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Molbank, Volume 2023, Issue 4

2023 December - 20 articles

Cover Story: Although the triethylammonium betaine of squaric acid was first reported almost 30 years ago, its structure has remained unpublished until now. The crystal structure determination via the use of Hirshfeld atom refinement reveals that the compound is best described as a resonance hybrid structure with a partial enolate character of the two lateral squaric acid C=O groups. The solid-state supramolecular structure features weak intermolecular C–H···O hydrogen bonds. The present study provides the first structural characterization of a betaine of squaric acid containing a four-coordinate nitrogen atom directly attached to the four-membered ring. View this paper
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Articles (20)

  • Short Note
  • Open Access
2,821 Views
4 Pages

18 December 2023

The reaction of 8-(4-bromobenzoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-1,6,7-trione with benzylamine in acetonitrile at room temperature afforded a good yield of (Z)-1-benzyl-5-(4-bromophenyl)-5-hydroxy-4-(2-oxomorpholin-3-ylidene)pyrrolidine-2...

  • Short Note
  • Open Access
2,812 Views
9 Pages

4-(5-Benzyl-3-((4-fluorophenyl)sulfonyl)-5-methyl-4,5-dihydrofuran-2-yl)-2-nitrobenzamide

  • Oscar Leonardo Avendaño Leon,
  • Christophe Curti,
  • Hussein El-Kashef,
  • Youssef Kabri,
  • Sébastien Redon and
  • Patrice Vanelle

15 December 2023

As part of our ongoing attempt to broaden the applications of the amidoxime moiety as a potential source of new antileishmanial agents, this study focuses on the product 4-(5-Benzyl-3-((4-fluorophenyl)sulfonyl)-5-methyl-4,5-dihydrofuran-2-yl)-2-nitro...

  • Short Note
  • Open Access
2,212 Views
7 Pages

13 December 2023

The reaction of 3-benzoylpyrrolo[2,1-c][1,4]benzothiazine-1,2,4-trione with 2,3-dimethylquinoxaline afforded 3-benzoyl-2-hydroxy-3a-[(3-methylquinoxalin-2-yl)methyl]-1H-pyrrolo[2,1-c][1,4]benzothiazine-1,4(3aH)-dione in a moderate yield. The compound...

  • Communication
  • Open Access
3,422 Views
11 Pages

Building Triazolated Macrocycles from Bis-Propargylated Calix[4]arenes and Bis-Azidomethylated Azobenzene or Stilbene

  • Ivan Lentin,
  • Ilia Korniltsev,
  • Alexander Gorbunov,
  • Dmitry Cheshkov,
  • Stanislav Bezzubov,
  • Vladimir Kovalev and
  • Ivan Vatsouro

7 December 2023

Copper(I)-catalyzed azide-alkyne cycloaddition was employed to construct biscalixarene assemblies from the calix[4]arene dipropargyl ethers and 4,4′-bis-azidomethylated azobenzene or stilbene. Three bis(calixarenes) having the calix[4]arene cor...

  • Communication
  • Open Access
2 Citations
3,718 Views
12 Pages

5,8-Quinolinedione Attached to Quinone Derivatives: XRD Diffraction, Fourier Transform Infrared Spectra and Computational Analysis

  • Arkadiusz Sokal,
  • Roman Wrzalik,
  • Joanna Klimontko,
  • Elwira Chrobak,
  • Ewa Bębenek and
  • Monika Kadela-Tomanek

28 November 2023

Quinoline and isoquinoline moieties occur in many natural and synthetic compounds exhibiting high biological activity. The purpose of this study was to analyze the chemical structures of 5,8-quinolinedione and 5,8-isoquinoline derivatives using FT-IR...

  • Short Note
  • Open Access
1 Citations
2,714 Views
6 Pages

2-(4-(Fluorosulfonyloxy)phenyl)benzoxazole

  • Nadezhda V. Danilenko,
  • Mariia O. Lutsuk,
  • Svetlana E. Patlasova,
  • Elena I. Korotkova and
  • Andrei I. Khlebnikov

27 November 2023

New 2-(4-(fluorosulfonyloxy)phenyl)benzoxazole (2) was synthesized through the SuFEx click reaction in a two-chamber reactor. The effect of silylation on the yield of the target compound was investigated. The fluorescent properties of compound 2 were...

  • Communication
  • Open Access
1 Citations
2,317 Views
7 Pages

Synthesis and In Silico Drug-Likeness Modeling of 5-FU/ASA Hybrids

  • Wilson Castrillón-López,
  • Andrés F. Yepes and
  • Wilson Cardona-Galeano

27 November 2023

A series of 5-FU-ASA hybrids were synthesized with good yields using click chemistry as the key step. The structures of these compounds were elucidated by spectroscopic analysis. Finally, an optimal pharmacokinetic profile was also estimated for each...

  • Short Note
  • Open Access
3,035 Views
5 Pages

1-(2,5-Dimethoxy-4-nitrophenyl)piperidine

  • Tanjia M. Syeda,
  • Muadh R. Al-Shaidi,
  • Ibtihal Basri,
  • Mahboub Merzouk and
  • Fawaz Aldabbagh

27 November 2023

Treatment of the non-purified mixture of dinitro isomers obtained from the nitration of 1,4-dimethoxybenzene with piperidine led to the isolation of novel but minor adduct, 1-(2,5-dimethoxy-4-nitrophenyl)piperidine (2b) in 15% yield. Yields of nucleo...

  • Communication
  • Open Access
3 Citations
2,322 Views
8 Pages

Synthesis of Norabietyl and Nordehydroabietyl Imidazolidine-2,4,5-Triones and Their Activity against Tyrosyl-DNA Phosphodiesterase 1

  • Kseniya S. Kovaleva,
  • Olga I. Yarovaya,
  • Irina A. Chernyshova,
  • Alexandra L. Zakharenko,
  • Sergey V. Cheresiz,
  • Amirhossein Azimirad,
  • Andrey G. Pokrovsky,
  • Olga I. Lavrik and
  • Nariman F. Salakhutdinov

9 November 2023

New imidazolidine-2,4,5-triones with norabietic, nordehydroabietic, and adamantane substituents were synthesized by reacting oxalyl chloride and the corresponding ureas, providing good yields. Bioisosteric replacement of the ureide group with a parab...

  • Short Note
  • Open Access
2 Citations
2,725 Views
7 Pages

4,4′,4″-(Benzene-1,3,5-triyltris(ethyne-2,1-diyl))tris(1-methylpyridin-1-ium) Iodide

  • Lorenza Romagnoli,
  • Andrea D’Annibale and
  • Alessandro Latini

8 November 2023

Despite having been known for a long time, quaternary 4,4′-bipyridinium salts, or viologens, are still a highly inspiring class of compounds, thanks to their peculiar redox and charge transfer properties. However, more complex structures contai...

  • Short Note
  • Open Access
1,934 Views
6 Pages

28-O-Acetyl-3-O’-(Phenylpropynoyl)Betulin

  • Ewa Bębenek,
  • Monika Kadela-Tomanek,
  • Beata Filip-Psurska and
  • Elwira Chrobak

24 October 2023

New derivative of 28-acetylbetulin containing a phenylpropynoyl moiety at the C-3 position was obtained by Steglich method. The chemical structure of this compound has been determined through 1H NMR, 13C NMR, IR, EI MS and HRMS. The antiproliferative...

  • Communication
  • Open Access
2 Citations
1,946 Views
7 Pages

18 October 2023

In this study, the synthesis and biological activities of previously and newly synthesized oleanolic acid derivatives containing seven-membered cyclic amines at the C28 position were described. The obtained compounds were fully characterized via 1H a...

  • Short Note
  • Open Access
1,963 Views
5 Pages

2-(1-Methoxycarbonyl-2-phenyleth-1-yl)-1-benzylpyridin-1-ium Bromide

  • Lorenzo Suigo,
  • Valentina Straniero and
  • Ermanno Valoti

16 October 2023

In this work, we report the unexpected conversion of a pyridine derivative into the corresponding N-benzylated pyridinium salt due to the presence of unreacted benzyl bromide in the crude product. This transformation was observed at room temperature...

  • Communication
  • Open Access
1 Citations
2,597 Views
10 Pages

Structural Elucidation of the Triethylammonium Betaine of Squaric Acid

  • Paul R. Palme,
  • Richard Goddard,
  • Markus Leutzsch,
  • Adrian Richter,
  • Peter Imming and
  • Rüdiger W. Seidel

16 October 2023

Betaines of squaric acid have gained research interest because of their structural and spectral properties. We elucidated the crystal and molecular structure of the triethylammonium betaine of squaric acid (1) by X-ray crystallography, IR, and NMR sp...

  • Short Note
  • Open Access
2 Citations
2,267 Views
6 Pages

Diethyl (5-Benzyl-2-(4-(N′-hydroxycarbamimidoyl)phenyl)-5-methyl-4,5-dihydrofuran-3-yl)phosphonate

  • Oscar Leonardo Avendaño Leon,
  • Christophe Curti,
  • Fabiana Maia Santos Urbancg Moncorvo,
  • Youssef Kabri,
  • Sébastien Redon,
  • Eduardo Caio Torres-Santos,
  • Romain Paoli-Lombardo and
  • Patrice Vanelle

13 October 2023

As part of our ongoing research into the antileishmanial properties of amidoxime derivatives, we report a preliminary assessment of the antiparasitic properties of a novel compound, diethyl (5-benzyl-2-(4-(N′-hydroxycarbamimidoyl)phenyl)-5-meth...

  • Communication
  • Open Access
2,244 Views
9 Pages

Potassium 6-Oxo-7,13,16,22-tetraazatetracyclo[12.6.2.18,12.017,21]tricosa-1(20),8(23),9,11,14,16,18,21-octaen-2-yne-15-carboxylate

  • Camille Blouet,
  • Stéphanie Letast,
  • Thomas Robert,
  • Stéphane Bach,
  • Noël Pinaud,
  • Nicolas Joubert,
  • Marie-Claude Viaud-Massuard,
  • Jean Guillon,
  • Cédric Logé and
  • Caroline Denevault-Sabourin

9 October 2023

Potassium 6-oxo-7,13,16,22-tetraazatetracyclo[12.6.2.18,12.017,21]tricosa-1(20),8(23),9,11,14,16,18,21-octaen-2-yne-15-carboxylate was synthesized through a multi-step pathway, starting from commercially available 3-iodo-1,2-phenylenediamine. Structu...

  • Short Note
  • Open Access
3 Citations
1,793 Views
6 Pages

(2aR,2a1S,5aR,9bR)-4-Isopropyl-7,8-dimethoxy-2a1-methyl-2,2a,2a1,3,5a,9b-hexahydrofluoreno[9,1-bc]furan

  • Irina V. Ilyina,
  • Nikolai S. Li-Zhulanov,
  • Yuri V. Gatilov,
  • Konstantin P. Volcho,
  • Alexander Yu. Sidorenko,
  • Vladimir E. Agabekov and
  • Nariman F. Salakhutdinov

9 October 2023

The development of highly efficient methods for the synthesis of chemical products by using renewable raw materials is one of the topical areas of medicinal chemistry. The paper presents the synthesis of (2aR,2a1S,5aR,9bR)-4-isopropyl-7,8-dimethoxy-2...

  • Short Note
  • Open Access
2 Citations
2,293 Views
6 Pages

3 October 2023

Viologens are a highly advantageous class of compounds for the synthesis of functional materials. Owing to their versatile structure, they can embed additional conjugated moieties, thus representing a convenient platform, for example for organic semi...

  • Short Note
  • Open Access
3,149 Views
7 Pages

(3-(4-Chlorophenyl)-4,5-dihydroisoxazol-5-yl)methyl Benzenesulfonate

  • Loubna Mokhi,
  • Karim Chkirate,
  • Xiaodong Zhang,
  • Mohsine Driowya and
  • Khalid Bougrin

22 September 2023

A novel single crystal of (3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl)methyl benzenesulfonate has been synthetized via a one-pot sequential strategy under sonication. The single crystal has been investigated using X-ray diffraction analysis. Hydroge...

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Molbank - ISSN 1422-8599