Molbank

Open AccessShort Note

N′-(3-Bromo-7-oxo-7H-benzo[de]anthracen-9-yl)-N,N-dimethylimidoformamide

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Molbank 2022, 2022(1), M1323; https://doi.org/10.3390/M1323 - 25 Jan 2022

Abstract

We report a synthesis of 3-bromo-9-N′-(N,N-dimethylformamidino)benzanthrone in good yield by a condensation reaction of 3-bromo-9-aminobenzanthrone with dimethylformamide in the presence of phosphorous oxychloride. The structure of the synthesized amidine was characterized by FTIR-ATR, NMR experiments, and elemental analysis. The [...] Read more.

We report a synthesis of 3-bromo-9-N′-(N,N-dimethylformamidino)benzanthrone in good yield by a condensation reaction of 3-bromo-9-aminobenzanthrone with dimethylformamide in the presence of phosphorous oxychloride. The structure of the synthesized amidine was characterized by FTIR-ATR, NMR experiments, and elemental analysis. The title compound was analyzed by UV-Vis and fluorescence spectroscopy in various organic solvents. Full article

(This article belongs to the Section Organic Synthesis)

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Figure 1

Open AccessCommunication

Reaction of 4,5-Dichloro-1,2,3-dithiazolium Chloride with 2-(Phenylsulfonyl)acetonitrile

by

Konstantinos Plakas

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Andreas S. Kalogirou

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Andreas Kourtellaris

and

Panayiotis A. Koutentis

Molbank 2022, 2022(1), M1322; https://doi.org/10.3390/M1322 - 24 Jan 2022

Abstract

The reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with 2-(phenylsulfonyl)acetonitrile (1 equiv) in the presence of pyridine (2 equiv) gave S-(3-chloro-5-cyanoisothiazol-4-yl)benzenesulfonothioate and (Z)-2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-2-(phenylsulfonyl)acetonitrile in 19% and 23% yield, respectively. The compounds were fully characterized and the mechanistic rationale is proposed for [...] Read more.

The reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with 2-(phenylsulfonyl)acetonitrile (1 equiv) in the presence of pyridine (2 equiv) gave S-(3-chloro-5-cyanoisothiazol-4-yl)benzenesulfonothioate and (Z)-2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-2-(phenylsulfonyl)acetonitrile in 19% and 23% yield, respectively. The compounds were fully characterized and the mechanistic rationale is proposed for the formation of the benzensulfonate. Full article

(This article belongs to the Section Organic Synthesis)

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Figure 1

Open AccessCommunication

Reactions of 4H-1,2,6-Thiadiazine Sulfides

by

Andreas S. Kalogirou

and

Panayiotis A. Koutentis

Molbank 2022, 2022(1), M1321; https://doi.org/10.3390/M1321 - 21 Jan 2022

Abstract

3,5-Dichloro-4H-1,2,6-thiadiazin-4-one reacts with benzo[d]thiazole-2-thiol (1 equiv) and triethylamine (1 equiv) to give 3-(benzo[d]thiazol-2-ylthio)-5-chloro-4H-1,2,6-thiadiazin-4-one in 71% yield. The reactivity of this compound with methoxide is explored and compared with that of 3-chloro-5-(phenylthio)-4H-1,2,6-thiadiazin-4-one. Full article

(This article belongs to the Section Organic Synthesis)

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Figure 1

Open AccessShort Note

2,6-exo-8,10-exo-4-Butyl-9-oxa-4-azatetracyclo[5.3.1.0^2,6.0^8,10]undecane-3,5-dione

by

R. Alan Aitken

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Fiona M. Fotherby

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Alexandra M. Z. Slawin

Molbank 2022, 2022(1), M1320; https://doi.org/10.3390/M1320 - 20 Jan 2022

Abstract

The title epoxide was obtained by spontaneous epoxidation of the corresponding unsaturated imide in air or by peracid oxidation. Unambiguous assignment of the ¹H- and ¹³C-NMR spectra is achieved by comparison between analogous compounds and its X-ray structure confirms the exo,exo-configuration. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessShort Note

(±)-2-(2-Fluoro-[1,1′-biphenyl]-4-yl)-N-(1-phenylpropan-2-yl)propanamide

by

Stanimir Manolov

,

Iliyan Ivanov

and

Dimitar Bojilov

Molbank 2022, 2022(1), M1319; https://doi.org/10.3390/M1319 - 17 Jan 2022

Abstract

2-(2-fluoro-[1,1′-biphenyl]-4-yl)-N-(1-phenylpropan-2-yl)propanamide was synthesized by a reaction between amphetamine and flurbiprofen in high yields. The newly obtained hybrid molecule was fully analyzed and characterized via ¹H, ¹³C, UV, IR, HPLC, and mass spectral data. Full article

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Graphical abstract

Open AccessShort Note

1,3-Dimethyl-3′,5-diphenyl-1,5-dihydro-2H,5′H-spiro[furo[2,3-d]pyrimidine-6,4′-isoxazole]-2,4,5′(3H)-trione

by

Yuliya E. Ryzhkova

,

Varvara M. Kalashnikova

,

Fedor V. Ryzhkov

and

Michail N. Elinson

Molbank 2022, 2022(1), M1317; https://doi.org/10.3390/M1317 - 14 Jan 2022

Abstract

Michael addition–halogenation–intramolecular ring-closing (MHIRC) reactions are processes in which a halogen atom as a leaving group can attach to substrates or reactants during the reaction, which then undergoes intramolecular ring closure. In this communication the MHIRC transformation of 4-benzylidene-3-phenylisoxazol-5(4H)-one and 1,3-dimethylbarbituric [...] Read more.

Michael addition–halogenation–intramolecular ring-closing (MHIRC) reactions are processes in which a halogen atom as a leaving group can attach to substrates or reactants during the reaction, which then undergoes intramolecular ring closure. In this communication the MHIRC transformation of 4-benzylidene-3-phenylisoxazol-5(4H)-one and 1,3-dimethylbarbituric acid in the presence of N-bromosuccinimide and sodium acetate in EtOH at room temperature was carefully investigated to give novel 1,3-dimethyl-3′,5-diphenyl-1,5-dihydro-2H,5′H-spiro[furo[2,3-d]pyrimi- dine-6,4′-isoxazole]-2,4,5′(3H)-trione in a good yield. The structure of the new compound was confirmed by the results of elemental analysis as well as mass, nuclear magnetic resonance, and infrared spectroscopy. Full article

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Graphical abstract

Open AccessShort Note

2,2′-(Ethane-1,2-diyl)bis(4-chlorophenol)

by

R. Alan Aitken

,

Anna L. G. Gidlow

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Russel S. Ramsewak

and

Alexandra M. Z. Slawin

Molbank 2022, 2022(1), M1318; https://doi.org/10.3390/M1318 - 14 Jan 2022

Abstract

The X-ray structure of the title compound, obtained as a byproduct in a natural product synthesis, has been determined and shows an unusual pattern featuring chains of molecules with both intra- and intermolecular hydrogen bonding of the OH groups. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

Open AccessCommunication

Synthesis, Crystal Structure and Cyclic Voltammetric Behavior of N-aroyl-N′-(4′-cyanophenyl)thioureas

by

Fatma Aydin

and

N. Burcu Arslan

Molbank 2022, 2022(1), M1316; https://doi.org/10.3390/M1316 - 14 Jan 2022

Abstract

Herein, two title compounds, N-benzoyl-N′-(4′-cyanophenyl)thiourea (1) and N-(4-nitrobenzoyl)-N′-(4′-cyanophenyl)thiourea (2) were synthesized in a high yield, via different applications of aroyl isocyanate and 4-aminobenzonitrile. The structure of the prepared compounds was characterized by elemental [...] Read more.

Herein, two title compounds, N-benzoyl-N′-(4′-cyanophenyl)thiourea (1) and N-(4-nitrobenzoyl)-N′-(4′-cyanophenyl)thiourea (2) were synthesized in a high yield, via different applications of aroyl isocyanate and 4-aminobenzonitrile. The structure of the prepared compounds was characterized by elemental analysis and FT-IR, ¹H, and ¹³C-NMR spectroscopic methods. The crystal structure of the title compound 1 was determined by an X-ray single-crystal technique and an intramolecular C=O…H-N hydrogen bond and intermolecular C=S…H-N and C=S…H-C hydrogen interactions, which were observed for the crystal structure. The molecular electrostatic potential (MEP) and the Mulliken atomic charges of title compounds 1 and 2 were theoretically calculated and interpreted. Cyclic voltammetric (CV) experiments for the compounds were performed with the glassy carbon electrode. The reduction in potential values of the different functional groups such as nitro and cyano in title compounds were investigated using CV curves. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessShort Note

(E)-1-(3-Benzoyl-4-phenyl-1H-pyrrol-1-yl)-3-phenylprop-2-en-1-one

by

Viola Noti

and

Dimitra Hadjipavlou-Litina

Molbank 2022, 2022(1), M1314; https://doi.org/10.3390/M1314 - 13 Jan 2022

Abstract

Over the last decade, there has been an increasing effort to fight inflammatory conditions establishing new multitarget approaches. Chronic inflammation is implicated in many multifactorial diseases, constituting a great economic burden and a chronic health problem. In an attempt to develop new potent [...] Read more.

Over the last decade, there has been an increasing effort to fight inflammatory conditions establishing new multitarget approaches. Chronic inflammation is implicated in many multifactorial diseases, constituting a great economic burden and a chronic health problem. In an attempt to develop new potent multifunctional anti-inflammatory agents, a cinnamic-pyrrole hybrid (6) was synthesized and screened for its antioxidant and anti-Lipoxygenase potential. The new compound, in comparison with its pyrrole precursor (4), showed improved biological activities. In silico calculations were performed to predict its drug-likeness. The examined derivative is considered orally bioavailable according to Lipinski’s rule of five. Compound 6 could be used as a lead for the synthesis of more effective hybrids. Full article

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Figure 1

Open AccessShort Note

2-(2-(4-Methoxyphenyl)furo[3,2-h]quinolin-3-yl)acetic Acid

by

Boris V. Lichitsky

,

Andrey N. Komogortsev

and

Valeriya G. Melekhina

Molbank 2022, 2022(1), M1315; https://doi.org/10.3390/M1315 - 13 Jan 2022

Abstract

A simple and efficient protocol for the synthesis of the previously unknown 2-(2-(4-methoxyphenyl)furo[3,2-h]quinolin-3-yl)acetic acid was elaborated. The suggested method is based on the telescoped multicomponent reaction of 8-hydroxyquinoline, 4-methylglyoxal, and Meldrum’s acid. The studied process includes the initial interaction of the [...] Read more.

A simple and efficient protocol for the synthesis of the previously unknown 2-(2-(4-methoxyphenyl)furo[3,2-h]quinolin-3-yl)acetic acid was elaborated. The suggested method is based on the telescoped multicomponent reaction of 8-hydroxyquinoline, 4-methylglyoxal, and Meldrum’s acid. The studied process includes the initial interaction of the starting compounds in MeCN followed by intramolecular cyclization to the target product in refluxing acetic acid. The advantage of this approach is the application of readily available starting materials, atom economy, and a simple work-up procedure. The structure of the synthesized furylacetic acid derivative was proven by ¹H, ¹³C, 2D-NMR, IR spectroscopy, and high-resolution mass spectrometry. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessEditorial

Synthesis of Flavonoids or Other Nature-Inspired Small Molecules

by

Giovanni Ribaudo

Molbank 2022, 2022(1), M1313; https://doi.org/10.3390/M1313 - 10 Jan 2022

Abstract

Natural compounds are endowed with an intriguing variety of scaffolds, functional groups and stereochemical properties [...] Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

Open AccessCommunication

2-(4-(Dimethylamino)phenyl)-3,3-difluoro-4,6-diphenyl-3,4-dihydro-1,2,4,5,3-tetrazaborinin-2-ium-3-ide

by

Ida A. Lupanova

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Dzhamilya N. Konshina

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Nikita A. Elkov

and

Valery V. Konshin

Molbank 2022, 2022(1), M1312; https://doi.org/10.3390/M1312 - 31 Dec 2021

Abstract

Reaction of 1-(4-(dimethylamino)phenyl)-3,5-diphenylformazane with boron trifluoride diethyl etherate (5 equiv) in the presence of triethylamine (3 equiv) in toluene medium gave “boratetrazine”—2-(4-(dimethylamino)phenyl)-3,3-difluoro-4,6-diphenyl-3,4-dihydro -1,2,4,5,3-tetrazaborinin-2-ium-3-ide in a 58% yield. Full article

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Figure 1

Open AccessCommunication

Synthesis and Characterisation of 1,1′-{[3,5-Bis(dodecyloxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) Dibromide

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Molbank 2022, 2022(1), M1311; https://doi.org/10.3390/M1311 - 24 Dec 2021

Abstract

In the present work, construction of double-charged cationic amphiphilic 1,1′-{[3,5-bis(dodecyl¬oxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) dibromide (7) was performed in four steps. Dodecyl 3-oxobutanoate (1) was condensed with thiophene-3-carbaldehyde (2) which was necessary for Hantzsch cyclisation dodecyl (E/Z)-3-oxo-2-(thiophen-3-ylmethylene)butanoate (3 [...] Read more.

In the present work, construction of double-charged cationic amphiphilic 1,1′-{[3,5-bis(dodecyl¬oxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) dibromide (7) was performed in four steps. Dodecyl 3-oxobutanoate (1) was condensed with thiophene-3-carbaldehyde (2) which was necessary for Hantzsch cyclisation dodecyl (E/Z)-3-oxo-2-(thiophen-3-ylmethylene)butanoate (3). Two-component Hantzsch type cyclisation of dodecyl (E/Z)-3-aminobut-2-enoate (4) and dodecyl (E/Z)-3-oxo-2-(thiophen-3-ylmethylene)butanoate (3) gave 3,5-bis(dodecyloxycarbonyl)-2,6-dimethyl-4-(thiophen-3-yl)-1,4-dihydropyridine (5). Bromination of compound 5 followed by nucleophilic substitution of bromine with pyridine gave the desired cationic amphiphilic 1,4-dihydropyridine 7. The obtained target compound 7 and new intermediates 3, 5 and 6 were fully characterised by IR, UV, ¹H NMR, ¹³C NMR, HRMS or microanalysis. Characterisation of nanoparticles formed by the cationic 1,4-dihydropyridine 7 in an aqueous solution was performed by DLS measurements. Full article

(This article belongs to the Section Organic Synthesis)

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Scheme 1

Open AccessShort Note

6′-Amino-5,7-dibromo-2-oxo-3′-(trifluoromethyl)-1′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-5′-carbonitrile

by

Yuliya E. Ryzhkova

,

Varvara M. Kalashnikova

and

Michail N. Elinson

Molbank 2022, 2022(1), M1309; https://doi.org/10.3390/M1309 - 23 Dec 2021

Abstract

The multicomponent reactions are environmentally benign synthetic methods of building-up of complex molecules and several levels of structural diversity for diverse applications. Spirooxindoles are an important synthetic target possessing extended biological activity and drug discovery applications. In this communication, the multicomponent transformation of [...] Read more.

The multicomponent reactions are environmentally benign synthetic methods of building-up of complex molecules and several levels of structural diversity for diverse applications. Spirooxindoles are an important synthetic target possessing extended biological activity and drug discovery applications. In this communication, the multicomponent transformation of 5,7-dibromoisatin, malononitrile, and 5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one in EtOH at reflux in the presence of sodium acetate was carefully investigated to give 6′-amino-5,7-dibromo-2-oxo-3′-(trifluoromethyl)-1′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-5′-carbonitrile in excellent yield. The structure of the new compound was established by means of elemental analysis, mass and nuclear magnetic resonance, and infrared spectroscopy. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessShort Note

7,7’-(4,4-Bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b’]dithiophene-2,6-diyl)bis(4-bromobenzo[c][1,2,5]thiadiazole)

by

Nikita S. Gudim

,

Ekaterina A. Knyazeva

and

Oleg A. Rakitin

Molbank 2022, 2022(1), M1310; https://doi.org/10.3390/M1310 - 23 Dec 2021

Abstract

2,6-Bis(benzo[c][1,2,5]thiadiazol-4-yl)-4H-cyclopenta[2,1-b:3,4-b’]dithiophenes are of interest for the synthesis of molecules which can be employed in optoelectronic devices. In this communication, 7,7’-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b’]dithiophene-2,6-diyl)bis(4-bromobenzo[c][1,2,5]thiadiazole) was obtained by direct C–H cross-coupling of [...] Read more.

2,6-Bis(benzo[c][1,2,5]thiadiazol-4-yl)-4H-cyclopenta[2,1-b:3,4-b’]dithiophenes are of interest for the synthesis of molecules which can be employed in optoelectronic devices. In this communication, 7,7’-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b’]dithiophene-2,6-diyl)bis(4-bromobenzo[c][1,2,5]thiadiazole) was obtained by direct C–H cross-coupling of 4,7-dibromobenzo[c][1,2,5]thiadiazole with 4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b’]dithiophene in the presence of palladium(II)acetate and potassium pivalate. The structure of newly synthesized compound was established by means of elemental analysis, high-resolution mass spectrometry, ¹H, ¹³C NMR, IR and UV spectroscopy. Full article

(This article belongs to the Section Organic Synthesis)

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Scheme 1

Open AccessCommunication

Methylation of 2-Aryl-2-(3-indolyl)acetohydroxamic Acids and Evaluation of Cytotoxic Activity of the Products

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Molbank 2022, 2022(1), M1307; https://doi.org/10.3390/M1307 - 22 Dec 2021

Abstract

2-Aryl-2-(3-indolyl)acetohydroxamic acids demonstrate promising antitumor activity, but quickly metabolize in vivo via glucuronidation of hydroxamic acid residue. In an attempt to improve their pharmacokinetics, methyl esters were synthesized via a newly developed protocol for chemoselective mono-methylation of hydroxamic acids. The cytotoxicity of these [...] Read more.

2-Aryl-2-(3-indolyl)acetohydroxamic acids demonstrate promising antitumor activity, but quickly metabolize in vivo via glucuronidation of hydroxamic acid residue. In an attempt to improve their pharmacokinetics, methyl esters were synthesized via a newly developed protocol for chemoselective mono-methylation of hydroxamic acids. The cytotoxicity of these derivatives against the HeLa cell line was evaluated and found to be inferior compared to the parent lead compounds. Full article

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Graphical abstract

Open AccessShort Note

Dimethyl 2-(2,4-Diamino-3-cyano-5H-chromeno[2,3-b]pyridin-5-yl)malonate

by

Yuliya E. Ryzhkova

,

Oleg I. Maslov

and

Michail N. Elinson

Molbank 2022, 2022(1), M1308; https://doi.org/10.3390/M1308 - 22 Dec 2021

Abstract

Dimethyl sulfoxide (DMSO) is widely used as a solvent in organic synthesis and in pharmacology because of its low cost, stability, and non-toxicity. Multicomponent reactions are a powerful synthetic tool for the rapid and efficient construction of complicated molecular frameworks. In this communication, [...] Read more.

Dimethyl sulfoxide (DMSO) is widely used as a solvent in organic synthesis and in pharmacology because of its low cost, stability, and non-toxicity. Multicomponent reactions are a powerful synthetic tool for the rapid and efficient construction of complicated molecular frameworks. In this communication, the multicomponent transformation of salicylaldehyde, malononitrile dimer, and dimethyl malonate in DMSO at room temperature was carefully investigated to give dimethyl 2-(2,4-diamino-3-cyano-5H-chromeno[2,3-b]pyridin-5-yl)malonate with good yield. The structure of the new compound was established by means of elemental analysis and mass, nuclear magnetic resonance, and infrared spectroscopy. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessCommunication

New Derivatives of Lupeol and Their Biological Activity

by

Hoang-Thuy-Tien Le

,

Quoc-Cuong Chau

,

Thuc-Huy Duong

,

Quyen-Thien-Phuc Tran

,

Nguyen-Kim-Tuyen Pham

,

Thi-Hoai-Thu Nguyen

,

Ngoc-Hong Nguyen

and

Jirapast Sichaem

Molbank 2021, 2021(4), M1306; https://doi.org/10.3390/M1306 - 10 Dec 2021

Abstract

The natural product lupeol (1) was isolated from Bombax ceiba leaves, which were used as starting material in the semisynthetic approach. Three new derivatives (2a, 2b, and 3) were synthesized using oxidation and aldolization. Their chemical structures [...] Read more.

The natural product lupeol (1) was isolated from Bombax ceiba leaves, which were used as starting material in the semisynthetic approach. Three new derivatives (2a, 2b, and 3) were synthesized using oxidation and aldolization. Their chemical structures were elucidated by spectroscopic analyses (HRESIMS and NMR). Compounds 3 showed significant α-glucosidase inhibition with an IC₅₀ value of 202 µM, whereas 2a and 2b were inactive. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

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Figure 1

Open AccessShort Note

2-(2-(4-Methoxyphenyl)-4,9-dimethyl-7-oxo-7H-furo[2,3-f]chromen-3-yl)acetic Acid

by

Boris V. Lichitsky

,

Andrey N. Komogortsev

and

Valeriya G. Melekhina

Molbank 2021, 2021(4), M1304; https://doi.org/10.3390/M1304 - 09 Dec 2021

Abstract

For the first time, we describe a new approach towards the synthesis of previously unknown 2-(2-(4-methoxyphenyl)-4,9-dimethyl-7-oxo-7H-furo[2,3-f]chromen-3-yl)acetic acid. The presented method is based on the multicomponent condensation of 5-hydroxy-4,7-dimethyl-2H-chromen-2-one, 4-methoxyphenylglyoxal and Meldrum’s acid. It was shown that the [...] Read more.

For the first time, we describe a new approach towards the synthesis of previously unknown 2-(2-(4-methoxyphenyl)-4,9-dimethyl-7-oxo-7H-furo[2,3-f]chromen-3-yl)acetic acid. The presented method is based on the multicomponent condensation of 5-hydroxy-4,7-dimethyl-2H-chromen-2-one, 4-methoxyphenylglyoxal and Meldrum’s acid. It was shown that the studied reaction proceeds in two steps including the initial interaction of starting materials in MeCN and the final formation of furylacetic acid moiety in acidic media. The structures of the obtained compound were established by ¹H, ¹³C-NMR spectroscopy and high-resolution mass spectrometry. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

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