General Scope of 1,4‐Diastereoselective Additions to a 2(3H)‐Quinazolinone: Practical Preparation of HIV Therapeutics.

Magnus, Nicholas A.; Confalone, Pat N.; Storace, Louis; Patel, Mona; Wood, Christopher C.; Davis, Wayne P.; Parsons, Rodney L.

doi:10.1002/chin.200324123

Cited by 3 publications

(3 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Attempts to deprotect 4-methoxybenzyl at the same time as reducing the nitro group failed. However, deprotection of 4-methoxybenzyl was achieved in the presence of (NH 4 ) 2 Ce(NO 3 ) 6 (CAN) 17 to provide the desired quinazolinedione 3v in 82% yield. Lastly, we obtained the quinazolinedione building block IV in 85% yield from a reduction of nitro via hydrogenation in the presence of Pd/C in methanol.…”

Section: Table 1 Optimization Of Reaction Conditions Fo...mentioning

confidence: 99%

DMAP-Catalyzed Domino Reactions of α-Chloroaldoxime O-Methanesulfonates and 2-Aminobenzoic Acids for the Synthesis of Quinazolinediones

Kaeobamrung,

Kaewman

2023

Synlett

View full text Add to dashboard Cite

Quinazolinedione derivatives were obtained from 2-aminobenzoic acids and bench-stable α-chloroaldoxime O-methanesulfonates via DMAP-catalyzed domino reactions under mild reaction conditions in one-pot fashion. Chemical transformations involved nucleophilic substitution, Tiemann rearrangement and cyclic urea formation. The strength of nitrogen nucleophile of 2-aminobenzoic acids and the high level of carbon electrophile of α-chloroaldoxime O-methanesulfonates were crucial for the reaction outcome. An application to synthesize a quinazolinedione building block was introduced.

show abstract

Section: Table 1 Optimization Of Reaction Conditions Fo...mentioning

confidence: 99%

DMAP-Catalyzed Domino Reactions of α-Chloroaldoxime O-Methanesulfonates and 2-Aminobenzoic Acids for the Synthesis of Quinazolinediones

Kaeobamrung,

Kaewman

2023

Synlett

View full text Add to dashboard Cite

show abstract

“…The 4(3H)-quinazolinone derivatives (a derivative of the parent compound quinazoline) have been shown as a group of compounds of broad medical interest. Quinazolinones are reported to exhibit antibacterial [7], antiviral [8], anticancer [9], antihypertensive [10] and anti-inflammatory activities [11]. The antihyperlipidemic and antihypercholesterolemic activities of quinazolinone derivatives are reported and the activities of the tested compounds were almost equal to that of β-sitosterol (a plant sterol of hypolipidemic activity) [1,12].…”

Section: Introductionmentioning

confidence: 99%

The antihyperlipidemic activities of 4(3H) quinazolinone and two halogenated derivatives in rats

et al. 2005

View full text Add to dashboard Cite

In the present study, the effects of subchronic treatments (4 weeks) of hypercholesterolemic (single) and diabetic-hypercholesterolemic (combined) rats with 4 (3H) quinazolinone and 2 halogenated derivatives (6, 8-dibromo-2-methy-4 (3H) quinazolinone and 6-iodo-2-methyl-4(3H) quinazolinone) at a sublethal dose level (2 mg/Kg) on cholesterol metabolism were investigated. Bezafibrate, a hypolipidemic drug was used as a reference compound for data comparison. Treatment of rats with single and combined hypercholesterolemia with quinazolinone compounds gave rise to highly significant reductions in serum total cholesterol and cholesterol ester levels, whereas serum triacylglycerol level was significantly reduced only after treatment with halogen-substituted quinazolinones in single hyper-cholesterolemia, compared to the control group. The effects of different quinazolinones and bezafibrate on reduction of serum LDL-C level were comparable in single hypercholesterolemia but significantly different in combined hypercholesterolemia. Results obtained from this study suggest that the antihyperlipidemic effect of quinazolinone compounds was brought about by inhibition of dietary cholesterol absorption and / or intestinal ACAT activity.

show abstract

“…When R = trifluoroethyl, it was not possible to isolate the dehydrated product 7. Therefore, the procedure of Magnus et al 17 was employed whereby treatment of the mixture of 5 and 6 with thionyl chloride and triethylamine in THF generates intermediate 7 in situ, followed by addition of a large excess of the Grignard reagent to afford the 4,4-disubstituted quinazolinones 8 where R = trifluoroethyl.…”

mentioning

confidence: 99%

Discovery of 4,4-Disubstituted Quinazolin-2-ones as T-Type Calcium Channel Antagonists

Barrow¹,

Rittle²,

Reger³

et al. 2010

ACS Med. Chem. Lett.

View full text Add to dashboard Cite

A novel series of quinazolinone T-type calcium channel antagonists have been prepared and evaluated using in vitro and in vivo assays. Optimization of the screening hit 3 by modifications of the 3- and 4-positions of the quinazolinone ring afforded potent and selective antagonists that displayed in vivo central nervous system efficacy in epilepsy and tremor models, as well as significant effects on rat active wake as measured by electrocorticogram.

show abstract

General Scope of 1,4‐Diastereoselective Additions to a 2(3H)‐Quinazolinone: Practical Preparation of HIV Therapeutics.

Cited by 3 publications

References 1 publication

DMAP-Catalyzed Domino Reactions of α-Chloroaldoxime O-Methanesulfonates and 2-Aminobenzoic Acids for the Synthesis of Quinazolinediones

DMAP-Catalyzed Domino Reactions of α-Chloroaldoxime O-Methanesulfonates and 2-Aminobenzoic Acids for the Synthesis of Quinazolinediones

The antihyperlipidemic activities of 4(3H) quinazolinone and two halogenated derivatives in rats

Discovery of 4,4-Disubstituted Quinazolin-2-ones as T-Type Calcium Channel Antagonists

Contact Info

Product

Resources

About