Synthesis and SAR of the antistaphylococcal natural product nematophin from Xenorhabdus nematophila

• Frank Wesche,
• Hélène Adihou,
• Thomas A. Wichelhaus and
• Helge B. Bode

Beilstein J. Org. Chem. 2019, 15, 535–541, doi:10.3762/bjoc.15.47

• relationship of the simple and antistaphylococcal amide nematophin from Xenorhabdus nematophila and synthetic derivatives are described. Moreover, the synthesis of intrinsic fluorescent derivatives, incorporating azaindole moieties was achieved for the first time. Keywords: azaindole; fluorescent dye; MRSA

• ; nematophin; Staphylococcus aureus; Introduction Microorganisms present a rich source of bioactive natural products of pharmacological importance against an emerging number of multiresistant bacteria [1]. Such examples are Xenorhabdus sp., Gram-negative entomopathogenic bacteria which live in symbiosis with

• , like xenocoumacins [12][13]. The quite simple amide nematophin (1) is another well-known member of natural products common in all Xenorhabdus nematophila strains and was first described by Li et al. in 1997 for their antimicrobial properties [14]. Simply, 1 is the condensation product of 3-methyl-2