Molbank

Open AccessShort Note

N-isobutyl-1,8-bis(isobutylamino)-naphthalimide

by

Rossella Santonocito

,

Ivana Maria Caruso

and

Giuseppe Trusso Sfrazzetto

Molbank 2023, 2023(1), M1568; https://doi.org/10.3390/M1568 - 27 Jan 2023

Abstract

Naphthalimides make up a class of organic molecules characterised by excellent spectroscopic properties due to their extended conjugate system. Furthermore, various asymmetric or symmetric compounds can be obtained from naphthalimides by the different functionalization that can be performed on the nitrogen and/or on [...] Read more.

Naphthalimides make up a class of organic molecules characterised by excellent spectroscopic properties due to their extended conjugate system. Furthermore, various asymmetric or symmetric compounds can be obtained from naphthalimides by the different functionalization that can be performed on the nitrogen and/or on the aromatic rings. The introduction of a wide range of substituents in different positions allows chemical and spectroscopic properties to be regulated. In this contribution, we report the synthesis and characterization of a new 4,5-amino-1,8-naphthalimide bearing three isobutyl substituents. Full article

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Open AccessShort Note

2-{9-(10-Bromoanthracenyl)}-1,3-dihydro-1H-[d]-1,3,2-benzodiazaborole

by

Siphamandla Sithebe

Molbank 2023, 2023(1), M1569; https://doi.org/10.3390/M1569 - 27 Jan 2023

Abstract

In this paper, a synthesis and characterization of a novel three coordinate 2-{9-(10-Bromoanthracenyl)}-1,3-dihydro-1H-[d]-1,3,2-benzodiazaborole from a cyclo-condensation reaction of o-phenylenediamine and 10-bromoanthracene-9-boronic acid is described. The desired product was obtained in 0.343 g (92% yields) with its structure characterized [...] Read more.

In this paper, a synthesis and characterization of a novel three coordinate 2-{9-(10-Bromoanthracenyl)}-1,3-dihydro-1H-[d]-1,3,2-benzodiazaborole from a cyclo-condensation reaction of o-phenylenediamine and 10-bromoanthracene-9-boronic acid is described. The desired product was obtained in 0.343 g (92% yields) with its structure characterized by ¹H, ¹¹B, ¹³C NMR, HRMS and FT-IR. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Scheme 1

Open AccessShort Note

2-Furyl-6-nitro-1,2,4-triazolo [1,5-a]pyrimidin-7-one

by

Victor V. Fedotov

,

Konstantin V. Savateev

,

,

,

and

Molbank 2023, 2023(1), M1563; https://doi.org/10.3390/M1563 - 23 Jan 2023

Abstract

A sodium salt of 2-(fur-2-yl)-6-nitro-1,2,4-triazolo[1,5-a]pyrimidin-7-one as a close structural analogue of ZM-241385 was obtained. This heterocycle can serve as an effector for A_2a adenosine receptors and possesses antiseptic activity. The structures of compounds were confirmed based on the data of [...] Read more.

A sodium salt of 2-(fur-2-yl)-6-nitro-1,2,4-triazolo[1,5-a]pyrimidin-7-one as a close structural analogue of ZM-241385 was obtained. This heterocycle can serve as an effector for A_2a adenosine receptors and possesses antiseptic activity. The structures of compounds were confirmed based on the data of ¹H, ¹³C NMR spectroscopy, IR spectroscopy, and an elemental analysis. The structure of sodium salt 2-furyl-6-nitro-1,2,4-triazolo[1,5-a]pyrimidin-7-one was confirmed by an X-ray diffraction analysis. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

Cis-(3-benzyloxy-1,1-cyclobutanedicarboxylato κ²O,O′)bis(1-methyl-1H-pyrazole)platinum(II)

by

,

,

,

,

and

Molbank 2023, 2023(1), M1564; https://doi.org/10.3390/M1564 - 23 Jan 2023

Abstract

A huge variety of types of cancer makes it necessary to search for new effective drugs with a defined molecular target. Modification of substituents in ligands based on 3-hydroxy-1,1-cyclobutanedicarboxylic acid are one of the effective directions to design a better version of carboplatin. [...] Read more.

A huge variety of types of cancer makes it necessary to search for new effective drugs with a defined molecular target. Modification of substituents in ligands based on 3-hydroxy-1,1-cyclobutanedicarboxylic acid are one of the effective directions to design a better version of carboplatin. In the present study, we combined in one molecule a derivative of 3-hydroxycyclobutane-1,1-dicarboxylic acid and N-methylpyrazole as a carrier ligand. The antiproliferative of the novel complex Pt(II) was established for cell lines HCT116, MCF7, A549, and WI38 by means of a standard MTT colorimetric assay. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

by

,

,

,

Ekaterina N. Chernova

,

Mariya A. Skryl’nikova

,

Vadim A. Baigildin

,

Aleksandra M. Puzyk

,

Alexander A. Oskorbyn

,

Rostislav E. Trifonov

,

Pavel A. Aleshunin

and

Vladimir A. Ostrovskii

Molbank 2023, 2023(1), M1565; https://doi.org/10.3390/M1565 - 23 Jan 2023

Abstract

Highly purified 5-vinyl-1H-tetrazole was synthesized, which is in great demand in modern medicine and industry as a monomer for obtaining nitrogen-rich macromolecular compounds and a reagent for the complete synthesis of biological compounds. The molecular structure was studied experimentally with sequential [...] Read more.

Highly purified 5-vinyl-1H-tetrazole was synthesized, which is in great demand in modern medicine and industry as a monomer for obtaining nitrogen-rich macromolecular compounds and a reagent for the complete synthesis of biological compounds. The molecular structure was studied experimentally with sequential X-ray diffraction analysis and theoretically with ab initio quantum chemical calculations. The data from differential scanning calorimetry, nuclear magnetic resonance (¹H, ¹³C, ¹H-¹⁵N, HMBC), high-resolution mass spectrometry and vibrational spectroscopy were analyzed. The results are useful for evaluating the possibility of extending the polymerization of 5-vinyl-1H-tetrazole to synthesize polymers with predictable molecular weight and thermodynamic parameters. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

(4-(Adamantan-1-yl)-1-(isopropyl)-1H-imidazol-2-yl)methanol

by

Ryan B. Gaynor

,

Baylee N. McIntyre

and

Sidney E. Creutz

Molbank 2023, 2023(1), M1566; https://doi.org/10.3390/M1566 - 23 Jan 2023

Abstract

(4-(Adamantan-1-yl)-1-(isopropyl)-1H-imidazol-2-yl)methanol was prepared through a five-step process starting from commercially available 1-acetyladamantane. Each step proceeded in moderate-to-excellent yields and the overall yield across five steps was 28%. The compound was identified and characterized by ¹H and ¹³C{¹H} [...] Read more.

(4-(Adamantan-1-yl)-1-(isopropyl)-1H-imidazol-2-yl)methanol was prepared through a five-step process starting from commercially available 1-acetyladamantane. Each step proceeded in moderate-to-excellent yields and the overall yield across five steps was 28%. The compound was identified and characterized by ¹H and ¹³C{¹H} NMR, high-resolution mass spectroscopy, and elemental analysis. This compound and its derivatives have the potential to be used as precursors to the synthesis of biomimetic chelating ligands. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessCommunication

Synthesis of Pentacycloundecane (PCUD) Based Spiro-Pyrano-Cage Framework via Ring-Closing Metathesis

by

Sambasivarao Kotha

,

Mohammad Salman

and

Subba Rao Cheekatla

Molbank 2023, 2023(1), M1567; https://doi.org/10.3390/M1567 - 23 Jan 2023

Abstract

Here, we demonstrate a short synthetic route to pyrano cage systems containing pentacycloundecane units by employing ring-closing metathesis (RCM) as a key step. These cage systems were constructed starting with readily available starting materials by adopting atomic economic processes such as cycloadditions (Diels-Alder [...] Read more.

Here, we demonstrate a short synthetic route to pyrano cage systems containing pentacycloundecane units by employing ring-closing metathesis (RCM) as a key step. These cage systems were constructed starting with readily available starting materials by adopting atomic economic processes such as cycloadditions (Diels-Alder reaction and [2+2] cycloaddition), Grignard addition, and olefin metathesis. The key building block, such as hexacyclic cage dione, was prepared from 1,4-naphthoquinone derivative and freshly cracked 1,3-cyclopentadiene. Some of these heterocyclic motifs are useful in biological chemistry and valuable as key synthons for high-energy-density materials. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Open AccessCommunication

Carboxybetaine and Carboxybetaine Ester Derivatives of Tetra(dodecyloxyphenyl)-calix[4]resorcinarene: Synthesis, Self-Assembly and In Vitro Toxicity

by

Julia E. Morozova

,

Zuchra R. Gilmullina

,

Victor V. Syakaev

,

Alexandra D. Voloshina

,

Anna P. Lyubina

,

Syumbelya K. Amerhanova

,

Olga B. Babaeva

,

Vasily M. Babaev

and

Igor S. Antipin

Molbank 2023, 2023(1), M1562; https://doi.org/10.3390/M1562 - 22 Jan 2023

Abstract

Amphiphilic calix[4]resorcinarenes are a class of macrocyclic compounds with broad potential utility including nanomedicine. Here the synthesis of new carboxybetaine and carboxybetaine ester calix[4]resorcinarene bearing 4-(dodecyloxy)phenyl groups on the lower rim is presented. The compounds were characterized by ¹H-NMR, ¹³C-NMR, 2D [...] Read more.

Amphiphilic calix[4]resorcinarenes are a class of macrocyclic compounds with broad potential utility including nanomedicine. Here the synthesis of new carboxybetaine and carboxybetaine ester calix[4]resorcinarene bearing 4-(dodecyloxy)phenyl groups on the lower rim is presented. The compounds were characterized by ¹H-NMR, ¹³C-NMR, 2D NMR, IR, ESI and elemental analysis. The critical association concentration values are 1.00 × 10⁻⁵ and 1.18 × 10⁻⁵ mol·L⁻¹ for carboxybetain and ester, respectively. The hemolytic activity of the macrocycles and their cytotoxicity against normal (WI-38, Chang liver) and tumor cells (M-HeLa) are also estimated. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessShort Note

(R)-N-Benzyl-N-(1-phenylethyl)cyclohexanamine

by

Ángel García-González

,

Leland Belda

,

Alejandro Manchado

,

Carlos T. Nieto

and

Narciso Martín Garrido

Molbank 2023, 2023(1), M1561; https://doi.org/10.3390/M1561 - 20 Jan 2023

Abstract

The preparation and characterization of a new chiral tertiary dibenzylamine are described. These molecules are well known in the literature for their high neuropharmacological potential. The general synthetic pathway is based on asymmetric Aza–Michael addition of chiral (R)-N-benzyl-N [...] Read more.

The preparation and characterization of a new chiral tertiary dibenzylamine are described. These molecules are well known in the literature for their high neuropharmacological potential. The general synthetic pathway is based on asymmetric Aza–Michael addition of chiral (R)-N-benzyl-N-(α-methylbenzyl)amide to methyl cyclohex-1-en-carboxilate obtaining the β-amino ester, followed by carboxylic acid hydrolysis and subsequent Barton descarboxylation. Interestingly, it is a general synthetic procedure of a wide range of chiral amines by careful choice of insaturated esters and alkylation of the chiral enolate in the initial reaction. The new tertiary dibenzylamine molecule is fully characterized by NMR Spectroscopy (¹H and ¹³C), as well by High-Resolution Mass Spectrometry and Infrared Spectroscopy. Full article

(This article belongs to the Section Organic Synthesis)

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Scheme 1

Open AccessShort Note

Methyl 3-Bromo-5-carbamoylisothiazole-4-carboxylate

by

Andreas S. Kalogirou

and

Panayiotis A. Koutentis

Molbank 2023, 2023(1), M1560; https://doi.org/10.3390/M1560 - 19 Jan 2023

Abstract

Reaction of methyl 3-bromo-5-cyanoisothiazole-4-carboxylate with conc. H₂SO₄ gave methyl 3-bromo-5-carbamoylisothiazole-4-carboxylate in 93% yield. The compound was fully characterized. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessCommunication

Obtainment of Threo and Erythro Isomers of the 6-Fluoro-3-(2,3,6,7,8,9-hexahydronaphtho[2,3-b][1,4]dioxin-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxamide

by

,

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and

Molbank 2023, 2023(1), M1559; https://doi.org/10.3390/M1559 - 18 Jan 2023

Abstract

2,6-difluorobenzamides have been deeply investigated as antibacterial drugs in the last few decades. Several 3-substituted-2,6-difluorobenzamides have proved their ability to interfere with the bacterial cell division cycle by inhibiting the protein FtsZ, the key player of the whole process. Recently, we developed a [...] Read more.

2,6-difluorobenzamides have been deeply investigated as antibacterial drugs in the last few decades. Several 3-substituted-2,6-difluorobenzamides have proved their ability to interfere with the bacterial cell division cycle by inhibiting the protein FtsZ, the key player of the whole process. Recently, we developed a novel family of 1,4-tetrahydronaphthodioxane benzamides, having an ethoxy linker, which reached sub-micromolar MICs towards Gram-positive Staphylococcus aureus and Bacillus subtilis. A further investigation of their mechanism of action should require the development of a fluorescent probe, and the consequent definition of a synthetic pathway for its obtainment. In the present work, we report the obtainment of an unexpected bicyclic side product, 6-fluoro-3-(2,3,6,7,8,9-hexahydronaphtho[2,3-b][1,4]dioxin-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxamide, coming from the substitution of one aromatic fluorine by the in situ formed alkoxy group, in the final opening of an epoxide intermediate. This side product was similarly achieved, in good yields, by opening the ring of both erythro and threo epoxides, and the two compounds were fully characterized using HRMS, ¹H-NMR, ¹³C-NMR, HPLC and DSC. Full article

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

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Open AccessShort Note

3-(1-Ethylamino-ethylidene)-1-methyl-pyrrolidine-2,4-dione

by

Plamen Angelov

,

Paraskeva Terziyska

and

Danail Georgiev

Molbank 2023, 2023(1), M1556; https://doi.org/10.3390/M1556 - 17 Jan 2023

Abstract

3-(1-Ethylamino-ethylidene)-1-methyl-pyrrolidine-2,4-dione was obtained as an unexpected product in a three-step synthesis starting with o-nitrobenzoyl sarcosine, acetoacetanilide and ethylamine. The compound showed moderate antibacterial activity against S. aureus and E. coli. Full article

(This article belongs to the Section Organic Synthesis)

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Scheme 1

Open AccessShort Note

2,3-Bis((E)-4-hydroxybenzylidene)-N1,N4-bis(4-methylbenzyl)succinamide

by

Claudia Sciacca

,

Nunzio Cardullo

and

Vera Muccilli

Molbank 2023, 2023(1), M1558; https://doi.org/10.3390/M1558 - 17 Jan 2023

Abstract

Lignans and neolignans are dimeric natural products with an extraordinary variety of structures and biological properties. Diphenylbutadienes are a subclass of lignans rarely found in nature with cannabisin G being the most representative example. This lignan, found in Cannabis sativa seed, has shown [...] Read more.

Lignans and neolignans are dimeric natural products with an extraordinary variety of structures and biological properties. Diphenylbutadienes are a subclass of lignans rarely found in nature with cannabisin G being the most representative example. This lignan, found in Cannabis sativa seed, has shown anti-inflammatory and antioxidant activity among other biological properties. Different methodologies have been reported for the synthesis of cannabis G to be employed in new biological studies. We report herein a green and concise procedure based on the use of Trametes versicolor laccase for the synthesis of a new diphenylbutadiene. The developed procedure may be employed for the synthesis of cannabisin G and other analogues. Full article

(This article belongs to the Section Natural Products)

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Open AccessCommunication

Synthesis of 3-Bromo-4-phenylisothiazole-5-carboxylic Acid and 3-Bromoisothiazole-5-carboxylic Acid

by

Andreas S. Kalogirou

and

Panayiotis A. Koutentis

Molbank 2023, 2023(1), M1557; https://doi.org/10.3390/M1557 - 17 Jan 2023

Abstract

Reactions of 3-bromo-4-phenylisothiazole-5-carboxamide and 3-bromoisothiazole-5-carboxamide with NaNO₂ (4 equiv.), in TFA, at ca. 0 °C gave the carboxylic acid products in 99% and 95% yields, respectively. The two compounds were fully characterized. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

5,5,7,7-Tetrametyl-6,7-dihydro-5H-dibenzo[c,e]azepine

by

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and

Molbank 2023, 2023(1), M1554; https://doi.org/10.3390/M1554 - 16 Jan 2023

Abstract

5,5,7,7-Tetrametyl-6,7-dihydro-5H-dibenzo[c,e]azepine has been synthesized as a possible pro-chiral (or tropos) unit for the construction of a chiral catalyst and as a molecular chirality sensor for the absolute configuration assignment by chiroptical spectroscopy. A straightforward synthetic strategy [...] Read more.

5,5,7,7-Tetrametyl-6,7-dihydro-5H-dibenzo[c,e]azepine has been synthesized as a possible pro-chiral (or tropos) unit for the construction of a chiral catalyst and as a molecular chirality sensor for the absolute configuration assignment by chiroptical spectroscopy. A straightforward synthetic strategy for the preparation of the title compound in high overall yield through sequential addition of the four methyl groups on benzylic positions has been described. A VT-NMR study was used to determine the rotational barrier of the aryl–aryl bond in this biphenylazepine, revealing its torsional flexibility at room temperature, which makes the biphenylazepine suitable as both a chirality probe and a tropos moiety in chiral ligands. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessEditorial

Acknowledgment to the Reviewers of Molbank in 2022

by Molbank Editorial Office

Molbank 2023, 2023(1), M1555; https://doi.org/10.3390/M1555 - 16 Jan 2023

Abstract

High-quality academic publishing is built on rigorous peer review [...] Full article

Open AccessShort Note

3-Chloro-4-(p-tolyl)isothiazole-5-carbonitrile

by

Andreas S. Kalogirou

and

Panayiotis A. Koutentis

Molbank 2023, 2023(1), M1553; https://doi.org/10.3390/M1553 - 13 Jan 2023

Abstract

A reaction of 3-chloroisothiazole-5-carbonitrile with 1-iodo-4-methylbenzene (2 equiv.) produced 3-chloro-4-(p-tolyl)isothiazole-5-carbonitrile in a 60% yield. The compound was fully characterized. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessCommunication

Synthesis of Bis(1,2,3-triazolyl)alkanes in Superbasic and Solvent-Free Conditions

by

Roman D. Marchenko

and

Andrei S. Potapov

Molbank 2023, 2023(1), M1551; https://doi.org/10.3390/M1551 - 13 Jan 2023

Abstract

Nucleophilic substitution reactions between 1,2,3-triazole and dibromomethane or 1,2-dirbomoethane in a superbasic medium potassium hydroxide–dimethyl sulfoxide gave mixtures of the isomeric bis(1,2,3-triazolyl)alkanes, in which (1,2,3-triazol-1-yl)(1,2,3-triazol-2-yl)alkanes and bis(1,2,3-triazol-2-yl)alkanes were the dominating products, while bis(triazol-1-yl)alkanes were detected only in trace amounts. The same products could [...] Read more.

Nucleophilic substitution reactions between 1,2,3-triazole and dibromomethane or 1,2-dirbomoethane in a superbasic medium potassium hydroxide–dimethyl sulfoxide gave mixtures of the isomeric bis(1,2,3-triazolyl)alkanes, in which (1,2,3-triazol-1-yl)(1,2,3-triazol-2-yl)alkanes and bis(1,2,3-triazol-2-yl)alkanes were the dominating products, while bis(triazol-1-yl)alkanes were detected only in trace amounts. The same products could also be obtained under solvent-free conditions in a neat reaction mixture. The proposed methods are economically feasible, do not require using toxic solvents or catalysts, and make the (1,2,3-triazol-2-yl)-derivatives, inaccessible by alkyne-azide cycloaddition (click) reactions, readily available. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Graphical abstract

Open AccessShort Note

3-(3,4-Dichlorophenyl)-5-(1H-indol-5-yl)-1,2,4-oxadiazole

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and

Molbank 2023, 2023(1), M1552; https://doi.org/10.3390/M1552 - 13 Jan 2023

Abstract

3-(3,4-Dichlorophenyl)-5-(1H-indol-5-yl)-1,2,4-oxadiazole was synthesized via the condensation of 3,4-dichlorobenzamidoxime and methyl 1H-indole-5-carboxylate using a superbasic medium (NaOH/DMSO). The compound was tested as a potential inhibitor of human monoamine oxidase (MAO) A and B. It demonstrated a notable inhibition with an [...] Read more.

3-(3,4-Dichlorophenyl)-5-(1H-indol-5-yl)-1,2,4-oxadiazole was synthesized via the condensation of 3,4-dichlorobenzamidoxime and methyl 1H-indole-5-carboxylate using a superbasic medium (NaOH/DMSO). The compound was tested as a potential inhibitor of human monoamine oxidase (MAO) A and B. It demonstrated a notable inhibition with an IC₅₀ value of 0.036 μM for the MAO-B and isoform specificity. The product was characterized by ¹H-NMR, ¹³C-NMR, and HRMS. In conclusion, the new active MAO-B inhibitor may serve as a candidate for the future discovery of therapeutic agents for neurodegenerative disorders such as Parkinson’s disease. Full article

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