Brasan aus Naphthalin

Abstract

0.1347 g Sbst.: 025S g,COr, 0.0379 g HsO. -0.1071 g Sbst.: 0 ccni N. C1,HlsO,As. Ber. C 52.17, H 4.66, N 0. Gef. D 51.67, D 4.77, D 0. 402. St. v. Kostanecki und V. Lampe: Brasan auB Naphthalln.Vor fiinf Jahren haben K o s t a n e c k i und L l o y d ' ) ein Umwandlungsprodukt der Muttersubstmz des Brasilins, das sogenannte B r as a n , beschrieben, dem sie auf Grund der Brasilinforrnel von F e u e rs t e i n und K o s t a n e c k i die Formel des B&Phenylen-naphthylen-oxyds (1) zuerteilt haben : 1) Diese Berichte 36, 2193 [1903j. a) Eine Besprechung der Bemerkungen Herzigs (Monatah. fur Chem. Y5, 875 [1904]) iiber die Arbeiten von Kostanecki nnd Lloyd halten wir nach wie vor fir zwecklos. 3) Kostanecki und Rost, diese Berichte 36, 2202 [1903]. 4) Kostanecki und Lampe, diese Berichte 41, 1333 [1908].

Design of antineoplastic agents on the basis of the 2-phenylnaphthalene-type structural pattern. 2. Synthesis and biological activity studies of benzo[b]naphtho[2,3-d]furan-6,11-dione derivatives

“…It is of interest to note that for quite a number of these compounds, which demonstrated inhibitory activity against SCLC, similar activity was also observed against the SCLC/ CDDP lines. This indicates that many compounds of this series are equally active against both the cisplatin-sensitive and cisplatin-resistant lines, which implies that these banzo [6]naphtho [2,3-d]furan-6,ll-dione derivatives do not exhibit cross-resistance with cisplatin against the smallcell lung cancer lines.…”

“…The hydroxyl function plays an important role with regard to biological activity. l,3-Dihydroxybenzo [6]naphtho [2,3-d]furan-6,11-dione (5b), which contains two hydroxyl functions, exhibited very good inhibitory activity against SCLC and SCLC/CDDP strains, and demonstrated higher topoisomerase II-mediated DNA cleavage than the anticancer agent teniposide (VM-26). However, the DNA cleavage pattern induced by compounds of this series is different from that induced by VM-26.…”

“…Anal. (CigHg04) C, H. l,3-Dihydroxybenzo [6]naphtho [2,3-d]furan-6,l 1-dione (5b). To a stirred solution of 315 mL of MeOH containing 12.6 g (0.225 mol) of KOH was added portionwise at 30 °C 10.2 g (0.045 mol) of powdered 2,3-dichloro-l,4-naphthoquinone (3).…”

“…5-Hydroxydimphtho[2,l-fc2,,3,-d]furan-8,13-dione (6). This compound was prepared from 5.3 g of 3 and 5.0 g of 1,3dihydroxynaphthalene in a manner similar to that for the preparation of 5a in 85% yield, mp > 300 °C.…”

Heterocyclic Quinones from 2,3-Dichloro-1,4-naphthoquinone.

“…Without offering substantial evidence, structure IX was preferred by Liebermann (48) first and by Kostanecky and Lampe (43) later. The accuracy of this choice was confirmed by Chatterjea (24), who prepared the methoxy derivative XI by an unambiguous route and found that the properties of XI are the same as those of the product obtained by alkylation of IX (43).…”