GLYOXYL ANALOGS OF INDOLE PHYTOALEXINS: SYNTHESIS AND ANTICANCER ACTIVITY

KUTSCHY, Peter; Andrej SÝKORA; Zuzana ČURILLOVÁ; Mária REPOVSKÁ; Martina PILÁTOVÁ; Ján MOJŽIŠ; Roman MEZENCEV; Pavel PAZDERA a Tatiana HROMJÁKOVÁ. GLYOXYL ANALOGS OF INDOLE PHYTOALEXINS: SYNTHESIS AND ANTICANCER ACTIVITY. Collection of Czechoslovak Chemical Communications. Prague: Inst Org Chem Biochem Czech Acad Sci, 2010, roč. 75, č. 8, s. 887–903, 12 s. ISSN 0010-0765.

Základní údaje

Originální název

GLYOXYL ANALOGS OF INDOLE PHYTOALEXINS: SYNTHESIS AND ANTICANCER ACTIVITY

Název česky

GLYOXYL ANALOGS OF INDOLE PHYTOALEXINS: SYNTHESIS AND ANTICANCER ACTIVITY

Autoři

KUTSCHY, Peter (703 Slovensko); Andrej SÝKORA (703 Slovensko); Zuzana ČURILLOVÁ (703 Slovensko); Mária REPOVSKÁ (703 Slovensko); Martina PILÁTOVÁ (703 Slovensko); Ján MOJŽIŠ (703 Slovensko); Roman MEZENCEV (703 Slovensko); Pavel PAZDERA (203 Česká republika, garant, domácí) a Tatiana HROMJÁKOVÁ (703 Slovensko)

Vydání

Collection of Czechoslovak Chemical Communications, Prague, Inst Org Chem Biochem Czech Acad Sci, 2010, 0010-0765

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Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Česká republika

Utajení

není předmětem státního či obchodního tajemství

Impakt faktor

Impact factor: 0.853

Kód RIV

RIV/00216224:14310/10:00044943

Organizační jednotka

Přírodovědecká fakulta

UT WoS

000281958400008

Klíčová slova česky

Heterocycles; Indoles; Natural products; Phytoalexins; Glyoxylindoles;

Klíčová slova anglicky

Heterocycles; Indoles; Natural products; Phytoalexins; Glyoxylindoles;

Příznaky

Mezinárodní význam, Recenzováno

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Anotace

V originále

Glyoxyl analogs of indole phytoalexins brassinin, 1-methoxybrassinin, brassitin, 1-methoxybrassitin and 1-methoxybrassenin B were prepared, using (1H-indol-3-yl)-, (1-methoxyindol- 3-yl)- and [1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indol-3-yl]glyoxyl chlorides as starting compounds. Synthesized products were examined for their antiproliferative activity against human cancer cell lines Jurkat (T-cell acute lymphoblastic leukemia), MCF-7 (breast adenocarcinoma, estrogen receptor-positive), MDA-MB-231 (breast adenocarcinoma, estrogen receptor-negative), HeLa (cervical adenocarcinoma), CCRF-CEM cell line (T-cell acute lymphoblastic leukemia) and A-549 cell line (lung adenocarcinoma), and their activity compared with natural phytoalexins and corresponding (1H-indol-3-yl)acetic acid derivatives. The highest potency with IC50 3.3-66.1 mímol l-1 was found for glyoxyl analogs of 1-methoxybrassenin B.

Česky

Glyoxyl analogs of indole phytoalexins brassinin, 1-methoxybrassinin, brassitin, 1-methoxybrassitin and 1-methoxybrassenin B were prepared, using (1H-indol-3-yl)-, (1-methoxyindol- 3-yl)- and [1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indol-3-yl]glyoxyl chlorides as starting compounds. Synthesized products were examined for their antiproliferative activity against human cancer cell lines Jurkat (T-cell acute lymphoblastic leukemia), MCF-7 (breast adenocarcinoma, estrogen receptor-positive), MDA-MB-231 (breast adenocarcinoma, estrogen receptor-negative), HeLa (cervical adenocarcinoma), CCRF-CEM cell line (T-cell acute lymphoblastic leukemia) and A-549 cell line (lung adenocarcinoma), and their activity compared with natural phytoalexins and corresponding (1H-indol-3-yl)acetic acid derivatives. The highest potency with IC50 3.3-66.1 mímol l-1 was found for glyoxyl analogs of 1-methoxybrassenin B.