Synthesis and Hypolipidemic Activities of Novel 2-[4-[(Diethoxyphosphoryl)methyl]phenyl]quinazolines and 4(3H)-Quinazolinones

Abstract

The novel compound NO-1886, 4-[(diethoxyphosphoryl)methyl]-N-(4-bromo-2-cyanophenyl)-ben zamide, is a hypolipidemic agent, which appears to increase lipoprotein lipase activity in rats. Various analogs of NO-1886 were synthesized to study the structure-activity relationship of this hypolipidemic drug. A novel series of quinazolines and 4(3H)-quinazolinones were prepared by cyclization of NO-1886 derivatives. Derivatives bearing a 4-[(diethoxyphosphoryl)-methyl]phenyl] group at the 2-position were found to lower triglyceride and total cholesterol levels. In accord with the decrease in log P*, quinazolines and 4(3H)-quinazolinones showed good absorption and hypolipidemic activity. When the quinazolinone ring system is substituted at positions 6 and 7 with methoxy groups, increased hypolipidemic activity was observed. The highest hypolipidemic activity was observed when the 3-position was substituted by a methyl or benzyl group.

Lipid lowering effect of synthetic phenolic compound in a high- fat diet (HFD) induced hyperlipidemic mice

“…This condition is an indicator of both coronary artery disease and atherosclerosis and is the main cause of cardiovascular disease worldwide. An accepted mean of treating the patients with hyperlipoproteinemia and atherosclerosis is lowering the serum triglycerides (TG) and increasing high-density lipoproteins (HDL) [2].…”

Amberlite IR-120 H+ Resin, an Efficient and Recyclable Solid Phase Catalyst for the Synthesis of 2, 3-Disubstituted Quinazolin-4(3H)-Ones: A Greener Approach

“…In general, these quinazolin-4(3H)-ones alkaloids have gained profound interest owing to their promising biological activity [1][2][3][4] viz., anticancer, 5 anti-convulsant, 6 anti-bacterial, 7 antiulcer, 8 anti-fungal, 9 analgesic, 10 anti-inflammatory 11 and anti-hypertensive. 12 Rutaecarpine (Fig.…”

Synthesis, spectro-analytical, computational and biological studies of novel 6-methyl-3-(1-(4-oxo-2-phenylquinazolin-3(4H)-ylimino) ethyl)-2H-pyran-2, 4(3H)-dione and its Co (II), Cu (II) and Hg (II) metal complexes

“…Quinazolinones are the heterocyclic compounds showing broad spectrum of biological significance such as anticancer [1], antitumour [2], antifungal [3,4], antibacterial [5,6], antitubercular [7], antihistaminic [8], antiinflammatory [9], anticonvulsant [10], immunotropic [11], hypolipidemic [12], antiulcer [13], analgesic [14,15] and CNS depressant [16] activities. The compound 3-acetyl-6-methyl-2H-Pyran-2, 4(3H)-dione upon complexation with transition metals exhibited numerous biological applications [17][18][19][20].…”