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

  • Chuanxiang Liu EMAIL logo , Fengping Yi EMAIL logo and Jianzhong Zou
Published/Copyright: August 1, 2012

Abstract

Novel heterocyclic enamine derivatives based on skeleton of neonicotinoids were designed and prepared by the substitution reaction between heterocyclic enamines with intermediates of neonicotinoids, which provides readily accessible neonicotinoid analogs for potential bioactivity assay.


Corresponding authors: Chuanxiang Liu and Fengping Yi, School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China; and School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai 201418, China

We are thankful for financial support from the Science Foundation of Shanghai Institute of Technology (YJ2010-49), the Key and Innovation Project of Shanghai Educational Committee (No. 11ZZ180), and the Project of Local University Ability Building of Shanghai Scientific and Technological Committee (No. 11520502600).

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/jm9905099Search 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/jo00003a014Search 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/s10158-005-0013-8Search 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/jf101303gSearch 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.56.362Search 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/jf0623440Search in Google Scholar PubMed

Moury, D. T. Mucochoric acid. II. Reactions of aldehyde group. J. Am Chem. Soc. 1953, 75, 1909–1912.10.1021/ja01104a038Search 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.2009.05.016Search 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/jf021185rSearch 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/jf103499xSearch 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.2007.01.047Search 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-XSearch in Google Scholar

Received: 2012-04-04
Accepted: 2012-05-13
Published Online: 2012-08-01
Published in Print: 2012-08-01

©2012 Walter de Gruyter GmbH & Co. KG, Berlin/Boston

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