Synthesis and anthelmintic activity of cyclohexadepsipeptides with cyclohexylmethyl side chains.
Cyclohexadepsipeptides (CHDPs) with cyclohexylmethyl side chains represent novel enniatins with in vivo activity against the parasitic nematode Haemonchus contortus Rudolphi in sheep. It was found that the replacement of benzylic by cyclohexylmethyl side chains on the enniatin skeleton can increase anthelmintic efficacy. Here we report on a simple total synthesis of the precursors for this type of CHDPs and an efficient chemical transformation of the benzylic into the corresponding cyclohexylmethyl side chains.
Jeschke
Peter
P
Bayer CropScience AG, Research Insecticides, Chemistry Insecticides, Monheim am Rhein, Germany. peter.jeschke@bayercropscience.com <peter.jeschke@bayercropscience.com>
Harder
Achim
A
Etzel
Winfried
W
Schindler
Michael
M
Thielking
Gerhard
G
D000818:Animals; D000871:Anthelmintics / Q000138:chemical synthesis* / Q000494:pharmacology*; D002384:Catalysis; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D015195:Drug Design; D006189:Haemonchus / Q000378:metabolism; D006801:Humans; D006859:Hydrogen / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008956:Models, Chemical; D010455:Peptides / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000737:chemistry; D012756:Sheep; D012757:Sheep Diseases / Q000188:drug therapy*
D000871:Anthelmintics; D010455:Peptides; D010456:Peptides, Cyclic; D006859:Hydrogen