Cytotoxic Mannich bases of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones

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

doi:10.1016/j.ejmech.2007.02.019

Cited by 62 publications

(54 citation statements)

References 15 publications

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“…These compounds reacted with various amines (piperidine in 1a, 2a, 3a; morpholine in 1b, 2b, 3b; Nmethylpiperazine in 1c, 2c, 3c) and paraformaldehyde to produce the corresponding bis Mannich bases (1a, 1b, 1c, 2a, 2b, 2c, 3a, 3b, 3c). Chemical structures of the compounds were confirmed by 1 H NMR, 13 C NMR, and HRMS spectra. 1 H NMR spectra of the compounds confirmed that amino methylation occured in the ortho positions to aryl hydroxy group and olefinic double bond assumed the E configuration (J ¼ 15.4-15.7 Hz) (see Supplementary File).…”

Section: Resultsmentioning

confidence: 87%

“…Melting points were determined using an Electrothermal 9100/IA9100 (Bibby Scientific Limited, Staffordshire, UK) instrument and are uncorrected. Chemical structures of the compounds were determined by 1 H NMR (400 MHz) and 13 C NMR (100 MHz) spectroscopies using a Varian Mercury Plus spectrometer (Varian Inc., Palo Alto, CA). Chemical shifts (d) are reported in ppm, and coupling constants (J) are expressed in hertz (Hz); HRMS-ESI Mass spectra were recorded on HPLC-TOF Waters Micromass LCT Premier XE (Waters Corporation, Milford, MA).…”

Section: Methodsmentioning

confidence: 99%

“…Cytotoxic chalcones and their analogs that interact with thiols which are not found in nucleic acids may be devoid of the side effects of certain anticancer drugs which interact with the hydroxy and amino groups of DNA and RNA 2,11,12 . Mechanisms of anticancer effects of chalcones appear to be complex and frequently multimodal and include cell cycle disruption, inhibition of angiogenesis, inhibition of tubulin polymerization, induction of apoptosis, inhibition of topoisomerase, and inhibition of kinases [13][14][15][16] . Mannich bases are generally formed by the reaction between a compound containing a reactive hydrogen atom, formaldehyde, and mostly secondary amine 2,17 .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and bioactivities of halogen bearing phenolic chalcones and their corresponding bis Mannich bases

Yamalı

Gül

Sakagami

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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Phenolic bis Mannich bases having the chemical structure of 1-[3,5-bis-aminomethyl-4-hydroxyphenyl]-3-(4-halogenophenyl)-2-propen-1-ones (1a-c, 2a-c, 3a-c) were synthesized (Numbers 1, 2, and 3 represent fluorine, chlorine, and bromine bearing compounds, respectively, while a, b, and c letters represent the compounds having piperidine, morpholine, and N-methyl piperazine) and their cytotoxic and carbonic anhydrase (CA, EC 4.2.1.1) enzyme inhibitory effects were evaluated. Lead compounds should possess both marked cytotoxic potencies and selective toxicity for tumors. To reflect this potency, PSE values of the compounds were calculated. According to PSE values, the compounds 2b and 3b may serve as lead molecules for further anticancer drug candidate developments. Although the compounds showed a low inhibition potency toward hCA I (25-43%) and hCA II (6-25%) isoforms at 10 mM concentration of inhibitor, the compounds were more selective (1.5-5.2 times) toward hCA I isoenzyme. It seems that the compounds need molecular modifications for the development of better CA inhibitors.

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Section: Resultsmentioning

confidence: 87%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and bioactivities of halogen bearing phenolic chalcones and their corresponding bis Mannich bases

Yamalı

Gül

Sakagami

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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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: 99%

(E)-3-Methyl-6-(3-oxo-3-(thiophen-2-yl)-1-propenyl)-2(3H)-benzothiazolone

Ivanova

Gerova

Chanev

et al. 2016

Molbank

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“…Selected Mannich bases induced programmed cell death in BV-173 at a concentration of 2.5 μM as evidenced by the encountered DNAladdering 34 .…”

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confidence: 99%

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2012

IJPSR

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Chalcones are 1, 3-diphenyl-2-propene-1-one, consist of two aromatic rings linked by a three carbon α, β-unsaturated carbonyl system. The chemistry of chalcones has generated intensive scientific studies throughout the world. Especially interest has been focused on the synthesis and biodynamic activities of chalcones. These are considered to be precursors of flavonoids and isoflavonoids. The aim of this review is to summarize chalcones and their diverse pharmacological activities like anticancer, antimicrobial, analgesic and antiviral activities etc.

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Cytotoxic Mannich bases of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones

Cited by 62 publications

References 15 publications

Synthesis and bioactivities of halogen bearing phenolic chalcones and their corresponding bis Mannich bases

Synthesis and bioactivities of halogen bearing phenolic chalcones and their corresponding bis Mannich bases

(E)-3-Methyl-6-(3-oxo-3-(thiophen-2-yl)-1-propenyl)-2(3H)-benzothiazolone

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