Journal Description
Molbank
Molbank
is an international, peer-reviewed, open access journal comprised of a unique collection of one-compound-per-paper short notes on synthetic compounds and natural products published quarterly online by MDPI.
- Open Access— free for readers, with article processing charges (APC) paid by authors or their institutions.
- High Visibility: indexed within Scopus, ESCI (Web of Science), Reaxys, CAPlus / SciFinder, and other databases.
- Rapid Publication: manuscripts are peer-reviewed and a first decision is provided to authors approximately 13.9 days after submission; acceptance to publication is undertaken in 3.8 days (median values for papers published in this journal in the first half of 2024).
- Recognition of Reviewers: reviewers who provide timely, thorough peer-review reports receive vouchers entitling them to a discount on the APC of their next publication in any MDPI journal, in appreciation of the work done.
Impact Factor:
0.6 (2023)
Latest Articles
Ac-[K-Aib-C(3,9-Acm; 6,12-SSNC(Acm)QENSDK)]4-NH2
Molbank 2024, 2024(4), M1900; https://doi.org/10.3390/M1900 (registering DOI) - 14 Oct 2024
Abstract
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Advances in synthetic peptide methodologies have enabled the development of macromolecules mimicking protein properties and have found applications in various fields, particularly in immunology. Furthermore, Sequential Oligopeptide Carriers (SOCn and CPSOC) have been designed as multi-functional core molecules, to which multiple bio-cargos
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Advances in synthetic peptide methodologies have enabled the development of macromolecules mimicking protein properties and have found applications in various fields, particularly in immunology. Furthermore, Sequential Oligopeptide Carriers (SOCn and CPSOC) have been designed as multi-functional core molecules, to which multiple bio-cargos can be anchored, allowing the construction of high molecular weight molecules (>3000 Da) capable of inducing a strong immune response. This study presents the design and synthesis of the Ac-[K-Aib-C(3,9-Acm; 6,12-SSNC(Acm)QENSDK)]4-NH2 peptide conjugate of branched architecture. The peptide epitope S128SNCQENSDK137 belongs to the V. berus basic phospholipase A2, a member of the European viper species’ most lethal protein families. The peptide epitope was synthesized according to the SPPS Fmoc/tBu strategy and characterized by HR-ESI-MS and NMR experiments, while the conjugate was purified by RP-HPLC and characterized by HR-ESI-MS.
Full article
Open AccessCommunication
1H NMR Chemical Shift Changes as a Result of Introduction of Carbonyl-Containing Protecting Groups Observed in Bornol and Isoborneol
by
Baohe Lyu, Honoka Sako, Mio Sugiura, Yoshikazu Hiraga, Ryukichi Takagi and Satomi Niwayama
Molbank 2024, 2024(4), M1899; https://doi.org/10.3390/M1899 - 11 Oct 2024
Abstract
Complete assignments of the 1H NMR chemical shifts for monoterpenes, borneol, and isoborneol, and their derivatives in which the secondary hydroxy group is protected with an acetyl group or a benzoyl group, have been made in CDCl3 and C6D
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Complete assignments of the 1H NMR chemical shifts for monoterpenes, borneol, and isoborneol, and their derivatives in which the secondary hydroxy group is protected with an acetyl group or a benzoyl group, have been made in CDCl3 and C6D6. Upon the protection of the hydroxy group with the carbonyl functional groups, or acetyl or benzoyl groups, many protons constituting the bicyclic ring exhibited downfield and upfield shifts in the chemical shift values, aiding in the unambiguous assignments of protons and carbons.
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(This article belongs to the Section Structure Determination)
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Open AccessShort Note
(4aS,5S,6aR,10aR,10bR)-5-Methoxy-9,9-dimethyl-4a,5,6a,7,10a,10b-hexahydro-12H-[1,3]dioxino[4′,5′:5,6]pyrano[4,3-b][1,2,3]triazolo[1,5-d][1,4]oxazine
by
Leticia Lomas Romero, Guillermo E. Negron Silva, Ricardo Corona-Sánchez, Elsie Ramírez-Domínguez, Atilano Gutiérrez-Carrillo and Alma Sánchez-Eleuterio
Molbank 2024, 2024(4), M1898; https://doi.org/10.3390/M1898 - 9 Oct 2024
Abstract
A new tetracyclic morpholine-fused[5,1-c]-triazole, (4aS,5S,6aR,10aR,10bR)-5-methoxy-9,9-dimethyl-4a,5,6a,7,10a,10b-hexahydro-12H-[1,3]dioxino[4′,5′:5,6]pyrano[4,3-b][1,2,3]triazolo[1,5-d][1,4]oxazine, was synthesized via a five-step sequence starting from methyl α-D-glucopyranoside by using, as a key step, an intramolecular copper(I) catalyzed alkyne-azide cycloaddition (CuAAC). The synthesized compound was fully characterized by 1H and 13C NMR, FT-IR, and HRMS.
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(This article belongs to the Section Organic Synthesis)
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Open AccessShort Note
2-(Butylamino)-6-chloro-4-[3-(7-chloro-4-quinolylamino)propylamino]-1,3,5-triazine
by
Zimo Ren, Yuzhu Guo, Yang Xiao, Alessandra Gianoncelli, Paolo Coghi and Giovanni Ribaudo
Molbank 2024, 2024(4), M1895; https://doi.org/10.3390/M1895 - 8 Oct 2024
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We herein report the synthesis of a 7-chloro-aminoquinoline triazine conjugate. The s-triazine library was generated by stepwise nucleophilic substitution of cyanuric chloride with butylamine. The structure of the compound was comprehensively determined using various analytical techniques, including proton nuclear magnetic resonance (1
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We herein report the synthesis of a 7-chloro-aminoquinoline triazine conjugate. The s-triazine library was generated by stepwise nucleophilic substitution of cyanuric chloride with butylamine. The structure of the compound was comprehensively determined using various analytical techniques, including proton nuclear magnetic resonance (1H NMR), carbon-13 nuclear magnetic resonance (13C NMR), heteronuclear single quantum coherence (HSQC), and Distortionless Enhancement by Polarization Transfer (DEPT-135) experiments. Additionally, ultraviolet (UV) spectroscopy, Fourier-transform infrared (FTIR) spectroscopy, and high-resolution mass spectrometry (HRMS) were employed for full characterization. Preliminary studies explored the potential interaction of the molecule with dihydrofolate reductase (DHFR) using molecular modeling. Furthermore, its drug-likeness was assessed by predicting relevant pharmacokinetic properties.
Full article
Figure 1
Open AccessShort Note
5-Diethoxymethyl-1,1-diethoxy-5-hydroxyundeca-3,6-diyn-2-one
by
Ludvik O. Espeland and Leiv K. Sydnes
Molbank 2024, 2024(4), M1896; https://doi.org/10.3390/M1896 - 8 Oct 2024
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As an extension of our study of the reactivity of derivatives of 3,3,4,4-tetraethoxybut-1-yne, attempts have been made to achieve acid-catalyzed deacetalization of the diethoxymethyl moieties in 5-diethoxymethyl-1,1,2,2-tetraethoxyundeca-3,6-diyn-5-ol. That was not achieved; instead, only deketalization occurred and afforded the title compound, indicating that the
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As an extension of our study of the reactivity of derivatives of 3,3,4,4-tetraethoxybut-1-yne, attempts have been made to achieve acid-catalyzed deacetalization of the diethoxymethyl moieties in 5-diethoxymethyl-1,1,2,2-tetraethoxyundeca-3,6-diyn-5-ol. That was not achieved; instead, only deketalization occurred and afforded the title compound, indicating that the triple bond activates the propargylic diethoxy moiety relative to the other acetal groups.
Full article
Scheme 1
Open AccessShort Note
4-(1H-Tetrazol-5-yl)-2-(p-tolyl)quinoline
by
Angelika Lásiková and Daniel Végh
Molbank 2024, 2024(4), M1897; https://doi.org/10.3390/M1897 - 8 Oct 2024
Abstract
The synthesis of 4-(1H-tetrazol-5-yl)-2-(p-tolyl)quinoline 4 as a possible modification of the biphenyltetrazole substructure of losartan 1 is described. The transformation of 2-(p-tolyl)quinoline-4-carbonitrile 3 to the corresponding tetrazole 4 was carried out by the reaction of trimethysilyl azide
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The synthesis of 4-(1H-tetrazol-5-yl)-2-(p-tolyl)quinoline 4 as a possible modification of the biphenyltetrazole substructure of losartan 1 is described. The transformation of 2-(p-tolyl)quinoline-4-carbonitrile 3 to the corresponding tetrazole 4 was carried out by the reaction of trimethysilyl azide and dibutyltin oxide as a catalyst in refluxing toluene. The title compound (4) was characterized by IR, 1H NMR, 13C NMR, and HRMS.
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(This article belongs to the Section Organic Synthesis)
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Supplementary File 1 (PDF, 870 KiB)
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Open AccessCommunication
Synthesis of Novel Thiazoles Based on (+)-Usnic Acid
by
Aleksandr S. Filimonov, Olga A. Luzina and Nariman F. Salakhutdinov
Molbank 2024, 2024(4), M1894; https://doi.org/10.3390/M1894 - 3 Oct 2024
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A series of usnic acid derivatives containing a thiazole ring with an amide substituent were synthesized. The convenient method for synthesis of these compounds is a reaction of 14-bromousnic acid with N-acylthioureas. Acylation of aminothiazole does not lead to the targeted compound.
Full article
Figure 1
Open AccessShort Note
Benzo[d][1,3]oxathiole-2-thione
by
R. Alan Aitken, David B. Cordes, Lauryne Cottineau and Aidan P. McKay
Molbank 2024, 2024(4), M1891; https://doi.org/10.3390/M1891 - 30 Sep 2024
Abstract
Although known for 120 years, the title compound has not been adequately characterised before. In this paper, it is fully characterised by 1H and 13C NMR and IR spectroscopy and its X-ray structure has been determined for the first time.
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(This article belongs to the Section Structure Determination)
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[(2-Chlorophenyl)-(4-fluorophenyl)methylene]-(4-fluorophenyl)amine
by
Salvador Vilchis-Valdés, Alberto Cedillo-Cruz, Marco A. García-Eleno, Diego Martínez-Otero and Erick Cuevas-Yañez
Molbank 2024, 2024(4), M1892; https://doi.org/10.3390/M1892 - 30 Sep 2024
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The formation of a N,1,1-triaryl imine derived from (2-chlorophenyl)-bis-(4-fluorophenyl)methanol is reported. The title compound is formed from a consecutive process which involves a nucleophilic substitution and subsequent Schmidt reaction. A description of the synthesized compound’s NMR spectra is presented and the structure
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The formation of a N,1,1-triaryl imine derived from (2-chlorophenyl)-bis-(4-fluorophenyl)methanol is reported. The title compound is formed from a consecutive process which involves a nucleophilic substitution and subsequent Schmidt reaction. A description of the synthesized compound’s NMR spectra is presented and the structure was unambiguously established by X-ray analysis. A Hirshfeld surface analysis is also included, confirming the presence of intermolecular H···F interactions involved in crystal packing.
Full article
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Supplementary material:
Supplementary File 1 (ZIP, 1076 KiB)
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Supplementary File 1 (ZIP, 1076 KiB)
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Open AccessShort Note
rac-2-(2′-Ferrocenyl-2′-hydroxy-n-propyl)-1,3-benzothiazole
by
Martin G. Zhen, Kathleen L. May and Robert A. Gossage
Molbank 2024, 2024(4), M1893; https://doi.org/10.3390/M1893 - 30 Sep 2024
Abstract
The synthesis and characterisation (UV-Vis, IR, HRESI-MS, 1H and 13C NMR spectroscopies, electrochemistry) is reported of the novel title material (1: alternatively named rac-1-(2′-benzothiazolyl)-2-ferrocenyl-2-propanol): a rare example of a ferrocenyl-benzothiazole hybrid species. Compound 1 is produced by the
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The synthesis and characterisation (UV-Vis, IR, HRESI-MS, 1H and 13C NMR spectroscopies, electrochemistry) is reported of the novel title material (1: alternatively named rac-1-(2′-benzothiazolyl)-2-ferrocenyl-2-propanol): a rare example of a ferrocenyl-benzothiazole hybrid species. Compound 1 is produced by the low temperature reaction of acetylferrocene (3) with a solution of the methyl anion derived via the deprotonation of 2-methyl-1,3-benzothiazole. The yield of 1 is moderate (34%) after purification and is an air and thermally stable solid under ambient conditions. Attempts to sublime 1, however, result in decomposition with one of the products being identified (NMR) as 3. The spectroscopic features of 1 are presented. Attempts to obtain suitable crystalline material of 1 for a single crystal X-ray diffraction study were unfortunately unsuccessful. Compound 1 also does not form stable coordination complexes with various metal salts (e.g., Ni[2+], Co[2+], etc.) under the conditions tested.
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(This article belongs to the Section Organic Synthesis)
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Scheme 1
Open AccessShort Note
(R)-2-Amino-1-hydroxyethylphosphonic Acid
by
Majid Motevalli, Isaac Abrahams, Peter Blakskjær, Caroline E. Wyatt and Peter B. Wyatt
Molbank 2024, 2024(4), M1888; https://doi.org/10.3390/M1888 - 26 Sep 2024
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(R)-2-Amino-1-hydroxyethylphosphonic acid 2 was prepared by hydrolytic kinetic resolution of rac-diethyl oxiran-2-ylphosphonate followed by reaction with benzylamine, acid hydrolysis, catalytic hydrogenolysis, and anion-exchange chromatography. Recrystallization from water-ethanol gave pure 2, which was characterized by IR, 1H NMR, 13
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(R)-2-Amino-1-hydroxyethylphosphonic acid 2 was prepared by hydrolytic kinetic resolution of rac-diethyl oxiran-2-ylphosphonate followed by reaction with benzylamine, acid hydrolysis, catalytic hydrogenolysis, and anion-exchange chromatography. Recrystallization from water-ethanol gave pure 2, which was characterized by IR, 1H NMR, 13C NMR, 31P NMR, polarimetry, elemental microanalysis, high-resolution mass spectrometry, and single-crystal X-ray diffraction. The acid 2 crystallized in the orthorhombic noncentrosymmetric space group P212121 with cell parameters a = 6.303 (2) Å, b = 7.104 (2) Å, c = 11.627 (3) Å. The X-ray crystal structure confirmed the (R)-configuration of 2 and revealed that 2 is zwitterionic in the solid state, with extensive intermolecular hydrogen bonding between the hydroxyl, ammonium cation, and phosphonate anion groups.
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Graphical abstract
Open AccessShort Note
Bis [4,4′-(1,3-Phenylenebis(azanylylidene))-bis(3,6-di-tert-butyl-2-oxycyclohexa-2,5-dien-1-one)-bis(dimethylsulfoxide)nickel(II)]
by
Irina N. Meshcheryakova, Nikolay O. Druzhkov, Ilya A. Yakushev, Kseniya V. Arsenyeva, Anastasiya V. Klimashevskaya and Alexandr V. Piskunov
Molbank 2024, 2024(4), M1890; https://doi.org/10.3390/M1890 - 26 Sep 2024
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A new cage-like dimeric nickel(II) complex Ni2L2(DMSO)4 based on a ditopic redox-active hydroxy-para-iminobenzoquinone type ligand LH2 (L is 4,4′-(1,3-phenylene-bis(azaneylylidene))-bis(3,6-di-tert-butyl-2-oxycyclohexa-2,5-dien-1-one dianion) was synthesized in DMSO at 120 °C. The molecular structure of
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A new cage-like dimeric nickel(II) complex Ni2L2(DMSO)4 based on a ditopic redox-active hydroxy-para-iminobenzoquinone type ligand LH2 (L is 4,4′-(1,3-phenylene-bis(azaneylylidene))-bis(3,6-di-tert-butyl-2-oxycyclohexa-2,5-dien-1-one dianion) was synthesized in DMSO at 120 °C. The molecular structure of the synthesized compound was determined by X-ray diffraction analysis. The complex Ni2L2(DMSO)4 is almost insoluble in all organic solvents, probably due to the presence of a large number of intermolecular contacts in its structure. The electronic spectrum and thermal stability of the crystalline compound have been studied.
Full article
Figure 1
Open AccessShort Note
Methyl 6,7-Difluoro-2-[(4-fluorobenzyl)sulfanyl]-4-hydroxyquinoline-3-carboxylate
by
Vladimir A. Potapov, Irina A. Novokshonova, Maxim V. Musalov, Svetlana V. Amosova and Oleg A. Rakitin
Molbank 2024, 2024(4), M1889; https://doi.org/10.3390/M1889 - 26 Sep 2024
Abstract
A convenient synthesis of a novel fluoroquinolone precursor, methyl 6,7-difluoro-2-[(4-fluorobenzyl)sulfanyl]-4-hydroxyquinoline-3-carboxylate, at a 78% yield starting from 3,4-difluorophenyl isothiocyanate was developed. The structure of the product was established by 1H, 13C, and 19F NMR spectroscopy, mass spectrometry, IR spectroscopy and confirmed
[...] Read more.
A convenient synthesis of a novel fluoroquinolone precursor, methyl 6,7-difluoro-2-[(4-fluorobenzyl)sulfanyl]-4-hydroxyquinoline-3-carboxylate, at a 78% yield starting from 3,4-difluorophenyl isothiocyanate was developed. The structure of the product was established by 1H, 13C, and 19F NMR spectroscopy, mass spectrometry, IR spectroscopy and confirmed by elemental analysis. The title compound, containing the pharmacophoric 4-fluorobenzyl group, will be used in the synthesis of novel fluoroquinolone derivatives.
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(This article belongs to the Section Organic Synthesis)
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Open AccessShort Note
Ac-[K-Aib-C(3,9-Acm; 6,12-DFLC(Acm)KKESEK)]4-NH2
by
Vasiliki Moulasioti, Evgenia Fotou, Vassilios Moussis and Vassilios Tsikaris
Molbank 2024, 2024(4), M1887; https://doi.org/10.3390/M1887 - 25 Sep 2024
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Chemoselective reactions have played a crucial role in the development of high-molecular-weight (>3000 Da) macromolecules with a branched architecture, particularly as peptides and epitope-based vaccines have emerged as promising tools for drug development. Based on this, in this study, we designed and synthesized
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Chemoselective reactions have played a crucial role in the development of high-molecular-weight (>3000 Da) macromolecules with a branched architecture, particularly as peptides and epitope-based vaccines have emerged as promising tools for drug development. Based on this, in this study, we designed and synthesized the peptide macromolecule CH3CO-[K-Aib-C(3,9-CH2NHCOCH3; 6,12-DFLC(CH2NHCOCH3)KKESEK)]4-NH2 [Ac-K-Aib-C(3,9-Acm); 6,12-epitope)]4-NH2] using chemoselective thioether bond formation between the peptide carrier CPSOC (3,9 Acm) and the IAc-DFLC(Acm)KKESEK-NH2 peptide epitope. The conjugate was purified via RP-HPLC and characterized via HR-ESI-MS. The epitope D128FLCKKESEK137 derives from the lethal toxin, ammodytoxin A, from the V. ammodytes snake species, and it was synthesized using the SPPS Fmoc/tBu methodology and characterized via HR-ESI-MS and NMR techniques.
Full article
Figure 1
Open AccessCommunication
Synthesis and Characterization of N-Nitroso-3-morpholinosydnonimine as NO Radical Donor
by
Nathalie Saffon-Merceron, Christian Lherbet and Pascal Hoffmann
Molbank 2024, 2024(4), M1886; https://doi.org/10.3390/M1886 - 24 Sep 2024
Abstract
N-Nitroso-3-morpholinosydnonimine 3 was prepared by nitrosation of SIN-1 and characterized by 1H-NMR, 13C-NMR, and HRMS. Its structure, confirmed by single crystal X-ray diffraction analysis, was found to be in agreement with its mesoionic and aromatic character. Unlike 3-morpholino-sydnonimine (SIN-1), which
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N-Nitroso-3-morpholinosydnonimine 3 was prepared by nitrosation of SIN-1 and characterized by 1H-NMR, 13C-NMR, and HRMS. Its structure, confirmed by single crystal X-ray diffraction analysis, was found to be in agreement with its mesoionic and aromatic character. Unlike 3-morpholino-sydnonimine (SIN-1), which releases both nitric oxide and superoxide radical, decomposition of this nitrosylated sydonimine could yield nitric oxide as the only decomposition product, and thus without the formation of toxic peroxynitrite.
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(This article belongs to the Section Organic Synthesis)
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Open AccessShort Note
2-Methylpropan-2-ammonium [(3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-[(2S)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-heptanoate
by
Ioana-Georgeta Grosu, Alexandru Turza, Xenia Filip and Maria-Olimpia Miclaus
Molbank 2024, 2024(3), M1885; https://doi.org/10.3390/M1885 - 24 Sep 2024
Abstract
Pravastatin is a popular statin agent with applications in the treatment of cardiovascular diseases for patients with an abnormal lipid panel. The starting form of pravastatin is amorphous and following recrystallization, it becomes a crystalline solid with tert-butylamine salt molecules embedded within the
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Pravastatin is a popular statin agent with applications in the treatment of cardiovascular diseases for patients with an abnormal lipid panel. The starting form of pravastatin is amorphous and following recrystallization, it becomes a crystalline solid with tert-butylamine salt molecules embedded within the lattice. Its molecular and crystal structure were elucidated based on single-crystal X-ray diffraction and characterized by ss-NMR.
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(This article belongs to the Section Structure Determination)
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Open AccessShort Note
4-(10-Phenyl-9-Anthracenyl)-1,2-Benzenediol
by
Nicola Edwards and Kelsey Harris
Molbank 2024, 2024(3), M1884; https://doi.org/10.3390/M1884 - 23 Sep 2024
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The title compound, 4-(10-phenyl-9-anthracenyl)-1,2-benzenediol, was synthesized using a two-step protocol. In the first step, 9-phenyl,10-bromoanthracene was coupled to 3,4-dimethoyphenylboronic acid by employing Pd(PPh3)4 as the catalyst and potassium carbonate as the base. Methoxy group removal was effected using HBr in
[...] Read more.
The title compound, 4-(10-phenyl-9-anthracenyl)-1,2-benzenediol, was synthesized using a two-step protocol. In the first step, 9-phenyl,10-bromoanthracene was coupled to 3,4-dimethoyphenylboronic acid by employing Pd(PPh3)4 as the catalyst and potassium carbonate as the base. Methoxy group removal was effected using HBr in the presence of acetic acid in the second step. Overall, two novel 9,10-diphenylanthracence-based compounds were synthesized in this work; standard spectroscopic techniques and high-resolution mass spectrometry were employed in their characterization. The photophysical properties of these compounds are also reported. These compounds are potentially useful as sensors, catalysts and building blocks for larger architectures.
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Supplementary material:
Supplementary File 1 (PDF, 6565 KiB)
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Supplementary File 1 (PDF, 6565 KiB)
Supplementary File 2 (MOL, 5 KiB)
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Open AccessCommunication
Thiazolylketol Acetates as Glycosyl Donors: Stereoselective Synthesis of a C-Ketoside
by
Clark Ferrari, Alessandro Dondoni and Alberto Marra
Molbank 2024, 2024(3), M1883; https://doi.org/10.3390/M1883 - 23 Sep 2024
Abstract
We have already proven that thiazolylketol acetates, synthetised by addition of 2-lithiothiazole to sugar lactones followed by acetylation, are efficient glycosyl donors in the presence of O-, N-, and P-nucleophiles. We describe here their first use in the C-glycosidation using
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We have already proven that thiazolylketol acetates, synthetised by addition of 2-lithiothiazole to sugar lactones followed by acetylation, are efficient glycosyl donors in the presence of O-, N-, and P-nucleophiles. We describe here their first use in the C-glycosidation using trimetylsilyl cyanide as the acceptor in order to prepare, after thiazole-to-formyl unmasking and reduction, the corresponding C-ketosides.
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(This article belongs to the Section Organic Synthesis)
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Open AccessCommunication
The Effects of Ceric Ammonium Nitrate in the Oxidation of 2-Benzyl-1,4-dimethoxybenzene Derivatives
by
Marcello Casertano, Anna Aiello, Marialuisa Menna and Concetta Imperatore
Molbank 2024, 2024(3), M1882; https://doi.org/10.3390/M1882 - 16 Sep 2024
Abstract
The one- or two-electron reduction in quinone compounds gives rise to semiquinones and hydroquinones, respectively, which, in turn, can be oxidized back to quinones, generating a cyclic redox system with the production of reactive oxygen species (ROS). For these reasons, quinone derivatives participate
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The one- or two-electron reduction in quinone compounds gives rise to semiquinones and hydroquinones, respectively, which, in turn, can be oxidized back to quinones, generating a cyclic redox system with the production of reactive oxygen species (ROS). For these reasons, quinone derivatives participate in various biological processes in metabolic pathways, such as oxidative reactions and electron transport. In addition, natural quinone compounds as well as their semisynthetic and/or synthetically produced derivatives are of great pharmacological interest for the discovery and design of new drugs. As a result, their chemical reactivity as well as new methods for their synthesis are being investigated on an ongoing basis. Herein, a mild and efficient synthesis to obtain 2-(4-benzyl substituted)-1,4-dimethoxybenzene derivatives is reported. In addition, an evaluation of the effects on the quinone/diquinone ratio in the reaction product in relation to different ways of adding the oxidant CAN to the arene solution is discussed.
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(This article belongs to the Section Organic Synthesis)
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Scheme 1
Open AccessShort Note
rel-(2R,3S)-2-((Diphenylmethylene)amino)-5-oxo-5-phenyl-3-(thiophen-2-yl)pentanenitrile
by
Donka N. Tasheva and Vesela M. Mihaylova
Molbank 2024, 2024(3), M1881; https://doi.org/10.3390/M1881 - 11 Sep 2024
Abstract
The reaction of 2-((diphenylmethylene)amino)acetonitrile with (E)-1-phenyl-3-(thiophen-2-yl)prop-2-en-1-one was performed by using 33% NaOH in CH3CN for 30 min at 0 °C. The main product—rel-(2R,3S)-2-((diphenylmethylene)amino)-5-oxo-5-phenyl-3-(thiophen-2-yl)pentanenitrile—was isolated and characterized by IR, 1H NMR, 13C NMR, 1H-1H COSY, and high-resolution mass spectrometry (HRMS).
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(This article belongs to the Section Organic Synthesis)
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