Hypolipidemic alkoxybenzoic acids

dichloromethane (25 mL). The tan solid was filtered off and suspended in cold (0 °C) DMF (50 mL). Anhydrous ammonia was bubbled through for 10 min, and the resulting solution was allowed to stand at room temperature overnight. The DMF solution was evaporated to dryness under reduced pressure, and the residue was washed with CH2C12 and ether and dried: yield 3.0 g; mp 340-345 °C dec. Method M.7-Chloro-4,9-dihydro-4-methyl-9-oxopyrazolo[5,l-h]quinazoline-2-carbonitrile. 7-Chloro-4,9-dihydro-4-methyl-9-oxopyrazolo[5,l-6]quinazoline-2-carboxamide (3 g, 0.011 mol) was heated at 56 °C with thionyl chloride (1.6 mL, 0.022 mol) and DMF (35 mL) for 18 h. The resulting clear solution was evaporated to dryness, and the residue was treated with water (600 mL). After the solution was left standing for 1 h, the crude nitrile was filtered off, washed with water, and recrystallized from a DMF-EtOH mixture: yield 2.4 g (84%);

Section: Discussionmentioning

confidence: 99%

N-(Aminophenyl)oxamic acids and esters as potent, orally active antiallergy agents

Klaubert¹,

Sellstedt²,

Guinosso³

et al. 1981

“…Bicyclo[3.2.1]octane-3-spiro-5'-hydantoins. (a) Bucherer Product (2). A solution of bicyclo[3.2.1]octan-3-one (1; 12.9 g, 0.10 mol), KCN (11.85 g, 0.18 mol), and (NH4)2C03 (29.95 g, 0.31 mol) in EtOH (52 mL) and water (52 mL) was placed in a sealed vessel and heated at 60-65 °C for 4 days.…”

Section: Methodsmentioning

confidence: 99%

“…The assignments were in accordance with those expected from a detailed consideration of steric effects on either a thermodynamically determined product (the Strecker product) or a kinetically determined product (the Bucherer-Bergs product). These considerations showed that the spirohydantoin derived by the Strecker route (3) (Scheme I) should have its 4'-carbonyl group in the axial orientation and that the spirohydantoin derived by the conventional Bucherer-Bergs route (2) should have this group in the equatorial orientation (The EJ rule).26…”

mentioning

confidence: 99%

Synthesis and transport applications of 3-aminobicyclo[3,2,1]octane-3-carboxylic acids

Hn¹,

Me²,

Jv³

et al. 1983

The isomeric 3-aminobicyclo[3.2.1]octane-3-carboxylic acids were synthesized and compared with the widely used (1R,2S,4S)-2-aminobicyclo[2.2.1]heptane-2-carboxylic acid as to specificity to the Na+-independent membrane transport system L of the Ehrlich ascites tumor cell and of the rat hepatoma cell line HTC. The presence of an additional methylene group in the ring system leads to an optically symmetrical amino acid, with the advantages that the product is devoid of isomeric contamination. Hence, optical resolution is not necessary to secure a homogeneous test substrate for discrimination of amino acid transport systems. Through its inhibitory action on the cellular uptake of known system-specific amino acids, the bicyclo[3.2.1]octane amino acid proved more reactive than the bicycloheptane analogue with the Na+-independent amino acid transport system of the test cells and not perceptibly reactive with the accompanying Na+-dependent systems. Recent evidence of the presence of a second component of Na+-independent amino acid transport, beyond system L, increases the importance of securing a variety of possibly discriminatory model substrates.

“…While this work was in progress the hypolipidemic activity of alkoxybenzoic acids was reported in the patent literature2 and more recently further results were published in this Journal. 3 Chemistry. The compounds were prepared by standard methods as detailed in Table I and in the Experimental Section.…”

mentioning

confidence: 99%

“…The target compound, 10-thia-5,8-deazafolic acid (2a), was prepared as shown in Scheme I. The sodium salt of diethyl 4-mercaptobenzoyl-L-glutamate (3) was generated according to the literature procedure2 and…”

mentioning

confidence: 99%

Hypolipidemic analogs of ethyl 4-benzyloxybenzoate

Baggaley¹,

Fears²,

Hindley³

et al. 1977

A series of compounds related to ethyl 4-benzyloxybenzoate was synthesized and evaluated for potential hypolipidemic activity in rats. Structure--activity relationships are discussed in terms of cholesterol-lowering activity together with effects on weight gain and liver lipids. A number of the compounds inhibited cholesterol and free fatty acid biosynthesis from [1-14C]acetate in rat liver slices in vitro. Ethyl 4-benzyloxybenzoate, ethyl-4-benzyloxybenzoic acid, ethyl 4-p-bromobenzyloxybenzoates, and 4-o-methoxybenzyloxyphenyl acetate exhibited the most favorable spectrum of activity.