Conjugate 16 (22-[4-(6-((6-(Piperazin-1-yl)-9H-purin-9-yl)methyl)pyridin-3-yl)-1H-1,2,3-triazol-1-yl]-22-deoxypleuromutilin)

Class: Pleuromutilin

Spectrum of activity:	Gram-positive
Details of activity:	Active against Staphylococcus aureus, Streptococcus pneumoniae, Enterococcus faecalis, vancomycin-resistant Enterococcus faecium
Propensity to select resistant mutants:	Yes, at 6 to 4.4 x 10^9 mutation frequency at 4xMIC
Description:	Synthetic compound with triaromatic C22-conjugated pleuromutilin scaffold; efficacious in reducing Staphylococcus aureus burden in a mouse infection model; oral solution and current form (2 HCl) makes bioavailability of compound unfavourable (likely poor intestinal solubility or high metabolism in mice and pigs); derivatives reported
Institute where first reported:	Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, DK-5230 Odense M, Denmark
Year first mentioned:	2024
Development status:	Experimental

Chemical structure(s):
Canonical SMILES:	C=C[C@]1(C)C[C@H]([C@]2(C)[C@H](C)CC[C@]3(CCC(=O)[C@@H]23)[C@@H](C)[C@@H]1O)OC(=O)CN4C=C(C5=CN=C(C=C5)CN6C=NC7=C6N=CN=C7N8CCNCC8)N=N4
Isomeric SMILES:	C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@@]1([C@@H](C[C@@]([C@H]([C@@H]3C)O)(C)C=C)OC(=O)CN4C=C(N=N4)C5=CN=C(C=C5)CN6C=NC7=C6N=CN=C7N8CCNCC8)C
InChI:	InChI=1S/C39H50N10O4/c1-6-37(4)17-30(38(5)24(2)9-11-39(25(3)34(37)52)12-10-29(50)33(38)39)53-31(51)21-49-20-28(45-46-49)26-7-8-27(41-18-26)19-48-23-44-32-35(42-22-43-36(32)48)47-15-13-40-14-16-47/h6-8,18,20,22-25,30,33-34,40,52H,1,9-17,19,21H2,2-5H3/t24-,25+,30-,33+,34+,37-,38+,39+/m1/s1
InChI Key:	JMWFCYTVJBGCRD-ODXCVMAQSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/168841449

External links:
Main Source:	https://pubs.acs.org/doi/10.1021/acs.jmedchem.3c02153