Über Derivate des Amino‐2‐pyridins, des Amino‐2‐chinolins und des Amino‐4‐chinolins. Aus dem chemischen Universitätslaboratorium Erlangen

Diepolder, E.; Dachlauer, K.; Deuerlein, E.; Wölfel, E.

doi:10.1002/prac.19231060105

Cited by 12 publications

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References 7 publications

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“…Moreover, we did not succeed in converting this aminoquinoline to the corresponding isothiocyanate, a potential intermediate to biguanide derivatives (1, 2). These failures may be attributed to the distinct character of the 4-amino group in the quinoline nucleus (3,4,5,6).…”

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BIGUANIDE AND THIOUREA DERIVATIVES OF QUINOLINE¹

May¹,

Mosettig²

1947

J. Org. Chem.

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The outstanding value, as antimalarials, of Chloroquin2 and Plasmochin3 on the one hand and the exceedingly interesting properties, in experimental and clinical malaria, of Paludrine4 on the other, prompted us to attempt the synthesis of drugs carrying a biguanidyl group in place of the side chain in Chloroquin and Plasmochin. In view of the low toxicity of Paludrine and of its analogs in the phenanthrene series (1, 2), one could reasonably expect a similar property in the planned compounds.Many attempts, under varied conditions, to induce 4-amino-7-chloroquinoline to react with cyanoguanidine or isopropylcyanoguanidine failed. Moreover, we did not succeed in converting this aminoquinoline to the corresponding isothiocyanate, a potential intermediate to biguanide derivatives (1, 2). These failures may be attributed to the distinct character of the 4-amino group in the quinoline nucleus (3,4,5,6).

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“…7-Chloro-4-(4-diethylamino-l-methylbutylamino)quinoline 3. 6-Methoxy-8-(4-diethylamino-l-methylbutylamino)quinoline 4. l-(p-ChIorophenyl)-5-isopropylbiguanide 6.…”

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