Design and synthesis of heterocyclic enamine derivatives based on skeleton of neonicotinoids

References

Butera, J. A.; Antane, M. M.; Antane, S. A.; Argentieri, T. M.; Freeden, C.; Graceffa, R. F.; Hirth, B.H.; Jenkins, D.; Lennox, J. R.; Matelan, E. Design and SAR of novel potassium channel openers targeted for urge urinary incontinence. 1. N-cyanoguanidine bioisosteres possessing in vivo bladder selectivity. J. Med. Chem. 2000, 43, 1187–1202.10.1021/jm9905099Suche in Google Scholar PubMed

Cheikh, A. B.; Chuche, J.; Manisse, N.; Pommelet, J. C.; Netsch, K. P.; Lorencak, P.; Wentrup, C. Synthesis of α-cyano carbonyl compounds by flash vacuum thermolysis of (alkylamino)methylene derivatives of meldrum's acid. Evidence for facile 1,3-shifts of alkylamino and alkylthio groups in imidoylketene intermediates. J. Org. Chem. 1991, 56, 970–975.10.1021/jo00003a014Suche in Google Scholar

Jepson, J. E. C.; Brown, L. A.; Sattelle, D. B. The actions of the neonicotinoid imidacloprid on cholinergic neurons of Drosophila melanogaster. Invert. Neurosci. 2006, 6, 33–40.10.1007/s10158-005-0013-8Suche in Google Scholar PubMed

Jeschke, P.; Nauen, R.; Schindler, M.; Elbert, A. Overview of the status and global strategy for noenicotinoids. J. Agric. Food Chem. 2011, 59, 2897–2908.10.1021/jf101303gSuche in Google Scholar PubMed

Kagabu, S.; Moriya, K.; Shibuya, K.; Hattori, Y.; Tsuboi, S.; Shiokawa, K. 1-(6-Halonicotinyl)-2-nitromethylene-imidaz olidines as potential new insecticides. Biosci. Biotech. Biochem. 1992, 56, 362–363.10.1271/bbb.56.362Suche in Google Scholar

Kagabu, S.; Ishihara, R.; Hieda, Y.; Nishimura, K.; Naruse, Y. Insecticidal and neuroblocking potencies of variants of the imidazolidine moiety of imidacloprid-related neonicotinoids and the relationship to partition coefficient and charge density on the pharmacophore. J. Agric. Food Chem. 2007, 55, 812–818.10.1021/jf0623440Suche in Google Scholar PubMed

Moury, D. T. Mucochoric acid. II. Reactions of aldehyde group. J. Am Chem. Soc. 1953, 75, 1909–1912.10.1021/ja01104a038Suche in Google Scholar

Ohno, I.; Tomizawaa, M.; Durkin, K. A.; Casida, J. E.; Kagabu, S. Bis-neonicotinoid insecticides: observed and predicted binding interactions with the nicotinic receptor. Bioorg. Med. Chem. Lett. 2009, 19, 3449–3452.10.1016/j.bmcl.2009.05.016Suche in Google Scholar PubMed

Samaritoni, J. G.; Demeter, D. A.; Gifford, J. M.; Watson, G.B.; Kempe, M.S.; Bruce, T.J. Dihydropiperazine neonicotinoid compounds. Synthesis and insecticidal activity. J. Agric. Food Chem. 2003, 51, 3035–3042.10.1021/jf021185rSuche in Google Scholar PubMed

Shao, X. S.; Lee, P. W.; Liu, Z. W.; Xu, X. Y.; Li, Z.; Qian, X. H. cis-Configuration: a new tactic/rationale for neonicotinoid molecular design. J. Agric. Food Chem. 2011, 59, 2943–2949.10.1021/jf103499xSuche in Google Scholar PubMed

Wang, Y. L.; Cheng, J. G.; Qian, X. H.; Li, Z. Actions between neonicotinoids and key residues of insect nAChR based on an ab initio quantum chemistry study: hydrogen bonding and π-π interaction. Bioorg. Med. Chem. 2007, 15, 2624–2630.10.1016/j.bmc.2007.01.047Suche in Google Scholar PubMed

Zhou, H. B.; Zhang, J.; Lu, S. M.; Xie, R. G.; Zhou, Z. Y.; Choi, M. C. K.; Chan, A. S. C.; Yang, T. K. Design, synthesis and structure of new chiral squaric acid monoaminoalcohols and diaminoalcohols and their use as catalysts in asymmetric reduction of ketones and diketones. Tetrahedron 2001, 57, 9325–9334.10.1016/S0040-4020(01)00936-XSuche in Google Scholar