Design, synthesis and activities of 4/5-acyl-2-aminoimidazolyl analogues of oroidin for biofilm inhibition

Sivappa Rasapalli; Abasaheb Dhawane; Christiaan Rees; James A. Golen; Bal Ram Singh; Shuowei Cai; Jerry Jasinski; Steven M. Kwasny; Donald T. Moir; Timothy J. Opperman; Terry L. Bowlin

doi:10.1039/C3MD00143A

Design, synthesis and activities of 4/5-acyl-2-aminoimidazolyl analogues of oroidin for biofilm inhibition†

Sivappa Rasapalli,*^a Abasaheb Dhawane,^a Christiaan Rees,^a James A. Golen,^a Bal Ram Singh,^a Shuowei Cai,^a Jerry Jasinski,^b Steven M. Kwasny,^c Donald T. Moir,^c Timothy J. Opperman^c and Terry L. Bowlin^c

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^a Department of Chemistry and Biochemistry, University of Massachusetts Dartmouth, North Dartmouth, MA 02747, USA
E-mail: srasapalli@umassd.edu

^b Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA

^c Microbiotix, Inc., One Innovation Drive, Worcester, MA 01605, USA

Abstract

Herein, we report the synthesis and the screening results of the unique acyl imidazopyrimidinyl and acyl imidazolyl structural analogues of oroidin as inhibitors of biofilm formation that have minimal or no microbicidal effect. A focused library based on the marine natural product oroidin scaffold was synthesized and assayed for antibacterial and anti-biofilm activity against medically relevant bacterial pathogens. Based on the structure–activity relationship (SAR) studies, it is concluded that the most active analogues are those that contained a 2-aminoimidazole motif and a brominated pyrrolecarboxamide subunit with a carbonyl functionality in the side chain.

MedChemComm

Design, synthesis and activities of 4/5-acyl-2-aminoimidazolyl analogues of oroidin for biofilm inhibition†

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Design, synthesis and activities of 4/5-acyl-2-aminoimidazolyl analogues of oroidin for biofilm inhibition

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