N-Cyano sulfilimine functional group as a nonclassical amide bond bioisostere in the design of a potent analogue to anthranilic diamide insecticide

On-Yu Kang; Eunsil Kim; Won Hyung Lee; Do Hyun Ryu; Hwan Jung Lim; Seong Jun Park

doi:10.1039/d2ra06988a

N-Cyano sulfilimine functional group as a nonclassical amide bond bioisostere in the design of a potent analogue to anthranilic diamide insecticide

RSC Adv. 2023 Jan 11;13(3):2004-2009. doi: 10.1039/d2ra06988a. eCollection 2023 Jan 6.

Authors

On-Yu Kang^{1

2}, Eunsil Kim^{1

3}, Won Hyung Lee⁴, Do Hyun Ryu², Hwan Jung Lim^{1

5}, Seong Jun Park^{1

5}

Affiliations

¹ Data Convergence Drug Research Center, Korea Research Institute of Chemical Technology Daejeon 34114 Republic of Korea sjunpark@krict.re.kr +82-42-860-7160 +82-42-860-7175.
² Department of Chemistry, Sungkyunkwan University 2066 Seobu-ro Suwon 16419 Republic of Korea.
³ Department of Chemistry, Sogang University 35 Baekbeom-ro Seoul 04107 Republic of Korea.
⁴ Central Research Institute, Kyung Nong Co. Ltd 34-14 Summeori-gil Kyongju 38175 Kyongsangbuk-do Republic of Korea.
⁵ Department of Medicinal Chemistry and Pharmacology, University of Science & Technology 217 Gajeong-ro Daejeon 34113 Republic of Korea.

Abstract

To explore the potential of the N-cyano sulfilimine group as an amide bond isostere, a derivative of the blockbuster anthranilic diamide, chlorantramiliprole, was synthesized and evaluated with regard to its physicochemical properties, permeability, and biological activity. Given the combination of N-cyano sulfilimine chlorantraniliprole 1 and its strong hydrogen bond acceptor character, high permeability, and excellent insecticidal activity, the N-cyano sulfilimine functional group could be considered as an amide bond isostere.