Functionally Optimized Neuritogenic Farinosone C Analogs: SAR-Study and Investigations on Their Mode of Action

Burch, Patrick; Chicca, Andrea; Gertsch, Jürg; Gademann, Karl (2014). Functionally Optimized Neuritogenic Farinosone C Analogs: SAR-Study and Investigations on Their Mode of Action. ACS medicinal chemistry letters, 5(2), pp. 172-177. American Chemical Society 10.1021/ml400435h

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Several natural products derived from entomopathogenic fungi have been shown to initiate neuronal differentiation in the rat pheochromocytoma PC12 cell line. After the successful completion of the total synthesis program, the reduction of structural complexity while retaining biological activity was targeted. In this study, farinosone C served as a lead structure and inspired the preparation of small molecules with reduced complexity, of which several were able to induce neurite outgrowth. This allowed for the elaboration of a detailed structure-activity relationship. Investigations on the mode of action utilizing a computational similarity ensemble approach suggested the involvement of the endocannabinoid system as potential target for our analogs and also led to the discovery of four potent new endocannabinoid transport inhibitors.

Item Type:

Journal Article (Original Article)


04 Faculty of Medicine > Pre-clinic Human Medicine > Institute of Biochemistry and Molecular Medicine

Graduate School:

Graduate School for Cellular and Biomedical Sciences (GCB)

UniBE Contributor:

Chicca, Andrea and Gertsch, Jürg


500 Science > 570 Life sciences; biology
600 Technology > 610 Medicine & health




American Chemical Society




Kevin Marc Rupp

Date Deposited:

12 May 2015 10:15

Last Modified:

16 Oct 2015 09:52

Publisher DOI:


PubMed ID:


Uncontrolled Keywords:

Neurite outgrowth; natural products; endocannabinoid membrane transport; CB1 receptor; SAR; truncated




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