New Synthetic Chalcones: Cytotoxic Mannich Bases of 6-(4-Chlorocinnamoyl)-2(3H)-benzoxazolone

Petrov, Ognyan; Ivanova, Yordanka; Momekov, Georgi; Kalcheva, V.

doi:10.2174/157018008785777342

Cited by 8 publications

(5 citation statements)

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“…20), which had high to moderate cytotoxicity (IC 50 between 5 and 40 mM) towards human pre-B-cell leukemia cell line BV-173 and chronic myeloid leukemia K-562, and appear to exert their cytotoxic action at least in part through induction of apoptosis [128]. Replacement of the methoxy substituent in compounds 100 with chlorine led to a marginal improvement of IC 50 values [129]. A series of Mannich bases 101 Fig.…”

Section: Anticancer and Cytotoxic Activitymentioning

confidence: 99%

Mannich bases in medicinal chemistry and drug design

Roman¹

2015

European Journal of Medicinal Chemistry

271

110

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The biological activity of Mannich bases, a structurally heterogeneous class of chemical compounds that are generated from various substrates through the introduction of an aminomethyl function by means of the Mannich reaction, is surveyed, with emphasis on the relationship between structure and biological activity. The review covers extensively the literature reports that have disclosed Mannich bases as anticancer and cytotoxic agents, or compounds with potential antibacterial and antifungal activity in the last decade. The most relevant studies on the activity of Mannich bases as antimycobacterial agents, antimalarials, or antiviral candidates have been included as well. The review contains also a thorough coverage of anticonvulsant, anti-inflammatory, analgesic and antioxidant activities of Mannich bases. In addition, several minor biological activities of Mannich bases, such as their ability to regulate blood pressure or inhibit platelet aggregation, their antiparasitic and anti-ulcer effects, as well as their use as agents for the treatment of mental disorders have been presented. The review gives in the end a brief overview of the potential of Mannich bases as inhibitors of various enzymes or ligands for several receptors.

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Section: Anticancer and Cytotoxic Activitymentioning

confidence: 99%

Mannich bases in medicinal chemistry and drug design

Roman¹

2015

European Journal of Medicinal Chemistry

271

110

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“…The (E)-3-methyl-6-(3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-en-1-yl)-2(3H)-benzothiazolone, was synthesized both by an acid-and base-catalyzed aldol condensation of 3-methyl-2(3H)benzothiazolone-6-carbaldehyde and 3,4,5-trimethoxyacetophenone, as presented in Scheme 1. The Claisen-Schmidt condensation was carried out in ethanol in the presence of aqueous KOH and the acid-catalyzed condensation was performed using SOCl 2 /EtOH [11,12]. The reactions were monitored using thin-layer chromatography.…”

Section: Resultsmentioning

confidence: 99%

“…A series of heterocyclic chalcones containing an oxazole or a thiazole cycle were synthesized by this method. The compounds displayed good cytotoxic activity against BV-173, MCF-7 and MDA-MB-231 cells in an MTT-dye reduction assay [8][9][10][11][12]. Especially promising results were obtained with chalcones that contained a fused azole cycle on ring A and more than one methoxy group on ring B.…”

Section: Introductionmentioning

confidence: 99%

(E)-3-Methyl-6-(3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-en-1-yl)-2(3H)-benzothiazolone

Ivanova

Gerova

Chanev

et al. 2016

Molbank

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“…In continuation of our previous studies on the synthesis of heterocyclic chalcone derivatives with benzoxazolone [5] or benzothiazolone ring [6][7][8], in this work we report the preparation of a novel (E)-3-methyl-6-(3-oxo-3-(thiophen-2-yl)-1-propenyl)-2(3H)-benzothiazolone. The compound consists of thiophene and benzothiazolone heterocycles, connected via α,β-unsaturated carbonyl system, a key framework of chalcones.…”

Section: Introductionmentioning

confidence: 91%