Vincent, Michel; Marchand, Bernard; Remond, Georges; Jaguelin-Guinamant, Sylvie; Damien, Gerard; Portevin, Bernard; Baumal, Jean Yves; Volland, Jean Paul; Bouchet, Jean Paul published the artcile< Synthesis and ACE inhibitory activity of the stereoisomers of perindopril (S 9490) and perindoprilate (S 9780)>, Related Products of 145513-91-3, the main research area is ACE inhibitor stereoisomer perindopril perindoprilate preparation; angiotensin converting enzyme perindopril perindoprilate stereoisomer.
Preindopril, a powerful ACE (angiotensin converting enzyme) inhibitor contains 5 chiral carbons, and thus there is the possibility of 25 = 32 stereoisomers for the general structure I. These 32 stereoisomers were prepared by crosscoupling the 8 stereoisomers of benzyl perhydroindole-2-carboxylate with the 4 stereoisomers of 2-(1-carbethoxybutylamino)propionic acid, and hydrogenating the resulting benzyl esters. Each stereoisomer of perindopril furnished by saponification of the corresponding diacid stereoisomer (II) of perindoprilate which is the active form of perindopril. For each of the 32 stereoisomers of II, the in vitro ACE inhibitory potency was determined Four of them, including perindoprilate, had activities in the nanomolar range, and 4 more were ca. 10-fold less active. The 4 acid esters of I corresponding resp. to the 4 most active diacids II, in vitro were studied (1 mg/kg via the oral route) for their in vivo activity in dogs. The oral absorption of the active acid esters I and their activation to the active diacid II depended only on the chiralities of the 2 ring junction carbons of the perhydroindole ring.
Drug Design and Discovery published new progress about Chirality. 145513-91-3 belongs to class indole-building-block, and the molecular formula is C9H15NO2, Related Products of 145513-91-3.
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles