Molbank

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

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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6 pages, 1031 KiB

Open AccessShort Note

3,4,6-Tri-O-acetyl-1-S-acetyl-2-deoxy-2-S-phenylthio-α-d-mannopyranoside

by Jack Porter and Gavin J. Miller

Molbank 2025, 2025(1), M1981; https://doi.org/10.3390/M1981 - 17 Mar 2025

Abstract

The title compound was isolated as the unexpected reaction product from a reaction attempting to access a glycosyl 1-phosphate. The product was isolated in good yield, as one diastereoisomer, and was characterised by ¹H, ¹³C, and 2D NMR, alongside HRMS analysis. Full article

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7 pages, 1278 KiB

Open AccessShort Note

Ethyl 4-Ene-4-ferrocenyl-5,5-bis-(4-hydroxyphenyl)-pentanoate

by Jérémy Forté and Pascal Pigeon

Molbank 2025, 2025(1), M1980; https://doi.org/10.3390/M1980 - 13 Mar 2025

Abstract

The ferrociphenol family is a group of molecules in which a ferrocenyl moiety is connected to at least one 4-hydroxyphenyl group through a C-C double bond. Among them, ferrocidiphenols in which the double bond is substituted by two gem 4-hydroxyphenyl groups have been [...] Read more.

The ferrociphenol family is a group of molecules in which a ferrocenyl moiety is connected to at least one 4-hydroxyphenyl group through a C-C double bond. Among them, ferrocidiphenols in which the double bond is substituted by two gem 4-hydroxyphenyl groups have been largely studied, demonstrating interesting anticancer properties. The fourth available position of the double bond could be substituted by a simple ethyl group (1a) inherited from Tamoxifen, but also by ethyl or methyl acetate, propionate, butanoate, pentanoate (1b-g), hydroxyethyl or hydroxypropyl (1h–i). Ethyl 4-ene-4-ferrocenyl-5,5-bis-(4-hydroxyphenyl)-pentanoate 1e shows an IC₅₀ on the MDA-MB-231 breast cancer cell line very close to that of 1a. These compounds were synthesized in moderate to good yields by McMurry coupling reaction from the corresponding ketones. Ethyl 4-ene-4-ferrocenyl-5,5-bis-(4-hydroxyphenyl)-pentanoate (1e) was fully characterized by ¹H NMR (including COSY), ¹³C NMR (including DEPT135), low resolution mass spectrometry, HRMS, infrared spectroscopy, elemental analysis, and X-ray diffraction (XRD). The data of already published crystal structures of five structurally related ferrocidiphenols are also included for comparison purposes. Full article

(This article belongs to the Section Structure Determination)

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5 pages, 1473 KiB

Open AccessShort Note

(Z)-1-(3,5-Dichloro-2H-pyrrol-2-ylidene)-N,N-dimethylmethanamine

by Daniil Rykunov, Alina Sonina and Aleksey Vorob’ev

Molbank 2025, 2025(1), M1979; https://doi.org/10.3390/M1979 - 11 Mar 2025

Abstract

The Vilsmeier–Haack reaction is a convenient method for the formylation of electron-rich aromatic compounds. However, this interaction sometimes gives specific side products. We report the isolation and structural characterization of a novel compound (Z)-1-(3,5-dichloro-2-pyrrolylidene)-N,N-dimethylmethanamine obtained as a [...] Read more.

The Vilsmeier–Haack reaction is a convenient method for the formylation of electron-rich aromatic compounds. However, this interaction sometimes gives specific side products. We report the isolation and structural characterization of a novel compound (Z)-1-(3,5-dichloro-2-pyrrolylidene)-N,N-dimethylmethanamine obtained as a side product during the formylation of 2-chloropyrrole. The product was characterized using NMR spectroscopy and X-ray crystallography. Full article

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

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5 pages, 767 KiB

Open AccessShort Note

(S)-2-Hydroxy-3-(((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)propyl (E)-8-Hydroperoxyhexadec-6-enoate

by Botao Zhang, Mana Horiuchi, Ryoya Kawabe, Hajime Uchida, Masayuki Satake and Hiroshi Nagai

Molbank 2025, 2025(1), M1978; https://doi.org/10.3390/M1978 - 4 Mar 2025

Abstract

A new oxylipin (1) was isolated from cyanobacteria collected at Tokyo Bay, Japan. The structure of 1 was elucidated based on spectroscopic data including 1D and 2D NMR, as well as high-resolution mass spectrometry. The structure of 1 was elucidated to [...] Read more.

A new oxylipin (1) was isolated from cyanobacteria collected at Tokyo Bay, Japan. The structure of 1 was elucidated based on spectroscopic data including 1D and 2D NMR, as well as high-resolution mass spectrometry. The structure of 1 was elucidated to be (S)-2-hydroxy-3-(((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)propyl (E)-8-hydroperoxyhexadec-6-enoate. Full article

(This article belongs to the Section Natural Product Chemistry)

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12 pages, 897 KiB

Open AccessCommunication

Microwave-Assisted Synthesis of 1-(5-Substituted-4-hydroxy-2-methyl-1H-pyrrol-3-yl)ethan-1-ones from 2-Amino Acid-Derived Enamine-Type Schiff Bases

by Diego Quiroga, Sergio Torres-Cortés and Ericsson Coy-Barrera

Molbank 2025, 2025(1), M1975; https://doi.org/10.3390/M1975 - 3 Mar 2025

Abstract

Pyrrole-type compounds are widely known for their potential biological activity. However, methods for synthesizing 2,3,4,5-tetrasubstituted pyrroles remain limited. This study explores an intramolecular cyclocondensation of 2-amino acid-derived enamines to yield novel 1-(5-substituted-4-hydroxy-2-methyl-1H-pyrrol-3-yl)ethan-1-ones. Using ʟ-alanine, ʟ-tyrosine, ʟ-phenylalanine, and ʟ-tryptophan, the corresponding 2-amino [...] Read more.

Pyrrole-type compounds are widely known for their potential biological activity. However, methods for synthesizing 2,3,4,5-tetrasubstituted pyrroles remain limited. This study explores an intramolecular cyclocondensation of 2-amino acid-derived enamines to yield novel 1-(5-substituted-4-hydroxy-2-methyl-1H-pyrrol-3-yl)ethan-1-ones. Using ʟ-alanine, ʟ-tyrosine, ʟ-phenylalanine, and ʟ-tryptophan, the corresponding 2-amino esters were synthesized, converted into enamines, and cyclized under microwave irradiation (55–86% yield). The highest yield was obtained from methyl ʟ-phenylalaninate (R¹ = CH₂Ph, R⁴ = Me). Steric hindrance from bulkier groups reduced yields, while the electronic nature of R¹ influenced reactivity. Structural analysis (NMR, HR-ESI-MS) confirmed product identities, and a 5-exo-trig cyclization mechanism explained base-mediated deprotonation and steric effects. These findings highlight steric and electronic factors in this cyclocondensation, guiding reaction optimization for valuable heterocycles. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Graphical abstract

6 pages, 1450 KiB

Open AccessShort Note

2-[3,5-Bis(5-bromothien-2-yl)-4H-1,2,6-thiadiazin-4-ylidene]-malononitrile

by Andreas S. Kalogirou, Andreas Kourtellaris and Panayiotis A. Koutentis

Molbank 2025, 2025(1), M1977; https://doi.org/10.3390/M1977 - 3 Mar 2025

Abstract

Bromination of 2-[3,5-di(thien-2-yl)-4H-1,2,6-thiadiazin-4-ylidene]-malononitrile with N-bromosuccinimide in THF, at ca. 20 °C for 24 h gave 2-[3,5-bis(5-bromothien-2-yl)-4H-1,2,6-thiadiazin-4-ylidene]-malononitrile in 82% yield. The latter is intended as a scaffold for preparing donors for organic photovoltaics. Full article

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

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8 pages, 2461 KiB

Open AccessShort Note

3-(4-Ethynylphenyl)-1,5-diphenylformazan

by Ida A. Lupanova, Dzhamilya N. Konshina, Igor V. Sukhno, Ekaterina S. Spesivaya and Valery V. Konshin

Molbank 2025, 2025(1), M1976; https://doi.org/10.3390/M1976 - 3 Mar 2025

Abstract

The structure of the “clickable” formazan, 3-(4-ethynylphenyl)-1,5-diphenylformazan, has been determined for the first time in a single crystal. The synthesis of 3-(4-ethynylphenyl)-1,5-diphenylformazan was carried out by coupling 4-(trimethylsilyl)ethynylbenzaldehyde phenylhydrazone with diazotized aniline, followed by desilylation, with a total yield of 54%. Full article

(This article belongs to the Section Structure Determination)

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