ChemInform Abstract: New Potent Prolyl Endopeptidase Inhibitors: Synthesis and Structure‐ Activity Relationships of Indan and Tetralin Derivatives and Their Analogues.

Abstract

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Low molecular weight inhibitors of Prolyl Oligopeptidase: a review of compounds patented from 2003 to 2010

“…Moreover, heterocycles containing an sp 2 nitrogen atom in the beta position result in an increase in potency, as a consequence of the formation of a hydrogen bond between this atom and the histidine of the catalytic triad [81]. Nitriles [68,84] were proposed to form imino ethers with the hydroxyl group of the serine, and were also studied as reversible covalent inhibitors [85,86].…”

“…Proline, proline derivatives [58,60,[65][66][67][68][69] or natural a-amino acids, both neutral and charged, are fitted [70][71][72]. Moreover, a wide variety of cyclic or bicyclic scaffolds are compatible [73][74][75] while open chains can also be fitted.…”

“…Other cyclic and bicyclic systems were included at N-terminal position, as well as modifications in the proline or pyrrolidine rings, as exemplified by Z-321 (3) [67,68,[90][91][92].…”

Stereochemical switch driven by crystallization: Interplay between stoichiometry and configuration of the products

“…A solid product was filtered off, washed with 1,4‐dioxane (20 ml), and dried. A pale‐yellow powder of acid 3 was obtained after recrystallization from 1,4‐dioxane (23.4 g, 82%) (the acid 3 was prepared by a modified procedure of the following reference: Tanaka et al 22 ). Mp 203–206°C; 1 H NMR (400 MHz, DMSO‐ d 6 , δ): 13.09 (bs, 1H), 7.81–7.72 (m, 2H), 7.67 (d, J = 7.7 Hz, 1H), 7.48 (dt, J = 7.7, 1.1 Hz, 1H), 6.54 (t, J = 2.4 Hz, 1H), 4.08 (d, J = 2.4 Hz, 2H); 13 C NMR (101 MHz, DMSO‐ d 6 , δ): 193.1, 166.9, 150.8, 148.8, 136.5, 136.1, 127.9, 127.0, 124.0, 121.3, 32.0.…”

“…A solid product was filtered off, washed with 1,4-dioxane (20 ml), and dried. A pale-yellow powder of acid 3 was obtained after recrystallization from 1,4-dioxane (23.4 g, 82%) (the acid 3 was prepared by a modified procedure of the following reference: Tanaka et al 22…”