Some N-(β-Substituted Ethyl)-N,N-dibenzylamines

Kaye, Irving Allan; Horn, Herman

doi:10.1021/ja01123a514

Cited by 4 publications

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“…The syntheses of a number of derivatives of 2-aminolepidine have also been reported (481,483,484,486,490). S. Alkylation, arylation, and heterylation of alkylated quinolines The sodium and potassium derivatives of quinaldine (88,492,672) and lepidine (88,197,492) have been condensed with alkyl halides (88, 672), benzyl and nuclear-substituted benzyl halides (88), dialkylaminoalkyl halides (197), and heterocyclic halides (492).…”

Section: /X Zxmentioning

confidence: 98%

“…gives 2-amino-4-methylthiazole (675). CH3 -N sgJcH,C,He 2-Aminothiazole and a number of its A-alkylated derivatives have been alkylated with alkyl, benzyl, and dialkylaminoalkyl halides (483,486,487,490,491). -N…”

Section: Cooc2hsmentioning

confidence: 99%

“…2-Aminopyrimidine (6,259,497, 559, 584), a few nuclear-substituted 2-aminopyrimidines (6, 444, 562), and several A-substituted 2-aminopyrimidines (298,483,486) have been condensed with dialkylaminoalkyl halides (6,298,444,483,486,559,562), benzyl halides (497, 584), thenyl halides (497), and 2-chlorothiazole (259). The reaction of acridine with sodium amide in refluxing dimethylaniline gives 9-aminoacridine (72 per cent) (57).…”

Section: Qch3mentioning

confidence: 99%

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The Chemistry of the Alkali Amides.

Levine¹,

Fernelius²

1954

Chem. Rev.

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This review of the chemistry of the alkali amides is a continuation of two earlier reviews (17) which have appeared on this subject. In the present review the authors have summarized the work on the inorganic and organic chemistry of the alkali amides which has appeared in the literature from 1937 through 1952. In addition, a considerable amount of previously unpublished material is discussed. Whenever possible, the authors have tried to interpret and evaluate critically the material presented and to call attention to those areas of research which have not been investigated or which should be studied further. Although it has not been convenient to discuss all of the present material under the same headings as were used previously, the changes have not been so extensive as to make cross references difficult.

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Section: /X Zxmentioning

confidence: 98%

Section: Cooc2hsmentioning

confidence: 99%

Section: Qch3mentioning

confidence: 99%

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The Chemistry of the Alkali Amides.

Levine¹,

Fernelius²

1954

Chem. Rev.

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Aminopyridines

and¹,

Starker²

1962

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Structure−Activity Relationship of Diaryl Phosphonate Esters as Potent Irreversible Dipeptidyl Peptidase IV Inhibitors

et al. 1999

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The previously reported diphenyl 1-(S)-prolylpyrrolidine-2(R, S)-phosphonate (5) was used as a lead compound for the development of potent and irreversible inhibitors of dipeptidyl peptidase IV (DPP IV, EC 3.4.14.5). The synthesis of a series of diaryl 1-(S)-prolylpyrrolidine-2(R,S)-phosphonates with different substituents on the aryl rings (hydroxyl, methoxy, acylamino, sulfonylamino, ureyl, methoxycarbonyl, and alkylaminocarbonyl) started from the corresponding phosphites. A good correlation was found between the electronic properties of the substituent and the inhibitory activity and stability. The most striking divergence of this correlation was the high potency combined with a high stability of the 4-acetylamino-substituted derivative 11e. This compound shows low cytotoxicity in human peripheral blood mononuclear cells and also has favorable properties in vivo. Therefore bis(4-acetamidophenyl) 1-(S)-prolylpyrrolidine-2(R,S)-phosphonate (11e) is considered as a major improvement and will be a highly valuable DPP IV inhibitor for further studies on the biological function of the enzyme and the therapeutic value of its inhibition.

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Some N-(β-Substituted Ethyl)-N,N-dibenzylamines

Cited by 4 publications

References 0 publications

The Chemistry of the Alkali Amides.

The Chemistry of the Alkali Amides.

Aminopyridines

Structure−Activity Relationship of Diaryl Phosphonate Esters as Potent Irreversible Dipeptidyl Peptidase IV Inhibitors

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