Behavior of Certain Pyridines, Quinolines, and Isoquinolines with Amino or Hydrazino Substituents Toward N-Acylamino Acids Under the Influence of Papain Catalysis

Abernethy, John Leo; Kilday, Warren

doi:10.1021/jo01081a025

Cited by 2 publications

(1 citation statement)

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“…First, the coupling of 5-aminoquinoline (5-AQ) with compound 6 was attempted, but use of DEPC failed to give the desired product. The coupling agent PyBroP was next used under standard conditions, but only starting material ( 6 and 5-AQ) was detected after 100 h. The activity of the aminoquinolines varies with the position of the amino group, 13a,17 and they are in general poor nucleophiles. Therefore, we considered a route involving an activated intermediate preformed from the amino acid.…”

Section: Resultsmentioning

confidence: 99%

Antineoplastic Agents. 592. Highly Effective Cancer Cell Growth Inhibitory Structural Modifications of Dolastatin 10

2011

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The dolastatin series of unique peptides, originally discovered as constituents of the sea hare Dolabella auricularia, is of increasing importance in providing biological leads, especially to new and useful anticancer drugs. Dolastatin 10 and three analogues, minor structural modifications designated auristatins, are currently in human cancer clinical trials. The present study was undertaken to explore delivery to the cancer sites by way of phosphate or quinoline modifications. The initial objectives, auristatin TP as sodium phosphate 3b (GI50 10−2–10−4 μg/mL), auristatin 2-AQ (4, GI50 10−2–10−3 μg/mL), and auristatin 6-AQ (5, GI50 10−4 μg/mL), exhibited superior cancer cell growth inhibitory properties.

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Section: Resultsmentioning

confidence: 99%