Molbank

5 pages, 350 KiB

Open AccessShort Note

5,7-Diiodoquinolin-8-yl (E)-3-(3,4-dihydroxyphenyl)acrylate

by Marcin Cybulski, Michał Zieliński, Marek Kubiszewski and Olga Michalak

Molbank 2025, 2025(2), M2000; https://doi.org/10.3390/M2000 (registering DOI) - 28 Apr 2025

We report the synthesis of 5,7-diiodoquinolin-8-yl ester of caffeic acid and its O,O-diallyl-protected analogue. The compounds from the hybrid class were fully characterised using NMR spectroscopy and high-resolution mass spectrometry. Full article

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Scheme 1

8 pages, 644 KiB

Open AccessShort Note

4,4′-(Anthracene-9,10-diylbis(ethyne-2,1-diyl))bis(1-benzyl-1-pyridinium) Bromide

by Valentina Novelli, Andrea D’Annibale, Fabrizio Casano, Alessandro Latini and Lorenza Romagnoli

Molbank 2025, 2025(2), M1998; https://doi.org/10.3390/M1998 (registering DOI) - 27 Apr 2025

Abstract

Viologens, i.e., quaternary 4,4′-bipyridinum salts, are a well-known class of functional organic compounds that have attracted in the past few decades a great deal of attention for their peculiar chemical and electrochemical properties and have therefore found numerous applications ranging from herbicides to [...] Read more.

Viologens, i.e., quaternary 4,4′-bipyridinum salts, are a well-known class of functional organic compounds that have attracted in the past few decades a great deal of attention for their peculiar chemical and electrochemical properties and have therefore found numerous applications ranging from herbicides to electrochromic devices. In this paper, the synthesis and characterization of a novel viologen derivative are described. In the reported compound, the pyridinium nitrogen atoms have been quaternarized with the benzyl group and an additional unsaturated moiety, namely a 9,10-diethynylanthracene core, has been inserted between the charged pyridinium rings to extend the conjugation. Characterization by means of absorbance and diffuse reflectance UV–visible spectroscopy suggested intriguing optical and electronic properties, making this extended viologen a potential candidate for different optoelectronic applications. Full article

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11 pages, 1146 KiB

Open AccessCommunication

1-(Pyrrolidin-1-yl)naphtho[1,2-d]isoxazole

by Ioannis E. Gerontitis, Abdul kadar Shaikh, Dimitrios Alivertis, Panteleimon G. Takis, Anastassios N. Troganis, Petros G. Tsoungas and George Varvounis

Molbank 2025, 2025(2), M1999; https://doi.org/10.3390/M1999 (registering DOI) - 27 Apr 2025

Abstract

In this study, we examined the oxidation of (E)-2-hydroxy-1-naphthaldehyde oxime with lead tetraacetate in tetrahydrofuran that produced novel (E)-7a,8,9,10-tetrahydro-12H-naphtho[1,2-e]pyrrolo[2,1-b][1,3]oxazin-12-one oxime and 1-(pyrrolidin-1-yl)naphtho[1,2-d]isoxazole and known 7a,8,9,10-tetrahydro-12H-naphtho[1,2-e]pyrrolo-[2,1-b][1,3]oxazin-12-one [...] Read more.

In this study, we examined the oxidation of (E)-2-hydroxy-1-naphthaldehyde oxime with lead tetraacetate in tetrahydrofuran that produced novel (E)-7a,8,9,10-tetrahydro-12H-naphtho[1,2-e]pyrrolo[2,1-b][1,3]oxazin-12-one oxime and 1-(pyrrolidin-1-yl)naphtho[1,2-d]isoxazole and known 7a,8,9,10-tetrahydro-12H-naphtho[1,2-e]pyrrolo-[2,1-b][1,3]oxazin-12-one in 15, 18, and 10% yields, respectively. The oxime is partially hydrolyzed to its corresponding ketone. Modifying the oxidants and reaction conditions did not improve the product yields. Based on previous studies in our laboratory, we proposed that the reactions proceed via the formation of an o-naphthoquinone nitrosomethide intermediate; 1D and 2D NMR, HRMS, IR, and UV-VIS spectra provided information that supported the structure of the products. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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7 pages, 958 KiB

Open AccessShort Note

(E)-4,2′,4′-Trimethoxychalcone (Z)-N-Tosyl Hydrazone

by Sonia Berenguel Gómez, Irene Moreno-Gutiérrez, Manuel Muñoz-Dorado, Míriam Álvarez-Corral and Ignacio Rodríguez-García

Molbank 2025, 2025(2), M1997; https://doi.org/10.3390/M1997 (registering DOI) - 27 Apr 2025

Abstract

The synthesis and structural characterization of (E)-4,2′,4′-trimethoxychalcone (Z)-N-tosyl hydrazone, a conjugated tosylhydrazone derivative, is described. The compound was obtained via the condensation of (E)-1-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one with p-toluenesulfonylhydrazide in methanol under mild conditions, yielding a yellow [...] Read more.

The synthesis and structural characterization of (E)-4,2′,4′-trimethoxychalcone (Z)-N-tosyl hydrazone, a conjugated tosylhydrazone derivative, is described. The compound was obtained via the condensation of (E)-1-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one with p-toluenesulfonylhydrazide in methanol under mild conditions, yielding a yellow solid in a 66% yield. The structure of the product was confirmed through ¹H NMR, ¹³C NMR, IR spectroscopy, mass spectrometry, and single-crystal X-ray diffraction analysis, which revealed a non-planar molecular conformation and a Z configuration for the C=N double bond. This work is part of our ongoing research on carbene-mediated transformations. Full article

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Graphical abstract

6 pages, 1255 KiB

Open AccessShort Note

(3a,8b)-5-Acetyl-3a-fluoro-6,8-dihydroxy-7,8b-dimethyl-3,3a-dihydrofuro[3,2-b]benzofuran-2(8bH)-one

by Aleksandr S. Filimonov, Stepan P. Zernov, Olga A. Luzina and Nariman F. Salakhutdinov

Molbank 2025, 2025(2), M1995; https://doi.org/10.3390/M1995 - 24 Apr 2025

Abstract

Usnetic acid is a dibenzofuran-2-ylacetic acid that can be obtained by alkaline degradation of a secondary lichen metabolite—usnic acid. In the present paper, the product of the reaction of usnetic acid with a mild fluorinating agent, Selectfluor^®, was obtained. The structure [...] Read more.

Usnetic acid is a dibenzofuran-2-ylacetic acid that can be obtained by alkaline degradation of a secondary lichen metabolite—usnic acid. In the present paper, the product of the reaction of usnetic acid with a mild fluorinating agent, Selectfluor^®, was obtained. The structure of the product was proved by a set of physical methods, including ¹H, ¹³C, ¹⁹F NMR, HMBC, HSQC, HRMS and IR spectroscopy. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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6 pages, 1285 KiB

Open AccessShort Note

2,2′-((5,5′,6,6′-Tetramethoxy-[1,1′-biphenyl]-3,3′-diyl)bis(methanylylidene))dimalononitrile

by David Gendron and Josée Labrecque

Molbank 2025, 2025(2), M1996; https://doi.org/10.3390/M1996 (registering DOI) - 24 Apr 2025

Abstract

This report discusses the synthesis of a biosourced divanillin derivative obtained by Knoevenagel condensation. The compound was fully characterized by proton (¹H), carbon (¹³C), heteronuclear single quantum coherence (HSQC), homonuclear correlation spectroscopy (COSY), and heteronuclear multiple bond correlation (HMBC) [...] Read more.

This report discusses the synthesis of a biosourced divanillin derivative obtained by Knoevenagel condensation. The compound was fully characterized by proton (¹H), carbon (¹³C), heteronuclear single quantum coherence (HSQC), homonuclear correlation spectroscopy (COSY), and heteronuclear multiple bond correlation (HMBC) NMR, as well as high-resolution mass spectroscopy (HRMS). We also investigated the optical properties through UV-visible spectroscopy and Fourier-transform infrared (FTIR) spectroscopy. At last, the thermal properties of this divanillin derivative were evaluated by thermogravimetric analysis (TGA) as well as differential scanning calorimetry (DSC). Full article

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7 pages, 603 KiB

Open AccessShort Note

6-(7,8-Dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)hexyl 5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate

by Simona Marincean, Diana Nichols, Rachael Schulz, Travis Branscum and Marilee Benore

Molbank 2025, 2025(2), M1994; https://doi.org/10.3390/M1994 - 23 Apr 2025

Abstract

Herein we report the synthesis of 6-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)hexyl 5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate. The compound was fully characterized by melting point, ¹H-, ¹³C-NMR spectroscopy, IR spectroscopy, UV-VIS spectroscopy, mass spectrometry, and elemental analysis. The obtained data confirmed the successful synthesis and structure of the novel molecule. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Graphical abstract

4 pages, 482 KiB

Open AccessShort Note

N-(2,2-Diphenylethyl)furan-2-carboxamide

by Iliyan Ivanov, Diyana Dimitrova and Stanimir Manolov

Molbank 2025, 2025(2), M1993; https://doi.org/10.3390/M1993 - 16 Apr 2025

Abstract

We report the synthesis of N-(2,2-diphenylethyl)furan-2-carboxamide. The compound was fully characterized by melting point determination, ¹H and ¹³C NMR spectroscopy, infrared spectroscopy, and mass spectrometry. The combined analytical data confirm both the successful synthesis and the structural integrity of the target molecule. Full article

(This article belongs to the Section Structure Determination)

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5 pages, 932 KiB

Open AccessShort Note

N-(3-(tert-Butyl)-1-methyl-1H-pyrazol-5-yl)-4-methyl-N-tosylbenzenesulfonamide

by Diana Becerra and Juan-Carlos Castillo

Molbank 2025, 2025(2), M1992; https://doi.org/10.3390/M1992 - 15 Apr 2025

Abstract

N-(3-(tert-Butyl)-1-methyl-1H-pyrazol-5-yl)-4-methyl-N-tosylbenzenesulfonamide was efficiently synthesized in good yield through a triethylamine-mediated sulfonamidation reaction of 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine with 4-methylbenzenesulfonyl chloride in acetonitrile at room temperature. The pyrazole-based benzenesulfonamide was fully characterized using FT-IR, NMR, and HMRS techniques. Full article

(This article belongs to the Collection Heterocycle Reactions)

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6 pages, 1615 KiB

Open AccessShort Note

4-[2-(Chlorodiphenylstannyl)phenyl]-4-hydroxybutan-2-one

by Adrian-Alexandru Someșan and Richard A. Varga

Molbank 2025, 2025(2), M1991; https://doi.org/10.3390/M1991 - 9 Apr 2025

Abstract

An aldol condensation reaction between [2-(O=CH)C₆H₄]SnPh₂Cl and acetone gave [2-{CH₃C(=O)CH₂(OH)CH}C₆H₄]SnPh₂Cl (1). The compound was characterized in a solution using multinuclear NMR spectroscopy and HR-MS spectrometry [...] Read more.

An aldol condensation reaction between [2-(O=CH)C₆H₄]SnPh₂Cl and acetone gave [2-{CH₃C(=O)CH₂(OH)CH}C₆H₄]SnPh₂Cl (1). The compound was characterized in a solution using multinuclear NMR spectroscopy and HR-MS spectrometry and in a solid state using IR spectroscopy and single-crystal X-ray diffraction. The molecular structure revealed the presence of both enantiomers in the crystal. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

6 pages, 1256 KiB

Open AccessCommunication

Synthesis and Intramolecular Regioselective Cyclization of 2-Cyano-3,10-dioxo-1,10-seco-1,25-dinorlupan-28-yl Benzoate

by Irina Tolmacheva, Mikhail Nazarov and Victoria Grishko

Molbank 2025, 2025(2), M1990; https://doi.org/10.3390/M1990 - 7 Apr 2025

Abstract

The paper describes the synthesis of a new 1,10-seco-triterpenoid with a 2-cyano-3,10-diketone fragment and its further regioselective cyclization under acidic and basic conditions with the formation of 2S-cyanopyran-3-one derivative or A-pentacyclic alkene β-ketonitrile, respectively. Full article

(This article belongs to the Section Natural Product Chemistry)

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5 pages, 335 KiB

Open AccessCommunication

Synthesis of a 2-(2-Trifluoroethoxyphenyl)oxazoline

by R. Alan Aitken and Andrew D. Harper

Molbank 2025, 2025(2), M1989; https://doi.org/10.3390/M1989 - 2 Apr 2025

Abstract

The title compound has been prepared in four steps starting from ethyl 2-fluorobenzoate. The final product as well as the intermediates are fully characterised by spectroscopic methods with the ¹H and ¹³C NMR spectra, featuring coupling to ¹⁹F being particularly informative. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Scheme 1

11 pages, 1910 KiB

Open AccessCommunication

Synthesis and Characterization of cis-/trans-(±)-3-Alkyl-3,4-dihydro-6,7-dimethoxy-1-oxo-1H-isochromene-4-carboxylic Acids

by Savina Stoyanova and Milen G. Bogdanov

Molbank 2025, 2025(2), M1988; https://doi.org/10.3390/M1988 - 1 Apr 2025

Abstract

A series of new 3-alkyl substituted cis- and trans-(±)-3,4-dihydro-6,7-dimethoxy-1-oxo-1H-isochromene-4-carboxylic acids (cis-/trans-1–3) was synthesized through the reaction of 6,7-dimethoxyhomophthalic anhydride with aliphatic aldehydes of varying chain lengths. Their structure and configuration were [...] Read more.

A series of new 3-alkyl substituted cis- and trans-(±)-3,4-dihydro-6,7-dimethoxy-1-oxo-1H-isochromene-4-carboxylic acids (cis-/trans-1–3) was synthesized through the reaction of 6,7-dimethoxyhomophthalic anhydride with aliphatic aldehydes of varying chain lengths. Their structure and configuration were elucidated using spectral methods, including ¹H, ¹³C, DEPT-135 NMR, FTIR, UV-Vis, and HRMS analyses. A deductive conformational analysis was performed for determining the preferred conformations in solution and to explain the observed vicinal coupling constants. Full article

(This article belongs to the Section Structure Determination)

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9 pages, 761 KiB

Open AccessCommunication

2D Coordination Polymer [Fe(piv)₂(dab)₂]_n

by Vladimir A. Bushuev, Dmitriy S. Yambulatov, Stanislav A. Nikolaevskii, Mikhail A. Kiskin and Igor L. Eremenko

Molbank 2025, 2025(2), M1987; https://doi.org/10.3390/M1987 - 31 Mar 2025

Abstract

The interaction of preorganized iron(II) pivalate complexes with aromatic N-donor ligand (pyridine (py) or 2,2′-bipyridine (bpy)) and 1,4-diaminobutane (dab, putrescine) in anhydrous acetonitrile yielded a new 2D coordination polymer [Fe(piv)₂(dab)₂]_n (1, piv = Me₃CCO [...] Read more.

The interaction of preorganized iron(II) pivalate complexes with aromatic N-donor ligand (pyridine (py) or 2,2′-bipyridine (bpy)) and 1,4-diaminobutane (dab, putrescine) in anhydrous acetonitrile yielded a new 2D coordination polymer [Fe(piv)₂(dab)₂]_n (1, piv = Me₃CCO₂^–). The molecular structure of 1 in crystal was determined by single-crystal X-ray diffraction analysis and ATR-FTIR spectroscopy. Full article

(This article belongs to the Section Structure Determination)

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5 pages, 2383 KiB

Open AccessShort Note

(E,E)-1,5-Diethoxy-1,5-diphenylpenta-1,4-dien-3-one

by R. Alan Aitken, David B. Cordes, Verity Kennett and Aidan P. McKay

Molbank 2025, 2025(2), M1986; https://doi.org/10.3390/M1986 - 28 Mar 2025

Abstract

The title compound has been fully characterised for the first time. Fully assigned ¹H and ¹³C NMR spectra and the X-ray structure are presented. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

11 pages, 2423 KiB

Open AccessCommunication

Synthesis of N,N-Dimethylaminopropyl Derivative of A Blood Sugar Antigen

by Elena Di Marzo, Luigi Lay and Giuseppe D’Orazio

Molbank 2025, 2025(2), M1985; https://doi.org/10.3390/M1985 - 27 Mar 2025

Abstract

Gold nanoparticles (AuNPs) are a promising tool for drug delivery due to their unique chemical properties that make them biocompatible and easy to functionalize. However, when AuNPs are introduced into biological systems, they are coated by the so-called protein corona (PC), which affects [...] Read more.

Gold nanoparticles (AuNPs) are a promising tool for drug delivery due to their unique chemical properties that make them biocompatible and easy to functionalize. However, when AuNPs are introduced into biological systems, they are coated by the so-called protein corona (PC), which affects their biodistribution and limits their therapeutic efficacy. The functionalization of AuNPs with endogenous carbohydrates can be a possible strategy to reduce immune recognition, thus enhancing their biocompatibility and circulation time. Suitable candidates for this approach are the ABO blood sugar antigens, di- and tri-saccharides that represent the terminal portion of some glycolipids and glycoproteins present on the surface of human red blood cells and other tissues. In this work, we illustrate the synthesis of trisaccharide antigen A derivative, whose last step is worthy of investigation. During the final hydrogenolysis reaction, intended to remove protecting groups, an unexpected side reaction occurred, the isolated product bearing an N,N-dimethyl moiety on the anomeric propyl linker. This side reaction might be ascribed to the in situ formation of formaldehyde and successive imine formation and reduction. The obtained compound can be used as a monomeric control compound in biochemical and structural biology studies involving ABO blood sugar antigens. Full article

(This article belongs to the Collection Molecules from Side Reactions)

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6 pages, 7999 KiB

Open AccessShort Note

tert-Butyl (6-(3-(3-Fluorophenyl)ureido)hexyl)carbamate

by Daria Zapravdina, Konstantin Eremeev, Ilya A. Yakushev, Anna Maksimova, Jourdan Bynerie and Vladimir Burmistrov

Molbank 2025, 2025(2), M1984; https://doi.org/10.3390/M1984 - 26 Mar 2025

Abstract

The title compound, tert-butyl (6-(3-(3-fluorophenyl)ureido)hexyl)carbamate, was synthesized and characterized by NMR, MS, elemental analysis, and single-crystal X-ray diffraction. This urea can serve as a framework for the preparation of unsymmetrical diureas or compounds containing both urea and thiourea groups. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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4 pages, 502 KiB

Open AccessShort Note

Benzyl 2-Phenyl-1H-pyrrole-1-carboxylate

by Sung-Gon Kim

Molbank 2025, 2025(2), M1983; https://doi.org/10.3390/M1983 - 24 Mar 2025

Abstract

A highly novel method for the preparation of benzyl 2-phenyl-1H-pyrrole-1-carboxylate has been developed. The intramolecular reaction of benzyl (E)-(4-oxo-4-phenylbut-2-en-1-yl)carbamate with oxalyl chloride provided title compound in good yields. The structure of the newly synthesized compound was determined using ¹ [...] Read more.

A highly novel method for the preparation of benzyl 2-phenyl-1H-pyrrole-1-carboxylate has been developed. The intramolecular reaction of benzyl (E)-(4-oxo-4-phenylbut-2-en-1-yl)carbamate with oxalyl chloride provided title compound in good yields. The structure of the newly synthesized compound was determined using ¹H-, ¹³C-NMR, IR, and mass spectral data. Full article

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Scheme 1

10 pages, 676 KiB

Open AccessCommunication

Synthesis of a Hydrogen Isotope-Labeled SGLT1 C-Glucoside Ligand for Distribution and Metabolic Fate Studies

by Giuseppe D’Orazio and Barbara La Ferla

Molbank 2025, 2025(1), M1982; https://doi.org/10.3390/M1982 - 21 Mar 2025

Abstract

Over the last decades, a novel immunological function was established for the sodium–glucose co-transporter 1 (SGLT1), a protein involved in sugar absorption in the small intestine. High-glucose dosage and pharmacological concentrations of a C-glucoside analog showed a protective role in in vitro [...] Read more.

Over the last decades, a novel immunological function was established for the sodium–glucose co-transporter 1 (SGLT1), a protein involved in sugar absorption in the small intestine. High-glucose dosage and pharmacological concentrations of a C-glucoside analog showed a protective role in in vitro and in vivo models of severe inflammation states; experimental evidence suggests the engagement of SGLT1 in these processes. The mechanism of action underlying the protection is still unclear. To enhance our understanding of the molecular mechanisms responsible for this protection, we have developed a synthesis for the preparation of hydrogen isotope-labeled versions of the C-glucoside hit compound. Specifically, we report the synthesis of the deuterium-labeled derivative, which can be utilized for mass spectrometry-based research to examine the compound’s metabolic pathway, distribution, and cellular/tissue localization. The synthetic method developed can be extended to produce the tritiated analog, serving as a radioactive tracer. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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