当前位置： SCI文献检索 > JOURNAL OF MEDICINAL CHEMISTRY期刊下所有文献 > New cyclopenta[a]naphthalene derivatives. Synthesis of 2-(carbamylmethyl)-8-hydroxy-3H-cyclopental[a]naphthalene as a possible deoxyribonucleic acid binding agent.

New cyclopenta[a]naphthalene derivatives. Synthesis of 2-(carbamylmethyl)-8-hydroxy-3H-cyclopental[a]naphthalene as a possible deoxyribonucleic acid binding agent.

Abstract：

:8-Methoxy-1-oxo-2,3-dihydro-1H-cyclopenta]a]naphthalene (4) was converted to the oxalyl derivative (7) by treatment with diethyl oxalate in the presence of sodium ethoxide. Compound 7 in the form of the sodium salt was alkylated with ethyl bromoacetate in DMF to 2-(carbethoxymethyl)-8-methoxy-1-oxo-2,3-dihydro-1H-cyclopenta[a]naphthalene (8). Treatment of 8 with methanolic ammonia yielded the corresponding amide (9). Dealkylation of 8 with 48% HBr and subsequent esterification gave compound 10. Ammonolysis of 10 led to the amide 11, which after reduction and subsequent dehydration of the reduced product afforded the desired compound, 2-(carbamylmethyl)-8-hydroxy-3H-cyclopenta[a]naphthalene (2). Compound 2 was found to be mildly growth inhibitory to L1210 and CCRF--CEM leukemic cells in culture. From thermal transition temperature studies, compound 2 was found to bind to calf thymus DNA and the poly(deoxyribonucleotides), e.g., poly(dG).poly(dC), poly(dG-dC), poly(dA).poly(dT), and poly(dA-dT).

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Kundu NG

doi

10.1021/jm00179a008

subject

Has Abstract

pub_date

1980-05-01 00:00:00

pages

512-6

issue

5

eissn

0022-2623

issn

1520-4804

journal_volume

23

pub_type

杂志文章

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