Open AccessCommunication
Straightforward Synthesis of 2(5H)-Furanones as Promising Cross-Coupling Partners: Direct Furanone Annulation Utilizing Ti-Mediated Aldol Addition
Molbank 2016, 2016(4), M908; doi:10.3390/M908 -
Abstract
Direct 2(5H)-furanone annulation produces promising cross-coupling partners incorporating m- or p-bromo- and p-tosyloxyphenyl groups into the 5-position of a notable 2(5H)-furanone pharmacore. The present one-pot annulation method involves two distinctive reactions: (i) a powerful and [...] Read more.
Direct 2(5H)-furanone annulation produces promising cross-coupling partners incorporating m- or p-bromo- and p-tosyloxyphenyl groups into the 5-position of a notable 2(5H)-furanone pharmacore. The present one-pot annulation method involves two distinctive reactions: (i) a powerful and crossed Ti-direct aldol addition and (ii) an acid-induced characteristic cyclo-condensation, leading to 2(5H)-furanones. Suzuki-Miyaura cross-coupling of 5-(4-bromophenyl)-furan-2(5H)-ones, 5-(4-tosyloxyphenyl)-3,4-dimethylfuran-2(5H)-ones and a furan derivative successfully afforded the corresponding products with the 2(5H)-furanone skeleton. Full article
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Open AccessCommunication
A Convenient Four-Step Synthesis of 1-{β-[3-(4-Methoxy-phenyl)Propoxy]-4-Methoxyphenethyl}-1H-Imidazole Hydrochloride as a Probing Tool for SOCE Assays
Molbank 2016, 2016(4), M909; doi:10.3390/M909 -
Abstract
1-{β-[3-(4-Methoxy-phenyl)propoxy]-4-methoxyphenethyl}-1H-imidazole hydrochloride 7, or SKF-96365, was synthesized in four steps with an overall yield of 9%. The structure of 7 was confirmed by 1H-, 13C-NMR, HRMS, and elemental analysis. The intermediates 3 and 4 were also isolated [...] Read more.
1-{β-[3-(4-Methoxy-phenyl)propoxy]-4-methoxyphenethyl}-1H-imidazole hydrochloride 7, or SKF-96365, was synthesized in four steps with an overall yield of 9%. The structure of 7 was confirmed by 1H-, 13C-NMR, HRMS, and elemental analysis. The intermediates 3 and 4 were also isolated and characterized by 1H-, 13C-NMR, and HRMS. Full article
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Open AccessShort Note
(E)-3-Methyl-6-(3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-en-1-yl)-2(3H)-benzothiazolone
Molbank 2016, 2016(3), M907; doi:10.3390/M907 -
Abstract The title compound, (E)-3-methyl-6-(3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-en-1-yl)-2(3H)-benzothiazolone, was synthesized by both an acid- and base-catalyzed aldol condensation of 3-methyl-6-acetyl-2(3H)-benzothiazolone and 3,4,5-trimethoxyacetophenone. The structure of the target compound was confirmed using 1H-NMR, 13C-NMR, IR, MS, and elemental analysis. Full article
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Open AccessShort Note
5,9,11-Trihydroxy-2,2-dimethyl-10-(3′-methyl-2′-butenyl)-3-(2″-methyl-3″-butenyl)pyrano[2,3-a]xanthen-12(2H)-one from the Stem Bark of Calophyllum pseudomole
Molbank 2016, 2016(3), M906; doi:10.3390/M906 -
Abstract 5,9,11-Trihydroxy-2,2-dimethyl-10-(3′-methyl-2′-butenyl)-3-(2″-methyl-3″-butenyl)-pyrano[2,3-a]xanthen-12(2H)-one (1) was isolated from the stem bark of Calophyllumpseudomole. The structure of 1 was established by spectroscopic analysis which included UV, IR, HRESIMS and NMR experiments. Full article
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Open AccessShort Note
1,3-Butanediol Dibenzoate
Molbank 2016, 2016(3), M905; doi:10.3390/M905 -
Abstract
Environmentally friendly and straightforward methods for creating biofuels are required to promote biofuel use. Therefore, we present here a convenient and environmentally friendly direct self-aldol reaction of acetaldehyde in 100 mM borate buffer (pH 10) affording the dimer of 3-hydroxybutanal with a [...] Read more.
Environmentally friendly and straightforward methods for creating biofuels are required to promote biofuel use. Therefore, we present here a convenient and environmentally friendly direct self-aldol reaction of acetaldehyde in 100 mM borate buffer (pH 10) affording the dimer of 3-hydroxybutanal with a good yield. The product can be easily converted into 1,3-butanediol and its benzoate; therefore, our results will have a positive impact in the field of biochemical production from ethanol. Full article
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Open AccessShort Note
Octanoic Hydrazide-Linked Chitooligosaccharides-2,5-Anhydro-d-Mannofuranose
Molbank 2016, 2016(3), M904; doi:10.3390/M904 -
Abstract
Chitooligosaccharide with one 2,5-anhydro-d-mannofuranose unit at the reducing end (COSamf) was prepared by nitrous acid depolymerization of chitosan. The reducing-end functionalization of COSamf by reductive amination with octanoic hydrazide in the presence of NaBH3CN was achieved in high [...] Read more.
Chitooligosaccharide with one 2,5-anhydro-d-mannofuranose unit at the reducing end (COSamf) was prepared by nitrous acid depolymerization of chitosan. The reducing-end functionalization of COSamf by reductive amination with octanoic hydrazide in the presence of NaBH3CN was achieved in high yield. The chemical structure of the targeted octanoic hydrazide-linked COSamf was fully characterized by NMR spectroscopy and MALDI-TOF mass spectrometry. This synthesis opens the way to a new generation of COSamf derivatives with potential amphiphilic properties. Full article
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Open AccessShort Note
N-[(1E)-(3-Bromophenyl)methylene]-N-(2-piperidin-1-ylethyl)amine
Molbank 2016, 2016(3), M903; doi:10.3390/M903 -
Abstract
N-[(1E)-(3-Bromophenyl)methylene]-N-(2-piperidin-1-ylethyl)amine Schiff base was prepared in good yield and characterized by the reflux of equivalent amounts of 2-(piperidin-1-yl)ethanamine with 3-bromobenzaldehyde. The structure of the desired Schiff base was analyzed based on: elemental analysis, EI-MS, TG/DTG, UV-visible, FT-IR, [...] Read more.
N-[(1E)-(3-Bromophenyl)methylene]-N-(2-piperidin-1-ylethyl)amine Schiff base was prepared in good yield and characterized by the reflux of equivalent amounts of 2-(piperidin-1-yl)ethanamine with 3-bromobenzaldehyde. The structure of the desired Schiff base was analyzed based on: elemental analysis, EI-MS, TG/DTG, UV-visible, FT-IR, 1H and 13C-NMR spectral analysis. The condensation reaction was monitored by FT-IR. Full article
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Open AccessShort Note
1,4-Phenylenebis[(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methanone]
Molbank 2016, 2016(3), M902; doi:10.3390/M902 -
Abstract
The compound named in the title was prepared from N1,N4-diphenethylterephthalamide 1. The resulting bis terephthalamide was subjected to an intramolecular α-amidoalkylation reaction with paraformaldehyde in the presence of heterogeneous catalyst TfOH/SiO2 to obtain 1,4-phenylenebis[(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1[...] Read more.
The compound named in the title was prepared from N1,N4-diphenethylterephthalamide 1. The resulting bis terephthalamide was subjected to an intramolecular α-amidoalkylation reaction with paraformaldehyde in the presence of heterogeneous catalyst TfOH/SiO2 to obtain 1,4-phenylenebis[(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methanone]. The structure of the newly synthesized compound was determined using 1H, 13C-NMR, UV, IR and mass spectral data. Full article
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Open AccessShort Note
6-[(4-Chlorophenyl)(1H-1,2,4-triazol-1-yl)methyl]-3-methyl-2(3H)-benzoxazolone
Molbank 2016, 2016(2), M901; doi:10.3390/M901 -
Abstract A new hybrid molecule containing a triazole and a benzoxazolone ring was synthesized. The structure of 6-[(4-chlorophenyl)(1H-1,2,4-triazol-1-yl) methyl]-3-methyl-2(3H)-benzoxazolone was confirmed by IR, 1H-, 13C-NMR, MS and elemental analysis. Full article
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Open AccessShort Note
2II-VII, 3I-VII, 6I-VII-Icosa-O-acetyl-2I-deoxy-cyclomaltoheptaose
Molbank 2016, 2016(2), M900; doi:10.3390/M900 -
Abstract Deoxygenation of a secondary hydroxy group on β-cyclodextrin was conducted to prepare the title compound 2II-VII, 3I-VII, 6I-VII-icosa-O-acetyl-2I-deoxy-cyclomaltoheptaose. The synthetic procedure comprised a two-step reaction—phenoxythiocarbonylation and Barton-McCombie deoxygenation. The synthesized compound was characterized by 1H-NMR, 13C-NMR, HRMS, and elemental analysis. Full article
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Open AccessShort Note
6-Nitro-4H-benzo[d][1,3]thiazin-2-amine
Molbank 2016, 2016(2), M899; doi:10.3390/M899 -
Abstract An efficient and cost-effective synthesis of 6-nitro-4H-benzo[d][1,3]thiazin-2-amine based on a sequential SN2-SNAr process is reported. The synthesis is accomplished with an overall yield of 80%. Full article
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Open AccessShort Note
5-(5-Bromo-2-hydroxy-3-methoxyphenyl)-7-methyl-4,5,6,7-tetrahydro[1,2,4]triazolo[1,5-a]pyrimidin-7-ol
Molbank 2016, 2016(2), M898; doi:10.3390/M898 -
Abstract The title compound was synthesized by multicomponent condensation of 3-amino-1,2,4-triazole, acetone and 5-bromo-2-hydroxy-3-methoxybenzaldehyde. The structure was established by 1H-NMR, 13C-NMR, IR spectroscopy and LC-MS. Full article
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Open AccessShort Note
(E)-3-Methyl-6-(3-oxo-3-(thiophen-2-yl)-1-propenyl)-2(3H)-benzothiazolone
Molbank 2016, 2016(2), M897; doi:10.3390/M897 -
Abstract The title compound, (E)-3-methyl-6-(3-oxo-3-(thiophen-2-yl)-1-propenyl)-2(3H)-benzothiazolone, was synthesized by Claisen-Schmidt condensation of 3-methyl-2(3H)-benzothiazolone-6-carbaldehyde with 2-acetylthiophene in 94% yield. The structure of the target compound was confirmed using 1H-NMR, 13C-NMR, IR, MS, and elemental analysis. Full article
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Open AccessShort Note
(5S)-5-[(4aR,8aS,9E,11S,13R,14S,16R,17R,19S)-11,19-Dihydroxy-8,10,13,16-tetramethyl-18-methylidene-3,4,5,6,8a,11,12,13,14,15,16,17,18,19,20,21-hexadecahydro-2H-14,17-epoxybenzo[2,3]cyclohexadeca[1,2-b]pyridine-7-yl]-3-methylfuran-2(5H)-one (12-Methylgymnodimine B)
Molbank 2016, 2016(2), M896; doi:10.3390/M896 -
Abstract A new member of the gymnodimine class of spiroimine toxins has been isolated from a laboratory culture strain of Alexandrium ostenfeldii. Extensive one-dimensional (1D) and two-dimensional (2D) NMR data analysis was used to elucidate its structure as 12-methylgymnodimine B. Full article
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Open AccessShort Note
2-O,O′,Oʺ,Oʺ′-Bis(1,2-dithiooxalato-S,S′)nickel(II)]bis[-O,O′-bis(1,2-dithiooxalato-S,S′)-nickel(II)pentaquaholmium(III)]hydrate, [Ho2Ni3(dto)6(H2O)10]
Molbank 2016, 2016(2), M895; doi:10.3390/M895 -
Abstract
Planar bis(1,2-dithiooxalato)nickelate(II), [Ni(dto)]2− reacts in aqueous solutions with lanthanide ions (Ln3+) to form pentanuclear, hetero-bimetallic complexes of the general composition [{Ln(H2O)n}2{Ni(dto)2}3]·xH2O. (n = 4 or 5; [...] Read more.
Planar bis(1,2-dithiooxalato)nickelate(II), [Ni(dto)]2− reacts in aqueous solutions with lanthanide ions (Ln3+) to form pentanuclear, hetero-bimetallic complexes of the general composition [{Ln(H2O)n}2{Ni(dto)2}3]·xH2O. (n = 4 or 5; x = 9–12). The complex [{Ho(H2O)5}2{Ni(dto)2}3]·10H2O, Ho2Ni3, was synthesized and characterized by single crystal X-ray structure analysis and powder diffraction. The Ho2Ni3 complex crystallizes as monoclinic crystals in the space group P21/c. The channels and cavities, appearing in the crystal packing of the complex molecules, are occupied by a varying amount of non-coordinated water molecules. Full article
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Open AccessShort Note
1-[2-(4-Methyl-7-coumarinyloxy)ethyl]-4-(5-{1-[2-(4-methyl-7-coumarinyloxy)ethyl]-1H-1,2,3-triazol-4-yl}pentyl)-1H-1,2,3-triazole
Molbank 2016, 2016(2), M894; doi:10.3390/M894 -
Abstract
Nature often produces compounds with a high degree of symmetry to reduce structural information and complexity. Synthesis of identical twin drugs, through the linkage of two identical pharmacophoric entities, is a classical strategy to produce more potent and/or selective drugs. Herein, two [...] Read more.
Nature often produces compounds with a high degree of symmetry to reduce structural information and complexity. Synthesis of identical twin drugs, through the linkage of two identical pharmacophoric entities, is a classical strategy to produce more potent and/or selective drugs. Herein, two units of the privileged core of the coumarin hymecromone were linked together using “click chemistry”. Synthesis of 1-[2-(4-Methyl-7-coumarinyloxy)ethyl]-4-(5-{1-[2-(4-methyl-7-coumarinyloxy)ethyl]-1H-1,2,3-triazol-4-yl}pentyl)-1H-1,2,3-triazole was achieved by coupling of two identical units of an azido coumarin with a symmetrical alkine using copper(I)-catalyzed alkyne-azide cycloaddition reaction, in good yields and with complete regioselectivity. Full article
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Open AccessShort Note
1,4-Bis[(N-acetyl-l-phenylalanyl-glycyl-l-alanyl)aminomethyl]benzene
Molbank 2016, 2016(2), M893; doi:10.3390/M893 -
Abstract
The title compound was prepared by inducing amide bond formation between 1,4-bis(aminomethyl)benzene and tripeptide Ac-Phe-Gly-Ala-OH. The structure of the synthesized compound was determined on the basis of its 1H-nuclear magnetic resonance (NMR), 13C-NMR, and mass spectral data. Furthermore, the compound's [...] Read more.
The title compound was prepared by inducing amide bond formation between 1,4-bis(aminomethyl)benzene and tripeptide Ac-Phe-Gly-Ala-OH. The structure of the synthesized compound was determined on the basis of its 1H-nuclear magnetic resonance (NMR), 13C-NMR, and mass spectral data. Furthermore, the compound's preferred structure in solution and calculated conformation are also reported. Full article
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Open AccessShort Note
5-(4-Fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-4,5-dihydro-1H-pyrazole
Molbank 2016, 2016(2), M891; doi:10.3390/M891 -
Abstract A new fluorinated 1-naphtyl pyrazoline (4) has been successfully synthesized by reacting a fluorinated 1-naphtyl chalcone (3) with phenyl hydrazine under microwave irradiation. The structure of compound 4 was characterized by UV-Vis, FTIR, HRMS, 1D NMR and 2D NMR spectroscopies. Full article
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Open AccessShort Note
Methyl 2,5-Dihydroxy-4-(3′-methyl-2′-butenyl)benzoate
Molbank 2016, 2016(2), M892; doi:10.3390/M892 -
Abstract Methyl 2,5-dihydroxy-4-(3′-methyl-2′-butenyl)benzoate (1) was isolated from the root of Erythrina subumbrans. The chemical structure of 1 has been elucidated based on spectroscopy UV-Vis, HRESIMS, 1D and 2D NMR analysis. Full article
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Open AccessShort Note
(S)-4-[(3aR,4S,7aR)-4-Methoxy-6-methyl-3-methylene-2-oxo-2,3,3a,4,7,7a-hexahydrobenzofuran-5-yl]pentyl Acetate
Molbank 2016, 2016(1), M890; doi:10.3390/M890 -
Abstract
A new etherified 1-O-acetylbritannilactone (ABL) analogue 2 was semi-synthesized by a mild etherification reaction. The structure of the newly synthesized analogue was identified by 1H-NMR, 13C-NMR and HR-ESI-MS analysis. 2 exhibited similar cytotoxicity against HCT116, SGC-7901 and HeLa [...] Read more.
A new etherified 1-O-acetylbritannilactone (ABL) analogue 2 was semi-synthesized by a mild etherification reaction. The structure of the newly synthesized analogue was identified by 1H-NMR, 13C-NMR and HR-ESI-MS analysis. 2 exhibited similar cytotoxicity against HCT116, SGC-7901 and HeLa human cancer cell lines with ABL. Full article
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