Article  Google Scholar 

  59. J.A. Joule, K. Mills, Heterocyclic Chemistry, vol 4 (Oxford, Blackwell, 2000)

  60. M. Al-Ghorbani, P. Thirusangu, H.D. Gurupadaswamy, V. Girish, H.G.S. Neralagundi, B.T. Prabhakar, S.A. Khanum, Bioorgan. Chem. 65, 73 (2016)

    Article  CAS  Google Scholar 

  61. G. Zeni, R.L. Larock, Chem. Rev. 106, 4644 (2006)

    Article  CAS  PubMed  Google Scholar 

  62. Zabiulla, V. Vigneshwaran, B.A. Begum, G.S. Pavankumar, B.T. Prabhakar, S.A. Khanum, Biomed. Pharm. 95, 419 (2017)

    Article  Google Scholar 

  63. C. Jared, G.L. Robert, A.B. JonathanEllman, J. Am. Chem. Soc. 129, 5332 (2007)

    Article  Google Scholar 

  64. P. Kiuru, J. Yli-Kauhaluoma, in Heterocycles in Natural Product Synthesis, ed. by K. Majumdar, S.K. Chattopadhyay (Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2011), pp. 267–297. https://doi.org/10.1002/9783527634880.ch8

  65. K.E. Bashford, M.B. Burton, S. Cameron, A.L. Cooper, R.D. Hogg, P.D. Kane, D.A. MacManus, C.A. Matrunola, C.J. Moody, A.A.B. Robertson, M.R. Warne, Tetrahedron Lett. 44, 1627 (2003)

    Article  CAS  Google Scholar 

  66. J.C. Lewis, R.G. Bergman, J.A.J. Ellman, J. Am. Chem. Soc. 129, 5332 (2007)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  67. C.K. Banerjee, J.D. Umarye, P.R. Kanjilal, Synth. Commun. 43, 2208 (2013)

    Article  CAS  Google Scholar 

  68. S.I. Scherbinina, O.V. Fedorov, V.V. Levin, V.A. Kokorekin, M.I. Struchkova, A.D. Dilman, J. Organ. Chem. 82, 12967 (2017)

    Article  CAS  Google Scholar 

  69. A.A. Altaf, A. Shahzad, Z. Gul, N. Rasool, A. Badshah, B. Lal, E. Khan, J. Drug Des. Med. Chem. 1, 1 (2015)

    Google Scholar 

  70. G. Sachs, J.M. Shin, C.W. Howden, Aliment. Pharmacol. Ther. 23, 2 (2006)

    Article  CAS  PubMed  Google Scholar 

  71. M.V.D. Almeida, M.V.D.N. Souza, N.R. Barbosa, F.P. Silva, G.W. Amarante, S.H. Cardoso, Lett. Drug Des. Discov. 4, 149 (2007)

    Article  Google Scholar 

  72. M.F. Ansari, D. Idrees, M.I. Hassan, K. Ahmad, F. Avecilla, A. Azam, Eur. J. Med. Chem. 144, 544 (2018)

    Article  CAS  PubMed  Google Scholar 

  73. B. Sun, Y. Dong, K. Lei, J. Wang, L. Zhao, M. Liu, Bioorgan. Med. Chem. 27, 2427 (2019)

    Article  CAS  Google Scholar 

  74. B. Jadhav, R. Kenny, Y. Nivid, M. Mandewale, R. Yamgar, Open J. Med. Chem. 6, 59 (2016)

    CAS  Google Scholar 

  75. M.S. Sondhi, M. Dinodia, A. Kumar, Bioorgan. Med. Chem. 14, 4657 (2006)

    Article  CAS  Google Scholar 

  76. R.C. Elderfield (ed.), Heterocyclic Compounds, vol. 6 (Wiley, New York, 1957)

  77. M. Shraddha, P.D. Kinjal, P.H. Rajesh, V.N. Shyamali, P.D. Hitesh, Patel, RSC Adv. 4, 24463 (2014)

  78. T. Prashanth, B.R. Vijay Avin, P.Thirusangu, V.L. Ranganatha, B.T. Prabhakar, J.N.N.S. Chandra, S.A. Khanum, Biomed. Pharm. 112, 108707 (2019)

  79. M. Ozyanik, S. Demirci, H. Bektas, N. Demirbas, A. Demirbas, S.A. Karaoglu, Turk. J. Chem. 36, 233 (2012)

    CAS  Google Scholar 

  80. P.R. Graves, J.J. Kwiek, P. Fadden, R. Ray, K. Hardeman, A.M. Coley, M. Foley, T.A. Haystead, Mol. Pharmacol. 62, 1364 (2002)

    Article  CAS  PubMed  Google Scholar 

  81. A.T. Vu, S.T. Cohn, E.S. Manas, H.A. Harris, R.E. Mewshaw, Bioorgan. Med. Chem. Lett. 15, 4520 (2005)

    Article  CAS  Google Scholar 

  82. Y. Li, X. Shi, N. Xie, Y. Zhao, S. Li, Med. Chem. Commun. 4, 367 (2013)

    Article  CAS  Google Scholar 

  83. J. Safari, S.H. Banitaba, S.S. Samiei, J. Chem. Sci. 121, 481 (2009)

    Article  CAS  Google Scholar 

  84. M. Qandalee, M. Alikarami, H. Mighani, S. Asghari, S. Beikjani, M. Hatami, Int. Nano Lett. 3, 49 (2013)

    Article  Google Scholar 

  85. B.C. Ranu, A. Hajra, U. Jana, Tetrahedron Lett. 41, 531 (2000)

    Article  CAS  Google Scholar 

  86. J. Wu, H.G. Xia, K. Gao, Organ. Biomol. Chem. 4, 126 (2006)

    Article  CAS  Google Scholar 

  87. M.A. Zolfgol, P. Salehi, A. Ghaderi, M. Shiri, J. Chin. Biochem. Soc. 54, 267 (2007)

    Article  Google Scholar 

  88. M.H. Sarvari, J. Iran. Chem. Soc. 8, 119 (2011)

    Article  Google Scholar 

  89. M.R. Heravi, Ultrason. Sonochem. 16, 361 (2009)

    Article  CAS  PubMed  Google Scholar 

  90. S. Kumar, S. Bawa, H. Gupta, Mini-Rev. Med. Chem. 9, 1648 (2009)

    Article  CAS  PubMed  Google Scholar 

  91. C. Vittorio, B. Guyen, Y. Opoku-Boahen, J. Mann, S.M. Gowan, M. Lloyd, A.R. Martin, N. Stephen, Bioorgan. Med. Chem. Lett. 10, 2063 (2000)

    Article  Google Scholar 

  92. W. Kemnitzer, J. Kuemmerle, S. Jiang, H.Z. Zhang, N. Sirisoma, S. Kasibhatla, C.C. Grundy, B. Tseng, J. Drewe, X.Z. Cai, Bioorgan. Med. Chem. Lett. 18, 6259 (2008)

    Article  CAS  Google Scholar 

  93. J.N. Delgado, W.A. Remers (ed.), Textbook of Organic Medicinal and Pharmaceutical Chemistry, 10th edn. (Lippincott-Raven, Philadelphia, PA, 1998). ISBN 0-397-51583-9

  94. S.A.A. Mohsen, Korean Chem. Soc. 26, 719 (2005)

    Article  Google Scholar 

  95. L.J. Guo, C.X. Wei, J.H. Jia, L.M. Zhao, Z.S. Quan, Eur. J. Med. Chem. 44, 954 (2009)

    Article  CAS  PubMed  Google Scholar 

  96. Y. Kohno, K. Awano, M. Miyashita, S. Fujimori, K. Kuriyama, Y. Sakoe, S. Kudoh, K. Saito, E. Kojima, Bioorgan. Med. Chem. Lett. 7, 1515 (1997)

    Article  CAS  Google Scholar 

  97. Y. Kohno, K. Awano, M. Miyashita, T. Ishizaki, K. Kuriyama, Y. Sakoe, S. Kudoh, K. Saito, E. Kojima, Bioorgan. Med. Chem. Lett. 7, 1519 (1997)

    Article  CAS  Google Scholar 

  98. J.M. McCall, R.E. Brink, B.V. Kamdar, L.L. Ska-Letzky, S.C. Perricone, R.C. Piper, Med. Chem. 29, 133 (1986)

    Article  CAS  Google Scholar 

  99. I. Sircar, S.J. Haleen, S.E. Burke, H. Barth, J. Med. Chem. 35, 4442 (1992)

    Article  CAS  PubMed  Google Scholar 

  100. A.K. Singh, R. Parthsarthy, J. Kshitiz, G. Mishra, Int. J. Sci. Innov. Discov. 3, 353 (2011)

    Google Scholar 

  101. S. Jalhan, A. Jindal, A. GuptaHemraj, Asian J. Pharm. Clin. Res. 3, 199 (2012)

    Google Scholar 

  102. H. Bhuva, D. Sahu, B.N. Shah, C.M. Dixit, M.B. Patel, Pharmacology 1, 528 (2011)

    Google Scholar 

  103. R. Tripathy, A. Ghose, J. Singh, E.R. Bacon, T.S. Angeles, S.X. Yang, Bioorgan. Med. Chem. Lett. 17, 1793 (2007)

    Article  CAS  Google Scholar 

  104. N. Siddiqui, P. Ahuja, W. Ahsan, S.N. Pandeya, S.M. Alam, J. Chem. Pharm. Res. 1, 19 (2009)

    CAS  Google Scholar 

  105. N. Foroughifar, A. Mobinikhaledi, S. Ebrahimi, H. Moghanian, B.M.A. Fard, Tetrahedron Lett. 50, 836 (2009)

    Article  CAS  Google Scholar 

  106. R.A. Bhat, A.T. Amir, I. Choi, F. Athar, Eur. J. Med. Chem. 46, 3158 (2011)

    Article  CAS  PubMed  Google Scholar 

  107. B.C. Chapleo, M. Myers, P.L. Myers, J.F. Saville, A.C.B. Smith, M.R. Stillingsm, J. Med. Chem. 29, 2273 (1986)

    Article  CAS  PubMed  Google Scholar 

  108. K.Y. Jung, S.K. Kim, Z.G. Gao, A.S. Gross, N. Melman, K.A. Jacobsonb, Bioorgan. Med. Chem. 12, 613 (2004)

    Article  CAS  Google Scholar 

  109. H.L. Shen, Y. Li, H.X.H. Shang, S. Tian, Y.S. Lai, L.J. Liu, Chin. Chem. Lett. 24, 299 (2013)

    Article  CAS  Google Scholar 

  110. M. Juszczak, J. Matysiak, M. Szeliga, P. Zarowski, N. Niewiadomy, J. Albrecht, Bioorgan. Med. Chem. Lett. 22, 5466 (2012)

    Article  CAS  Google Scholar 

  111. A.K. Kumar, V.G. Kumar, N. Renuka, Int. J. ChemTech. Res. 5, 239 (2013)

    Google Scholar 

  112. M.R. Mahendrasinh, H.V. Patel, M.R. Lata, N.K. Patel, Int. J. Pharm. Chem. Biol. Sci. 3, 814 (2013)

    Google Scholar 

  113. C.T. Supuran, A. Scozzafava, Curr. Med. Chem. Immunol. Endocr. Metab. Agents 1, 61 (2001)

    Article  CAS  Google Scholar 

  114. Y. Iizawa, K. Okonogi, R. Hayashi, T. Iwahi, T. Yamazaki, A. Imada, Antimicrob. Agents Chemother. 37, 100 (1993)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  115. M. Amir, A. Kumar, I. Ali, S.A. Khan, Indian J. Chem. 48B, 1288 (2009)

    CAS  Google Scholar 

  116. S.R. Pattan, B.S. Kittur, B.S. Sastry, S.G. Jadhav, D.K. Thakur, S.A. Madamwar, H.V. Shindhe, Indian J. Chem. 50B, 615 (2011)

    CAS  Google Scholar 

  117. N. Linganna, K.M.L. Rai, Synth. Commun. 28, 4611 (2006)

    Article  Google Scholar 

  118. N.C. Desai, A.M. Bhavsar, M.D. Shah, A.K. Saxena, Indian J. Chem. 47, 579 (2008)

    Google Scholar 

  119. K. Arvind, G.S. Mishra, K. Jyoti, J. Appl. Pharm. Sci. 1, 44 (2011)

    Google Scholar 

  120. A. Foroumadi, M. Sorkhi, M.H. Moshafi, M. Safavi, A. Rineh, F. Siavoshi, A. Shafiee, S. Emami, Med. Chem. 5, 529 (2009)

    Article  CAS  PubMed  Google Scholar 

  121. A. Rana, J.M. Alex, M. Chauhan, G. Joshi, R. Kumar, Med. Chem. Res. 24, 903 (2015)

    Article  CAS  Google Scholar 

  122. R. Siegel, D. Naishadham, A. Jemal, Cancer J. Clin. 62, 10 (2012)

    Article  Google Scholar 

  123. H.C. Zhao, Y.P. Shi, Y.M. Liu, C.W. Li, L.N. Xua, P. Wang, Bioorgan. Med. Chem. Lett. 23, 6577 (2013)

    Article  CAS  Google Scholar 

  124. J.Y. Chou, S.Y. Lai, S.L. Pan, G.M. Jow, J.W. Chern, J.H. Guh, Biochem. Pharmacol. 66, 115 (2003)

    Article  CAS  PubMed  Google Scholar 

  125. G. Shankar, R.A. Kallanagouda, V.A. Pranali, M.S. Sagar, H.C. Dilip, S.D. Amol, Shah, Bioorgan. Med. Chem. Lett. 22, 917 (2012)

  126. U.S. Goksen, N.G. Kelekci, O. Goktas, Y. Koysal, E. Kilic, S. Isik, G. Aktay, M. Ozalp, Bioorgan. Med. Chem. 15, 5738 (2007)

    Article  Google Scholar 

  127. S. Wiebe, N. Jette, Nat. Rev. Neurol. 8, 669 (2012)

    Article  CAS  PubMed  Google Scholar 

  128. C.M. Ulloa, F.G. Gilliam, Nat. Rev. Neurol. 7, 195 (2011)

    Article  PubMed  Google Scholar 

  129. W.H. Bergstom, R.F. Carzoli, C. Lombroso, D.T. Davidson, W.M. Wallace, Am. J. Dis. Child. 84, 771 (1952)

    CAS  Google Scholar 

  130. V.K. Archana, S.A. Kumar, Chem. Biol. Drug Des. 37, 873 (2002)

    CAS  Google Scholar 

  131. V.K. Archana, S.A. Kumar, Bioorgan. Med. Chem. 12, 1257 (2004)

    Article  CAS  Google Scholar 

  132. K. Tewari, A. Mishra, Bioorgan. Med. Chem. 9, 7150 (2001)

    Article  Google Scholar 

  133. S.L. Janus, A.Z. Magdif, B.P. Erik, N. Claus, Monatsheftefür Chemie-Chem. Month. 130, 1167 (1999)

    Google Scholar 

  134. E.V. Pimerova, E.V. Voronina, Pharm. Chem. J. 35, 602 (2001)

    Article  Google Scholar 

  135. I. Bouabdallah, L.A. Barret, A. Zyad, A. Ramadan, I. Zidane, A. Melhaoui, Nat. Prod. Res. 20, 1024 (2006)

    Article  CAS  PubMed  Google Scholar 

  136. N. Puttaswamy, N.D. Rekha, V.L. Ranganatha, T. Prashanth S.A. Khanum, J. Appl. Pharm. Sci. 8, 60 (2018) 

  137. C.K. Chu, J.J. Cutler, J. Hetrocycl. Chem. 23, 289 (1986)

    Article  CAS  Google Scholar 

  138. V. Michon, C.H. Du Penhoat, F. Tombret, J.M. Gillardin, F. Lepagez, L. Berthon, Eur. J. Med. Chem. 30, 147 (1995)

    Article  CAS  Google Scholar 

  139. M.J. Genin, C. Biles, B.J. Keiser, S.M. Poppe, S.M. Swaney, W.G. Tarpley, Y. Yagi, D.L. Romero, J. Med. Chem. 43, 1034 (2000)

    Article  CAS  PubMed  Google Scholar 

  140. Y.R. Huang, J.A. Katzenellenbogen, Organ. Lett. 2, 2833 (2000)

    Article  CAS  Google Scholar 

  141. S.R. Stauffer, C.J. Coletta, R. Tedesco, G. Nishiguchi, K. Carlson, J. Sun, B.S. Katzenellenbogen, J.A. Katzenellenbogen, J. Med. Chem. 43, 4934 (2000)

    Article  CAS  PubMed  Google Scholar 

  142. S. Ruiu, G.A. Pinna, G. Marchese, J.M. Mussinu, P. Saba, S. Tambaro, P. Casti, R. Vargiu, L. Pani, J. Pharmacol. Exp. Ther. 306, 363 (2003)

    Article  CAS  PubMed  Google Scholar 

  143. K. Du, Y. Mei, X.T. Cao, P.F. Zhang, H. Zheng, Int. J. Chem. Eng. Appl. 21, 238 (2013)

    Google Scholar 

  144. L. Knorr, German Patent 26, 429 (1883)

    Google Scholar 

  145. L. Knorr, Ber. Dtsch. Chem. Ges. 16, 2597 (1883)

    Article  Google Scholar 

  146. L. Knorr, A. Blank, Ber. Dtsch. Chem. Ges. 18, 311 (1885)

    Article  Google Scholar 

  147. Y.R. Girish, K.S.S. Kumar, H.S. Manasa, S. Shashikanth, J. Chin. Chem. Soc. 61, 1175 (2014)

    Article  CAS  Google Scholar 

  148. S. Ponnala, S.D. Prasad, Synth. Commun. 36, 2189 (2006)

    Article  Google Scholar 

  149. M.E. Braibante, H.T. Braibante, J.K. Da Roza, D.M. Henriques, T.L. de Carvalho, Synthesis 2003, 1160 (2003)

    Article  Google Scholar 

  150. P. Lokhande, K. Hasanzadeh, S.G. Konda, Eur. J. Chem. 2, 223 (2011)

    Article  CAS  Google Scholar 

  151. S. Ferfra, N.H. Ahabchane, B. Garrigues, E.M. Essassi, Comptes Rendus de and Académie des Sciences 4, 905 (2001)

    CAS  Google Scholar 

  152. S.D. Larsen, T.J. Poel, K.J. Filipski, J.T. Kohrt, J.A. Pfefferkorn, R.J. Sorenson, B.D. Tait, V. Askew, L. Dillon, J.C. Hanselman, G.H. Lu, A. Robertson, C. Sekerke, Kowala, M.C.B.J. Auerbach, Bioorgan. Med. Chem. Lett. 17, 5567 (2007) 

  153. M. Ichikawa, M. Ohtsuka, H. Ohki, M. Ota, N. Haginoya, M. Itoh, Y. Shibata, Y. Ishigai, K. Terayama, A. Kanda, K. Sugita, Med. Chem. Lett. 4, 932 (2013)

    Article  CAS  Google Scholar 

  154. E. Kick, R. Martin, Y. Xie, B. Flatt, E. Schweiger, T.L. Wang, B. Busch, M. Nyman, X.H. Gu, G. Yan, B. Wagner, M. Nanao, L. Nguyen, T. Stout, A. Plonowski, I. Schulman, J. Ostrowski, T. Kirchgessner, R. Wexler, R. Mohan, Bioorgan. Med. Chem. Lett. 25, 372 (2015)

    Article  CAS  Google Scholar 

  155. G.S. Hassan, S.M. Abou-Seri, G. Kamel, M.M. Ali, Eur. J. Med. Chem. 76, 482 (2016)

    Article  Google Scholar 

  156. R.D. Kamble, R.J. Meshram, S.V. Hese, R.A. More, S.S. Kamble, R.N. Gacche, B.S. Dawane, Comput. Biol. Chem. 61, 86 (2016)

    Article  CAS  PubMed  Google Scholar 

  157. J.N. Dominquez, J.E. Charris, M. Caparelli, F. Riggione, Arzneim-Forch, Drug Res. 52, 482 (2002)

    Google Scholar 

  158. E. Akbas, I. Berber, A. Sener, B. Hasanov, Farmaco 60, 23 (2005)

    Article  CAS  PubMed  Google Scholar 

  159. A.M. Vijesh, A.M. Isloor, S. Telkar, S.K. Peethambar, S. Rai, N. Isloor, Eur. J. Med. Chem. 46, 3531 (2011)

    Article  CAS  PubMed  Google Scholar 

  160. J. Wu, Q. Shi, Z. Chen, M. He, L. Jin, D. Hu, Molecules 17, 5139 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  161. R. Alam, D. Wahi, R. Singh, D. Sinha, V. Tandon, A. Grover, Bioorgan. Chem. 69, 77 (2016)

    Article  CAS  Google Scholar 

  162. J.B. Shi, W.J. Tang, R. Li, X.H. Liu, Eur. J. Med. Chem. 90, 889 (2015)

    Article  CAS  PubMed  Google Scholar 

  163. S.A. Galal, A.S. Abdelsamie, S.A. Shouman, Y.M. Attia, H.I. Ali, A. Tabll, R. El-Shenawye, Y.S. El Abd, M.M. Ali, A.E. Mahmoud, Eur. J. Med. Chem. 134, 392 (2017)

    Article  CAS  PubMed  Google Scholar 

  164. B.L. Plassman, K.M. Langa, G.G. Fisher, S.G. Heeringa, D.R. Weir, Neuroepidemiology 29, 125 (2007)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  165. A. Ott, M.M. Breteler, F. van Harskamp, J.J. Claus, T.J. van der Cammen, BMJ 310, 970 (1995)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  166. H.W. Querfurth, F.M. LaFerla, N. Engl. J. Med. 362, 329 (2010)

    Article  CAS  PubMed  Google Scholar 

  167. Y.T. Han, K. Kim, G.I. Choi, H. An, D. Son, H. Kim, H.J. Ha, J.H. Son, S.J. Chung, H.J. Park, Eur. J. Med. Chem. 79, 128 (2014)

    Article  CAS  PubMed  Google Scholar 

  168. A. Hetzhein, K. Mockel, Adv. Heterocycl. Chem. 7, 183 (1996)

    Article  Google Scholar 

  169. J. Sandstrom, Adv. Heterocycl. Chem. 9, 165 (1968)

    Article  CAS  PubMed  Google Scholar 

  170. B. Namratha, L. Santosh, Gaonkar, Int. J. Pharm. Pharm. Sci. 6, 73 (2014)

    CAS  Google Scholar 

  171. R.M. Balabin, J. Chem. Phys. 131, 1 (2009)

    Google Scholar 

  172. S.M.H. Al-Majidi, Z.S. Saeed, J. Al-Nahrain Univ. 16, 59 (2013)

    Article  Google Scholar 

  173. D. Prasad, N. Aggarwal, R. Kumar, M. Nath, J. Chem. 51B, 731 (2012)

    CAS  Google Scholar 

  174. S.G. Agalave, S.R. Maujan, V.S. Pore, Chem. Asian J. 6, 2696 (2011)

    Article  CAS  PubMed  Google Scholar 

  175. J.K. Sahu, S. Ganguly, A. Kaushik, J. Appl. Pharm. Sci. 4, 81 (2014)

    Article  CAS  Google Scholar 

  176. R.G. Lima-Neto, N.N.M. Cavalcante, R.M. Srivastava, F.J.B. Mendonça, A.G. Wanderley, R.P. Neves, J.V.D. Anjos, Molecules 17, 5882 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  177. C.M. Jamkhandi, J.I. Disouza, J. Pharm. Pharm. Sci. 5, 249 (2013)

    CAS  Google Scholar 

  178. V. Patil, W. Guerrant, P.C. Chen, B. Gryder, D.B. Benicewicz, S.I. Khan, B.L. Tekwani, A.K. Oyelere, Med. Chem. 18, 415 (2010)

    CAS  Google Scholar 

  179. R.C. Corrales, N.B. de Souza, L.S. Pinheiro, S. Abramo, E.S. Coimbra, A.D. Da Silva, Biomed. Pharmacother. 65, 198 (2011)

    Article  CAS  PubMed  Google Scholar 

  180. O.A. Naif, J. Al-Nahrain Univ. 15, 1 (2012)

    Google Scholar 

  181. Z.A.K. Al-Messri, Um-Salama Sci. J. 6, 200 (2009)

    Google Scholar 

  182. A. Mobinikhaledi, N. Foroughifar, M. Khanpour, S. Ebrahimi, Eur. J. Chem. 1, 33 (2010)

    Article  CAS  Google Scholar 

  183. A.M. Al-Azzawi, K.K. Hammud, Iraqi J. Sci. 54, 782 (2013)

    Google Scholar 

  184. A.M.N. Yahya, A.N. MohammadRafidain, J. Sci. 21, 39 (2010)

    Google Scholar 

  185. B.A. Ahmed, S.J. Mohammed, Rafidain. J. Sci. 20, 11 (2009)

    Google Scholar 

  186. H. Yoshioka, H. Sakai, S. Shibayama, Silver Halide Photographic Photosensitive Material and Production Method Thereof (Patent Application Publisher, United States, 2013)

  187. K. Jawad, Shneine, H. Yusra, Alaraji, Int. J. Sci. Res. 5, 1411 (2016)

  188. G. Pellizari, Gazzetta ChimicaItaliana 41, 20 (1911)

    Google Scholar 

  189. S.K. Younis, Rafidain J. Sci. 22, 62 (2011)

    Article  Google Scholar 

  190. R.H. Udupi, S. Bheemachari, N. Srinivasulu, R. Varnekar, Purushottamachar, Bull. Korean Chem. Soc. 28, 2235 (2007)

    Article  CAS  Google Scholar 

  191. D. Li, H. Bao, T. You, Heterocycles 65, 1957 (2005)

    Article  CAS  Google Scholar 

  192. S.I. Nagai, T. Ueda, S. Sugiura, A. Nagatsu, N. Murakami, J. Sakakibara, M. Fujita, Y. Hotta, J. Heterocyl. Chem. 35, 325 (1998)

    Article  CAS  Google Scholar 

  193. S. Pokuri, R.K. Singla, V.G. Bhat, G.G. Shenoy, Curr. Drug Metab. 15, 389 (2014)

    Article  CAS  PubMed  Google Scholar 

  194. E.M. Flefel, W.A. Tantawy, W.A. El-Sayed, H.H. Sayed, N.M. Fathy, J. Heterocycl. Chem. 2, 344 (2013)

    Article  Google Scholar 

  195. R.S. Keri, S.A. Patil, S. Budagumpi, B.M. Nagaraja, 86, 410 (2015) 

  196. S.G. Kucukguzel, P. Cikla-Suzgun, Eur. J. Med. Chem. 97, 830 (2015)

    Article  CAS  PubMed  Google Scholar 

  197. D.R. Godhani, A.A. Jogel, A.M. Sanghani, J.P. Mehta, Indian J. Chem. 54B, 556 (2015)

    CAS  Google Scholar 

  198. R. Tokala, S. Bale, I.P. Janrao, A. Vennela, N.P. Kumar, K.R. Senwar, C. Godugu, N. Shankaraiah, Bioorgan. Med. Chem. Lett. 28, 1919 (2018)

    Article  CAS  Google Scholar 

  199. G. Ayhan-Kilcigil, C. Kuş, T. Coban, B. Can-Eke, S. Ozbey, M. Iscan, J. Enzyme Inhib. Med. Chem. 20, 503 (2005)

  200. E. Thomas, M.G. Ghany, T.J. Liang, Antivir. Chem. Chemother. 23, 1 (2012)

    Article  CAS  PubMed  Google Scholar 

  201. K. Benci, T. Suhina, L. Mandic, S.K. Pavelic, A.T. Paravic, K. Pavelic, J. Balzarini, K. Wittine, M. Mintas, Antivir. Chem. Chemother. 21, 221 (2011)

    Article  CAS  PubMed  Google Scholar 

  202. K.D. Dobbs, J. Feldman, W.J. Marshall, S.J. McLain, J.S. Meth, G.D. Vo, Y. Wang, J. Phys. Chem. 118, 27763 (2014)

    CAS  Google Scholar 

  203. F.A. Hassan, K.W. Younus, Res. J. Biol. Sci. 7, 48 (2012)

    Article  Google Scholar 

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Acknowledgements

Zabiulla thankfully acknowledges the support provided by the Director and management of PG Department, St. Philomena's College (Autonomous), a recognized research center of University of Mysore, Mysore, Karnataka, India. Shaukath Ara Khanum thankfully acknowledges the financial support provided by VGST, Bangalore, under CISEE Programme [Project sanction order: No. VGST/ CISEE /282].

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Authors and Affiliations

  1. PG Department of Studies and Research Centre in Chemistry (A recognized research centre of University of Mysore), St. Philomena’s College Bannimantap, Mysuru, Karnataka, India

    Zabiulla & Asha M. S

  2. Department of Biochemistry, Faculty of Education and Science, Al-Baydha University, Al-Baydha, Yemen

    Fares Hezam Al-Ostoot

  3. Department of Chemistry, Yuvaraja’s College (Autonomous), University of Mysore, Mysore, Karnataka, India

    Fares Hezam Al-Ostoot & Shaukath Ara Khanum

  4. Department of Chemistry, Faculty of Science, Thamar University, Thamar, Yemen

    Mohammed Al-Ghorbani

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Zabiulla, Al-Ostoot, F.H., S, A.M. et al. Recent investigation on heterocycles with one nitrogen [piperidine, pyridine and quinoline], two nitrogen [1,3,4-thiadiazole and pyrazole] and three nitrogen [1,2,4-triazole]: a review. J IRAN CHEM SOC 19, 23–54 (2022). https://doi.org/10.1007/s13738-021-02293-x

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