Molbank

Open AccessShort Note

1-(4-Chlorophenyl)-2-methyl-2-phenyl-5-(thiophen-2-yl)-1,2-dihydro-3H-pyrrol-3-one

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Molbank 2022, 2022(4), M1520; https://doi.org/10.3390/M1520 - 06 Dec 2022

Abstract

1-(4-Chlorophenyl)-2-methyl-2-phenyl-5-(thiophen-2-yl)-1,2-dihydro-3H-pyrrol-3-one, was synthesized for the first time in 75% yield by the base-catalyzed intramolecular cyclization of 4-((4-chlorophenyl)amino)-4-phenyl-1-(thiophen-2-yl)pent-2-yn-1-one. The starting aminoacetylenic ketone was prepared by cross-coupling of available propargylamines with acyl chlorides in the presence of the PdCl₂/CuI/Ph₃P catalytic system. Full article

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Open AccessShort Note

4-Methoxyphenethyl (E)-3-(o-tolyl)acrylate

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Molbank 2022, 2022(4), M1519; https://doi.org/10.3390/M1519 - 05 Dec 2022

Abstract

4-Methoxyphenethyl (E)-3-(o-tolyl)acrylate (1) was obtained in a good yield by the reaction of 2-methylcinnamic acid, 4-methoxyphenethyl alcohol, 2-methyl-6-nitrobenzoic anhydride, 4-dimethylaminopyridine, and triethylamine at room temperature for 40 min. The structure of 4-methoxyphenethyl (E)-3-(o-tolyl)acrylate [...] Read more.

4-Methoxyphenethyl (E)-3-(o-tolyl)acrylate (1) was obtained in a good yield by the reaction of 2-methylcinnamic acid, 4-methoxyphenethyl alcohol, 2-methyl-6-nitrobenzoic anhydride, 4-dimethylaminopyridine, and triethylamine at room temperature for 40 min. The structure of 4-methoxyphenethyl (E)-3-(o-tolyl)acrylate (1) was established by FTIR, NMR, and the high resolution of mass spectroscopies. 4-Methoxyphenethyl (E)-3-(o-tolyl)acrylate (1) showed higher α-glucosidase inhibition activity than standard drug acarbose. The molecular docking study exhibited that the title compound 1 had a good affinity for α-glucosidase (PDB ID: 3W37) and formed some interactions with the α-glucosidase active site residue. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

Bis(3,4-diphenyl)(2-methythienyl)cyclopentadienyl Terbium Chloride

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Alexander A. Vinogradov

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Pavel D. Komarov

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Lada N. Puntus

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Konstantin A. Lyssenko

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Ilya E. Nifant’ev

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Evgenia A. Varaksina

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Ilya V. Taydakov

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Dmitrii M. Roitershtein

Molbank 2022, 2022(4), M1517; https://doi.org/10.3390/M1517 - 05 Dec 2022

Abstract

A new terbium(III) complex with a (3,4-diphenyl)(2-methylthienyl)cyclopentadienyl ligand was synthesized. Single-crystal X-ray analysis revealed a binuclear biscyclopentadienyl complex with a [TbCl₂K]₂ core. Luminescence properties of the terbium complex were analyzed. Full article

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Open AccessShort Note

3-Phenyl-10-(2,3,4-trimethoxyphenyl)-9,10-dihydro-4H,8H-pyrano [2,3-f]chromene-4,8-dione

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Boris V. Lichitsky

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Andrey N. Komogortsev

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Valeriya G. Melekhina

Molbank 2022, 2022(4), M1516; https://doi.org/10.3390/M1516 - 05 Dec 2022

Abstract

An efficient telescoped method for synthesis of 3-phenyl-10-(2,3,4-trimethoxyphenyl)-9,10-dihydro-4H,8H-pyrano[2,3-f]chromene-4,8-dione was elaborated. The presented protocol includes the one-pot multicomponent reaction of 7-hydroxy-3-phenyl-4H-chromen-4-one, 2,3,4-trimethoxybenzaldehyde and Meldrum’s acid. Advantages of this method are the application of readily available starting [...] Read more.

An efficient telescoped method for synthesis of 3-phenyl-10-(2,3,4-trimethoxyphenyl)-9,10-dihydro-4H,8H-pyrano[2,3-f]chromene-4,8-dione was elaborated. The presented protocol includes the one-pot multicomponent reaction of 7-hydroxy-3-phenyl-4H-chromen-4-one, 2,3,4-trimethoxybenzaldehyde and Meldrum’s acid. Advantages of this method are the application of readily available starting reagents, atom economy and easy procedure of preparation and purification of the target product. The structure of the synthesized polycyclic compound was proved by ¹H, ¹³C-NMR, IR spectroscopy and high-resolution mass spectrometry with electrospray ionization (ESI-HRMS). Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl (R)-4-methylbenzenesulfonimidate

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Arianna Tota

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Michael Andresini

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Marco Colella

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Roberta Savina Dibenedetto

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Leonardo Degennaro

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Renzo Luisi

Molbank 2022, 2022(4), M1518; https://doi.org/10.3390/M1518 - 05 Dec 2022

Abstract

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (R)-4-methylbenzenesulfonimidate was synthesized via the stereoselective NH-transfer to (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (S)-4-methylbenzenesulfinate. The reaction employed diacetoxyiodobenzene (DIB) and ammonium carbamate, and occurred in acetonitrile at room temperature. The [...] Read more.

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (R)-4-methylbenzenesulfonimidate was synthesized via the stereoselective NH-transfer to (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (S)-4-methylbenzenesulfinate. The reaction employed diacetoxyiodobenzene (DIB) and ammonium carbamate, and occurred in acetonitrile at room temperature. The imidation of sulfur proceeded with complete stereocontrol, and the reaction afforded the desired product as a single diastereoisomer and with high enantiocontrol (e.r. = 97:3) in 70% yield. The product was characterized by ¹H-NMR, ¹³C-NMR, COSY, HSQC, IR spectroscopy, HRMS, and the enantiomeric ratio was established by HPLC analysis at the chiral stationary phase. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessShort Note

3-(3-Bromophenyl)-7-acetoxycoumarin

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Petri A. Turhanen

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Liisa P. Nousiainen

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Juri M. Timonen

Molbank 2022, 2022(4), M1513; https://doi.org/10.3390/M1513 - 02 Dec 2022

Abstract

In natural product synthesis, the procurement of easily accessible starting materials is crucial. Chromenones and their subclass, coumarins, are a wide family of small, oxygen-containing aromatic heterocycles. Phenylcoumarins offer a particularly excellent starting point for a diverse chemical space of natural products, and [...] Read more.

In natural product synthesis, the procurement of easily accessible starting materials is crucial. Chromenones and their subclass, coumarins, are a wide family of small, oxygen-containing aromatic heterocycles. Phenylcoumarins offer a particularly excellent starting point for a diverse chemical space of natural products, and thus are excellent staring materials for more complex natural products. Herein, we report an efficient synthesis of an easily accessible 3-phenylcoumarin bearing two orthogonally substitutable groups, bromine, and an acetyl-protected phenylic hydroxyl group. Full article

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Scheme 1

Open AccessShort Note

2-(2,5-Dimethoxyphenoxy)isoindoline-1,3-dione

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Stanislav A. Paveliev

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Oleg O. Segida

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Alexander O. Terent’ev

Molbank 2022, 2022(4), M1514; https://doi.org/10.3390/M1514 - 02 Dec 2022

Abstract

In this work, the direct C-H functionalization reaction of 1,4-dimethoxybenzene with N-hydroxyphthalimide has been disclosed. A previously unknown product of the C-O coupling of 1,4-dimethoxybenzene and N-hydroxyphthalimide was obtained. The reaction proceeded under mild conditions, in which a commercially available manganese-based [...] Read more.

In this work, the direct C-H functionalization reaction of 1,4-dimethoxybenzene with N-hydroxyphthalimide has been disclosed. A previously unknown product of the C-O coupling of 1,4-dimethoxybenzene and N-hydroxyphthalimide was obtained. The reaction proceeded under mild conditions, in which a commercially available manganese-based oxidizing agent was used for generation of a phthalimide-N-oxyl radical. The obtained compound is a promising valuable precursor of O-aryl hydroxylamine. Full article

(This article belongs to the Section Organic Synthesis)

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Scheme 1

Open AccessShort Note

N,N′-4,5-Dimethoxy-1,2-phenylenebis(salicylideneiminato)nickel(II)

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Molbank 2022, 2022(4), M1512; https://doi.org/10.3390/M1512 - 02 Dec 2022

Abstract

The title compound, which is potentially interesting as a building block for electrochemically active metallopolymers, was synthesized and characterized by single-crystal X-ray diffraction, IR and NMR spectroscopies. Full article

(This article belongs to the Section Structure Determination)

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Open AccessShort Note

5-(4-Nitrophenyl)furan-2-carboxylic Acid

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Molbank 2022, 2022(4), M1515; https://doi.org/10.3390/M1515 - 02 Dec 2022

Abstract

The ever-evolving research in the field of antitubercular agents has led to the identification of several new potential drug classes. Among them, 5-phenyl-furan-2-carboxylic acids have emerged as innovative potential therapeutics, targeting iron acquisition in mycobacterial species. In our efforts to characterize the molecular [...] Read more.

The ever-evolving research in the field of antitubercular agents has led to the identification of several new potential drug classes. Among them, 5-phenyl-furan-2-carboxylic acids have emerged as innovative potential therapeutics, targeting iron acquisition in mycobacterial species. In our efforts to characterize the molecular interactions between these compounds and their protein target (MbtI from M. tuberculosis) by means of co-crystallization experiments, we unexpectedly obtained the structure of 5-(4-nitrophenyl)furan-2-carboxylic acid (1). Herein, we describe the preparation of the compound and its analysis by ¹H NMR, ¹³C NMR, HRMS, and SC-XRD. Full article

(This article belongs to the Section Structure Determination)

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Open AccessShort Note

2-Furanylmethyl N-(2-propenyl)carbamate

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Molbank 2022, 2022(4), M1510; https://doi.org/10.3390/M1510 - 01 Dec 2022

Abstract

The overexpression of protein phosphatase 5 (PP5) has been correlated to tumor cell reproduction, making it a candidate for small molecule drug therapy. Prior work has focused on functionalized and decorated scaffolds that maximize contacts within and around the active site. The assembly [...] Read more.

The overexpression of protein phosphatase 5 (PP5) has been correlated to tumor cell reproduction, making it a candidate for small molecule drug therapy. Prior work has focused on functionalized and decorated scaffolds that maximize contacts within and around the active site. The assembly and testing of cantharidin derivatives decorated with functionalized attachments has been our focus in order to affect the optimal binding of PP5. Condensation of 2-hydroxymethylfuran with allyl isocyanate meets the metrics of the rapid installment of functionality, as part of the core scaffold. Once condensed, cycloaddition followed by hydrogenation produces the desired derivative of norcantharidin in three synthetic steps. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessShort Note

6,6′-((Ethane-1,2-diylbis(azanediyl))bis(methylene))bis(2,4-bis(2-phenylpropan-2-yl)phenolate)zirconium(IV) Dichlorido

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Joana Hipólito

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Ana M. Martins

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Luis G. Alves

Molbank 2022, 2022(4), M1511; https://doi.org/10.3390/M1511 - 01 Dec 2022

Abstract

The salan zirconium complex of formula [(H₂N₂O₂)ZrCl₂] (H₂N₂O₂H₂ = HOPh’CH₂NH(CH₂)₂NHCH₂Ph’OH, where Ph’ = 2,4-(CMe₂Ph)C₆H₂) [...] Read more.

The salan zirconium complex of formula [(H₂N₂O₂)ZrCl₂] (H₂N₂O₂H₂ = HOPh’CH₂NH(CH₂)₂NHCH₂Ph’OH, where Ph’ = 2,4-(CMe₂Ph)C₆H₂) was synthesized and fully characterized by NMR and single-crystal X-ray diffraction. The solid-state molecular structure of [(H₂N₂O₂)ZrCl₂] shows distorted octahedral geometry around the zirconium center with the salan ligand adopting a β-Λ-cis conformation. Full article

(This article belongs to the Section Structure Determination)

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Open AccessCommunication

N-(p-Toluenesulfonyl)-1-(4′-acetylphenoxy)acrylimidate: Synthesis, Crystal Structure and Theoretical Studies

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Flor María Escandón-Mancilla

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Alberto Cedillo-Cruz

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Raúl Eduardo Gordillo-Cruz

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Diego Martínez-Otero

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M. V. Basavanag Unnamatla

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Erick Cuevas-Yañez

Molbank 2022, 2022(4), M1509; https://doi.org/10.3390/M1509 - 28 Nov 2022

Abstract

The formation of N-sulfonyl-1-aryloxy acrylimidate is described, for the first time, from a consecutive process, which involves a CuAAC reaction, a ketenimine formation and subsequent rearrangement between an aryl propargyl ether and a sulfonyl azide. The structure of this newly synthesized compound was [...] Read more.

The formation of N-sulfonyl-1-aryloxy acrylimidate is described, for the first time, from a consecutive process, which involves a CuAAC reaction, a ketenimine formation and subsequent rearrangement between an aryl propargyl ether and a sulfonyl azide. The structure of this newly synthesized compound was analyzed by NMR spectra and unambiguously established by X-ray analysis. In addition, theoretical calculations, which included a Hirshfeld surface, FMO, QTAIM and NCI indices analysis, corroborated the formation of π-π stacking interactions among aromatic rings, as well as C-H···O interactions between vinyl hydrogens with ketone carbonyl oxygen. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessCommunication

Novel Schiff Bases of C-Methylresorcinarene Derivatives

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Molbank 2022, 2022(4), M1505; https://doi.org/10.3390/M1505 - 25 Nov 2022

Abstract

The article presents the synthesis and properties of two new Schiff bases of resorcinarene derivatives. The Schiff bases were obtained by the reaction of formylresorcinarene with aromatic (o-aminophenol) and aliphatic (N,N-dimethyldiaminoethane) amines in chloroform. The synthesized Schiff [...] Read more.

The article presents the synthesis and properties of two new Schiff bases of resorcinarene derivatives. The Schiff bases were obtained by the reaction of formylresorcinarene with aromatic (o-aminophenol) and aliphatic (N,N-dimethyldiaminoethane) amines in chloroform. The synthesized Schiff bases exist in equilibrium of several tautomers, as evident from the IR, UV, NMR spectra and cyclic voltammetry data analysis. In DMF, methanol, and acetonitrile, the tautomeric equilibrium is shifted toward the enol-imine tautomers. Full article

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Open AccessShort Note

Dichloro[N-[(η⁶-phenyl)methyl]-4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8tetrahydronaphthalen-2-yl)vinyl)benzamide](1,3,5-triaza-7-phosphatricyclo [3.3.1.1^3,7]decane-κP⁷)ruthenium

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Molbank 2022, 2022(4), M1506; https://doi.org/10.3390/M1506 - 25 Nov 2022

Abstract

Bexarotene-tethered RuII(arene) compounds with 1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane (PTA) were prepared as an analog of RAPTA antitumor complexes in order to evaluate their in vitro antiproliferative activity against human cancer cell lines. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessCommunication

Synthesis of 6-Methyluracilpentylviologen Resorcinarene Cavitand

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Vyacheslav E. Semenov

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Igor S. Antipin

Molbank 2022, 2022(4), M1507; https://doi.org/10.3390/M1507 - 25 Nov 2022

Abstract

Resorcinarenes, as macrocyclic compounds, are widely used to recognize substrates and create supramolecular assemblies. Their bowl-like form organizes functional groups at the upper and lower rims, which has a substantial impact on the molecular recognition of various substrates. As a result, resorcinarenes make [...] Read more.

Resorcinarenes, as macrocyclic compounds, are widely used to recognize substrates and create supramolecular assemblies. Their bowl-like form organizes functional groups at the upper and lower rims, which has a substantial impact on the molecular recognition of various substrates. As a result, resorcinarenes make good drug nanocarrier candidates. This paper presents the synthesis of a new resorcinarene cavitand functionalized along the upper rim with methyluracil and viologen fragments for its potential use in drug delivery. Methyluracils and viologens are well-known receptor-targeted compounds capable of facilitating the vector transfer of drugs and increasing the effectiveness of their action on cells. The paper describes the synthesis of resorcinarene modified with methyluracil and viologen groups along with its structure determined by ¹H-, ¹³C-NMR and IR spectroscopy. Full article

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Scheme 1

Open AccessCommunication

Diverse Hydrogen-Bonded Structural Motifs in 1,4-Diazabicyclo[2.2.2]octane N,N’-Dioxide Salts with Oxoanions

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Ksenia D. Abasheeva

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Pavel A. Demakov

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Vladimir P. Fedin

Molbank 2022, 2022(4), M1508; https://doi.org/10.3390/M1508 - 25 Nov 2022

Abstract

Four new hybrid inorganic–organic salts of 1,4-diazabicyclo[2.2.2]octane N,N’-dioxide (odabco) with the formulae odabco·2HNO₃ (1), odabco·HClO₄ (2), odabco·H₂SO₄ (3) and odabco·2H₂SO₄ (4) were synthesized and characterized by single-crystal [...] Read more.

Four new hybrid inorganic–organic salts of 1,4-diazabicyclo[2.2.2]octane N,N’-dioxide (odabco) with the formulae odabco·2HNO₃ (1), odabco·HClO₄ (2), odabco·H₂SO₄ (3) and odabco·2H₂SO₄ (4) were synthesized and characterized by single-crystal x-ray diffraction (XRD), powder XRD and infrared spectroscopy. Compound 1 is based on the isolated (H₂odabco)²⁺ fragments, representing 0D structure. 2 is based on cationic 1D {Hodabco}_nⁿ⁺ hydrogen-bonded chains. Compound 3 comprising a strongly coordinated sulfate anion consists of two-component hydrogen-bonded {-H₂odabco-SO₄₋} fragments forming uncharged 1D helical chains. 4 contains both {-HSO₄-}_n^n– and {-HSO₄-H₂odabco-HSO₄₋} hydrogen bonding motifs, resulting in a 3D polymeric network. A comparative structural analysis of both the obtained and the previously reported cognate structures was performed to rationalize the impact of the degree of odabco protonation and the anion donor ability on the structural features and dimensionalities of odabco-based hydrogen-bonded lattices. Full article

(This article belongs to the Section Structure Determination)

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Open AccessShort Note

(E)-3-(2-(4-methylthiazol-2-yl)hydrazineylidene)chromane-2,4-dione

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Fatlinda Rahmani

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Aurélien Crochet

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Fabio Zobi

Molbank 2022, 2022(4), M1504; https://doi.org/10.3390/M1504 - 24 Nov 2022

Abstract

(E)-3-(2-(4-methylthiazol-2-yl)hydrazineylidene)chromane-2,4-dione was synthesized for the first time and the compound was characterized by ¹H and ¹³C spectroscopy, IR spectroscopy, and UV-Vis. The chemical structure and isomeric configuration of the molecule were confirmed by single-crystal X-ray diffraction. Full article

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Open AccessShort Note

2-Benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

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Ivette Morales-Salazar

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Mónica A. Rincón-Guevara

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Eduardo González-Zamora

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Alejandro Islas-Jácome

Molbank 2022, 2022(4), M1503; https://doi.org/10.3390/M1503 - 23 Nov 2022

Abstract

The new polyheterocyclic compound 2-benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (1) was synthesized via a one-pot process involving an Ugi-Zhu three-component reaction coupled to a cascade aza-Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration process, using toluene as the solvent, ytterbium (III) triflate as the [...] Read more.

The new polyheterocyclic compound 2-benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (1) was synthesized via a one-pot process involving an Ugi-Zhu three-component reaction coupled to a cascade aza-Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration process, using toluene as the solvent, ytterbium (III) triflate as the Lewis acid catalyst, and microwave-dielectric heating to increase the overall yield by up to 73%, while decreasing the reaction time to less than one hour. Product 1 was fully characterized by its physicochemical properties and using spectroscopic techniques (IR, HRMS and NMR). Full article

(This article belongs to the Collection Heterocycle Reactions)

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Graphical abstract

Open AccessShort Note

N²,N⁶-Bis(6-iodo-2-methyl-4-oxoquinazolin-3(4H)-yl)pyridine-2,6-dicarboxamide

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Maja Molnar

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Mario Komar

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Igor Jerković

Molbank 2022, 2022(4), M1500; https://doi.org/10.3390/M1500 - 21 Nov 2022

Abstract

A green chemistry method was applied in the synthesis of N²,N⁶-bis(6-iodo-2-methyl-4-oxoquinazolin-3(4H)-yl)pyridine-2,6-dicarboxamide. The desired compound was synthesized mechanochemically, using a choline chloride-based deep eutectic solvent as a catalyst. The synthesis took 20 min and the new compound was characterized using different spectral methods. Full article

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