Synthetic fibrinolytic agents. 1. N-Monoacyl, N-monoalkyl, and related bis(tetrahydroisoquinolines)

Buchanan, R. L.; Sprancmanis, V.; Jenks, T. A.; Crenshaw, R. R.; Luke, G. M.; Holava, Henry M.; Partyka, R. A.

doi:10.1021/jm00258a002

Cited by 6 publications

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“…1,1'-Tetramethylenebis(4,9-dihy dro-6-methoxy-3.fipyrido [3,[4][5][6]indole) (12) Dihydrochloride. A mixture of 8.50 g (0.0173 mol) of 10 and 64 ml of POCI3 was refluxed with stirring for 15 min.…”

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Synthesis and evaluation of 1,.omega.-diaryl-1,.omega.-alkanediamines related to the fibrinolytic bis(tetrahydroisoquinolines) and bis(benzylamines)

Fliedner¹,

Myers²,

Schor³

et al. 1976

J. Med. Chem.

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Since the previously investigated bis(tetrahydroisoquinolines) 1 and bis(benzylamines) 2 may be classified as 1,omega-diaryl-1,omega-alkanediamines, it appeared worthwhile to examine this structural concept as a guideline for predicting significant fibrinolytic activity. The prototype bis compounds 7, 14, 15, and 29-31, which were synthesized for this purpose, incorporate such molecular modifications as replacement of the tetrahydroisoquinoline nuclei of series 1 with tetrahydrobenzazepine (7) and tetrahydropyridoindole (14-15) nuclei. The latter compounds, as well as 29-31 which possess features common to both series 1 and 2, showed good to moderate activity in the standard rat (ip) screen. Significant departures from the 1,omega-diaryl-1,omega-alkanediamine structural concept led to compounds (35 and 40) of weak to moderate activity.

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“…Anal. l,l'-Tetramethylenebis(2,3,4,9-tetrahydro-6-methoxylff-pyrido [3,[4][5][6]indole) ( 14) Dihydrochloride. To a suspension of 6.50 g (0.0112 mol) of the above dihydrochloride salt of 12 in 500 ml of hot (70°) EtOH, H20 (total ca.…”

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confidence: 99%