Preparation of cyclic acetals and gem-dichlorocyclopropanes based on 1,2-dichloromethylbenzol

2021 ◽  
pp. 121-126
Author(s):  
Sh.Sh. Dzhumaev ◽  
◽  
Y.G. Borisova ◽  
G.Z. Raskil’dina ◽  
R.R. Daminev ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Cell Lines ◽  
Allyl Alcohol ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Research Database ◽  
Cyclic Acetals ◽  
Mcf 7 ◽  
Catamine Ab

Using 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane (sol-ketal) and 1,2-dichlomethylbenzene under the conditions of phase transfer catalysis, mono- and diesters containing cycloacetal fragments were synthesized. Also, with the help of dichloride, in the presence of benzene, mono- and diesters of allyl alcohol were obtained. Dichlorocyclopropanation of unsaturated ethers using chloroform, alkali and catamine AB catalyst made it possible to obtain compounds containing gem-dichlorocyclopropane fragments. O-alkylation of the sol-ketal with 1-[(alloxy)methyl]-2-(chloromethyl)benzene (mono-derivative of allyl alcohol) was used to synthesize an ether combining in its structure 1,3-dioxolane and gem-dichlorocyclopropane fragments simultaneously. The obtained substances were analyzed and confirmed by mass spectrometry («Chromatek-Kristall» instrument with Nist research database) and NMR spectroscopy («Bruker instrument»). It was found that among a number of compounds obtained, only 4-{[(2-{[(2,2-dichlorocyclopropyl) methoxy]methyl}-benzyl)oxy] methyl}-2,2-dimethyl-1,3-dioxolane exhibits cytological activity against the cell lines HEK293, SH-SY5Y, MCF-7 and A549.

scholarly journals Carbidopa Alters Tryptophan Metabolism in Breast Cancer and Melanoma Cells Leading to the Formation of Indole-3-Acetonitrile, a Pro-Proliferative Metabolite

Biomolecules ◽  
2019 ◽  
Vol 9 (9) ◽  
pp. 409
Author(s):  
Diana Duarte ◽  
Filipa Amaro ◽  
Isabel Silva ◽  
Dany Silva ◽  
Paula Fresco ◽  
...  
Keyword(s):  
Breast Cancer ◽  
Mass Spectrometry ◽  
Liquid Chromatography ◽  
Cell Lines ◽  
Lower Incidence ◽  
Metabolic Profile ◽  
Dopa Decarboxylase ◽  
Breast Cancers ◽  
Mcf 7 ◽  
A375 Cells

Carbidopa is used for the treatment of Parkinson’s disease (PD) as an inhibitor of DOPA decarboxylase, and PD patients taking carbidopa have a lower incidence of various tumors, except for breast cancer and melanoma. Recently, it was shown that carbidopa inhibits tryptophan-2,3-dioxygenase (TDO) and kynureninase enzymes. In the present study, the effect of carbidopa on the viability and metabolic profile of breast cancer MCF-7 and melanoma A375 cells was investigated. Carbidopa was not effective in inhibiting MCF-7 and A375 proliferation. Liquid chromatography and mass spectrometry revealed a new compound, identified as indole-3-acetonitrile (IAN), which promoted a concentration-dependent increase in the viability of both cell lines. The results suggest that treatment with carbidopa may alter tryptophan (Trp) metabolism in breast cancer and melanoma leading to the formation of a pro-proliferative Trp metabolite, which may contribute to its failure in reducing breast cancers and melanoma incidence in PD patients taking carbidopa.

scholarly journals A New Tocopherol Derivative and Cytotoxicity from the Leaves of Dalbergia velutina

2018 ◽  
Vol 13 (12) ◽  
pp. 1934578X1801301
Author(s):  
Sutin Kaennakam ◽  
Thammarat Aree ◽  
Kitiya Rassamee ◽  
Pongpun Siripong ◽  
Santi Tip-pyang
Keyword(s):  
Nmr Spectroscopy ◽  
Cell Lines ◽  
Cancer Cell ◽  
Spectroscopic Analysis ◽  
Cancer Cell Lines ◽  
The Absolute ◽  
Ht 29 ◽  
Mcf 7

A new tocopherol derivative, named (+)-α-tocuspirone (1), along with eleven known compounds, including six tocopherol derivatives (2–7) and five triterpenes (8–12) were isolated from the leaves of Dalbergia velutina. Their structures were determined by spectroscopic analysis especially NMR spectroscopy. The absolute configurations of 1 and 2 were assigned by NOESY experiments and ECD calculations. All isolated compounds were evaluated for their cytotoxicity against five cancer cell lines (KB, HeLa S-3, HT-29, MCF-7 and HepG-2). Dioslupecin A (10) showed potent cytotoxicity against all the five cancer cell lines with IC50 values in the range of 0.28–2.05 μM. In addition, caffeoxylupeol (12) showed potent cytotoxicity against KB cell with an IC50 value of 2.28 μM.

scholarly journals Acanthomine A, a new Pyrimidine-β-Carboline Alkaloid from the Sponge Acanthostrongylophora Ingens

2008 ◽  
Vol 3 (2) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Sabrin R. M. Ibrahim ◽  
RuAngelie Ebel ◽  
Rainer Ebel ◽  
Peter Proksch
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Ethyl Acetate ◽  
Cytotoxic Activity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Brine Shrimp ◽  
Ethyl Acetate Extract ◽  
Cancer Cell Lines ◽  
Chemical Investigation

Chemical investigation of the ethyl acetate extract of the sponge Acanthostrongylophora ingens afford one new pyrimidine-β-carboline alkaloid named acanthomine A (2), together with two known compounds annomontine (1) and 1,2,3,4-tetrahydronorharman-1-one (3). Their structures were unambiguously established on the basis of NMR spectroscopy (1H, 13C, 1H-1H COSY, HMQC and HMBC) and mass spectrometry. The isolated compounds were tested for cytotoxic activity using brine shrimp bioassay and different cancer cell lines.

scholarly journals Isolation and Structure Elucidation of Secondary Metabolites From an Endophytic Fungus Annulohypoxylon ilanense

2019 ◽  
Vol 14 (9) ◽  
pp. 1934578X1985790 ◽  
Author(s):  
Ming-Jen Cheng ◽  
Shuen-Shin Yang ◽  
Ming-Der Wu ◽  
Hsun-Hsuo Chang ◽  
Yueh-Hsiung Kuo ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Cell Lines ◽  
Endophytic Fungus ◽  
Structure Elucidation ◽  
Soluble Fraction ◽  
Mass Spectrometric ◽  
Ionization Mass ◽  
Cytotoxic Effects ◽  
Mcf 7

Fractionation of the EtOAc-soluble fraction of the liquid fermentation of an endophytic fungus Annulohypoxylon ilanense associated with the wood of medicinal plant Cinnamomum species resulted in the isolation of 1 new α-pyrone, ilanpyrone (1), along with 3 previously identified compounds, 2 to 4. Their structures were elucidated by means of spectroscopic and mass-spectrometric analyses, especially 1D and 2D nuclear magnetic resonance (NMR) spectroscopy as well as high-resolution electrospray ionization mass spectrometry. The isolated compounds were tested for their cytotoxicity against MCF-7, NCI-H460, and SF-268 cell lines using the MTT assay. Among them, compounds 1 and 4 were found to have moderate-to-weak cytotoxic effects against these 3 cell lines in vitro.

scholarly journals Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis

2020 ◽  
Vol 70 (2) ◽  
pp. 161-178 ◽  
Author(s):  
Yaser A. El-Badry ◽  
Mahr A. El-Hashash ◽  
Khalil Al-Ali
Keyword(s):  
Antitumor Activity ◽  
Cell Lines ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Human Tumor ◽  
Human Tumor Cell ◽  
Human Tumor Cell Lines ◽  
Solvent Free Conditions ◽  
Modest Activity

AbstractA series of nine new 2,3-disubstituted 4(3H)-quinazolin-4-one derivatives was furnished starting from the 2-propyl-4(3H)-quinazo-line-4-one (2). The reinvestigation of the key starting quinazolinone 2 was performed under microwave irradiation (MW) and solvent-free conditions. Combination of MW and phase-transfer catalysis using tetrabutylammonium benzoate (TBAB) as a novel neutral ionic catalyst was used for carrying out N-alkylation and condensation reactions of compound 2 as a simple, efficient and eco-friendly technique. The structure of the synthesized compounds was elucidated using different spectral and chemical analyses. In vitro antimicrobial activity of the compounds was investigated against four bacterial and two fungal strains; very modest activity was achieved. Some of the synthesized compounds were screened for their antitumor activity against different human tumor cell lines. The screened compounds exhibited a significant antitumor activity on some of the cancer cell lines, melanoma (SK-MEL-2), ovarian cancer (IGROV1), renal cancer (TK-10), prostate cancer (PC-3), breast cancer (MCF7) and colon cancer (HT29). The most active, even more active than the reference 5-fluorouracil, were found to be ethyl 4-[(4-oxo-2-propylquinazolin-3(4H)-yl)methyl]benzoate (3c), 3-{2-[6-(pyrrolidin-1-yl-sulfonyl)-1,2,3,4-tetrahydroquinoline]-2-oxoethyl}-2-propylquinazolin--4(3H)-one (3e), N’-[(E)-(2H-1,3-benzodioxo-5-yl)methylidene]-2-(4-oxo-2-propylquinazolin-3(4H)-yl)acetohydrazide (10a), N’-[(E)-(4-hydroxyphenyl)methylidene]-2-(4-oxo-2-propylquinazo-lin-3(4H) -yl)acetohydrazide (10b) and N’-[(E)-(4-nitrophenyl)methyl idene]-2-(4-oxo-2-propylquinazolin-3(4H)-yl)acetohydrazide (10c).

Xanthones from Polygala alpestris (Rchb.)

2004 ◽  
Vol 59 (5-6) ◽  
pp. 335-338 ◽  
Author(s):  
Stefano Dall’Acquaa ◽  
Giampietro Viola ◽  
Elsa Mariella Cappelletti ◽  
Gabbriella Innocenti
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
High Resolution ◽  
Tumor Cell ◽  
Cytotoxic Activity ◽  
Cell Lines ◽  
High Resolution Mass Spectrometry ◽  
Tumor Cell Lines ◽  
High Resolution Mass ◽  
Resolution Mass

Bioactivity-guided fractionation of Polygala alpestris L. (Rchb.) extracts led to the identification of two new xanthones, 1,3,7-trihydroxy-2,6-dimethoxyxanthone (1) and 2,3-methylenedioxy-4,7-dihydroxyxanthone (2). In addition five known compounds 3,4-dimethoxy-1,7-dihydroxyxanthone (3), 1,3-dihydroxy-7-methoxyxanthone (4), 1,7-dihydroxy-2,3-dimethoxyxanthone (5), 3′,6-O-disinapoyl sucrose (6) and 3′,5′-dimethoxybiphenyl-4-olo (7) were isolated. The structures of the isolated compounds were established by means of high resolution mass spectrometry, mono- and bi-dimensional NMR spectroscopy. All isolated compounds were tested for cytotoxic activity against three tumor cell lines (LoVo, HL-60, K 562).

scholarly journals Synthesis of alkyl-gem-dichlorocyclopropanes based on isoamylene fraction

2021 ◽  
Vol 15 (6) ◽  
pp. 9-15
Author(s):  
A. I. Musin ◽  
Yu. G. Borisova ◽  
G. Z. Raskil’dina ◽  
R. R. Daminev ◽  
R. U. Rabaev ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Nmr Spectroscopy ◽  
Quantitative Composition ◽  
Gas Liquid Chromatography ◽  
Qualitative And Quantitative ◽  
Hardware Complex ◽  
Complex Mass ◽  
Gasliquid Chromatography ◽  
Catamine Ab

Objectives. The study aims to analyze the dichlorocarbenation of the isoamylene fraction, which is a mixture of 2-methyl-butene-1 and 2-methyl-butene-2, in order to obtain the corresponding alkyl-gem-dichlorocyclopropanes in quantitative yield, and also to determine their structure.Methods. In order to determine the qualitative and quantitative composition of the reaction masses, the following analysis methods were used: gas-liquid chromatography (using the Crystal 2000 hardware complex), mass spectrometry (using a Chromatec-Crystal 5000M device with NIST 2012 database), and nuclear magnetic resonance (NMR) spectroscopy (using a Bruker AM-500 device at operating frequencies of 500 and 125 MHz).Results. Alkyl-gem-dichlorocyclopropanes were synthesized from an isoamylene fraction in the presence of catamine AB as a catalyst. Alternatively, isomeric alkenyl-gem-dichlorocyclopropanes were obtained on the basis of isoprene, and by reduction, the corresponding alkyl-gemdichlorocyclopropanes were synthesized. The synthesized substances were analyzed by gasliquid chromatography, mass spectrometry, and NMR spectroscopy, as previously mentioned above.Conclusions. The results show that the dichlorocyclopropanation of the isoamylene fraction proceeds quantitatively with the formation of a mixture of 2-methyl-2-ethyl-1,1dichlorocyclopropane and 2,3,3-trimethyl-1,1-dichlorocyclopropane. Using isoprene, countersynthesis through successive dichlorocarbenation and hydrogenation was used to synthesize 2-methyl-2-ethyl-1,1-dichlorocyclopropane, one of the products of dichlorocarbenation of the isoamylene fraction.

scholarly journals Antitumor, antibiotic and antileishmanial properties of the Pyranonaphthoquinone Psychorubrin from Mitracarpus frigidus

2012 ◽  
Vol 84 (4) ◽  
pp. 1081-1090 ◽  
Author(s):  
Rodrigo L. Fabri ◽  
Richard M. Grazul ◽  
Lidiane O. de Carvalho ◽  
Elaine S. Coimbra ◽  
Gabriele M.M. Cardoso ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Antimicrobial Activity ◽  
Biological Activity ◽  
Tumor Cell ◽  
Cell Lines ◽  
Leishmania Species ◽  
Antitumor Antibiotic ◽  
Tumor Cell Lines ◽  
Vis Spectroscopy ◽  
Mcf 7

The bioactivity guided fractionation of the dichloromethane extract of Mitracarpus frigidus afforded the pyranonaphthoquinone psychorubrin. This compound, hitherto unknown in the genus Mitracarpus, had its biological activity evaluated against one panel of bacteria and two fungi, three tumor cell lines (HL60, Jurkat and MCF-7) and four Leishmania species. Its identity was confirmed unambiguously by ¹H, 13C, ¹H-COSY, IR and UV-Vis spectroscopy and mass spectrometry. Psychorubrin displayed a very promising antitumor with IC50 of 4.5, 5.6 and 1.1 µM for HL60, Jurkat and MCF-7 cell lines, respectively. Antimicrobial activity, mainly against Cryptococcus neoformans (MIC of 87.3 µM) was observed. A pronounced antileishmanial potential was also verified with IC50 varying from 1.7 to 2.7 µM for the Leishmania species tested. This is the first report of the presence of pyranonapthoquinones in the Mitracarpus genus, which may serve as a chemotaxonomical marker.

scholarly journals Synthesis of ethers containing 1,3-dioxolane and gem-dichlorocyclopropane fragments

2021 ◽  
Vol 16 (2) ◽  
pp. 156-166
Author(s):  
Sh. Sh. Dzhumaev ◽  
Yu. G. Borisova ◽  
G. Z. Raskil’dina ◽  
U. Sh. Kuzmina ◽  
R. R. Daminev ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Magnetic Resonance Spectroscopy ◽  
Nuclear Magnetic Resonance Spectroscopy ◽  
Cell Lines ◽  
A549 Cell ◽  
Resonance Spectroscopy ◽  
Mcf 7 ◽  
Nuclear Magnetic

Objectives. This study aimed to obtain ethers containing gem-dichlorocyclopropane and 1,3-dioxolane fragments and evaluate their cytotoxic properties against HEK293, SH-SY5Y, MCF-7, and A549 cell lines.Methods. The qualitative and quantitative compositions of the reaction masses were determined using mass spectrometry (using a Chromatek-Kristall 5000M device with the 2012 National Institute of Standards and Technology, USA database) and nuclear magnetic resonance spectroscopy (using a Bruker AM-500 device with operating frequencies of 500 and 125 MHz).Results. Ethers containing gem-dichlorocyclopropane and 1,3-dioxolane fragments were synthesized in the presence of a catamine AB catalyst. The structures of the obtained substances were confirmed using gas-liquid chromatography, mass spectrometry, and nuclear magnetic resonance spectroscopy. The cytotoxicity of the esters was studied against HEK293, SH-SY5Y, MCF-7, and A549 cell lines.Conclusions. Ethers containing gem-dichlorocyclopropane and 1,3-dioxolane fragments were obtained in quantitative yields; however, only 4-{[(2,2-dichloro-3-{[(2,2-dichlorocyclopropyl) methoxy]methyl}cyclopropyl)methoxy]methyl}-2,2-dimethyl-1,3-dioxolane exhibited cytotoxic activity against HEK293, SH-SY5Y, MCF-7, and A549 cell lines. 

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