In:
ChemMedChem, Wiley, Vol. 11, No. 6 ( 2016-03-17), p. 600-611
Abstract:
The regioselective condensations of various 7‐hydroxyisoflavonoids with bis( N , N ‐dimethylamino)methane in a Mannich reaction provided C‐8 N , N ‐dimethylaminomethyl‐substituted isoflavonoids in good yield. Similar condensations of 7‐hydroxy‐8‐methylisoflavonoids led to the C‐6‐substituted analogs. Thermal eliminations of dimethylamine from these C‐6 or C‐8 N , N ‐dimethylaminomethyl‐substituted isoflavonoids generated ortho ‐quinone methide intermediates within isoflavonoid frameworks for the first time. Despite other potential competing outcomes, these ortho ‐quinone methide intermediates trapped dienophiles including 2,3‐dihydrofuran, 3,4‐dihydro‐2 H ‐pyran, 3‐( N , N ‐dimethylamino)‐5,5‐dimethyl‐2‐cyclohexen‐1‐one, 1‐morpholinocyclopentene, and 1‐morpholinocyclohexene to give various inverse electron‐demand Diels–Alder adducts. Several adducts derived from 8‐ N , N ‐dimethylaminomethyl‐substituted isoflavonoids displayed good activity in the 1–10 μ m concentration range in an in vitro proliferation assay using the PC‐3 prostate cancer cell line.
Type of Medium:
Online Resource
ISSN:
1860-7179
,
1860-7187
DOI:
10.1002/cmdc.201600008
Language:
English
Publisher:
Wiley
Publication Date:
2016
detail.hit.zdb_id:
2209649-8
SSG:
15,3
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