Author: Krzesiński, Paweł ; Pawłowska, Jolanta ; Skoczeń, Aleksandra ; Grela, Karol ; Kajetanowicz, Anna ; Baumert, Marcel E. ; Suska-Kauf, Ewa ; Nienałtowski, Tomasz

A number of metathesis reactions were successfully conducted in 4-methyltetrahydropyran, including both standard model dienes, as well as more complex substrates, such as analogues of biologically active compounds and active pharmaceutical ingredients. To place this solvent in a context of pharmaceutical R + D, larger-scale syntheses of SUAM 1221, a prolyl endopeptidase inhibitor with potential application in Alzheimer disease treatment, and a derivative of sildenafil, an analogue of the popular Viagra drug, were executed. In the latter case, despite all the setup being made in air, the metathesis reaction at a 33 g scale proceeded very well with relatively low catalyst loading and without need of aqueous workup or column chromatography.

01 Mar 2007·Bioorganic & Medicinal ChemistryQ3 · MEDICINE

2(S)-(Cycloalk-1-enecarbonyl)-1-(4-phenyl-butanoyl)pyrrolidines and 2(S)-(aroyl)-1-(4-phenylbutanoyl)pyrrolidines as prolyl oligopeptidase inhibitors

Q3 · MEDICINE

Article

Author: Johannes A.M. Christiaans ; Jouko Vepsäläinen ; Pekka T. Männistö ; Harri Leskinen ; Jarkko I. Venäläinen ; Erik A.A. Wallén ; Sami Poutiainen ; Elina M. Jarho ; Markus M. Forsberg

In order to replace the P2-P1 amide group, different 1-cycloalkenyls and 2-aryls were studied in the place of the P1 pyrrolidine group of a 4-phenylbutanoyl-L-Pro-pyrrolidine structure, which is a well-known prolyl oligopeptidase inhibitor SUAM-1221. The 1-cyclopentenyl and the 2-thienyl groups gave novel compounds, which were equipotent with the corresponding pyrrolidine-analog SUAM-1221. It was shown that the P2-P1 amide group of POP inhibitors can be replaced by an alpha,beta-unsaturated carbonyl group or the aryl conjugated carbonyl group.

01 Jun 2002·Bioorganic & Medicinal ChemistryQ3 · MEDICINE

Comparison of the Inhibition of Human and Trypanosoma cruzi Prolyl Endopeptidases

Q3 · MEDICINE

Article

Author: Christian Sergheraert ; Filip Goossens ; Sandrine Vendeville ; Marie Ange Debreu-Fontaine ; Valérie Landry ; Elisabeth Davioud-Charvet ; Simon Scharpe ; Philippe Grellier

Prolyl endopeptidases (PEPs) have been found in numerous species. Inhibitors of human enzyme could correct cognitive deficits in Alzheimer patients while inhibition of Trypanosoma cruzi PEP could prevent invasion phase in Chagas disease. A structure-activity relationship study carried out in a tetrahydroisoquinoline series allowed to obtain potent competitive inhibitors superior to SUAM-1221. Besides, inhibitors expected to act according to an irreversible mechanism revealed to be superior to JPT-4819, for applications linked to human enzyme inhibition.

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Indication	Highest Phase	Country/Location	Organization	Date
Amnesia	Discovery	HU	Chinoin Zrt.	-

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