Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules

Mohsin, Noor Ul Amin; AHMAD, MATLOOB

doi:10.3906/kim-1709-4

Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules

Noor-ul-Amin MOHSIN, (Government College University, Faculty of Pharmaceutical Sciences, Faisalabad, Pakistan)

Matloob AHMAD (Government College University, Department of Chemistry, Faisalabad, Pakistan)

Turkish Journal of Chemistry

4 0

Yıl: 2018 Cilt: 42 Sayı: 5 Sayfa Aralığı: 1191 - 1216 Metin Dili: İngilizce DOI: 10.3906/kim-1709-4 İndeks Tarihi: 23-10-2020

Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules

Öz:

The tetrahydropyridine (THP) ring system has received considerable focus due to its excellent ability to actas a pharmacophore. It is recognized as a major constituent in natural alkaloids. THP derivatives have been reportedfor a diverse range of biological activities. Recent synthetic works contain syntheses of monosubstituted, disubstituted,trisubstituted, highly functionalized, and condensed structures. In this review, we summarize the recent literature dealingwith the bioactive nature of this important heterocycle.

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Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

1. Arora, P.; Arora, V.; Lamba, H.; Wadhwa, D. Int. J. Pharm. Sci. Res. 2012, 3, 2947.
2. Chen, J.; Cantrell, C. L.; Shang, H. W.; Rojas, M. G. J. Agric. Food. Chem. 2009, 57, 3128-3133.
3. Kusano, G.; Takahashi, A.; Sugiyama, K.; Nozoe, S. Chem. Pharm. Bull. 1987, 35, 4862-4867.
4. Yang, Y. R.; Chang, K. C.; Chen, C. L.; Chiu, T. H. Chin. J. Physiol. 2000, 43, 23-28.
5. Christie, J. E.; Shering, A.; Ferguson, J.; Glen, A. I. Br. J. Psychiatry 1981, 138, 46-50.
6. Harmer, R. Food Chem. 1980, 5, 81-90.
7. Davis, G. C.; Williams, A. C.; Markey, S. P.; Ebert, M. H.; Caine, E. D.; Reichert, C. M.; Kopin, I. J. Psychiat. Res. 1979, 1, 249-254.
8. Gessner, W.; Brossi, A.; Shen, R. S.; Abell, C. W. J. Med. Chem. 1985, 28, 311-317.
9. Domino, K. B.; Anderson, E. A.; Polissar, N. L.; Posner, K. L. Anesth. Analg. 1999, 88, 1370-1379.
10. Mashkovskii, M.; Glushkov, R. Pharm. Chem. J. 2001, 35, 179-182.
11. Gangapuram, M.; Redda, K. K. J. Heterocycl. Chem. 2006, 43, 709-718.
12. Rao, K. N.; Redda, K. K.; Onayemi, F. Y.; Melles, H.; Choi, J. J. Heterocycl. Chem. 1995, 32, 307-315.
13. Goldmann, S.; Stoltefuss, J. Angew. Chem. Int. Ed. 1991, 30, 1559-1578.
14. Zhou, Y.; Gregor, V. E.; Ayida, B. K.; Winters, G. C.; Sun, Z.; Murphy, D.; Haley, G.; Bailey, D.; Froelich, J. M.; Fish, S. Bioorg. Med. Chem. Lett. 2007, 17, 1206-1210.
15. Dai, L.; Jacob, M. R.; Khan, S. I.; Khan, I. A.; Clark, A. M.; Li, X. C. J. Nat. Prod. 2011, 74, 2023-2026.
16. Prachayasittikul, S.; Worachartcheewan, A.; Lawung, R.; Ruchirawat, S.; Prachayasittikul, V. EXCLI J. 2009, 8, 107-114.
17. León, L. G.; Carballo, R. M.; Vega-Hernández, M. C.; Martín, V. S.; Padrón, J. I.; Padrón, J. M. Bioorg. Med. Chem. Lett. 2007, 17, 2681-2684.
18. Gizur, T.; Kiss, B.; Harsányi, K.; Kárpáti, E.; Pálosi, É.; Gere, A.; Lapis, E.; Laszlovszky, I.; Szabó, S.; Szporny, L. Eur. J. Med. Chem. 1994, 29, 349-355.
19. Messer, W. S.; Abuh, Y. F.; Liu, Y.; Periyasamy, S.; Ngur, D. O.; Edgar, M. A. N.; El-Assadi, A. A.; Sbeih; Dunbar, P. G.; Roknich, S. et al. J. Med. Chem. 1997, 40, 1230-1246.
20. Redda, K.; Corleto, L. A.; Knaus, E. E. J. Med. Chem. 1979, 22, 1079-1082.
21. Rao, K. N.; Redda, K. K.; Onayemi, F. Y.; Melles, H.; Choi, J. J. Heterocycl. Chem. 1995, 32, 307-315.
22. Redda, K. K.; Rao, K. N.; Heiman, A. S.; Onayemi, F. Y.; Clark, J. B. Chem. Pharm. Bull. 1991, 39, 786-791.
23. Mateeva, N.; Winfield, L.; Redda, K. Curr. Med. Chem. 2005, 12, 551-571.
24. Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Elsevier: Amsterdam, the Netherlands, 2012.
25. Ganem, B. Acc. Chem. Res. 2009, 42, 463-472.
26. Barry, B. Chem. Rev. 2009, 109, 4439-4486.
27. Han, R. G.; Wang, Y.; Li, Y. Y.; Xu, P. F. Adv. Synth. Catal. 2008, 350, 1474-1478.
28. Lee, H. S.; Kim, E. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2009, 50, 2274-2277.
29. Takizawa, S.; Inoue, N.; Sasai, H. Tetrahedron Lett. 2011, 52, 377-380.
30. Blumel, M.; Chauhan, P.; Hahn, R.; Raabe, G.; Enders, D. Org. Lett. 2014, 16, 6012-6015.
31. Aridoss, G.; Amirthaganesan, S.; Ashok Kumar, N.; Kim, J. T.; Lim, K. T.; Kabilan, S.; Jeong, Y. T. Bioorg. Med. Chem. Lett. 2008, 18, 6542-6548.
32. Aridoss, G.; Amirthaganesan, S.; Jeong, Y. T. Bioorg. Med. Chem. Lett. 2010, 20, 2242-2249.
33. Raju, S. K.; Stephen, M. R.; Subbu, P.; Debjani, B.; Perumal, Y.; Dharmarajan, S. Chem. Pharm. Bull. 2010, 58, 602-610.
34. Yankin, A.; Nosova, N.; Gein, V.; Tomilov, M. Russ. J. Gen. Chem. 2015, 85, 844-850.
35. Srivastava, B. K.; Solanki, M.; Mishra, B.; Soni, R.; Jayadev, S.; Valani, D.; Jain, M.; Patel, P. R. Bioorg. Med. Chem. Lett. 2007, 17, 1924-1929.
36. Lohray, B. B.; Lohray, V. B.; Srivastava, B. K.; Kapadnis, P. B.; Pandya, P. Biorg. Med. Chem. 2004, 12, 4557-4564.
37. Anusevičius, K.; Mickevičius, V.; Belyakov, S.; Šiugždaitė, J.; Kantminienė, K. Monats. Chem. 2014, 145, 1611- 1620.
38. Prachayasittikul, S.; Pingaew, R.; Worachartcheewan, A.; Ruchirawat, S.; Prachayasittikul, V. EXCLI J 2010, 9, 102-107.
39. Brown, B. S.; Keddy, R.; Zheng, G. Z.; Schmidt, R. G.; Koenig, J. R.; McDonald, H. A.; Bianchi, B. R.; Honore, P.; Jarvis, M. F.; Surowy, C. S. et al. Biorg. Med. Chem. 2008, 16, 8516-8525.
40. Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P. W.; Docter, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M. et al. J. Med. Chem. 1997, 40, 1347-1365.
41. Chowdhury, M. A.; Abdellatif, K. R. A.; Dong, Y.; Knaus, E. E. Biorg. Med. Chem. 2008, 16, 8882-8888.
42. Wu, W.; Li, Z.; Yang, G.; Teng, M.; Qin, J.; Hu, Z.; Hou, L.; Shen, L.; Dong, H.; Zhang, Y. et al. Bioorg. Med. Chem. Lett. 2017, 27, 2210-2215.
43. Choi, K. H. Expert. Opin. Drug. Dis. 2013, 8, 919-931.
44. Perez-Reyes, E. Physiol. Rev. 2003, 83, 117-161.
45. Lee, J. H.; Seo, S. H.; Lim, E. J.; Cho, N. C.; Nam, G.; Kang, S. B.; Pae, A. N.; Jeong, N.; Keum, G. Eur. J. Med. Chem. 2014, 74, 246-257.
46. Mochona, B.; Redda, K. K. J. Heterocycl. Chem. 2007, 44, 1383-1387.
47. Fujita, M.; Seki, T.; Ikeda, N. Bioorg. Med. Chem. Lett. 2002, 12, 1897-1900.
48. Gangapuram, M.; Mazzio, E.; Eyunni, S.; Soliman, K. F. A.; Redda, K. K. Arch. Pharm. 2014, 347, 360-369.
49. Yoon, K. J. P.; Kode, B.; Bowen, L.; Redda, K. K. J. Heterocycl. Chem. 2001, 38, 69-76.
50. Yoon, K. J. P.; Redda, K. K.; Mazzio, E.; Soliman, K. F. A. Drug Dev. Res. 2004, 61, 189-196.
51. Nakao, A.; Ohkawa, N.; Nagasaki, T.; Kagari, T.; Doi, H.; Shimozato, T.; Ushiyama, S.; Aoki, K. Bioorg. Med. Chem. Lett. 2009, 19, 4607-4610.
52. Nakao, A.; Ohkawa, N.; Nagasaki, T.; Kagari, T.; Doi, H.; Shimozato, T.; Ushiyama, S.; Aoki, K. Bioorg. Med. Chem. Lett. 2010, 20, 2435-2437.
53. Nakao, A.; Ohkawa, N.; Nagasaki, T.; Kagari, T.; Doi, H.; Shimozato, T.; Ushiyama, S.; Aoki, K. Bioorg. Med. Chem. Lett. 2010, 20, 4774-4778.
54. Gwaltney, S. L.; O’Connor, S. J.; Nelson, L. T.; Sullivan, G. M.; Imade, H.; Wang, W.; Hasvold, L.; Li, Q.; Cohen, J.; Gu, W. Z. Bioorg. Med. Chem. Lett. 2003, 13, 1359-1362.
55. Bell, I. M. Expert. Opin. Ther. Pat. 2000, 10, 1813-1831.
56. Aeluri, R.; Alla, M.; Bommena, V. R.; Murthy, R.; Jain, N. Asian J. Org. Chem. 2012, 1, 71-79.
57. Romagnoli, R.; Baraldi, P. G.; Carrion, M. D.; Cruz-Lopez, O.; Cara, C. L.; Tolomeo, M.; Grimaudo, S.; Di Cristina, A.; Pipitone, M. R.; Balzarini, J. et al. Bioorg. Med. Chem. Lett. 2008, 18, 5041-5045.
58. Narva, S.; Chitti, S.; Amaroju, S.; Bhattacharjee, D.; Rao, B. B.; Jain, N.; Alvala, M.; Sekhar, K. V. G. C. Bioorg. Med. Chem. Lett. 2017, 27, 3794-3801.
59. Lukevics, E.; Jansone, D.; Leite, L.; Popelis, J.; Andreeva, G.; Shestakova, I.; Domracheva, I.; Bridane, V.; Kanepe, I. Chem. Heterocycl. Comp. 2009, 45, 1226-1234.
60. Kamei, K.; Maeda, N.; Ogino, R.; Koyama, M.; Nakajima, M.; Tatsuoka, T.; Ohno, T.; Inoue, T. Bioorg. Med. Chem. Lett. 2001, 11, 595-598.
61. Kamei, K.; Maeda, N.; Katsuragi-Ogino, R.; Koyama, M.; Nakajima, M.; Tatsuoka, T.; Ohno, T.; Inoue, T. Bioorg. Med. Chem. Lett. 2005, 15, 2990-2993.
62. Conway, R. J.; Valant, C.; Christopoulos, A.; Robertson, A. D.; Capuano, B.; Crosby, I. T. Bioorg. Med. Chem. Lett. 2012, 22, 2560-2564.
63. Kikuchi, C.; Hiranuma, T.; Koyama, M. Bioorg. Med. Chem. Lett. 2002, 12, 2549-2552.
64. Graulich, A.; Léonard, M.; Résimont, M.; Huang, X. P.; Roth, B. L.; Liégeois, J. F. Aust. J. Chem. 2010, 63, 56-67.
65. Liegeois, J. F.; Lespagnard, M.; Meneses Salas, E.; Mangin, F.; Scuvee-Moreau, J.; Dilly, S. ACS Med. Chem. Lett. 2014, 5, 358-362.
66. Dilly, S.; Graulich, A.; Liégeois, J. F. Bioorg. Med. Chem. Lett. 2010, 20, 1118-1123.
67. Rajeswaran, W. G.; Cao, Y.; Huang, X. P.; Wroblewski, M. E.; Colclough, T.; Lee, S.; Liu, F.; Nagy, P. I.; Ellis, J.; Levine, B. A. et al. J. Med. Chem. 2001, 44, 4563-4576.
68. Cao, Y.; Zhang, M.; Wu, C.; Lee, S.; Wroblewski, M. E.; Whipple, T.; Nagy, P. I.; Takács-Novák, K.; Balázs, A.; Tőrös, S. et al. J. Med. Chem. 2003, 46, 4273-4286.
69. Tejada, F. R.; Nagy, P. I.; Xu, M.; Wu, C.; Katz, T.; Dorsey, J.; Rieman, M.; Lawlor, E.; Warrier, M.; Messer, W. S., Jr. J. Med. Chem. 2006, 49, 7518-7531.
70. Kiesewetter, D. O.; Jagoda, E. M.; Shimoji, K.; Ma, Y.; Eckelman, W. C. Nuclear Med. Biol. 2007, 34, 141-152.
71. van Oosten, E. M.; Wilson, A. A.; Mamo, D. C.; Pollock, B. G.; Mulsant, B. H.; Houle, S.; Vasdev, N. Can. J. Chem. 2010, 88, 1222-1232.
72. Sadashiva, C. T.; Chandra, J. N.; Kavitha, C. V.; Thimmegowda, A.; Subhash, M. N.; Rangappa, K. S. Eur. J. Med. Chem. 2009, 44, 4848-4854.
73. Anagnostaras, S. G.; Murphy, G. G.; Hamilton, S. E.; Mitchell, S. L.; Rahnama, N. P.; Nathanson, N. M.; Silva, A. J. Nat. Neurosci. 2003, 6, 51-58.
74. Zheng, G.; Smith, A. M.; Huang, X.; Subramanian, K. L.; Siripurapu, K. B.; Deaciuc, A.; Zhan, C. G.; Dwoskin, L. P. J. Med. Chem. 2013, 56, 1693-1703.
75. Misra, M.; Pandey, S. K.; Pandey, V. P.; Pandey, J.; Tripathi, R.; Tripathi, R. P. Biorg. Med. Chem. 2009, 17, 625-633.
76. Ramin, G. V.; Hajar, S. C. R. Chimie 2013, 16, 1047-1054.
77. Naranjo-Montoya, O. A.; Martins, L. M.; Silva-Filho, L. C. D.; Batagin-Neto, A.; Lavarda, F. C. J. Braz. Chem. Soc. 2015, 26, 255-265.
78. Nakazato, A.; Kumagai, T.; Okubo, T.; Tanaka, H.; Chaki, S.; Okuyama, S.; Tomisawa, K. Bioorg. Med. Chem. 2000, 8, 1183-1193.
79. Kumagai, T.; Okubo, T.; Kataoka-Okubo, H.; Chaki, S.; Okuyama, S.; Nakazato, A. Biorg. Med. Chem. 2001, 9, 1349-1355.
80. Krauze, A.; Vītolia, R.; Garaliene, V.; Sīle, L.; Kluša, V.; Duburs, G. Eur. J. Med. Chem. 2005, 40, 1163-1167.
81. Kálai, T.; Várbiró, G.; Bognár, Z.; Pálfi, A.; Hantó, K.; Bognár, B.; Ősz, E.; Sümegi, B.; Hideg, K. Biorg. Med. Chem. 2005, 13, 2629-2636.
82. Nguewa, P. A.; Fuertes, M. A.; Alonso, C.; Peréz, J. M. Mol. Pharmacol. 2003, 64, 1007.
83. Ishida, J.; Hattori, K.; Yamamoto, H.; Iwashita, A.; Mihara, K.; Matsuoka, N. Bioorg. Med. Chem. Lett. 2005, 15, 4221-4225.
84. Kálai, T.; Balog, M.; Szabó, A.; Gulyás, G.; Jekő, J.; Sümegi, B.; Hideg, K. J. Med. Chem. 2009, 52, 1619-1629.
85. Liu, Y. Q.; Yang, L.; Zhao, Y. L.; Li, H. Y. Pestic. Biochem. Physiol. 2010, 98, 219-223.
86. Tian, Z.; Shao, X.; Li, Z.; Qian, X.; Huang, Q. J. Agric. Food. Chem. 2007, 55, 2288-2292.
87. Zhang, W.; Chen, Y.; Chen, W.; Liu, Z.; Li, Z. J. Agric. Food. Chem. 2010, 58, 6296-6299.
88. Olesen, P. H.; Swedberg, M. D. B.; Rimvall, K. Biorg. Med. Chem. 1998, 6, 1623-1629.
89. Prasad, S. B. B.; Kumar, Y. C. S.; Kumar, C. S. A.; Sadashiva, C. T.; Vinaya, K.; Rangappa, K. S. Open Med. Chem. J. 2007, 1, 4-10.
90. Wichitnithad, W.; O’Callaghan, J. P.; Miller, D. B.; Train, B. C.; Callery, P. S. Bioorg. Med. Chem. 2011, 19, 7482-7492.
91. Borbe, H.; Niebch, G.; Nickel, B. In Proceedings of the 4th International Amine Oxidases Workshop; Würzburg, Germany; 1990. Springer Link: Berlin, Germany, 1990, pp. 131-137.
92. Flaherty, P.; Castagnoli, K.; Wang, Y. X.; Castagnoli, N., Jr. J. Med. Chem. 1996, 39, 4756-4761.
93. Das, D. K.; Sarkar, S.; Khan, A. T.; Saravanan, P.; Patra, S. RSC Adv. 2014, 4, 3581-3590.
94. Löber, S.; Hübner, H.; Gmeiner, P. Bioorg. Med. Chem. Lett. 2006, 16, 2955-2959.
95. Ramachandran, P. V.; Burghardt, T. E.; Bland-Berry, L. J. Org. Chem. 2005, 70, 7911-7918.
96. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
97. Krishna, P. R.; Reddy, P. S. J. Comb. Chem. 2008, 10, 426-435.
98. Heja, L.; Kovacs, I.; Szarics, E.; Incze, M.; Temesvarine-Major, E.; Dornyei, G.; Peredy-Kajtar, M.; Gacs-Baitz, E.; Szantay, C.; Kardos, J. J. Med. Chem. 2004, 47, 5620-5629.
99. Deskus, J. A.; Epperson, J. R.; Sloan, C. P.; Cipollina, J. A.; Dextraze, P.; Qian-Cutrone, J.; Gao, Q.; Ma, B.; Beno, B. R.; Mattson, G. K. et al. Bioorg. Med. Chem. Lett. 2007, 17, 3099-3104.
100. Zheng, Y. Y.; Weng, Z. J.; Xie, P.; Zhu, M. Y.; Xing, L. X.; Li, J. Q. Eur. J. Med. Chem. 2014, 86, 219-234.
101. Ito, S.; Satoh, A.; Nagatomi, Y.; Hirata, Y.; Suzuki, G.; Kimura, T.; Satow, A.; Maehara, S.; Hikichi, H.; Hata, M. et al. Bioorg. Med. Chem. 2008, 16, 9817-9829.
102. Mohammadi, A. A.; Taheri, S.; Amouzegar, A.; Ahdenov, R.; Halvagar, M. R.; Sadr, A. S. J. Mol. Struct. 2017, 1139, 166-174.
103. Ravindernath, A.; Reddy, M. S. Arab. J. Chem. 2017, 10 (Suppl. 1), S1172-S1179.
104. Soldatenkov, A. T.; Levov, A. N.; Mamyrbekova, Z. A.; Kolyadina, N. M.; Mobio, I. G.; Naumov, Y. I.; Komarova, A. I.; An, L. T. Pharm. Chem. J. 2004, 38, 361-363.
105. Long, S.; Stefani, F. R.; Biondi, S.; Ghiselli, G.; Panunzio, M. Bioorg. Med. Chem. 2013, 21, 5811-5822.
106. Dai, L.; Jacob, M. R.; Khan, S. I.; Khan, I. A.; Clark, A. M.; Li, X. C. J. Nat. Prod. 2011, 74, 2023-2026.
107. Marastoni, M.; McDonald, J.; Baldisserotto, A.; Canella, A.; De Risi, C.; Pollini, G. P.; Tomatis, R. Bioorg. Med. Chem. Lett. 2004, 14, 1965-1968.
108. Watanabe, R.; Mizoguchi, H.; Oikawa, H.; Ohashi, H.; Watashi, K.; Oguri, H. Bioorg. Med. Chem. 2017, 25, 2851-2855.
109. Kim, E.; Park, C. S.; Han, T.; Bae, M. H.; Chong, W.; Lee, C. H.; Shin, Y. A.; Ahn, B. N.; Kim, M. K.; Shin, C. Y. et al. Bioorg. Med. Chem. Lett. 2008, 18, 4993-4996.
110. Remeň, L. U.; Bezençon, O.; Richard-Bildstein, S.; Bur, D.; Prade, L.; Corminboeuf, O.; Boss, C.; Grisostomi, C.; Sifferlen, T.; Strickner, P. et al. Bioorg. Med. Chem. Lett. 2009, 19, 6762-6765.
111. Takai, T.; Hoashi, Y.; Tomata, Y.; Morimoto, S.; Nakamura, M.; Watanabe, T.; Igari, T.; Koike, T. Bioorg. Med. Chem. Lett. 2015, 25, 4245-4249.
112. Bringmann, G.; Feineis, D.; God, R.; Peters, K.; Peters, E. M.; Scholz, J.; Riederer, F.; Moser, A. Bioorg. Med. Chem. 2002, 10, 2207-2214.
113. Brisbare-Roch, C.; Dingemanse, J.; Koberstein, R.; Hoever, P.; Aissaoui, H.; Flores, S.; Mueller, C.; Nayler, O.; van Gerven, J.; de Haas, S. L. et al. Nat. Med. 2007, 13, 150-155.
114. Sifferlen, T.; Boss, C.; Cottreel, E.; Koberstein, R.; Gude, M.; Aissaoui, H.; Weller, T.; Gatfield, J.; Brisbare-Roch, C.; Jenck, F. Bioorg. Med. Chem. Lett. 2010, 20, 1539-1542.

APA	Mohsin N, AHMAD M (2018). Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules. , 1191 - 1216. 10.3906/kim-1709-4
Chicago	Mohsin Noor Ul Amin,AHMAD MATLOOB Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules. (2018): 1191 - 1216. 10.3906/kim-1709-4
MLA	Mohsin Noor Ul Amin,AHMAD MATLOOB Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules. , 2018, ss.1191 - 1216. 10.3906/kim-1709-4
AMA	Mohsin N,AHMAD M Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules. . 2018; 1191 - 1216. 10.3906/kim-1709-4
Vancouver	Mohsin N,AHMAD M Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules. . 2018; 1191 - 1216. 10.3906/kim-1709-4
IEEE	Mohsin N,AHMAD M "Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules." , ss.1191 - 1216, 2018. 10.3906/kim-1709-4
ISNAD	Mohsin, Noor Ul Amin - AHMAD, MATLOOB. "Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules". (2018), 1191-1216. https://doi.org/10.3906/kim-1709-4

APA	Mohsin N, AHMAD M (2018). Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules. Turkish Journal of Chemistry, 42(5), 1191 - 1216. 10.3906/kim-1709-4
Chicago	Mohsin Noor Ul Amin,AHMAD MATLOOB Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules. Turkish Journal of Chemistry 42, no.5 (2018): 1191 - 1216. 10.3906/kim-1709-4
MLA	Mohsin Noor Ul Amin,AHMAD MATLOOB Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules. Turkish Journal of Chemistry, vol.42, no.5, 2018, ss.1191 - 1216. 10.3906/kim-1709-4
AMA	Mohsin N,AHMAD M Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules. Turkish Journal of Chemistry. 2018; 42(5): 1191 - 1216. 10.3906/kim-1709-4
Vancouver	Mohsin N,AHMAD M Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules. Turkish Journal of Chemistry. 2018; 42(5): 1191 - 1216. 10.3906/kim-1709-4
IEEE	Mohsin N,AHMAD M "Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules." Turkish Journal of Chemistry, 42, ss.1191 - 1216, 2018. 10.3906/kim-1709-4
ISNAD	Mohsin, Noor Ul Amin - AHMAD, MATLOOB. "Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules". Turkish Journal of Chemistry 42/5 (2018), 1191-1216. https://doi.org/10.3906/kim-1709-4