37464-90-7Relevant academic research and scientific papers
A SIMPLE SYNTHESIS OF (+/-) 4-DEMETHOXYDAUNOMYCINONE
Rao, Rama A. V.,Deshpande, V. H.,Reddy, Laxma N.
, p. 2661 - 2664 (1980)
A new and simple synthesis of 4-demethoxy-7-deoxydaunomycinone has been carried out essentially in three steps starting from 1,4-dimethoxy-6-tetralone.
Synthesis of anthracyclinone precursor: 5,12-dihydroxy-1,3,4- trihydronaphthacene-2,6,11-quinone
Tririya, Gasirat,Zanger, Murray
, p. 3047 - 3059 (2007/10/03)
Two practical and efficient approaches for preparing large quantities of 5,12-dihydroxy-1,3,4-trihydronaphthacene-2,6,11-quinone 9 are described. Both synthetic approaches involve a simple route with a fewer number of steps and utilize readily available and inexpensive starting materials. Large-scale production of this precursor may prove to be useful for further research involving the synthesis of antineoplastic anthracyclines and development of their analogs with increased activity and decreased toxicity.
Baker's Yeast Mediated Reduction of Aromatic Ring Substituted 2-Tetralones
Manitto, Paolo,Speranza, Giovanna,Monti, Diego,Fontana, Gabriele,Panosetti, Elisa
, p. 11531 - 11546 (2007/10/02)
2-Tetralones mono- and disubstituted with methoxy or hydroxy groups in the aromatic ring are hydrogenated to 2-tetralols in good yields by non-fermenting baker's yeast.The prevalent enantioform of the reduction product and its e.e. were found to depend on the substitution pattern.In one case, i.e. the biotransformation of 5-methoxy-2-tetralone into the corresponding 2-tetralol, an e.e. >/= 98percent was observed.A simple abstract model for explaining and predicting the stereochemical outcome in the yeast-mediated carbonyl reduction of 2-tetralones is proposed.
Synthesis and adrenergic properties of new duplicated analogs of methoxamine
Perez,Rosell,Mauleon,Carganico
, p. 1155 - 1166 (2007/10/02)
New duplicated analogs of the α1-selective agonist methoxamine and of its cyclic derivative 5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthylamine have been synthesized and tested for their adrenergic properties. All the compounds prepared, presenting a polymethylene spacer of varying length between two units of the active structure, turned out to be completely devoid of any α-stimulating activity. Surprisingly, some of them showed a marked β-adrenergic agonistic effect, being the most interesting compound active at nanomolar concentration.
P-aminophenols, derivatives thereof and method of use
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, (2008/06/13)
p-Aminophenols are provided having the structure STR1 wherein m is 0, 1 or 2; n is 0, 1, 2 or 3; R1 and R2 may be the same or different and are H, hydroxy or alkoxy; R3 is H, lower alkyl, alkanoyl or aroyl and R4 is H, lower alkyl or alkanoyl, and including acid-addition salts thereof. These compounds are useful as inhibitors of leukotriene production and as such are useful as antiallergy, anti-inflammatory and anti-psoriatic agents.
Model Studies for an Asymmetric Synthesis of (+)-4-Demethoxydaunomycinone
Mehendale, A. R.,Kulkarni, Alpana,Nagarajan, Geeta
, p. 305 - 307 (2007/10/02)
2-Hydroxymethyl-5,8-dimethoxy-3,4-dihydronaphthalene (II) on t-butyl hydroperoxide oxidation followed by LAH reduction gives 2-hydroxy-2-hydroxymethyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene (IVa) in 85percent yield.The corresponding O-benzyl derivate (VI) on PDC oxidation affords 2-benzyloxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthyl-2-aldehyde (VII), which on Grignard reaction with methylmagnesium iodide followed by PDC oxidation affords the desired (+/-)-2-acetyl-2-O-benzyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene (IXa) in 70percent yield.Friedel-Crafts condensation of IXa with phthalic anhydride in the presence of AlCl3-NaCl melt furnishes (+/-)-4-demethoxy-7-deoxydaunomycinone (Ia) in 74percent yield, which on 7-hydroxylation affords the desired (+/-)-4-demethoxydaunomycinone (Ib) in 40percent yield.
Simple Preparation of β-Tetralones and β-Indanones by a 1,2-Carbonyl Group Transposition
Braun, Manfred,Bernhard, Carlo
, p. 435 - 437 (2007/10/02)
By a four-step procedure, the ketones 3 are converted into the β-tetralones 7a-d and the β-indanones 7e, f via the intermediates 4, 5, and 6.
8-Hydroxy-2-(alkylamino)tetralins and related compounds as central 5-hydroxytryptamine receptor agonists
Arvidsson,Hacksell,Johansson,Nilsson,Lindberg,Sanchez,Wikstroem,Svensson,Hjorth,Carlsson
, p. 45 - 51 (2007/10/02)
A series of 2-(alkylamino)tetralins related to 8-hydroxy-2-(di-n-propylamino)tetralin (21) were prepared and tested as dopamine (DA) and 5-hydroxytryptamine (5-HT) receptor agonists. Several of the compounds were potent 5-HT agonists devoid of DA-mimetic effects. N-Ethyl or N-propyl substitution of 8-hydroxy-2-aminotetralin gave the most potent agonists. It was shown that the most potent compound, (+)-21, has the 2R configuration. 5,8-Dimethoxy-2-(di-n-propylamino)tetralin (31) was found to be a weak DA agonist devoid of 5-HT activity. The corresponding indan derivative, 4,7-dimethoxy-2-(di-n-propylamino)indan (39), has been reported to be active on both DA and 5-HT receptors. The 5-HT-stimulating properties of compounds 21 and 39 as compared to the incapability of compound 31 to activate the 5-HT receptor is tentatively explained by the assumed mode of binding of the compounds to the 5-HT receptor.
