1-Methyl-3-pyrrolines and 2-methylisoindolines: new classes of cyclic tertiary amine monoamine oxidase B substrates

Bioorganic & Medicinal Chemistry
Y X WangN Castagnoli

Abstract

Both 1-methyl-3-pyrrolines and 2-methylisoindolines are substrates for MAO-B with Vmax/Km values ranging from 200 to 2000 min-1 mM-1 at 37 degrees C. These compounds represent new classes of cyclic tertiary amine substrates for this flavoenzyme. The only other known cyclic amines that are MAO-B substrates are 1,4-disubstituted 1,2,3,6-tetrahydropyridinyl derivatives. The presence of an allylic (benzylic) amino functionality in all of these compounds may be linked to their substrate properties since related piperidinyl and pyrrolidinyl analogs are stable in the presence of MAO-B. This paper discusses energetic and geometric features of these compounds in relationship to their substrate properties and in anticipation of their utility to probe the active site of this flavoenzyme.

References

Oct 1, 1978·Journal of Medicinal Chemistry·C R RasmussenJ Marakowski
Nov 9, 1992·Journal of Medicinal Chemistry·A S Kalgutkar, N Castagnoli
Dec 31, 1991·Biochemical and Biophysical Research Communications·A K TanT P Singer
Sep 1, 1989·Chemical Research in Toxicology·M K ShigenagaN Castagnoli
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Citations

Apr 28, 1999·Bioorganic & Medicinal Chemistry·J Yu, N Castagnoli
Jun 29, 2000·Annual Review of Biochemistry·C KhoslaD E Cane
Jul 28, 2007·Life Sciences·Modupe O OgunrombiJacobus P Petzer
Sep 7, 2002·Drug Metabolism Reviews·Neal CastagnoliJackie Shang
Jul 5, 2005·Bioorganic & Medicinal Chemistry·John M RimoldiNeal Castagnoli
Jan 18, 2013·Angewandte Chemie·Jenna L JeffreyRichmond Sarpong
Sep 26, 2014·Organic & Biomolecular Chemistry·Egon HeusonLennart Bunch
Sep 19, 2008·Bioorganic & Medicinal Chemistry·Anél PretoriusJacobus P Petzer

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