C-Formylation of Some 2(3H)-Benzazolones and 2H-1,4-Benzoxazin-3(4H)-one

Petrov, Ognyan; Kalcheva, V.; Antonova, Antonina

doi:10.1135/cccc19970494

Cited by 8 publications

(4 citation statements)

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“…Methoxy substituted benzaldehydes 5-8 are commercially available and inexpensive. As previously described by us [35], 3-methyl-2(3H)-benzothiazolone-6-carbaldehyde (9) was obtained by Duff reaction. The main challenge was the synthesis of the phosphonium Methoxy substituted benzaldehydes 5-8 are commercially available and inexpensive.…”

Section: Chemistrymentioning

confidence: 99%

“…The main challenge was the synthesis of the phosphonium Methoxy substituted benzaldehydes 5-8 are commercially available and inexpensive. As previously described by us [35], 3-methyl-2(3H)-benzothiazolone-6-carbaldehyde (9) was obtained by Duff reaction. The main challenge was the synthesis of the phosphonium salts 11-13, obtained in three steps from the corresponding 4-, 5-, or 6-methyl-2(3H)-benzothiazolones 28-30 (Scheme 2).…”

Section: Chemistrymentioning

confidence: 99%

“…Path B. Following the general procedure 4.1.6., diastereomers 26Z and 26E were obtained by reaction of (3,4,5-trimethoxybenzyl)triphenylphosphonium bromide (14) [74] and 3-methyl-2(3H)-benzothiazolone-6-carbaldehyde (9) [35]. Separation by flash column chromatography afforded pure stilbenes 26Z (40% yield) and 26E (36% yield).…”

Section: General Procedures For the Stilbene Syntheses 15-27mentioning

confidence: 99%

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New Heterocyclic Combretastatin A-4 Analogs: Synthesis and Biological Activity of Styryl-2(3H)-benzothiazolones

et al. 2021

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Here, we describe the synthesis, characterization, and biological activities of a series of 26 new styryl-2(3H)-benzothiazolone analogs of combretastatin-A4 (CA-4). The cytotoxic activities of these compounds were tested in several cell lines (EA.hy926, A549, BEAS-2B, MDA-MB-231, HT-29, MCF-7, and MCF-10A), and the relations between structure and cytotoxicity are discussed. From the series, compound (Z)-3-methyl-6-(3,4,5-trimethoxystyryl)-2(3H)-benzothiazolone (26Z) exhibits the most potent cytotoxic activity (IC50 0.13 ± 0.01 µM) against EA.hy926 cells. 26Z not only inhibits vasculogenesis but also disrupts pre-existing vasculature. 26Z is a microtubule-modulating agent and inhibits a spectrum of angiogenic events in EA.hy926 cells by interfering with endothelial cell invasion, migration, and proliferation. 26Z also shows anti-proliferative activity in CA-4 resistant cells with the following IC50 values: HT-29 (0.008 ± 0.001 µM), MDA-MB-231 (1.35 ± 0.42 µM), and MCF-7 (2.42 ± 0.48 µM). Cell-cycle phase-specific experiments show that 26Z treatment results in G2/M arrest and mitotic spindle multipolarity, suggesting that drug-induced centrosome amplification could promote cell death. Some 26Z-treated adherent cells undergo aberrant cytokinesis, resulting in aneuploidy that perhaps contributes to drug-induced cell death. These data indicate that spindle multipolarity induction by 26Z has an exciting chemotherapeutic potential that merits further investigation.

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Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: General Procedures For the Stilbene Syntheses 15-27mentioning

confidence: 99%

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New Heterocyclic Combretastatin A-4 Analogs: Synthesis and Biological Activity of Styryl-2(3H)-benzothiazolones

et al. 2021

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“…3-Methyl-2(3H)-benzothiazolone-6-carbaldehyde (1) was synthesized as described previously [9]. Reactions were monitored by thin-layer chromatography (TLC) on silica gel plates (Kieselgel 60 F 254 ) using hexane/acetone (2:1 v/v) as eluent.…”

Section: General Informationmentioning

confidence: 99%