1,4-disubstituted anthracene antitumor agents

Bhashyam S. Iyengar, Robert T Dorr, David S Alberts, Anikó M. Sólyom, Mary Krutzsch, William A. Remers

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Three different types of 1,4-disubstituted anthracenes were synthesized, and their cytotoxicity in a panel of tumor cells was compared with that of the corresponding 9,10-disubstituted anthracenes. The panel contained human myeloma, melanoma, colon, and lung cancer cells and sensitive and multidrug- resistant murine L1210 leukemia cells. These compounds had [[(dimethylamino)ethyl]amino]methyl, N-[(dimethylamino)ethyl]carbamoyl, and carboxaldehyde (4,5-dihydro-1H-imidazol-2-yl)hydrazone side chains. The 1,4- diamide was more potent across the tumor panel than the corresponding 9,10- isomer, but the 1,4-diamine and the 1,4-hydrazone were less potent than their 9,10-isomers. Although the 1,4-hydrazone was active against P388 leukemia in mice, it was inactive against L1210 leukemia. Within each pair of compounds, the one with greater average potency against tumor cells gave a greater increase in the transition melt temperature of DNA.

Original languageEnglish (US)
Pages (from-to)3734-3738
Number of pages5
JournalJournal of Medicinal Chemistry
Volume40
Issue number23
DOIs
StatePublished - 1997

Fingerprint

Hydrazones
Anthracenes
Antineoplastic Agents
Tumors
Cells
Leukemia L1210
Isomers
Diamide
Diamines
Leukemia P388
Cytotoxicity
Neoplasms
Transition Temperature
Colonic Neoplasms
Melanoma
Lung Neoplasms
DNA
anthracene
Temperature

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Iyengar, B. S., Dorr, R. T., Alberts, D. S., Sólyom, A. M., Krutzsch, M., & Remers, W. A. (1997). 1,4-disubstituted anthracene antitumor agents. Journal of Medicinal Chemistry, 40(23), 3734-3738. https://doi.org/10.1021/jm970308+

1,4-disubstituted anthracene antitumor agents. / Iyengar, Bhashyam S.; Dorr, Robert T; Alberts, David S; Sólyom, Anikó M.; Krutzsch, Mary; Remers, William A.

In: Journal of Medicinal Chemistry, Vol. 40, No. 23, 1997, p. 3734-3738.

Research output: Contribution to journalArticle

Iyengar, BS, Dorr, RT, Alberts, DS, Sólyom, AM, Krutzsch, M & Remers, WA 1997, '1,4-disubstituted anthracene antitumor agents', Journal of Medicinal Chemistry, vol. 40, no. 23, pp. 3734-3738. https://doi.org/10.1021/jm970308+
Iyengar, Bhashyam S. ; Dorr, Robert T ; Alberts, David S ; Sólyom, Anikó M. ; Krutzsch, Mary ; Remers, William A. / 1,4-disubstituted anthracene antitumor agents. In: Journal of Medicinal Chemistry. 1997 ; Vol. 40, No. 23. pp. 3734-3738.
@article{bf3e48b6521442f2a17814e283a04fa3,
title = "1,4-disubstituted anthracene antitumor agents",
abstract = "Three different types of 1,4-disubstituted anthracenes were synthesized, and their cytotoxicity in a panel of tumor cells was compared with that of the corresponding 9,10-disubstituted anthracenes. The panel contained human myeloma, melanoma, colon, and lung cancer cells and sensitive and multidrug- resistant murine L1210 leukemia cells. These compounds had [[(dimethylamino)ethyl]amino]methyl, N-[(dimethylamino)ethyl]carbamoyl, and carboxaldehyde (4,5-dihydro-1H-imidazol-2-yl)hydrazone side chains. The 1,4- diamide was more potent across the tumor panel than the corresponding 9,10- isomer, but the 1,4-diamine and the 1,4-hydrazone were less potent than their 9,10-isomers. Although the 1,4-hydrazone was active against P388 leukemia in mice, it was inactive against L1210 leukemia. Within each pair of compounds, the one with greater average potency against tumor cells gave a greater increase in the transition melt temperature of DNA.",
author = "Iyengar, {Bhashyam S.} and Dorr, {Robert T} and Alberts, {David S} and S{\'o}lyom, {Anik{\'o} M.} and Mary Krutzsch and Remers, {William A.}",
year = "1997",
doi = "10.1021/jm970308+",
language = "English (US)",
volume = "40",
pages = "3734--3738",
journal = "Journal of Medicinal Chemistry",
issn = "0022-2623",
publisher = "American Chemical Society",
number = "23",

}

TY - JOUR

T1 - 1,4-disubstituted anthracene antitumor agents

AU - Iyengar, Bhashyam S.

AU - Dorr, Robert T

AU - Alberts, David S

AU - Sólyom, Anikó M.

AU - Krutzsch, Mary

AU - Remers, William A.

PY - 1997

Y1 - 1997

N2 - Three different types of 1,4-disubstituted anthracenes were synthesized, and their cytotoxicity in a panel of tumor cells was compared with that of the corresponding 9,10-disubstituted anthracenes. The panel contained human myeloma, melanoma, colon, and lung cancer cells and sensitive and multidrug- resistant murine L1210 leukemia cells. These compounds had [[(dimethylamino)ethyl]amino]methyl, N-[(dimethylamino)ethyl]carbamoyl, and carboxaldehyde (4,5-dihydro-1H-imidazol-2-yl)hydrazone side chains. The 1,4- diamide was more potent across the tumor panel than the corresponding 9,10- isomer, but the 1,4-diamine and the 1,4-hydrazone were less potent than their 9,10-isomers. Although the 1,4-hydrazone was active against P388 leukemia in mice, it was inactive against L1210 leukemia. Within each pair of compounds, the one with greater average potency against tumor cells gave a greater increase in the transition melt temperature of DNA.

AB - Three different types of 1,4-disubstituted anthracenes were synthesized, and their cytotoxicity in a panel of tumor cells was compared with that of the corresponding 9,10-disubstituted anthracenes. The panel contained human myeloma, melanoma, colon, and lung cancer cells and sensitive and multidrug- resistant murine L1210 leukemia cells. These compounds had [[(dimethylamino)ethyl]amino]methyl, N-[(dimethylamino)ethyl]carbamoyl, and carboxaldehyde (4,5-dihydro-1H-imidazol-2-yl)hydrazone side chains. The 1,4- diamide was more potent across the tumor panel than the corresponding 9,10- isomer, but the 1,4-diamine and the 1,4-hydrazone were less potent than their 9,10-isomers. Although the 1,4-hydrazone was active against P388 leukemia in mice, it was inactive against L1210 leukemia. Within each pair of compounds, the one with greater average potency against tumor cells gave a greater increase in the transition melt temperature of DNA.

UR - http://www.scopus.com/inward/record.url?scp=0030729479&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0030729479&partnerID=8YFLogxK

U2 - 10.1021/jm970308+

DO - 10.1021/jm970308+

M3 - Article

C2 - 9371238

AN - SCOPUS:0030729479

VL - 40

SP - 3734

EP - 3738

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

SN - 0022-2623

IS - 23

ER -