Molbank

5 pages, 409 KiB

Open AccessShort Note

9,10-Dimethoxy-4-oxo-1-phenyl-1,3,4,6,7,11b-hexahydro-[1,4]thiazino[3,4-a]isoquinoline-1-carboxylic Acid

by Valentin Petrov, Teodora Aleksandrova and Aleksandar Pashev

Molbank 2025, 2025(1), M1955; https://doi.org/10.3390/M1955 (registering DOI) - 21 Jan 2025

The synthesis of the compound 9,10-dimethoxy-4-oxo-1-phenyl-1,3,4,6,7,11b-hexahydro-[1,4]thiazino[3,4-a]isoquinoline-1-carboxylic acid (4) was described for the first time using a reaction between 6,7-dimethoxy-3,4-dihydroisoquinoline and phenyl-substituted thiodiacetic anhydride 3. The reaction proceeded in excellent yield and furnished the compound 4 as a single diastereomer. The [...] Read more.

The synthesis of the compound 9,10-dimethoxy-4-oxo-1-phenyl-1,3,4,6,7,11b-hexahydro-[1,4]thiazino[3,4-a]isoquinoline-1-carboxylic acid (4) was described for the first time using a reaction between 6,7-dimethoxy-3,4-dihydroisoquinoline and phenyl-substituted thiodiacetic anhydride 3. The reaction proceeded in excellent yield and furnished the compound 4 as a single diastereomer. The structure and relative configuration of 4 was elucidated using a combination of spectroscopic techniques–¹H, ¹³C, COSY, HSQC, HMBC, and NOESY NMR spectra, as well as elemental analysis. Full article

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Scheme 1

7 pages, 1437 KiB

Open AccessShort Note

(E)-N-(4-Methoxyphenyl)-1-(4′-(trifluoromethyl)-[1,1′-biphenyl]-4-yl)methanimine

by Mario Rico-Molina, David Peña-García, Joaquín Altarejos and Sofía Salido

Molbank 2025, 2025(1), M1953; https://doi.org/10.3390/M1953 (registering DOI) - 17 Jan 2025

Abstract

The title compound (1) was obtained within a project aimed at synthesizing inhibitors of the human enzyme lactate dehydrogenase A (hLDHA). Compound 1 was synthesized by Suzuki cross-coupling of (E)-1-(4-bromophenyl)-N-(4-methoxyphenyl)methanimine (2a) or ( [...] Read more.

The title compound (1) was obtained within a project aimed at synthesizing inhibitors of the human enzyme lactate dehydrogenase A (hLDHA). Compound 1 was synthesized by Suzuki cross-coupling of (E)-1-(4-bromophenyl)-N-(4-methoxyphenyl)methanimine (2a) or (E)-1-(4-iodophenyl)-N-(4-methoxyphenyl)methanimine (2b) with 4-(trifluoromethyl)phenylboronic acid (3) using Pd(PPh₃)₄ as a catalyst in 86% and 87% yields, respectively. Halo-imines 2a and 2b were previously obtained by condensation reaction between p-anisidine (4) and 4-bromo-benzaldehyde (5a) or 4-iodo-benzaldehyde (5b), respectively. The structure of compound 1 was established by 1D and 2D NMR spectroscopy, infrared and ultraviolet spectroscopies, and high-resolution mass spectrometry. Full article

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Graphical abstract

7 pages, 2421 KiB

Open AccessShort Note

(E)-3-Mesityl-1-(2,3,5,6-tetramethylphenyl)prop-2-en-1-one

by Aidan P. McKay, David B. Cordes, Iain A. Smellie and Brian A. Chalmers

Molbank 2025, 2025(1), M1952; https://doi.org/10.3390/M1952 (registering DOI) - 17 Jan 2025

Abstract

We report the synthesis and characterisation of the previously unknown (E)-3-Mesityl-1-(2,3,5,6-tetramethylphenyl)prop-2-en-1-one by NMR spectroscopy, IR spectroscopy, melting point, mass spectrometry, and X-ray crystallography. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

5 pages, 646 KiB

Open AccessShort Note

3-Benzoyl-1′,3′,6-trimethyl-2′H,3H,4H-spiro[furo[3,2-c]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′H,3′H)-tetraone

by Michail N. Elinson, Varvara M. Kalashnikova, Yuliya E. Ryzhkova and Oleg A. Rakitin

Molbank 2025, 2025(1), M1951; https://doi.org/10.3390/M1951 - 15 Jan 2025

Abstract

We describe an approach towards the synthesis of previously unknown 3-benzoyl-1′,3′,6-trimethyl-2′H,3H,4H-spiro[furo[3,2-c]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′H,3′H)-tetraone. The presented method is based on the cyclization of 5-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione. It was [...] Read more.

We describe an approach towards the synthesis of previously unknown 3-benzoyl-1′,3′,6-trimethyl-2′H,3H,4H-spiro[furo[3,2-c]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′H,3′H)-tetraone. The presented method is based on the cyclization of 5-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione. It was shown that the presented reaction proceeds through the stage of bromination of the starting compound followed by O-nucleophilic attack. The structures of the obtained compound were established by ¹H, ¹³C NMR and IR spectroscopy, and high-resolution mass spectrometry. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Scheme 1

9 pages, 773 KiB

Open AccessCommunication

A New Pyrrole Alkaloid from Capsicum annuum L. var. palmera Grown in La Palma (Canary Islands, Spain)

by Jesús G. Díaz, María A. de Buergo and David Díaz Díaz

Molbank 2025, 2025(1), M1950; https://doi.org/10.3390/M1950 - 15 Jan 2025

Abstract

Capsicum annuum, commonly known as pepper, is a widely cultivated crop valued for its nutritional and economic significance. Among its varieties, the small red bell pepper, locally known as “pimienta palmera”, is a unique cultivar from La Palma in the [...] Read more.

Capsicum annuum, commonly known as pepper, is a widely cultivated crop valued for its nutritional and economic significance. Among its varieties, the small red bell pepper, locally known as “pimienta palmera”, is a unique cultivar from La Palma in the Canary Islands, renowned for its distinctive flavor and use in traditional dishes. Despite its cultural importance, limited research exists on the chemical composition of this pepper variety. This study investigates the chemical constituents of dichloromethane and n-butanol fractions extracted from the pericarp of Capsicum annuum var. palmera. Isolation and structural elucidation of compounds were achieved using high-resolution mass spectrometry (HREIMS), nuclear magnetic resonance spectroscopy (NMR), and chromatographic techniques. A previously unreported pyrrolo-lactone compound, 2-(6-formyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazin-4-yl)acetic acid, was identified alongside other metabolites, including α-tocopherol, β-sitosterol, and oleic acid. This alkaloid adds to the chemical diversity of Capsicum species and highlights the unique bioactive potential of this regional pepper. These findings enhance the understanding of pimienta palmera’s composition and suggest potential applications in nutraceuticals and pharmacology due to the biological activity associated with pyrrole alkaloids. The characterization of this compound underscores the need to further explore the phytochemical richness of traditional crops with limited prior research. Full article

(This article belongs to the Section Natural Product Chemistry)

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5 pages, 579 KiB

Open AccessShort Note

(1R)-2,3,4,6-Tetra-O-benzyl-1-C-allyl-1-deoxy-1-C-(2-thiazolyl)-d-galactopyranose

by Clark Ferrari, Alessandro Dondoni and Alberto Marra

Molbank 2025, 2025(1), M1949; https://doi.org/10.3390/M1949 - 8 Jan 2025

Abstract

We have previously reported that thiazolylketol acetates, synthesized by the addition of 2-lithiothiazole to sugar lactones followed by acetylation, are efficient glycosyl donors affording O-, N-, P-, and C-glycosides. After the first example of C-glycosidation recently described by [...] Read more.

We have previously reported that thiazolylketol acetates, synthesized by the addition of 2-lithiothiazole to sugar lactones followed by acetylation, are efficient glycosyl donors affording O-, N-, P-, and C-glycosides. After the first example of C-glycosidation recently described by us, we report here on the unexpected outcome of the reaction of a thiazolylketol acetate with allyltrimethylsilane in the presence of trimethylsilyl triflate. The obtained intermediate, an intramolecular N-thiazolium salt, could be stereoselectively converted into the desired allyl C-thiazolylketoside. Full article

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

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Graphical abstract

9 pages, 2079 KiB

Open AccessShort Note

Bis{µ-(2,2′-bipyridine-1κ²N,N′)-(6,6′-dicarbonyl-1κ²O,O′:2κO′)bis(N,N-diethylthioureato-2κS)}(acetato-1κO)(µ-acetato-1κO:2-κO′)(methanol-2κO)thoriumnickel

by Christelle Njiki Noufele, Chien Thang Pham and Ulrich Abram

Molbank 2025, 2025(1), M1948; https://doi.org/10.3390/M1948 - 6 Jan 2025

Abstract

Reactions of 2,2′-bipyridine-6,6′-dicarbonyl-bis(N,N-diethylthiourea), H₂L^bipy, with a mixture of thorium nitrate hydrate and nickel acetate hydrate in methanol with NEt₃ as a supporting base yield brown single crystals of the bimetallic complex [ThNi(L^bipy)₂(CH [...] Read more.

Reactions of 2,2′-bipyridine-6,6′-dicarbonyl-bis(N,N-diethylthiourea), H₂L^bipy, with a mixture of thorium nitrate hydrate and nickel acetate hydrate in methanol with NEt₃ as a supporting base yield brown single crystals of the bimetallic complex [ThNi(L^bipy)₂(CH₃COO)₂(MeOH)]. Two 2,2′-bipyridine-centered bis(aroylthioureato) ligands connect the metal atoms in a way that the thorium atom is coordinated by two O,N,N,O donor atom sets, while the nickel atom establishes two S,O chelate rings in its equatorial coordination plane. The metal atoms are connected by a bridging acetato ligand, and their coordination spheres are completed by one methanol ligand (nickel) and a monodentate acetato ligand (thorium). A distorted octahedral coordination environment is established around the Ni²⁺ ion, while the Th⁴⁺ ion is in first approximation a 10-coordinate with a diffusely defined coordination polyhedron. Full article

(This article belongs to the Section Structure Determination)

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Figure 1

6 pages, 1208 KiB

Open AccessShort Note

2-((Diphenylmethylene)amino)ethyl N-(Cyclohexyl)carbamate

by Bailey N. Baxter, Mary Helene Marmande, Alyssa M. Albers, Manisha R. Gangasani, Hao N. Le, Omar E. Molokhia, Juanita Monteiro-Pai, Kyndall V. Ransom and David C. Forbes

Molbank 2025, 2025(1), M1947; https://doi.org/10.3390/M1947 - 6 Jan 2025

Abstract

Lipid-like nanoparticles (LLNPs) have been shown to be an effective encapsulation and delivery tool for therapeutic molecules. While the preclinical development of lipid nanoparticle formulations has been of paramount importance, next-generation LLNPs present an opportunity of enhanced biocompatibility. With the change in amido [...] Read more.

Lipid-like nanoparticles (LLNPs) have been shown to be an effective encapsulation and delivery tool for therapeutic molecules. While the preclinical development of lipid nanoparticle formulations has been of paramount importance, next-generation LLNPs present an opportunity of enhanced biocompatibility. With the change in amido functionality as part of the core backbone, our target, carbamate functionality within the LLNP core scaffold, was realized upon reaction of a protected amino alcohol onto the isocyanate generated in situ via a Curtius rearrangement. The single-step assembly of carbamate functionality starting from cyclohexane carboxylic acid in the presence of diphenylphosphoryl azide (DPPA) exceeds the metrics set forth for the rapid installment and enhanced biodegradability of next-generation lipid-like nanoparticles. Full article

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

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Figure 1

6 pages, 2436 KiB

Open AccessCommunication

Crystal Structure of 5-Nitro-4-(4-methoxyphenoxy)phthalonitrile

by Dmitry Erzunov, Anastasia Rassolova, Igor Abramov, Vladimir Maizlish, Roman Rumyantsev and Arthur Vashurin

Molbank 2025, 2025(1), M1946; https://doi.org/10.3390/M1946 - 3 Jan 2025

Abstract

This article presents findings on the synthesis and crystal structure analysis of 5-nitro-4-(4-methoxyphenoxy)phthalonitrile. The crystal structure was meticulously refined using X-ray diffraction techniques, which allowed for a detailed examination of the molecular arrangement within the crystal. The manuscript elaborates on the significant intermolecular [...] Read more.

This article presents findings on the synthesis and crystal structure analysis of 5-nitro-4-(4-methoxyphenoxy)phthalonitrile. The crystal structure was meticulously refined using X-ray diffraction techniques, which allowed for a detailed examination of the molecular arrangement within the crystal. The manuscript elaborates on the significant intermolecular and intramolecular interactions that contribute to the overall crystal packing, highlighting how these interactions influence the stability and properties of the material. Full article

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Figure 1

5 pages, 1051 KiB

Open AccessShort Note

Octahedral Oxo-Bridged Tri-Nickel(II) Complex with 1,3,5-Tris(2-hydroxyphenyl)-2,4-diazapenta-1,3-diene

by Daniil R. Bazanov, Egor D. Korolyov, Konstantin A. Lyssenko and Natalia A. Lozinskaya

Molbank 2025, 2025(1), M1945; https://doi.org/10.3390/M1945 - 27 Dec 2024

Abstract

An octahedral nickel(II) complex of 1,3,5-tris(2-hydroxyphenyl)-2,4-diazapenta-1,3-diene was obtained and characterized by X-ray crystallography. The organic ligand was obtained by the reaction of 2-hydroxybenzaldehyde with aqueous ammonia solution. Full article

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Figure 1

8 pages, 1262 KiB

Open AccessCommunication

From Dienophiles to Dienes: Catalysis by Polystyrene-Supported Triphenylphosphine with Pentane-2,4-dione as Co-Catalyst

by Ludvik O. Espeland and Leiv K. Sydnes

Molbank 2025, 2025(1), M1944; https://doi.org/10.3390/M1944 - 24 Dec 2024

Abstract

Three 1,1-diethoxyalk-3-yn-2-ones underwent isomerization and gave only the corresponding (3E,5E)-alkadienones in 72–87% yield when subjected to polystyrene-supported triphenylphosphine at 60 °C using acetylacetone as a co-catalyst. As a first step to make the dienes electron richer, the diethoxyacetyl moiety [...] Read more.

Three 1,1-diethoxyalk-3-yn-2-ones underwent isomerization and gave only the corresponding (3E,5E)-alkadienones in 72–87% yield when subjected to polystyrene-supported triphenylphosphine at 60 °C using acetylacetone as a co-catalyst. As a first step to make the dienes electron richer, the diethoxyacetyl moiety was reduced with sodium borohydride under Luche conditions and afforded the corresponding alcohols, with a 92% yield in the best case. Full article

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

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Figure 1

4 pages, 759 KiB

Open AccessShort Note

Bis(1,1,1,3,3,3-hexafluoropropan-2-yl) [1,1′-biphenyl]-4,4′-dicarboxylate

by Ethan T. Mercier, Manisha Sharma, Adam M. Graichen and Nicholas E. Leadbeater

Molbank 2024, 2024(4), M1943; https://doi.org/10.3390/M1943 - 20 Dec 2024

Abstract

The oxidative esterification of 4,4′-Biphenyldicarboxaldehyde with hexafluoroisopropanol is reported. The methodology, making a novel hexafluoroisopropyl ester uses a green, recyclable oxoammonium salt along with easily obtained sodium persulfate. Full article

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

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Graphical abstract

3 pages, 360 KiB

Open AccessShort Note

5-Bromo-N′-(2-oxoindolin-3-ylidene)furan-2-carbohydrazide

by Nur Pasca Aijijiyah, Arif Fadlan, Sri Ningsih and Mardi Santoso

Molbank 2024, 2024(4), M1941; https://doi.org/10.3390/M1941 - 19 Dec 2024

Abstract

5-Bromo-N′-(2-oxoindolin-3-ylidene)furan-2-carbohydrazide (1) was successfully synthesized in 79.4% yield by reaction of isatin with 5-bromofuran-2-carbohydrazide in acidic conditions under reflux. The structure of synthesized compound 1 was confirmed by ¹H and ¹³C NMR, FTIR, and HRMS spectrometers. It [...] Read more.

5-Bromo-N′-(2-oxoindolin-3-ylidene)furan-2-carbohydrazide (1) was successfully synthesized in 79.4% yield by reaction of isatin with 5-bromofuran-2-carbohydrazide in acidic conditions under reflux. The structure of synthesized compound 1 was confirmed by ¹H and ¹³C NMR, FTIR, and HRMS spectrometers. It is necessary to evaluate compound 1 as an anti-inflammatory agent. Full article

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

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Scheme 1

4 pages, 575 KiB

Open AccessShort Note

6-Amino-7-((4-methoxybenzyl)thio)quinazolin-4(3H)-one

by Susila Thapa and Jeanne L. Bolliger

Molbank 2024, 2024(4), M1942; https://doi.org/10.3390/M1942 - 19 Dec 2024

Abstract

The titular compound, 6-amino-7-((4-methoxybenzyl)thio)quinazolin-4(3H)-one, was prepared from 7-fluoro-6-nitroquinazolin-4(3H)-one via a nucleophilic aromatic substitution reaction followed by a reduction of the nitro group. Characterization of the target compound via ¹H NMR, ¹³C NMR, and HRMS confirmed its structure. Full article

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Graphical abstract

8 pages, 1246 KiB

Open AccessShort Note

3-(4-Ferrocenyl-1H-1,2,3-triazol-1-yl)cholic Acid

by Valeria D’Annibale, Venanzio Raglione, Francesco Lisi, Elisa Verdirosi, Lorenza Romagnoli, Danilo Dini, Luciano Galantini and Andrea D’Annibale

Molbank 2024, 2024(4), M1940; https://doi.org/10.3390/M1940 - 19 Dec 2024

Abstract

Surfactants are very important compounds that are ubiquitous in biological systems and detergents. Among them, ferrocene surfactants are a very valuable class of stimuli-responsive materials since the presence of ferrocene moiety discloses the chance to control and even modify their amphiphilic properties via [...] Read more.

Surfactants are very important compounds that are ubiquitous in biological systems and detergents. Among them, ferrocene surfactants are a very valuable class of stimuli-responsive materials since the presence of ferrocene moiety discloses the chance to control and even modify their amphiphilic properties via a redox-induced change in the surfactant charge. In this paper, we report a new ferrocene-based surfactant: a ferrocene C-3 derivative of cholic acid, a non-classical surfactant. The title compound of this work was meant to show the significant self-assembly behaviour typical of bile salts, improved by the presence of the aromatic ferrocene subunit. We intended to demonstrate that the presence of the redox mediator should provide the derivative with sensitivity to an oxidative stimulus and control over the aggregation properties. The title compound was prepared in two steps from easily accessible precursors, and its optical properties were investigated through UV-Vis absorption spectroscopy. The determination of its critical micellar concentration and redox potential confirmed this derivative’s amphiphilic nature and its tendency to be reversibly oxidized. Full article

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

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Figure 1

6 pages, 1541 KiB

Open AccessCommunication

Ethyl 4H-Pyran-4-one-2-carboxylate

by R. Alan Aitken, Alexander J. B. Nelson and Alexandra M. Z. Slawin

Molbank 2024, 2024(4), M1939; https://doi.org/10.3390/M1939 - 16 Dec 2024

Abstract

The title compound was characterised for the first time by ¹³C NMR, including the determination of CH coupling constants, and its X-ray structure was determined, showing double ribbons of molecules in the crystal held together by weak CH to O=C hydrogen bonds. Full article

(This article belongs to the Section Structure Determination)

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Figure 1

5 pages, 836 KiB

Open AccessShort Note

(E)-1-(Benzo[d][1,3]dioxol-5-yl)-5,6,6-trimethylhept-4-en-3-one

by Mario Rico-Molina, Joaquín Altarejos and Sofía Salido

Molbank 2024, 2024(4), M1938; https://doi.org/10.3390/M1938 (registering DOI) - 11 Dec 2024

Abstract

The title compound (1) was obtained within a project to synthesize analogs of the antiepileptic drug stiripentol. Compound 1 was synthesized by aldol addition of the lithium enolate of 4-(benzo[d][1,3]dioxol-5-yl)butan-2-one (2) to 3,3-dimethylbutan-2-one (3), followed [...] Read more.

The title compound (1) was obtained within a project to synthesize analogs of the antiepileptic drug stiripentol. Compound 1 was synthesized by aldol addition of the lithium enolate of 4-(benzo[d][1,3]dioxol-5-yl)butan-2-one (2) to 3,3-dimethylbutan-2-one (3), followed by the dehydration of the resulting β-hydroxy-ketone under acid processing. The structure of 1 was established by 1D and 2D NMR spectroscopy and high-resolution mass spectrometry. Full article

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Figure 1

5 pages, 927 KiB

Open AccessShort Note

5,10-Diiododibenzo[a,e]pentalene

by Natsumi Ohara, Chinatsu Ogiwara and Takuya Kuwabara

Molbank 2024, 2024(4), M1937; https://doi.org/10.3390/M1937 - 10 Dec 2024

Abstract

The crystal structure and the improved synthesis of the title compound (1) are presented. Treatment of 5,10-disilyldibenzo[a,e]pentalenes (2a and 2b) with iodine chloride (ICl) readily provided 1 in good yields. Recrystallization from a dichloromethane/hexane solution [...] Read more.

The crystal structure and the improved synthesis of the title compound (1) are presented. Treatment of 5,10-disilyldibenzo[a,e]pentalenes (2a and 2b) with iodine chloride (ICl) readily provided 1 in good yields. Recrystallization from a dichloromethane/hexane solution afforded single crystals suitable for X-ray diffraction studies. In the packing structure, iodine···iodine interactions classified as type II halogen bonding were found, forming the zigzag I…I chains along the ac-plane. Full article

(This article belongs to the Section Structure Determination)

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Figure 1

6 pages, 1240 KiB

Open AccessCommunication

Synthesis of (5Z)-3-Allyl-5-{[5-(4-methoxyphenyl)thiophen-2-yl]methylidene}-2-sulfanylidene-1,3-thiazolidin-4-one in L-Proline-Based Deep Eutectic Solvent

by Stéphanie Hesse, Isabelle Jourdain, Abderrahim Khatyr and Michael Knorr

Molbank 2024, 2024(4), M1936; https://doi.org/10.3390/M1936 - 10 Dec 2024

Abstract

3-N-allylrhodanine was condensed with 5-(4-methoxyphenyl)-thiophene-2-carbaldehyde in an L-proline-based deep eutectic solvent (DES) to obtain the π-conjugated heterocyclic rhodanine compound (5Z)-3-allyl-5-{[5-(4-methoxyphenyl)thiophen-2-yl]methylidene}-2-sulfanylidene-1,3-thiazolidin-4-one (2). Compound 2 was characterized by NMR spectroscopy, and its UV-vis spectrum was compared with that of [...] Read more.

3-N-allylrhodanine was condensed with 5-(4-methoxyphenyl)-thiophene-2-carbaldehyde in an L-proline-based deep eutectic solvent (DES) to obtain the π-conjugated heterocyclic rhodanine compound (5Z)-3-allyl-5-{[5-(4-methoxyphenyl)thiophen-2-yl]methylidene}-2-sulfanylidene-1,3-thiazolidin-4-one (2). Compound 2 was characterized by NMR spectroscopy, and its UV-vis spectrum was compared with that of the related derivative 3-allyl-5-(4-methoxybenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one (1). Preliminary results revealed that compound 2 is emissive at room temperature in solution. Full article

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

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