New thiophene substituted 10-deazaaminopterins: synthesis and biological evaluation.
Analogues of 10-deazaaminopterin (10-DAM) and 4-amino-4-deoxy-10-deazapteroyl-gamma-methylene glutamic acid (MDAM) in which the benzene ring was replaced with a thiophene ring have been synthesized and evaluated for their antitumor activity. These analogues were N-([5-(2,4-diamino-6-pteridinyl)ethyl]-2-thenoyl)-L- glutamic acid (1) and N-([5-(2,4-diamino-6-pteridinyl)ethyl]-2-thenoyl)-gamma-meth ylene glutamic acid (2).
Abraham
A
A
University of South Alabama, Mobile 36688.
McGuire
J J
JJ
Galivan
J
J
Vishnuvajjala
B R
BR
Nair
M G
MG
D000630:Aminopterin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology / Q000633:toxicity; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology / Q000633:toxicity*; D002455:Cell Division / Q000187:drug effects; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D004353:Drug Evaluation, Preclinical; D005260:Female; D005493:Folic Acid Antagonists / Q000494:pharmacology* / Q000633:toxicity*; D005971:Glutamates / Q000494:pharmacology / Q000633:toxicity*; D006801:Humans; D008297:Male; D008727:Methotrexate / Q000633:toxicity; D051379:Mice; D011622:Pterins / Q000494:pharmacology / Q000633:toxicity*; D051381:Rats; D013329:Structure-Activity Relationship; D013876:Thiophenes; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D005493:Folic Acid Antagonists; D005971:Glutamates; C085589:N-((5-(2,4-diamino-6-pteridinyl)-ethyl)-2-thenoyl)-gamma-methyleneglutamic acid; C085588:N-((5-(2,4-diamino-6-pteridinyl)ethyl)-2-thenoyl)glutamic acid; D011622:Pterins; D013876:Thiophenes; D000630:Aminopterin; C017178:10-deazaaminopterin; D008727:Methotrexate