Substituted tetralins I: Synthesis and Analgesic Activities of Some 2-Aminotetralins

Martin, Arnold R.; Parulkar, Anilkumar P.; Gusseck, David J.; Anderson, Leray J.; Grunewald, Gary L.; White, A. I.

doi:10.1002/jps.2600580312

Cited by 17 publications

(10 citation statements)

References 15 publications

(2 reference statements)

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“…2 the unit cell. The relative configuration assigned previously (Martin et al, 1969) was easily verified. The absolute configuration in Fig.…”

supporting

confidence: 56%

“…Martin, 1973), was shown to be correct when it gave an R factor of 0-038 compared with 0-041 for the other enantiomer. As the other three stereoisomers have been unambiguously correlated with this one (Martin et al, 1969;Kandeel & Martin, 1973), their configurations are also verified. The most potent analgetic of the four [(-)-(Ia)] is thus the one most closely related to morphine in structure.…”

mentioning

confidence: 54%

“…In connection with our continuing interest in aminotetralins as potential analgetics of the morphine type (Martin, Parulkar, Gusseck, Anderson, Grunewald & White, 1969;Kandeel & Martin, 1973;Galpin, Kandeel & Martin, 1978), we have sought to determine the stereochemical and conformational relationships among the N,N-dimethyl-4-methyl-4-phenyl-l,2,3,4-tetrahydro-2-naphthylamines (I). The two racemates, (+)-(Ia) and (+)-(Ib), exhibit analgetic potency similar to codeine in mice (Kandeel & Martin, 1973).…”

mentioning

confidence: 99%

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Absolute configurations of the stereoisomeric N,N-dimethyl-4-methyl-4-phenyl-1,2,3,4-tetrahydro-2-naphthylamines

Arora¹,

Bates²,

Kriek³

et al. 1979

Acta Crystallogr Sect B

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“…2 the unit cell. The relative configuration assigned previously (Martin et al, 1969) was easily verified. The absolute configuration in Fig.…”

supporting

confidence: 56%

mentioning

confidence: 54%

mentioning

confidence: 99%

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Absolute configurations of the stereoisomeric N,N-dimethyl-4-methyl-4-phenyl-1,2,3,4-tetrahydro-2-naphthylamines

Arora¹,

Bates²,

Kriek³

et al. 1979

Acta Crystallogr Sect B

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“…Thus, the starting material chosen for the sequence was m-methoxy- 1 Substitution of an oxygen function in the 6-position of the tetralin system corresponds to a 3-oxygen function in the morphine series. hydratroponitrile (IV), which was prepared by the procedure of Kugita and Oine (4).…”

Section: Methodsmentioning

confidence: 99%

“…A fivestep sequence, beginning with a glyoxylation and ending with a Curtius reaction (26% overall yield), has been described previously (1). A more direct route, the isonitrosation of 1 -tetralones followed by a catalytic reduction using the methods of Kindler and Peschke (2) and Rosenmund and Karg (3), appeared to be more suitable for the preparation of 4-carbonyl-2-aminotetralins.…”

Section: I1mentioning

confidence: 99%

Substituted Tetralins II: Preparation of 2-Amino-4-carbamyl-6-methoxy-4-methyltetralin

Green

Martin

White

1970

Journal of Pharmaceutical Sciences

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Derivate des 2‐Amino‐1,2,3,4‐tetrahydronaphthalins. I. Synthese einiger N‐substituierter trans‐2‐Amino‐3‐hydroxy‐1,2,3,4‐tetrahydronaphthaline

Dantchev¹,

Ivanov²

1974

Archiv der Pharmazie

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Derivate des 2-Amino-I ,2,3,4-tetrahydronaphthalins I. S ynthese einiger N-substituierter trans-2-Amino-3-hydroxy-1,2,3,4-tetrahydronaphthaline Durch Ankniipfung einiger Aminoalkohole, Aminophenole, Aminosiuren und cyclischer Amine an das 2,3-Epoxytetralin wurden 10 neue N-substituierte trans-2-Arnino-3-hydroxy-l.2,3,4tetrahydronaphthaline (1-10) erhalten. Beim Erhitzen der Xthyleniminbase 9 bildet sich das Dimer 11. Die Konfiguration dieser Verbindungen wird erortert.Derivatives of 2-Amino-1,2,3,4-tetrahydronaphthalene. I. Synthesis of Some N-Substituted trans-2-Amino-3-hydroxy 1,2,3,4-tetrahydronaphthalenes By addition of some aminoalcohols, aminophenoh, amino acids and cyclic amines 2,3-epoxytetralin, ten new N-substituted trans-2-amino-3-hydroxy-l,2,3,4-tctrahydronaphthalenes (1 -10) are obtained. The heating of the ethyleneimine base 9 leads to its dimer 11. The configuration of these compounds is discussed.

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Substituted tetralins I: Synthesis and Analgesic Activities of Some 2-Aminotetralins

Cited by 17 publications

References 15 publications

Absolute configurations of the stereoisomeric N,N-dimethyl-4-methyl-4-phenyl-1,2,3,4-tetrahydro-2-naphthylamines

Absolute configurations of the stereoisomeric N,N-dimethyl-4-methyl-4-phenyl-1,2,3,4-tetrahydro-2-naphthylamines

Substituted Tetralins II: Preparation of 2-Amino-4-carbamyl-6-methoxy-4-methyltetralin

Derivate des 2‐Amino‐1,2,3,4‐tetrahydronaphthalins. I. Synthese einiger N‐substituierter trans‐2‐Amino‐3‐hydroxy‐1,2,3,4‐tetrahydronaphthaline

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