Synthesis of aminoalkylglyoxal derivatives. II. Aminoalkyglyoxal derivatives of <sub>L</sub>-alanine, β-alanine, and <sub>L</sub>-tyrosine

Balenović, K.; Cerar, D.; Filipović, Lana

doi:10.1021/jo50013a015

Cited by 14 publications

(7 citation statements)

References 2 publications

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“…Removal of the phthalyl group by the method of Zng and Manske [48] yields aminopyruvaldehyde derivatives [49], which can be reduced very reidily with H2/Pt02 to rJ-amino-cr-hydroxypropaldehydes [50] and 3-aminopropane-l,2-diols [50,53]; with o-phenylenediamine, the pyruvaldehyde derivatives give arninoalkylquinoxalines, e.g. (39) [51].…”

Section: Alkmentioning

confidence: 99%

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Syntheses Using Pyridinium Salts (IV)

Kröhnke

1963

Angew. Chem. Int. Ed. Engl.

130

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Cleavage of N-phenylpyridinium or N-vinylpyridinium salts with secondary aliphatic amines leads to aromatic amino compounds or enamines which are often unobtainable by other routes. The other fragment, glutacondialdehyde or its rnonoanil, gives azulenes, as shown by Ziegler and Hafner, as well as Konig; these compounds can also be prepared from alkylpyridinium salts with cyclopentadienylsodium (Hafner). Syntheses of labile aldehydes which are otherwise dijjjcult to obtain and of a-ketocarboxylic acids, starting from pqiridinium salts and proceeding via nitrones or a-cyanoanils, are illustrated by many wcw examples. Benzimidazoles, benzothiazoles, and amidines are accessible from pyridinium salts via nitrones or a-cyanoanils; cyanoanils can be transformed into guinoxalines (including xanthopterine), perimidines, etc. Furthermore, nitrosonaphthols and nitrosonaphthylamines react with pyridinium salts containing an active iizethylene group on the nitrogq leading to new ring syslems. Further syn fhetic possihilities arise from nucleophilic &isplacements of the pyridine in pyriditiium salts by SN2 reactions. Combination of the route via nitrones with the methods of Arndt-Eistert, Ortoleva-King, or with chloromethylation constitutes a significant enlargement of its range of'application. The forniation of a-cyanoanils from diazoketones permits synthesis of a-keto-0-umino acids from a-amino acids, or of phenylglyoxylic acids from benzoic acids by chain extension.

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Section: Alkmentioning

confidence: 99%

“…153 "C, is formed in 50 % yield in the usual manner, as is the a-keto-aldehyde, (-)-cr-phthalimidomethyl pyruvaldehyde [49] ; the yield of aldehyde, based on the nitrone, is 80 %,, cci? = I .34 i 0.4 O (in ether) [53].…”

Section: Preparation Of ( -)-I -Bromo-3-phthalimido-2-butanonementioning

confidence: 99%

Syntheses Using Pyridinium Salts (IV)

Kröhnke

1963

Angew. Chem. Int. Ed. Engl.

130

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“…Geiparvarin (1),* 12 jatrophone (2),3 and eremantholides A, B, and C (3)4 constitute a group of compounds of considerable current interest. The stimulus for this interest arises from observations that these compounds display significant inhibitory activity against a variety of cell lines including sarcoma 180, Lewis lung carcinoma, P-388 lymphocytic leukemia, and Walker 256 carcinosarcoma.5" 7 The common central structural feature of these molecules is the 3(2H)-furanone ring which seems to be responsible for the biological action of this class of compounds. Smith and co-workers5 postulated that 1,6 conjugate addition (Michael addition) of bionucleophiles to the 3(2H)furanone ring system could be the basis for the possible mode of action of this class of compounds.…”

Section: Introductionmentioning

confidence: 99%

“…In these studies a simple and efficient synthetic route to 1 was utilized based on a new approach toward isoxazole chemistry;8,9 moreover, modifications of the basic 3(2/f)-furanone ring system were carried out.10 Geiparvarin Jatrophone Eremantholide A: R = iPr B: R = sec-Bu C: R = CMesCHj * Correspondence should be addressed to Professor D. Simoni, Dipartimento di Scienze Farmaceutiche, Universitá di Ferrara, Via Scandiana 21, 44100 Ferrara, Italy. 7 Universita di Ferrara. 1 Universita di Bologna.…”

Section: Introductionmentioning

confidence: 99%

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Geiparvarin analogs. 2. Synthesis and cytostatic activity of 5-(4-arylbutadienyl)-3(2H)-furanones and of N-substituted 3-(4-oxo-2-furanyl)-2-buten-2-yl carbamates

Daniele

Manfredini²,

Tabrizi³

et al. 1991

J. Med. Chem.

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In an attempt to determine some of the structural features of geiparvarin (1) that account for its cytostatic activity in vitro, a series of geiparvarin analogues (10a-i, 1, 12, and 14-16) which contain novel modifications in the region of the olefinic double bond and of the coumarin moiety have been designed and synthesized. Among the derivatives containing a carbamate moiety, only the analogues containing a carbamate group linked to an alkyl moiety 10b-i were endowed with potent cytostatic activity, whereas the corresponding benzene derivative 10a was devoid of any antiproliferative activity. 6-Methoxygeiparvarin 101 proved equally effective as geiparvin (1), while compounds containing an additional double bond at the side chain (12 and 14-16) were invariably 5-100-fold less effective than geiparvarin. Diene derivative 15, bearing a coumarin moiety, was essentially inactive against murine (L1210, FM3A) tumor cells but exhibited good activity against human (Molt/4F, MT-4) tumor cells.

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Hydrogen Bromide

Breton¹,

Kropp²

2001

Encyclopedia of Reagents for Organic Synthesis

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Synthesis of aminoalkylglyoxal derivatives. II. Aminoalkyglyoxal derivatives of _L-alanine, β-alanine, and _L-tyrosine

Cited by 14 publications

References 2 publications

Syntheses Using Pyridinium Salts (IV)

Syntheses Using Pyridinium Salts (IV)

Geiparvarin analogs. 2. Synthesis and cytostatic activity of 5-(4-arylbutadienyl)-3(2H)-furanones and of N-substituted 3-(4-oxo-2-furanyl)-2-buten-2-yl carbamates

Hydrogen Bromide

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Synthesis of aminoalkylglyoxal derivatives. II. Aminoalkyglyoxal derivatives of L-alanine, β-alanine, and L-tyrosine

Cited by 14 publications

References 2 publications

Syntheses Using Pyridinium Salts (IV)

Syntheses Using Pyridinium Salts (IV)

Geiparvarin analogs. 2. Synthesis and cytostatic activity of 5-(4-arylbutadienyl)-3(2H)-furanones and of N-substituted 3-(4-oxo-2-furanyl)-2-buten-2-yl carbamates

Hydrogen Bromide

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Synthesis of aminoalkylglyoxal derivatives. II. Aminoalkyglyoxal derivatives of _L-alanine, β-alanine, and _L-tyrosine