Total Synthesis and Monoamine Oxidase Inhibitory Activities of (±)-Entonalactam A and Its Derivatives

Abstract

The first total synthesis of isoindolinone (±)-entonalactam A (6), originally obtained from the fungus Entonaema sp., was achieved in 14 steps from commercially available 5-bromovanillin via benzophenone intermediates. Isoindolinone, phthalide, and benzophenone analogues of natural products were also synthesized. The monoamine oxidase (MAO) A and B inhibitory activities were tested. The isoindolinone derivative 30 exhibited inhibition of both MAO-A and -B (IC50 = 17.8 and 15.8 μM, respectively).

Multifaceted Behavior of 2‐Cyanobenzaldehyde and 2‐Acylbenzonitriles in the Synthesis of Isoindolinones, Phthalides and Related Heterocycles

“…Recently, Kamauchi and co‐workers reported the first total synthesis of isoindolinone (±)‐entonalactams A, B and C, originally isolated from the fungus Entonaema sp . The synthesis was achieved in 7 to 14 steps from commercially available 5‐bromovanillin 102 via 2‐cyanobenzophenone intermediates synthesis 107 , according to the Scheme 45 [42] . Cyanation of 106 was carried out by the use of CuCN, while cyclization of 107 was achieved under KOH promoted conditions similar to those of Scheme 42.…”

“…Cyanation of 106 was carried out by the use of CuCN, while cyclization of 107 was achieved under KOH promoted conditions similar to those of Scheme 42. Isoindolinone, phthalide, and benzophenone analogues of natural products were also synthesized in this work [42] …”

“…The synthesis was achieved in 7 to 14 steps from commercially available 5bromovanillin 102 via 2-cyanobenzophenone intermediates synthesis 107, according to the Scheme 45. [42] Cyanation of 106 was carried out by the use of CuCN, while cyclization of 107 was achieved under KOH promoted conditions similar to those of Scheme 42. Isoindolinone, phthalide, and benzophenone analogues of natural products were also synthesized in this work.…”

“…Isoindolinone, phthalide, and benzophenone analogues of natural products were also synthesized in this work. [42]…”

In‐depth analysis of the xanthine oxidase inhibitors of Cicer arietinum L.‐based receptor–ligand affinity coupled with complex chromatography

“…Compounds from plants with inhibitory activities are conventionally screened using in vitro assays. 11 Three types of activity methods were used to study potential XOD inhibitors in C. arietinum L. Firstly, a method based on ultrafiltration (UF) screening method based on receptor-ligand affinity has been proposed to overcome the limitations of in vitro methods and enhance the throughput of drug discovery. 12 Ultrafiltration liquid chromatography-mass spectrometry (UF-LC-MS) has been proven to be a powerful tool for screening and isolating biologically active compounds from botanical extracts because the step facilitates the separation of receptor-ligand complexes from unbound compounds.…”