Citation: Su Shimiao, Zhu Mo, Zhang Daqiang, Yuan Dekai. Synthesis and Biological Activity Study of Novel Cyano-containing Multi-substituted Pyrazoles Obtained via Strecker Reaction[J]. Chinese Journal of Organic Chemistry, ;2019, 39(7): 2026-2034. doi: 10.6023/cjoc201812019 shu

Synthesis and Biological Activity Study of Novel Cyano-containing Multi-substituted Pyrazoles Obtained via Strecker Reaction

Su Shimiao ^a ,
Zhu Mo ^b ,
Zhang Daqiang ^a ,
Yuan Dekai ^a,,

a.
Department of Applied Chemistry, Science College, China Agricultural University, Beijing 100193
b.
Department of Chemistry, Capital Normal University, Beijing 100048

Corresponding author: Yuan Dekai, yuandekai@cau.edu.cn; yuandekai@aliyun.com
Received Date: 11 December 2018
Revised Date: 28 February 2019
Available Online: 21 July 2019
Fund Project: Project supported by the National Natural Science Foundation of China (No. 20902107)the National Natural Science Foundation of China 20902107

In order to study the Strecker reaction of multi-substituted amino armorotic heterocycles and the biological activity of the target compounds, the reaction of 3, 5-disubstituted pyrazole-4-amine, TMSCN and aldehydes was realized for the first time by the catalysis of anhydrous ZnI₂ with 4 molecular seive. The reaction condition was preliminarily optimized and the substrate scop of aldehydes was studied. 20 target compounds of cyano-containing multi-substituted pyrazoles were obtained with the highest yield of 93.5%, and the sturctures of the compounds were confirmed via ¹H NMR, ¹³C NMR and HRMS methods. Priliminary bioassay of the target compounds showed that 13 target compounds possessed 100% larvicidal activity against mosquito at a concentration of 10×10^-3 g/L, and four compounds possessed over 40% larvicidal activity at 5×10^-3 g/L, and 10 compounds poccessed weak larvicidal activity against army worm at 500×10^-3 g/L with the highest activity of 40%; five compounds were confirmed poccessed good inactivation activity against tobacco mosaic virus (TMV) in vivo with the highest inhibition rate of 31.8%, and four compounds possessed moderate host-protection activity against TMV in vivo with the highest rate of 28.3%; in addition, at a concentration of 50×10^-3 g/L, three compounds showed moderate fungicidal activity against Pythium aphanidermatum, Phomopsis asparagi, Phytophora capsic and Rhizoctonia solani in vitro. 4-((1-cyanododecyl)amino)-5-ethyl-N-methyl-1H-pyrazole-3-carboxamide (3t) possessed the highest activity against Phytophora capsic of 62.3%. All the results showed that 3, 5-disubstitued pyrazole-4-amine could undergo Strecker reaction smoothly, and this study gave a useful example to explore the Strecker reaction of other multi-substituted aromatic hetreocyclic amines. Additionally, the larvicidal and anti-TMV activity of the target compounds gave some clues in design cyano-containing biological heterocycles.
- multi-substituted pyrazole-4-amine,
- Strecker reaction,
- anhydrous ZnI₂,
- cyano-containing pyrazoles,
- larvicidal activity,
- anti-TMV activity,
- fungicidal activity
1. [1]
  (a) Strecker, D. Ann. Chem. Pharm. 1850, 75, 27.
  (b) Kouznetsov, V. V.; Galvis, C. E. P. Tetrahedron 2018, 74, 773.
2. [2]
  (a) de Bruin, G.; Mock, E. D.; Hoogendoorn, S.; van den Nieuwendijk, A. M. C. H.; Mazurek, J.; van der Marel, G. A.; Florea, B. I.; Overkleeft, H. S. Chem. Commun. 2016, 52, 4064.
  (b) Hirata, T.; Ueda, A.; Oba, M.; Doi, M.; Demizu, Y.; Kurihara, M.; Nagano, M.; Suemune, H.; Tanaka, M. Tetrahedron 2015, 71, 2409.
3. [3]
  (a) Song, R. Z.; Han, Z. M.; He, Q. Q.; Fan, R. H. Org. Lett. 2016, 18, 5328.
  (b) Tay, G. C.; Sizemore, N.; Rychnovsky, S. D. Org. Lett. 2016, 18, 3050.
  (c) Guchhait, S. K.; Priyadarshani, G.; Gulghane, N. M. RSC Adv. 2016, 6, 56056.
  (d) Afraj, S. N.; Chen, C. P.; Lee, G. H. RSC Adv. 2016, 6, 29783.
4. [4]
  (a) Yashin, N. V.; Averina, E. B.; Sedenkova, K. N.; Kuznetsova, T. S.; Zefirov, N. S. Russ. Chem. Bull. 2013, 62, 928.
  (b) Acena, J. L.; Sorochinsky, A. E.; Soloshonok, V. A. Synthesis 2012, 44, 1591.
5. [5]
  (a) Malins, L. R.; deGruyter, J. N.; Robbins, K. J.; Scola, P. M.; Eastgate, M. D.; Ghadiri, M. R.; Baran, P. S. J. Am. Chem. Soc. 2017, 139, 5233.
  (b) Xing, J. H.; Brooks, A. F.; Fink, D.; Zhang, H. B.; Piert, M. R.; Scott, P. J. H.; Shao, X. Synlett 2017, 28, 371.
  (c) Cai, H. C.; Mangner, T. J.; Muzik, O.; Wang, M. W.; Chugani, D. C.; Chugani, H. T. ACS Med. Chem. Lett. 2014, 5, 1152.
  (d) Kokhan, S. O.; Tymtsunik, A. V.; Grage, S. L.; Afonin, S.; Babii, O.; Berditsch, M.; Strizhak, A. V.; Bandak, D.; Platonov, M. O.; Komarov, I. V.; Ulrich, A. S.; Mykhailiuk, P. K. Angew. Chem., Int. Ed. 2016, 55, 14788.
6. [6]
  (a) Katsuhiko, M.; Bilal, A. A.; Christopher, M. S.; Shajila, S.; Michio, K. J. Am. Chem. Soc. 2016, 138, 12975.
  (b) Dhanasekaran, S.; Suneja, A.; Bisai, V.; Singh, V. K. Org. Lett. 2016, 18, 634.
  (c) Chen, C. H.; Genapathy, S.; Fischer, P. M.; Chan, W. C. Org. Biomol. Chem. 2014, 12, 9764.
  (d) Aleiwi, B. A.; Schneider, C. M.; Kurosu, M. J. Org. Chem. 2012, 77, 3859.
7. [7]
  (a) Brahmachari, G.; Kumar, A.; Srivastava, A. K.; Gangwar, S.; Misra, N.; Gupta, V. K.; Rajnikant, R. RSC Adv. 2015, 5, 80967.
  (b) Luis, J. A. S.; De Aquino, T. M.; Lira, B.F.; Filho, P. F. A.; Scotti, M. T.; Scotti, L.; De Moura, R. O.; Mendonca, F. J. Acta Pharm. (Zagreb, Crotia) 2014, 64, 233.
8. [8]
  (a) Carreno Otero, A. L.; Vargas Mendez, L. Y.; Duque L., J. E.; Kouznetsov, V. V. Eur. J. Med. Chem. 2014, 78, 392.
  (b) Yu, X. H.; Wang, G. H.; Kong, X. L.; Huang, H. Y. CN 103183707, 2013[Chem. Abstr. 2013, 159, 229714].
  (c) Lamberth, C.; Dumeunier, R.; Trah, S.; Wendeborn, S.; Godwin, J.; Schneiter, P.; Corran, A. Bioorg. Med. Chem. 2013, 21, 127.
9. [9]
  (a) Parker, E. T.; Zhou, M. S.; Burton, A. S.; Glavin, D. P.; Dworkin, J. P.; Krishnamurthy, R.; Fernandez, F. M.; Bada, J. L. Angew. Chem., Int. Ed. 2014, 53, 8132.
  (b) Bolm, C.; Mocci, R.; Schumacher, C.; Turberg, M.; Puccetti, F.; Hernandez, J. G. Angew. Chem., Int. Ed. 2018, 57, 2423.
  (c) Riffet, V.; Frison, G.; Bouchoux, G. J. Phys. Chem. A 2018, 122, 1643.
10. [10]
  Li, P. C.; Zhang, Y. D.; Chen, Z. L.; Zhang, X. X. Tetrahedron Lett. 2017, 58, 1854. doi: 10.1016/j.tetlet.2017.03.087
11. [11]
  Reddy, V. V. R.; Saritha, B.; Ramu, R.; Varala, R.; Jayashree, A. Asian J. Chem. 2014, 26, 7439.
12. [12]
  Hajipour, A. R.; Dehbane, I. M. Iran. J. Catal. 2012, 2, 147.
13. [13]
  Wang, S. Y.; Xu, J. N.; Zheng, J. F.; Chen, X. D.; Shan, L.; Gao, L. J.; Wang, L.; Yu, M.; Fan, Y. Inorg. Chim. Acta 2015, 437, 81. doi: 10.1016/j.ica.2015.08.012
14. [14]
  (a) Chai, J.; Wang, P. C.; Jia, J.; Ma, B.; Sun, J.; Tao, Y. F.; Zhang, P.; Wang, L.; Fan, Y. Polyhedron 2018, 141, 369.
  (b) Ibanez, S.; Poyatos, M.; Peris, E. Chem. Comm. 2017, 53, 3733.
  (c) Prakash, G. K. S.; Mathew, T.; Panja, C.; Kulkarni, A.; Olah, G. A.; Harmer, M. A. Adv. Synth. Catal. 2012, 354, 2163.
15. [15]
  (a) Saravanan, S.; Khan, N. H.; Jakhar, A.; Ansari, A.; Kureshy, R. I.; Abdi, S. H. R.; Kumar, G. RSC Adv. 2015, 5, 99951.
  (b) Zhu, C.; Xia, J. Bao; Chen, C. Tetrahedron Lett. 2014, 55, 232.
16. [16]
  Costantini, N. V.; Bates, A. D.; Haun, G. J.; Chang, N. M.; Moura- Letts, G. ACS Sustainable Chem. Eng. 2016, 4, 1906. doi: 10.1021/acssuschemeng.6b00241
17. [17]
  Li, N. B.; Wang, J. Y.; Zhang, X. H.; Qiu, R. H.; Wang, X; Chen, J. Y.; Yin, S. F.; Xu, X. H. Dalton Trans. 2014, 43, 11696. doi: 10.1039/C4DT00549J
18. [18]
  Brahmachari, G.; Banerjee, B. Asian J. Org. Chem. 2012, 1, 251. doi: 10.1002/ajoc.201200055
19. [19]
  Zhang, X. L.; Wu, Q. P.; Zhang, Q. S. J. Chem. Res. 2013, 37, 690. doi: 10.3184/174751913X13814077309487
20. [20]
  Ghasemnejad-Bosra, H.; Arta, R. Org. Chem.: Indian J. 2015, 11, 399.
21. [21]
  Huber, R.; Bigler, R.; Mezzetti, A. Organometallics 2015, 34, 3374. doi: 10.1021/acs.organomet.5b00357
22. [22]
  Khalafi-Nezhad, A.; Divar, M.; Panahi, F. J. Org. Chem. 2013, 78, 10902. doi: 10.1021/jo401890g
23. [23]
  Ghafuri, H.; Roshani, M. RSC Adv. 2014, 4, 58280. doi: 10.1039/C4RA11957F
24. [24]
  Nammalwar, B.; Fortenberry, C.; Bunce, R. A. Tetrahedron Lett. 2014, 55, 379. doi: 10.1016/j.tetlet.2013.11.035
25. [25]
  (a) Khazdooz, L.; Zarei, A.; Hajipour, A. R.; Sheikhan, N. Iran. J. Catal. 2012, 2, 63.
  (b) Akbari, J. C. R. Chim. 2012, 15, 471.
26. [26]
  Sengupta, A.; Su, C. L.; Bao, C. L.; Nai, C. T.; Loh, K. P. ChemCatChem 2014, 6, 2507. doi: 10.1002/cctc.201402254
27. [27]
  Zhang, J.; Du, G. F.; Gu, C. Z.; Dai, B. J. Chin. Org. Chem. 2017, 37, 914(in Chinese).
28. [28]
  (a) Chen, W.; Peng, X. W.; Zhong, L. X.; Li, Y.; Sun, R. C. ACS Sustainable Chem. Eng. 2015, 3, 1366.
  (b) Dabral, S.; Turberg, M.; Wanninger, A.; Bolm, C.; Hernandez, J. G. Molecules 2017, 22, 146/1.
29. [29]
  Dekamin, M. G.; Azimoshan, M.; Ramezani, L. Green Chem. 2013, 15, 811. doi: 10.1039/c3gc36901c
30. [30]
  (a) Islami, M.; Dekamin, M. G.; Motlagh, L.; Maleki, A. Green Chem. Lett. Rev. 2018, 11, 36.
  (b) Reinares-Fisac, D.; Aguirre-Diaz, L. M.; Iglesias, M.; Snejko, N.; Gutierrez-Puebla, E.; Monge, M. A.; Gandara, F. J. Am. Chem. Soc. 2016, 138, 9089.
  (c) Xia, J.; Xu, J. N.; Fan, Y.; Song, T. Y.; Wang, L.; Zheng, J. F. Inorg. Chem. 2014, 53, 10024.
  (d) Chen, H.; Ju, J.; Meng, Q. P.; Su, J.; Lin, C.; Zhou, Z.Y.; Li, G. B.; Wang, W. L.; Gao, W. L.; Zeng, C. M.; Tang, C.; Lin, J. H.; Yang, T.; Sun, J. L. J. Am. Chem. Soc. 2015, 137, 7047.
  (e) Wang, W. L.; Wang, Y.; Wu, B.; Cong, R. H.; Gao, W. L.; Qin, B.; Yang, T. Catal. Commun. 2015, 58, 174.
31. [31]
  (a) Azizi, N.; Farhadi, E. Appl. Organomet. Chem. 2018, 32, e4188.
  (b) Arora, P.; Rajput, J. K.; Singh, H. RSC Adv. 2015, 5, 97212.
  (c) Indalkar, K. S.; Khatri, C. K.; Chaturbhuj, G. U. Tetrahedron Lett. 2017, 58, 2144.
  (d) Mobaraki, A.; Movassagh, B.; Karimi, B. ACS Comb. Sci. 2014, 16, 352.
  (e) Gawande, M. B.; Rathi, A. K.; Nogueira, I. D.; Varma, R. S.; Branco, P. S. Green Chem. 2013, 15, 1895.
32. [32]
  (a) Chen, D.; Xu, M. H. J. Org. Chem. 2014, 79, 7746.
  (b) Dekamin, M. G.; Mokhtari, Z. Tetrahedron 2012, 68, 922.
  (c) Yang, K.; Liu, L. J.; Liu, J. T. J. Org. Chem. 2014, 79, 3215.
  (d) Yuan, X. M.; Xu, J.; Liu, Z. J.; Yang, X. J.; Wang, L. M.; Zhang, Y.; Yang, X. Y.; He, X. P.; Liu, J. T. J. Fluorine Chem. 2012, 144, 102.
33. [33]
  Miao, Z. W. In Tools for Stereoselective Synthesis, Eds.: Martin, M.; Boysen, K., Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2013, Chapter 1, pp. 3~26.
34. [34]
  (a) Pellissier, H. Chem. Rev. 2013, 113, 442.
  (b) Sashikanth, S.; Raju, V.; Somaiah, S.; Rao, P. S.; Reddy, K. V. Synthesis 2013, 45, 621.
35. [35]
  Oliveira, M. T.; Lee, J. W. ChemCatChem 2017, 9, 377. doi: 10.1002/cctc.201601441
36. [36]
  (a) Sugiishi, T.; Matsugi, M.; Hamamoto, H.; Amii, H. RSC Adv. 2015, 5, 17269.
  (b) Sadhukhan, A.; Saravanan, S.; Khan, N. H.; Kureshy, R. I.; Abdi, S. H. R.; Bajaj, H. C. J. Org. Chem. 2012, 77, 7076.
  (c) Su, Z. S.; Li, W. Y.; Wang, J.; Hu, C. W.; Feng, X. M. Chem.- Eur. J. 2013, 19, 1637.
  (d) Wang, D.; Liang, J. Y.; Feng, J. C.; Wang, K. R.; Sun, Q. T.; Zhao, L.; Li, D.; Yan, W. J.; Wang, R. Adv. Synth. Catal. 2013, 355, 548.
37. [37]
  (a) Vesely, J.; Rios, R. Chem. Soc. Rev. 2014, 43, 611.
  (b) Liu, Y. L.; Yin, X. P.; Zhou, J. Chin. J. Chem. 2018, 36, 321.
  (c) Iwanejko, J.; Wojaczynska, E. Org. Biomol. Chem. 2018, 16, 7296.
38. [38]
  Yan, H. L.; Oh, J. S.; Lee, J. W.; Song, C. E. Nat. Commun. 2012, 3, 2216/1.
39. [39]
  (a) Kaur, J.; Chimni, S. S. Org. Biomol. Chem. 2018, 16, 3328.
  (b) Wang, H. Y.; Zheng, C.W.; Chai, Z.; Zhang, J. X.; Zhao, G. Nat. Commun. 2016, 7, 12720.
40. [40]
  (a) Karahan, S.; Tanyeli, C. Tetrahedron Lett. 2018, 59, 3725.
  (b) Zhao, B. L.; Li, J. H.; Du, D. M. Chem. Rec. 2017, 17, 1.
41. [41]
  Agnew-Francis, K. A.; Williams, C. M. Adv. Synth. Catal. 2016, 358, 675. doi: 10.1002/adsc.201500949
42. [42]
  Xue, H. S.; Tan, C. H.; Wong, M. W. Can. J. Chem. 2016, 94, 1099. doi: 10.1139/cjc-2016-0307
43. [43]
  Agarwal, J. Org. Biomol. Chem. 2016, 14, 10747. doi: 10.1039/C6OB01462C
44. [44]
  (a) Hatano, M.; Ishihara, K. Asian J. Org. Chem. 2014, 3, 352.
  (b) Ma, J. A.; Zhang, G. W. In Tools for Stereoselective Synthesis, Eds.: Martin, M.; Boysen K., Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2013, Chapter 16, pp. 351~370.
45. [45]
  Hou, Y. L.; Sun, R. W. Y.; Zhou, X. P.; Wang, J. H.; Li, D. Chem. Commun. 2014, 50, 2295. doi: 10.1039/C3CC47996J
46. [46]
  Mendoza, J. H. Q.; Henao, J. A.; Otero, A. L. C.; Kouznetsov, V. V. Powder Diffr. 2016, 31, 149. doi: 10.1017/S0885715616000075
47. [47]
  Martinez-Ariza, G.; Nunez-Rios, J.; Lee, Y. S.; Hulme, C. Tetrahedron Lett. 2015, 56, 1038. doi: 10.1016/j.tetlet.2014.12.127
48. [48]
  Hu, X. C.; Li, R. Z; Li, Z. J. Chem. Res. 2014, 38, 432. doi: 10.3184/174751914X14030207593683
49. [49]
  (a) Hall, R. G.; Edmunds, A.; Jeanguenat, A. WO 2014166795, 2014[Chem. Abstr. 2014, 161, 613546].
  (b) Buysse, A. M.; Niyaz, N. M.; Demeter, D. A.; Zhang, Y.; Walsh, M. J.; Kubota, A.; Hunter, R.; Trullinger, T. K.; Lowe, C. T.; Knueppel, D.; Patny, A.; Garizi, N.; Leplae, P. R. J.; Wessels, F.; Ross, R. J.; Deamicis, C.; Borromeo, P. US 20140213448, 2014[Chem. Abstr. 2014, 161, 275906].
  (c) Dai, H.; Xiao, Y.-S.; Li, Z.; Xu, X.-Y.; Qian, X.-H. Chin. Chem. Lett. 2014, 25, 1014.
50. [50]
51. [51]
52. [52]
  Xu, G. F.; Liu, Y. H.; Yang, X. L.; Wang D. Q.; Yuan, D. K. Chem. J. Chin. Univ. 2016, 37, 486(in Chinese).
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