Linked Life Data

11975545

Source:http://linkedlifedata.com/resource/pubmed/id/11975545

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
9
pubmed:dateCreated
2002-4-26
pubmed:abstractText
A number of substituted 9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrones have been synthesized and their anticancer and antimalarial activities evaluated. A one-pot synthesis of 2,5,8-trimethoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4-dione (4) was achieved by heating a mixture of 1,4-dimethoxyanthracene, methoxyhydroquinone, silver oxide, and zinc iodide in toluene. Regioselective bromination of 4 and 2-methoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrone (7) with N-bromosuccinimide provided 2-bromo-3,5,8-trimethoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4-dione and 2-bromo-3-methoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrone (1), respectively. The reactions of 1 with aliphatic primary amines and secondary amines, respectively, produced different products, a result most likely attributed to the different basicities (or nucleophilicities) and steric effects of the two kinds of amines. The structure of the displacement product, 2-bromo-3-[2-(tert-butoxycarbonyl)ethylamino]-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrone, from the reaction of 1 with tert-butyl 3-aminopropanoate was unequivocally determined by a single-crystal X-ray analysis. IC(50) values of triptycene bisquinones for the inhibition of L1210 leukemia cell viability are in the 0.11-0.27 microM range and for the inhibition of Plasmodium falciparum 3D7 are in the 4.7-8.0 microM range.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
May
pubmed:issn
0022-3263
pubmed:author
pubmed:issnType
Print
pubmed:day
3
pubmed:volume
67
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
2907-12
pubmed:dateRevised
2007-11-14
pubmed:meshHeading
pubmed-meshheading:11975545-Amines, pubmed-meshheading:11975545-Animals, pubmed-meshheading:11975545-Antimalarials, pubmed-meshheading:11975545-Antineoplastic Agents, pubmed-meshheading:11975545-Benz(a)Anthracenes, pubmed-meshheading:11975545-Catalysis, pubmed-meshheading:11975545-Crystallography, X-Ray, pubmed-meshheading:11975545-Drug Screening Assays, Antitumor, pubmed-meshheading:11975545-Hydrocarbons, Brominated, pubmed-meshheading:11975545-Inhibitory Concentration 50, pubmed-meshheading:11975545-Leukemia, pubmed-meshheading:11975545-Mice, pubmed-meshheading:11975545-Molecular Conformation, pubmed-meshheading:11975545-Molecular Structure, pubmed-meshheading:11975545-Plasmodium falciparum, pubmed-meshheading:11975545-Structure-Activity Relationship, pubmed-meshheading:11975545-Tumor Cells, Cultured
pubmed:year
2002
pubmed:articleTitle
Syntheses and bioactivities of substituted 9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrones. Unusual reactivities with amines.
pubmed:affiliation
Department of Chemistry, Kansas State University, Manhattan, Kansas 66506, USA. duy@ksu.edu
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, P.H.S., Research Support, U.S. Gov't, Non-P.H.S., Research Support, Non-U.S. Gov't