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5 pages, 966 KiB

Open AccessShort Note

5,5′-Bis[9-(2-ethylhexyl)-9H-carbazol-3-yl]-4,4′-diphenyl-2,2′-bithiazole

by

Andreas S. Kalogirou

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Panayiotis A. Koutentis

Molbank 2024, 2024(1), M1761; https://doi.org/10.3390/M1761 - 11 Jan 2024

Viewed by 299

Abstract

Stille coupling between 5,5′-dibromo-4,4′-diphenyl-2,2′-bithiazole and 9-(2-ethylhexyl)-3-(tributylstannyl)-9H-carbazole in the presence of Pd(Ph₃P)₂Cl₂ in toluene, heated at reflux for 2 h, gave 5,5′-bis[9-(2-ethylhexyl)-9H-carbazol-3-yl]-4,4′-diphenyl-2,2′-bithiazole in 85% yield. Full article

(This article belongs to the Section Organic Synthesis)

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7 pages, 824 KiB

Open AccessShort Note

4-(2-(5-(2-(tert-Butoxycarbonyl)hydrazinecarbonyl)-2-methylthiophen-3-yl)cyclopent-1-enyl)-5-methylthiophene-2-carboxylic Acid

by

Marija Matković

Molbank 2024, 2024(1), M1760; https://doi.org/10.3390/M1760 - 11 Jan 2024

Viewed by 227

Abstract

Diarylethene (DAE) molecular photoswitches draw attention as building units in the preparation of diverse photoactive molecules. An interesting class of these molecules are photoactive peptides. A way to build DAE moiety into peptides/peptidomimetics is via DAE amino acids, an example of which has [...] Read more.

Diarylethene (DAE) molecular photoswitches draw attention as building units in the preparation of diverse photoactive molecules. An interesting class of these molecules are photoactive peptides. A way to build DAE moiety into peptides/peptidomimetics is via DAE amino acids, an example of which has been demonstrated in bioactive cyclic peptides, wherein the DAE Fmoc-amino acid was prepared and used. Herein, the preparation of DAE Boc-amino acid is presented using a modified method of synthesis. This contribution to the DAE amino acid collection could be useful in the further enhancement of diversity in designing different routes to photoactive peptides. Full article

(This article belongs to the Section Organic Synthesis)

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5 pages, 1363 KiB

Open AccessShort Note

9-Ethyl-6,6-dimethyl-8-[4-(morpholin-4-yl)piperidin-1-yl]-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile Hydrochloride

by

Petr A. Buikin

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Anna V. Vologzhanina

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Roman A. Novikov

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Alexander A. Korlyukov

Molbank 2024, 2024(1), M1759; https://doi.org/10.3390/M1759 - 05 Jan 2024

Viewed by 383

Abstract

Alectinib hydrochloride is an anticancer medication used for the first-line treatment of non-small cell lung cancer. Although it was approved for medical use ten years ago, and three polymorphs of this substance were proposed based on X-ray diffraction patterns, their crystal structures remained [...] Read more.

Alectinib hydrochloride is an anticancer medication used for the first-line treatment of non-small cell lung cancer. Although it was approved for medical use ten years ago, and three polymorphs of this substance were proposed based on X-ray diffraction patterns, their crystal structures remained unknown to date. The main problem was the preparation of high quality single crystals due to the very low solubility of the salt. Herein, we report on the molecular and crystal structure of form I of alectinib hydrochloride as obtained using powder X-ray diffraction data from a laboratory source. Short Cl…N distances between the anion and the nitrogen atoms of the morpholine and benzo[b]carbazole rings indicate the positions of the H(N) atoms. As a result, the cation and anion form infinite Cl…H(N)-bonded chains. Full article

(This article belongs to the Section Structure Determination)

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8 pages, 1472 KiB

Open AccessCommunication

(5Z,9Z)-14-[(3,28-Dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic Acid with Cytotoxic Activity

by

Regina A. Tuktarova

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Lilya U. Dzhemileva

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Usein M. Dzhemilev

Molbank 2024, 2024(1), M1758; https://doi.org/10.3390/M1758 - 02 Jan 2024

Viewed by 446

Abstract

For the first time, a synthetic analogue of natural (5Z,9Z)-dienoic acid has been synthesized in the form of a hybrid molecule containing a fragment of oleanolic acid and (5Z,9Z)-tetradeca-5.9-dienedicarboxylic acid, synthesized using a new reaction of Ti-catalyzed homo-cyclomagnesiation 1,2-dienes. The high cytotoxic activity [...] Read more.

For the first time, a synthetic analogue of natural (5Z,9Z)-dienoic acid has been synthesized in the form of a hybrid molecule containing a fragment of oleanolic acid and (5Z,9Z)-tetradeca-5.9-dienedicarboxylic acid, synthesized using a new reaction of Ti-catalyzed homo-cyclomagnesiation 1,2-dienes. The high cytotoxic activity of (5Z,9Z)-14-[(3,28-dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic acid against tumor cells Jurkat, K562, U937 and HL60 was established. This compound is also an inducer of apoptosis, affects the cell cycle and inhibits human topoisomerase I. Full article

(This article belongs to the Section Natural Products)

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4 pages, 1252 KiB

Open AccessShort Note

3-(4-Bromophenyl)-1-carbamothioyl-5-(2-carbamothioylhydrazinyl)-4,5-dihydro-1H-pyrazole-5-carboxylic Acid

by

Anastasia A. Andreeva

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Maksim V. Dmitriev

and

Andrey N. Maslivets

Molbank 2024, 2024(1), M1757; https://doi.org/10.3390/M1757 - 02 Jan 2024

Viewed by 487

Abstract

The reaction of 4-(4-bromophenyl)-2,4-dioxobutanoic acid with thiosemicarbazide, in a ratio of 1:2, when boiled in ethanol gives 3-(4-bromophenyl)-1-carbamothioyl-5-(2-carbamothioylhydrazinyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid with a good yield. This compound was fully characterized. Full article

(This article belongs to the Collection Heterocycle Reactions)

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5 pages, 811 KiB

Open AccessShort Note

(1R/S,7aS/R)-1-Benzyl-1-[2,8-bis(trifluoromethyl)quinolin-4-yl]-hexahydro-oxazolo[3,4-a]pyridin-3-one

by

Dawid J. Kucharski

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Przemysław J. Boratyński

Molbank 2024, 2024(1), M1756; https://doi.org/10.3390/M1756 - 30 Dec 2023

Viewed by 491

Abstract

An unexpected diastereoselective C-alkylation of a mefloquine derivative in up to 57% yield was the result of an attempted Williamson etherification of Boc-mefloquine. The domino reaction involved oxazolidinone ring closure, deprotonation, and stereoselective carbon–carbon bond formation. The structure was confirmed with 2D NMR [...] Read more.

An unexpected diastereoselective C-alkylation of a mefloquine derivative in up to 57% yield was the result of an attempted Williamson etherification of Boc-mefloquine. The domino reaction involved oxazolidinone ring closure, deprotonation, and stereoselective carbon–carbon bond formation. The structure was confirmed with 2D NMR experiments. Full article

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

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13 pages, 6062 KiB

Open AccessCommunication

Unexpected Formation of the Iodobismuthate Salt (C₁₄H₁₅S₂N₂)₂(C₉H₁₀SN)₂[Bi₄I₁₆] upon Reaction of the Unsaturated Ligand Z-PySCH₂CH=CHCH₂SPy with BiI₃

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Molbank 2024, 2024(1), M1755; https://doi.org/10.3390/M1755 - 29 Dec 2023

Viewed by 315

Abstract

The olefinic dithioether (Z)-1,4-bis(pyridin-2-ylthio)but-2-ene Z-PyS(CH₂CH=CHCH₂)SPy (L) was prepared by the treatment of cis-ClCH₂CH=CHCH₂Cl with in situ generated potassium pyridine-2-thiolate Py-SK and analyzed by IR and NMR spectroscopy. To investigate [...] Read more.

The olefinic dithioether (Z)-1,4-bis(pyridin-2-ylthio)but-2-ene Z-PyS(CH₂CH=CHCH₂)SPy (L) was prepared by the treatment of cis-ClCH₂CH=CHCH₂Cl with in situ generated potassium pyridine-2-thiolate Py-SK and analyzed by IR and NMR spectroscopy. To investigate the chemistry of polynuclear iodobismuthate complexes, two equivalents of BiI₃ were reacted with L in the MeOH solution to afford the anionic tetranuclear title compound (C₁₄H₁₅S₂N₂)₂(C₉H₁₀SN)₂[Bi₄I₁₁₆] with a N-protonated (Z)-1,4-bis(pyridin-2-ylthio)but-2-ene as a counterion. Compound 1 was characterized by IR and UV spectroscopy; the formation of a tetranuclear framework was ascertained by a single-crystal X-ray diffraction study performed at 100 K. Furthermore, an unusual Bi(III)-meditated cyclization of one Z-PyS(CH₂CH=CHCH₂)SPy ligand occurred, affording the bicyclic pyridinium salt 3-vinyl-2,3-dihydrothiazolo[3,2-a]pyridinium bearing a terminal vinyl group, compensating the second negative charge of the Bi₄I₁₆⁴⁻ cluster anion. The SCXRD characterization was completed by a Hirshfeld surface analysis, revealing some secondary interactions occurring in the crystal. Full article

(This article belongs to the Section Structure Determination)

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8 pages, 890 KiB

Open AccessCommunication

New Antimicrobial Accramycins from Streptomyces sp. MA37 Variant

by

Aziz Alabed

,

Kwaku Kyeremeh

and

Hai Deng

Molbank 2024, 2024(1), M1754; https://doi.org/10.3390/M1754 - 28 Dec 2023

Viewed by 401

Abstract

In our continued desire to isolate more bioactive compounds from the Streptomyces sp. MA37 variant, ΔaccJ, three new accramycin derivatives have been successfully characterised. The structures of accramycin L-N (1–3) were established by high-resolution mass spectrometry and 1D and 2D nuclear [...] Read more.

In our continued desire to isolate more bioactive compounds from the Streptomyces sp. MA37 variant, ΔaccJ, three new accramycin derivatives have been successfully characterised. The structures of accramycin L-N (1–3) were established by high-resolution mass spectrometry and 1D and 2D nuclear magnetic resonance. The antimicrobial evaluation of accramycin L-N against Staphylococcus aureus, Klebsiella pneumoniae, and Enterobacter cloacae showed minimum inhibitory concentration (MIC) values ranging from 0.77 to 13.02 µg/mL. Accramycin L exhibited the most significant activity against S. aureus. In addition, accramycin L-N (1–3) displayed significant activity against K. pneumoniae at the MIC values of 0.81, 0.77, and 0.79 µg/mL, respectively. Full article

(This article belongs to the Section Natural Products)

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7 pages, 1434 KiB

Open AccessShort Note

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Molbank 2024, 2024(1), M1753; https://doi.org/10.3390/M1753 - 22 Dec 2023

Viewed by 473

Abstract

N,N′-Dipropyloxamide (1) was synthesised by the reaction between diethyloxalate and n-propylamine in ethanol. Compound 1 was fully characterised by both microanalytical (elemental analysis, melting point determination) and spectroscopic means (FT-IR and NMR spectroscopy). Crystals suitable for single [...] Read more.

N,N′-Dipropyloxamide (1) was synthesised by the reaction between diethyloxalate and n-propylamine in ethanol. Compound 1 was fully characterised by both microanalytical (elemental analysis, melting point determination) and spectroscopic means (FT-IR and NMR spectroscopy). Crystals suitable for single crystal X-ray diffraction were isolated by the slow evaporation of a methyl alcohol solution of the compound. The resulting crystal structure shows the prominent role exerted by intermolecular hydrogen bonds in the crystal packing. Full article

(This article belongs to the Section Structure Determination)

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8 pages, 2129 KiB

Open AccessShort Note

Bis(2,6-di(pyridin-2-yl)pyridin-4-yl)-6,6′-(1,2-diselanediyl)dihexanoate

by

Evelyn Popa

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Adelina A. Andelescu

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Valentin Badea

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Paula Svera (m. Ianăşi)

and

Elisabeta I. Szerb

Molbank 2024, 2024(1), M1752; https://doi.org/10.3390/M1752 - 20 Dec 2023

Viewed by 407

Abstract

The present paper describes the preparation and characterization of a new dinuclear ligand based on terpyridine featuring a diselenide unit. This new compound was synthesized in a two-step procedure that first involved the insertion of the diselenide moiety on a carboxylic acid and [...] Read more.

The present paper describes the preparation and characterization of a new dinuclear ligand based on terpyridine featuring a diselenide unit. This new compound was synthesized in a two-step procedure that first involved the insertion of the diselenide moiety on a carboxylic acid and was followed by a Steglich esterification reaction between the biscarboxylic acid containing the diselenide unit and 2,6-di(pyridin-2-yl)pyridin-4-ol (tpyOH). The title compound was characterized via FT-IR, Raman, NMR (1D and 2D), and UV-Vis spectroscopies and elemental analysis. Emission properties were investigated. Full article

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4 pages, 1379 KiB

Open AccessShort Note

(Z)-1-Benzyl-5-(4-bromophenyl)-5-hydroxy-4-(2-oxomorpholin-3-ylidene)pyrrolidine-2,3-dione

by

Nikita A. Tretyakov

and

Andrey N. Maslivets

Molbank 2023, 2023(4), M1751; https://doi.org/10.3390/M1751 - 18 Dec 2023

Viewed by 616

Abstract

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-2,3-dione. The compound was fully characterized. Full article

(This article belongs to the Collection Heterocycle Reactions)

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9 pages, 1120 KiB

Open AccessShort Note

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

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Oscar Leonardo Avendaño Leon

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Molbank 2023, 2023(4), M1750; https://doi.org/10.3390/M1750 - 15 Dec 2023

Viewed by 507

Abstract

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-nitrobenzamide. This unexpected amide was obtained in an 85% yield as the major product with [...] Read more.

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-nitrobenzamide. This unexpected amide was obtained in an 85% yield as the major product with a conventional amidoxime synthesis protocol (Ethanol/Na₂CO₃) involving the reaction of hydroxylamine and a nitrile group. The formation of this amide derivative instead of the expected amidoxime can be attributed to two complementary effects: the strong electron effect of the nitro group and the influence of ethanol, a polar protic solvent. Alternatively, the desired amidoxime derivative, 4-(5-benzyl-3-((4-fluorophenyl)sulfonyl)-5-methyl-4,5-dihydrofuran-2-yl)-N′-hydroxy-2-nitrobenzimidamide, was obtained in an 80% yield by an alternative protocol (DMSO/KOtBu). This original compound, featuring a nitro group in the ortho position to the amidoxime, will be further evaluated, both in the field of medicinal chemistry and in other relevant areas, highlighting an unusual method to access amidoximes from hindered substrates. Full article

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

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7 pages, 4926 KiB

Open AccessShort Note

3-Benzoyl-2-hydroxy-3a-[(3-methylquinoxalin-2-yl)methyl]-1H-pyrrolo[2,1-c][1,4]benzothiazine-1,4(3aH)-dione

by

Ekaterina A. Lystsova

and

Ekaterina E. Khramtsova

Molbank 2023, 2023(4), M1749; https://doi.org/10.3390/M1749 - 13 Dec 2023

Viewed by 534

Abstract

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 was fully characterized. Full article

(This article belongs to the Collection Heterocycle Reactions)

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11 pages, 3280 KiB

Open AccessCommunication

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

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Molbank 2023, 2023(4), M1748; https://doi.org/10.3390/M1748 - 07 Dec 2023

Viewed by 734

Abstract

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 cores linked to each other by pairs of (E)-azobenzene/stilbene units through four triazole groups were obtained as [...] Read more.

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 cores linked to each other by pairs of (E)-azobenzene/stilbene units through four triazole groups were obtained as confirmed by NMR, HRMS and X-ray diffraction data. Nevertheless, the formation of larger macrocycles and polymeric/oligomeric products was found to be the major competing process that seriously limited the applicability of the one-step macrocyclization approach for the construction of photoresponsive biscalixarene assemblies linked by pairs of azobenzene/stilbene units. Full article

(This article belongs to the Section Organic Synthesis)

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12 pages, 1961 KiB

Open AccessCommunication

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

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Monika Kadela-Tomanek

Molbank 2023, 2023(4), M1747; https://doi.org/10.3390/M1747 - 28 Nov 2023

Viewed by 628

Abstract

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 spectroscopy supplemented with theoretical DFT calculations. Spectroscopic measurements were conducted [...] Read more.

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 spectroscopy supplemented with theoretical DFT calculations. Spectroscopic measurements were conducted using the attenuated total reflection (ATR) mode in the frequency range of 4000–400 cm⁻¹. An analysis of FT-IR spectra was carried out, assigning the characteristic vibration frequencies of various functional groups to individual peaks. It was found that the experimental and calculated FT-IR spectra showed a good correlation for all the compounds under study. The most significant difference in the spectra occurred in the region of carbonyl bands. For compounds with the 5,8-quinolinedione moiety, two separated C=O vibration peaks were observed, while for compounds with the 5,8-isoquinolinedione moiety, the carbonyl vibrations created only one peak. This difference makes it possible to distinguish between the 5,8-quinolinedione and 5,8-isoquinolinedione derivatives. Full article

(This article belongs to the Section Structure Determination)

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