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Open AccessShort Note

(E)-2-(1,3-Diphenylallyl)-3,5-dimethoxyphenol

by

Lara Mollà-Guerola

and

Alejandro Baeza

Molbank 2023, 2023(3), M1709; https://doi.org/10.3390/M1709 - 04 Aug 2023

Viewed by 233

Abstract

The synthesis of (E)-2-(1,3-diphenylallyl)-3,5-dimethoxyphenol is described by means of the reaction of 3,5-dimethoxyphenol with (E)-1,3-diphenylprop-2-en-1-ol in 1,1,1,3,3,3-hexafluoroispropanol (HFIP), which acts as a solvent and reaction promoter. The reaction proceeds smoothly to afford the mentioned compound in high yield under [...] Read more.

The synthesis of (E)-2-(1,3-diphenylallyl)-3,5-dimethoxyphenol is described by means of the reaction of 3,5-dimethoxyphenol with (E)-1,3-diphenylprop-2-en-1-ol in 1,1,1,3,3,3-hexafluoroispropanol (HFIP), which acts as a solvent and reaction promoter. The reaction proceeds smoothly to afford the mentioned compound in high yield under a metal and additive-free procedure. The corresponding allylated phenol has been fully characterized. Full article

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Open AccessShort Note

Isoamyl (E)-3-(3,4-Dimethoxyphenyl)acrylate

by

Egar Pamela

,

Lukman Atmaja

and

Mardi Santoso

Molbank 2023, 2023(3), M1708; https://doi.org/10.3390/M1708 - 02 Aug 2023

Viewed by 221

Abstract

Isoamyl (E)-3-(3,4-dimethoxyphenyl)acrylate (1) was obtained from the 2-methyl-6-nitrobenzoic anhydride (MNBA)/4-dimethylaminopyridine (DMAP)-catalyzed reaction at room temperature for 190 min in dichloromethane with a yield of 95%. The structure of isoamyl (E)-3-(3,4-dimethoxyphenyl)acrylate (1) was elucidated using NMR, [...] Read more.

Isoamyl (E)-3-(3,4-dimethoxyphenyl)acrylate (1) was obtained from the 2-methyl-6-nitrobenzoic anhydride (MNBA)/4-dimethylaminopyridine (DMAP)-catalyzed reaction at room temperature for 190 min in dichloromethane with a yield of 95%. The structure of isoamyl (E)-3-(3,4-dimethoxyphenyl)acrylate (1) was elucidated using NMR, FTIR, and high-resolution mass spectrometry. In vitro sun protection factor evaluation exhibited a value of 37.10 ± 0.03 which indicates that isoamyl (E)-3-(3,4-dimethoxyphenyl)acrylate (1) is a sunscreen agent with high protection. Full article

(This article belongs to the Section Organic Synthesis)

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Scheme 1

Open AccessCommunication

Synthesis of Novel Diterpenic Peptides via the Ugi Reaction and Their Anticancer Activities

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,

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and

Molbank 2023, 2023(3), M1707; https://doi.org/10.3390/M1707 - 01 Aug 2023

Viewed by 156

Abstract

Novel diterpenic peptide derivatives were synthesized via the Ugi four-component reaction at ambient temperature. The protocol employed a reaction between formaldehyde, benzyl amine, the corresponding diterpene acid, and ethyl 2-isocyanoacetate. The anticancer properties of the compounds were studied in vitro. Full article

(This article belongs to the Section Organic Synthesis)

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Scheme 1

Open AccessShort Note

N′-(5-Bromofuran-2-carbonyl)isonicotinohydrazide

by

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and

Molbank 2023, 2023(3), M1706; https://doi.org/10.3390/M1706 - 01 Aug 2023

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Abstract

N′-(5-bromofuran-2-carbonyl)isonicotinohydrazide (1) was obtained in the form of a colorless solid from the 2-methyl-6-nitrobenzoic anhydride (MNBA)/4-dimethylaminopyridine (DMAP)-catalyzed reaction of 5-bromofuran-2-carboxylic acid and isoniazid in dichloromethane at room temperature with a yield of 83%. The structure of N′-(5-bromofuran-2-carbonyl)isonicotinohydrazide (1 [...] Read more.

N′-(5-bromofuran-2-carbonyl)isonicotinohydrazide (1) was obtained in the form of a colorless solid from the 2-methyl-6-nitrobenzoic anhydride (MNBA)/4-dimethylaminopyridine (DMAP)-catalyzed reaction of 5-bromofuran-2-carboxylic acid and isoniazid in dichloromethane at room temperature with a yield of 83%. The structure of N′-(5-bromofuran-2-carbonyl)isonicotinohydrazide (1) was elucidated using ¹H NMR, ¹³C NMR, FTIR, and high-resolution mass spectrometry. Molecular docking screening of the title compound (1) on cyclooxygenase-2 (COX-2) protein (PDB ID: 5IKR) indicated that compound (1) has a good binding affinity, suggesting that further structure optimization and in-depth research can be carried out on compound (1) as a potential COX-2 inhibitor. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

4-(4-ethoxyphenyl)-5-(4-methoxyphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

by

Ion Burcă

,

Valentin Badea

,

Calin Deleanu

,

Vasile-Nicolae Bercean

and

Francisc Péter

Molbank 2023, 2023(3), M1705; https://doi.org/10.3390/M1705 - 01 Aug 2023

Viewed by 180

Abstract

A new triazol-3-one resulted unexpectedly from the reduction reaction of a heterocyclic thioketone using sodium borohydride in pyridine containing a small amount of water. The structure of the new compound was characterised using FT-IR, 1D and 2D NMR, and HRMS spectroscopic methods. Full article

(This article belongs to the Special Issue Molecules from Side Reactions II)

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Open AccessCommunication

N-(((1S,5R)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)-3-dodecan/tetradecanamido-N,N-dimethylpropan-1-aminium Bromide

by

Liliya E. Nikitina

,

Ilmir R. Gilfanov

,

Roman S. Pavelyev

,

Svetlana A. Lisovskaya

,

Elena Y. Trizna

,

Ilfat Z. Rakhmatullin

,

,

,

,

,

Olga V. Ostolopovskaya

,

Larisa L. Frolova

and

Airat R. Kayumov

Molbank 2023, 2023(3), M1704; https://doi.org/10.3390/M1704 - 26 Jul 2023

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Abstract

The syntheses of the title compounds were performed using lauric and myristic acids. The compounds obtained were characterized using ¹H-, ¹³C-NMR and 2D ¹H-¹H COSY, ¹H-¹³C HSQC NMR, IR, and high-resolution mass spectrometry. Both compounds [...] Read more.

The syntheses of the title compounds were performed using lauric and myristic acids. The compounds obtained were characterized using ¹H-, ¹³C-NMR and 2D ¹H-¹H COSY, ¹H-¹³C HSQC NMR, IR, and high-resolution mass spectrometry. Both compounds exhibited bactericidal activity on S. aureus comparable to that of a reference drug (miramistin). Compound 10, with lauric acid fragment, had a 16-fold higher activity on P. aeruginosa compared to compound 11, which in turn contains myristic acid fragment (with minimum inhibitory concentrations of 32 and 512 μg/mL, respectively). Compound 11 exhibited a pronounced activity against all types of fungi (higher than the activity of miramistin), while the activity of compound 10 was considerably lower. Thus, compound 11 can serve as a promising antimicrobial agent for the treatment of various fungal and staphylococcal infections, while compound 10 is of interest to treat P. aeruginosa-associated infections. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

2,7-Bis(pyridin-4-ylethynyl)-9H-carbazole

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and

Molbank 2023, 2023(3), M1703; https://doi.org/10.3390/M1703 - 24 Jul 2023

Viewed by 247

Abstract

2,7-Bis(pyridin-4-ylethynyl)-9H-carbazole (1) was synthesized by reacting 4-ethynylpyridine hydrochloride with 2,7-dibromo-9H-carbazole. The full characterization of compound 1 is presented, and the crystal structure of its monohydrate was determined by single-crystal XRD analysis. Full article

(This article belongs to the Section Structure Determination)

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Open AccessShort Note

6,7-Dihydroxy-5,8-dimethoxy-2H-chromen-2-one

by

Olga I. Adaeva

,

Dmitry V. Demchuk

and

Victor V. Semenov

Molbank 2023, 2023(3), M1702; https://doi.org/10.3390/M1702 - 23 Jul 2023

Viewed by 248

Abstract

This article presents a novel approach for synthesizing a new 5,8-dimethoxy derivative of esculetin via the selective cleavage of the methylene bridge in sabandin—naturally occurring and easily synthetically accessible methoxylated coumarin. A high selectivity is achieved by using acetoxylation of methylenedioxy group with [...] Read more.

This article presents a novel approach for synthesizing a new 5,8-dimethoxy derivative of esculetin via the selective cleavage of the methylene bridge in sabandin—naturally occurring and easily synthetically accessible methoxylated coumarin. A high selectivity is achieved by using acetoxylation of methylenedioxy group with lead tetraacetate. Natural coumarin sabandin as a starting compound was prepared in a few simple steps from 5-allyl-4,7-dimethoxybenzo[d][1,3]dioxole (apiol), which is readily available from parsley and dill seed extracts. The developed method enables an efficient and straightforward synthesis of a new derivative of esculetin with potential medicinal and therapeutic applications. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

5-((4-(-Phenyldiazenyl)phenyl)diazenyl)quinolin-8-ol

by

Ion Burcă

,

Alexandra-Mihaela Diaconescu

,

Valentin Badea

and

Francisc Péter

Molbank 2023, 2023(3), M1701; https://doi.org/10.3390/M1701 - 21 Jul 2023

Viewed by 215

Abstract

A new azo compound was synthesized via an azo coupling reaction between 4-(phenyldiazenyl)benzenediazonium chloride and 8-hydroxyquinoline (8-Hq). The new diazene compound can be used to synthesize metal complexes as a derivative of 8-Hq. The structure of the new compound was characterized using UV–Vis, [...] Read more.

A new azo compound was synthesized via an azo coupling reaction between 4-(phenyldiazenyl)benzenediazonium chloride and 8-hydroxyquinoline (8-Hq). The new diazene compound can be used to synthesize metal complexes as a derivative of 8-Hq. The structure of the new compound was characterized using UV–Vis, FT-IR, and 2D NMR spectroscopic methods. Full article

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Scheme 1

Open AccessShort Note

4-(2,5-Dimethyl-1H-pyrrol-1-yl)-1,2,5-oxadiazol-3-amine

by

Natalia V. Obruchnikova

and

Oleg A. Rakitin

Molbank 2023, 2023(3), M1700; https://doi.org/10.3390/M1700 - 20 Jul 2023

Viewed by 180

Abstract

1,2,5-Oxadiazol-3-amines with a heterocyclic substituent in the 4-position are being intensively investigated as compounds with valuable pharmacological activity. In this communication, the reaction of 1,2,5-oxadiazole-3,4-diamine with 2,5-hexanedione was shown to selectively give 4-(2,5-dimethyl-1H-pyrrol-1-yl)-1,2,5-oxadiazol-3-amine as a product of the Paal–Knorr reaction. The [...] Read more.

1,2,5-Oxadiazol-3-amines with a heterocyclic substituent in the 4-position are being intensively investigated as compounds with valuable pharmacological activity. In this communication, the reaction of 1,2,5-oxadiazole-3,4-diamine with 2,5-hexanedione was shown to selectively give 4-(2,5-dimethyl-1H-pyrrol-1-yl)-1,2,5-oxadiazol-3-amine as a product of the Paal–Knorr reaction. The structure of the synthesized compound was established by elemental analysis, high-resolution mass spectrometry, ¹H and ¹³C NMR, and IR spectroscopy. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Scheme 1

Open AccessShort Note

(2S,2’S,4R,5S,5’R)-2,2’-Di-tert-butyl-4-hydroxy-5,5’-dimethyl-4,5’-bi(1,3-dioxolanyl)-4’-one

by

R. Alan Aitken

,

Lynn A. Power

and

Alexandra M. Z. Slawin

Molbank 2023, 2023(3), M1699; https://doi.org/10.3390/M1699 - 20 Jul 2023

Viewed by 225

Abstract

The product formed by base-induced dimerisation of (2S,5S)-2-tert-butyl-5-methyl-1,3-dioxolan-4-one is shown by X-ray diffraction to be the title compound and not the isomeric fused-ring 1,3-dioxolane/1,3-dioxane-4-one structure proposed by previous researchers. The analogous compound derived from (2S,5S)-5-benzyl-2-tert-butyl-1,3-dioxolan-4-one has also been obtained and characterised. Full article

(This article belongs to the Section Structure Determination)

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Open AccessShort Note

[μ-1,2-Bis(dipheylphosphino)ethane-κ²P,P’]bis(3-mercapto-1,2-propanediolato-κS-gold(I))

by

Taichi Baba

and

Nobuto Yoshinari

Molbank 2023, 2023(3), M1698; https://doi.org/10.3390/M1698 - 19 Jul 2023

Viewed by 271

Abstract

A new dinuclear gold(I) complex, possessing a bridging diphosphine ligand (1,2-bis(diphenylphosphino)ethane) and two terminal thiol ligands (1-thioglycerol), was synthesized and fully characterized by IR, ¹H and ³¹P NMR, fluorescence, ESI-mass, and diffuse reflection spectroscopy, together with X-ray diffraction and elemental analyses. [...] Read more.

A new dinuclear gold(I) complex, possessing a bridging diphosphine ligand (1,2-bis(diphenylphosphino)ethane) and two terminal thiol ligands (1-thioglycerol), was synthesized and fully characterized by IR, ¹H and ³¹P NMR, fluorescence, ESI-mass, and diffuse reflection spectroscopy, together with X-ray diffraction and elemental analyses. The compound formed a 1D chain supramolecular structure through intermolecular aurophilic interactions in the crystal structure, leading to photoluminescence in the solid state. Full article

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Open AccessShort Note

Methyl-4-hydroxy-2-(2-hydroxypropan-2-yl)-6-methyl-2,3-dihydrobenzofuran-5-carboxylate

by

Rishi Vachaspathy Astakala

,

Gagan Preet

,

Rainer Ebel

and

Marcel Jaspars

Molbank 2023, 2023(3), M1697; https://doi.org/10.3390/M1697 - 19 Jul 2023

Viewed by 382

Abstract

Microorganisms are an important source of compounds that are pharmaceutically active, both as leads and as scaffolds for synthesis. Often, interesting chemistry is uncovered by exploring new biomes, of which the Chilean Atacama Desert is a prime example. This paper describes the isolation [...] Read more.

Microorganisms are an important source of compounds that are pharmaceutically active, both as leads and as scaffolds for synthesis. Often, interesting chemistry is uncovered by exploring new biomes, of which the Chilean Atacama Desert is a prime example. This paper describes the isolation and structural characterisation, using HR-LCMS and 1D and 2D NMR, of a new compound belonging to a family of compounds called radstrictins. The compound was isolated from a fungus, that had itself been isolated from a soil sample from the Atacama Desert. The compound was tested against pathogenic strains associated with bovine mastitis, but was found to be devoid of antimicrobial activity. Full article

(This article belongs to the Section Natural Products)

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Open AccessShort Note

28-O-Acetyl-3-O′-(prop-2-enoyl)betulin

by

Ewa Bębenek

,

Elwira Chrobak

and

Monika Kadela-Tomanek

Molbank 2023, 2023(3), M1696; https://doi.org/10.3390/M1696 - 14 Jul 2023

Viewed by 227

Abstract

28-Acetylbetulin is a good starting compound for the synthesis of 3- or 3,28-substituted betulin derivatives with biological activity. The final product of the reaction of 28-acetylbetulin and acrylic acid under Steglich esterification conditions produced a new 3-alkenyl betulin derivative. The structure of the [...] Read more.

28-Acetylbetulin is a good starting compound for the synthesis of 3- or 3,28-substituted betulin derivatives with biological activity. The final product of the reaction of 28-acetylbetulin and acrylic acid under Steglich esterification conditions produced a new 3-alkenyl betulin derivative. The structure of the obtained compound was confirmed based on the analysis of NMR, IR, EI MS, and HRMS spectra. Selected pharmacokinetic parameters related to the absorption and distribution were calculated for the new betulin derivative using in silico methods. Full article

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Open AccessShort Note

1-[(1S)-(4-Fluorophenyl)-((1′S)-1′-naphthalen-1-yl-ethylamino)-methyl]-naphthalen-2-trifluoromethanesulfonate

by

Cosimo Cardellicchio

and

Maria Annunziata M. Capozzi

Molbank 2023, 2023(3), M1695; https://doi.org/10.3390/M1695 - 14 Jul 2023

Viewed by 215

Abstract

The complex structure of aminobenzylnaphthols can be easily obtained with the useful Betti reaction. These valuable compounds can give rise to chiral intermediates, that found wide application in asymmetric synthesis. 1-[(1S)-(4-Fluorophenyl)-((1′S)-1′-naphthalen-1-yl-ethylamino)-methyl]-naphthalen-2-ol 1 was treated with triflic anhydride to yield [...] Read more.

The complex structure of aminobenzylnaphthols can be easily obtained with the useful Betti reaction. These valuable compounds can give rise to chiral intermediates, that found wide application in asymmetric synthesis. 1-[(1S)-(4-Fluorophenyl)-((1′S)-1′-naphthalen-1-yl-ethylamino)-methyl]-naphthalen-2-ol 1 was treated with triflic anhydride to yield the corresponding (S,S)-triflate 2, which is a valuable intermediate in the future synthesis of aminophosphine, to be used in asymmetric catalysis. Preliminarily structural considerations based upon H(1)-NMR spectroscopy are also reported. Full article

(This article belongs to the Collection Molecules from Catalytic Processes)

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