Alanine, /?-2-thienyl

Alanine, ( )-/3-(2-amino-1,3-selenazol-4-yl)-synthesis, 6, 343 Alanine, phenyl-p-hydroxylation, 7, 565 Alanine, selenienyl-synthesis, 4, 964 Alanine, /3-2-selenienyl-applications, 4, 970 Alanine, /3-3-selenienyl-applications, 4, 970 Alanine, /3-2-thienyl-biological activity, 4, 911 Alanine, /3-3-thienyl-biological activity, 4, 912 L-Alanine, y-L-glutamyl-jS-pyrazolyl-occurrence, 5, 303 L-Alanine, /3-pyrazolyl-occurrence, 5, 303 Alanine racemase inhibition, 1, 266 Albendazole... 

The sequence with oxazole 73 also proves to be applicable to systems in which the double bond of the allylic alcohol fragment is incorporated into a heteroaromatic ring, such as in furfuryl alcohol (77a) and thiophene-2-methanol (77b).28 After hydrolysis of the oxazolone ring with water, V-benzoyl-3,3,3-trifluoro-2-(2-methyl-3-furyl)alanine (79a) and /V-benzoyl-3,3,3-trifluoro-2-(2-melhyl-3-thienyl)alanine (79b) are obtained. The 2-methylene helerocyclcs 78 originally formed in the Claisen rearrangement undergo rearomatizalion under the reaction conditions. 

In one of the steps in the synthesis of thienopyridine metalloprotease inhibitors possessing anticancer and antiinflammatory activities, the pyridine ring is constructed by treating (3-(2-thienyl)-D-alanine (274) with formaline in an acidic medium (1998EUP803505, 1999PCT9906410). In particular, this method was used to prepare 6-(R)-amino acid 275 in 91% yield. AT-Cbz-(3-(2-Thienyl)-L-alanine amide 276 was transformed into 4,5,6,7-tetrahydrothienopyridine-(65f)-carboxamide by dimeth-oxymethane in the presence of an acid (1996USP5480887). Compound 277 serves as an intermediate in the synthesis of anti-AIDS drugs. 

Andersen OA, Flatmark T, Hough E Crystal structure of the ternary complex of the catalytic domain of human phenylalanine hydroxylase with tetrahydrobiopterin and 3-(2-thienyl)-L-alanine, and its implications for the mechanism of catal-... 

C21H3602 pregnane-3,20-diol, (3alpha,5beta,20S) 80-92-2 25.00 1.1500 1 33189 C22H19N04S (R)-N-fmoc-2-thienyl alanine 201532-42-5 25.00 1.2813 2... 

C7H803 3-methylfuroic acid, methyl ester 6141-57-7 474.75 41.463 2 11011 C7H9N02S 2-thienyl alanine 139-86-6 378.40 32.335 1,2... 

Cady SG, Sono M (1991) 1-Methyl-DL-tryptophan, beta-(3-benzofuranyl)-DL-alanine (the oxygen ana-log of tryptophan), and beta-[3-benzo. (b)thienyl]-DL-alanine (the sulfur analog of tryptophan) are com-petitive inhibitors for indoleamine 2, 3-dioxygenase. Arch Biochem Biophys 291 326-333... 

A new mild and convenient method for esterification of a-keto-acids has been applied to 2-thienylglyoxylic acid. A convenient method for the resolution of j8-(2-thienyl)alanine has been described. ... 

Amino acids are accessible by use of ethyl (acetylamino)malonate. Dittmer, Hert, and Chambers treated 2-(chloromethyl)thiophene with ethyl (acetyl-amino)malonate in the presence of sodium ethoxide, obtaining an 87% yield of -(acetylamino)-a>(2-thienyl)malonate which was converted into /3-(2-thienyl)alanine in 78% yield by boiling hydrobromic acid 390... 

Thienyl)-/S-alanine was obtained by resolving the iV-benzyloxycar-bonyl-DL-amino-acid with quinine and removing the protecting group. Its absolute configuration was determined by o.r.d. " ... 

An alternative route to induce complete desymmetrization of the oligopeptides was achieved by polymerization of the mixed qwasi-racemic crystals of (R)-PheNCA with (S)-PheNCA and (S)-ThieNCA, (3-(2-thienyl)-alanine-carboxyanhydride) (Scheme 8.8), of various compositions [66]. 

Scheme 8.8 Formulae PheNCA phenylalanine N-carboxyanhydride ThieNCA 3-(2-thienyl)-alanine N-carboxyanhydride oligopeptide product of the polymerization in mixed crystals of (RS)-PheNCA (S)-ThieNCA.

Fig. 9 shows some examples, the list of which might be expanded almost arbitrarily. The only limitation hes in the reactivity of the aryl cuprates, which means that pyridyl or thienyl residues cannot be introduced yet. On the other hand the flexibility of the bisepoxide method is demonstrated by the synthesis of 2,3-diamino-propionic acid (p-amino-alanine) which is a constituent of antibiotic cyclo-peptides like tuberactinomycin A or, in form of the N-methyl derivative L-BMAA, occurs in the seeds of the local sago palm and had notoriously caused the Guam disease [8], with a certain kind of Alzheimer and Parkinson symptoms, until the American conquest of the island in World War II led to a change in nutrition (Fig. 10). 

Diethyl 2-thenylacetamidomalonate suspended in an aq. soln. of an equal weight of Na2G03, refluxed 18 hrs., cautiously acidified with coned. HGl to pH 2, and boiled a few min. N-acetyl-j -2-thienyl-DL-alanine. Y 77-85%. F. W. Dunn, Biochem. Prep. 10, 159 (1963). 

Some aminobenzoic acid diuretics containing the thiophen ring have also been studied. The syntheses and lipid-lowering properties of (203) and (204) have been described. 3-j8-(2-Thienyl-alanine-8-lysine)vasopressine has been synthesized by the solution technique. A comparison of the bioavailability of [2,5- C]thiophen after oral and rectal administration in mice has been reported. The nitro-reduction of carcinogenic 5-nitro-thiophens by rat-tissues has been studied. Thiophen-ring-containing compounds with antiradiation, antidepressant, antiparasitic, " antibacterial, - antiviral, and broncho-dilator activity have been studied. A thia-steroid, 14,15-dehydro-A-nor-3-thiaequilenin, has been synthesized. In connection with studies on the syn-... 

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