Open AccessShort Note
3-(2-Hydroxyethyl)-2-methylbenzothiazolium Bromide
Molbank 2016, 2016(4), M920; doi:10.3390/M920 (registering DOI) -
Abstract A novel method for the preparation of 3-(2-hydroxyethyl)-2-methylbenzothiazolium bromide was developed. It consists of heating of 2-methylbenzothiazole, 2-bromoethanol and ethoxyethanol for 2 h. On the next day the precipitate was filtered and air dried. Full article
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Scheme 1

Open AccessShort Note
1,4-Dihydro-4-(nitromethyl)-2-phenyl-1-tosylquinoline-3-carbaldehyde
Molbank 2016, 2016(4), M918; doi:10.3390/M918 -
Abstract An aza-Michael/Michael cascade reaction of 2-((E)-2-nitrovinyl)-N-tosylbenzenamine with 3-phenylpropiolaldehyde catalyzed by pyrrolidine has produced a new compound, 1,4-dihydro-4-(nitromethyl)-2-phenyl-1-tosylquinoline-3-carbaldehyde. The structure of the newly synthesized compound was determined using 1H, 13C-NMR, IR, and mass spectral data. Full article
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Open AccessShort Note
3-Ethyl-2-(ethylimino)-4-methyl-2,3-dihydro-1,3-thiazole-5-carboxylate Ethyl Ester
Molbank 2016, 2016(4), M919; doi:10.3390/M919 (registering DOI) -
Abstract
An efficient procedure to obtain the new compound 1a from ethyl acetoacetate (2a), NBS and N,N′-diethylthiourea (4a) was reported. In comparison with the traditional method to synthesize its analogues, this efficient, catalyst-free, and one-pot synthetic method
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An efficient procedure to obtain the new compound 1a from ethyl acetoacetate (2a), NBS and N,N′-diethylthiourea (4a) was reported. In comparison with the traditional method to synthesize its analogues, this efficient, catalyst-free, and one-pot synthetic method is facile. The work-up procedure is easy and gives the pure target compound under milder reaction conditions in a relatively high yield of 75%. Full article
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Scheme 1

Open AccessShort Note
1,3,1′,3′-(Dinaphthalene-1,8-diyl)bisthiourea
Molbank 2016, 2016(4), M917; doi:10.3390/M917 -
Abstract
A new bisthiourea compound, 1,3,1′,3′-(dinaphthalene-1,8-diyl)bisthiourea, was synthesized. Its structure was characterized by elemental analysis, FT-IR and 1H-, 13C-NMR and MS spectroscopic techniques. The compound was found to selectively recognize fluoride anions among other halides as demonstrated by means of UV-vis absorption
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A new bisthiourea compound, 1,3,1′,3′-(dinaphthalene-1,8-diyl)bisthiourea, was synthesized. Its structure was characterized by elemental analysis, FT-IR and 1H-, 13C-NMR and MS spectroscopic techniques. The compound was found to selectively recognize fluoride anions among other halides as demonstrated by means of UV-vis absorption spectroscopic date and the naked eye. Full article
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Open AccessCommunication
2-C-Alkynyl and 2-C-cis-Alkenyl β-Mannosides with Acetal Protected γ-Aldehyde Functionality via 2-Uloside Alkynylation and Lindlar Hydrogenation
Molbank 2016, 2016(4), M916; doi:10.3390/M916 -
Abstract
Benzyl 3,4,6-tri-O-benzyl-β-d-arabino-hexos-2-ulo-1,5-pyranoside was subjected to manno-selective ketone alkynylation with propiolaldehyde dibenzyl acetal, resulting in the formation of a 2-C-alkynyl β-mannoside bearing a γ-dibenzyl acetal functionality. Subsequent transacetalization of the acetal moiety with methanol and
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Benzyl 3,4,6-tri-O-benzyl-β-d-arabino-hexos-2-ulo-1,5-pyranoside was subjected to manno-selective ketone alkynylation with propiolaldehyde dibenzyl acetal, resulting in the formation of a 2-C-alkynyl β-mannoside bearing a γ-dibenzyl acetal functionality. Subsequent transacetalization of the acetal moiety with methanol and 1,3-dihydroxypropane and acetylation of position 2, respectively, gave 4 different 2-C-alkynyl branched mannosides. Lindlar hydrogenation of the latter under optimized conditions in dimethylformamide afforded a series of 2-C-cis-alkenyl mannosides. X-ray molecular structures of benzyl 3,4,6-tri-O-benzyl-β-d-arabino-hexos-2-ulo-1,5-pyranoside and of the branched glycoside benzyl 3,4,6-tri-O-benzyl-2-C-((Z)-3,3-dibenzyloxyprop-1-en-1-yl)-β-d-mannopyranoside are reported. Full article
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Open AccessShort Note
(3,5-Dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]methanone
Molbank 2016, 2016(4), M915; doi:10.3390/M915 -
Abstract
In an attempt to enhance cytotoxic activity of pyrazolo[3,4-d]pyrimidine core, we synthesized (3,5-dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]methanone (4) by reacting 4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)benzohydrazide (3) with acetylacetone. Antiproliferative activity of this compound was screened against breast
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In an attempt to enhance cytotoxic activity of pyrazolo[3,4-d]pyrimidine core, we synthesized (3,5-dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]methanone (4) by reacting 4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)benzohydrazide (3) with acetylacetone. Antiproliferative activity of this compound was screened against breast (MCF-7), colon (HCT-116), and liver (HEPG-2) cancer cell lines. The tested compound exhibited cytotoxic activity with IC50 = 5.00–32.52 μM. Moreover, inhibitory activity of this compound was evaluated against the epidermal growth factor receptor (EGFR), the fibroblast growth factor receptor (FGFR), the insulin receptor (IR), and the vascular endothelial growth factor receptor (VEGFR). This target compound showed potent inhibitory activity, especially against FGFR with IC50 = 5.18 μM. Full article
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Open AccessShort Note
4,4′-Bis[4-(4′-hydroxyphenyl)phenylazo]diphenyl Ether
Molbank 2016, 2016(4), M914; doi:10.3390/M914 -
Abstract 4,4′-Bis[4-(4′-hydroxyphenyl)phenylazo]diphenyl ether (3) was prepared by diazotization coupling of 4,4′-oxy dianiline (1) and biphenyl-4-ol (2). The synthesized compound (3) was characterized by elemental analysis, UV-Visible, FTIR and 1H-NMR (nuclear magnetic resonance) spectroscopic studies. Full article
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Open AccessCommunication
4-Acetyl-2-hydroxy-2,5-dimethylfuran-3(2H)-one
Molbank 2016, 2016(4), M913; doi:10.3390/M913 -
Abstract The facile synthesis of 4-acetyl-2-hydroxy-2,5-dimethylfuran-3(2H)-one (4) was achieved by the Mn(OAc)3-mediated aerobic oxidation of 2,4-pentanedione or the direct reaction of Mn(acac)3 in AcOH-TFE at room temperature under a dried air stream. Full article
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Open AccessShort Note
Benzyl 2-((E)-Tosyliminomethyl)phenylcarbamate
Molbank 2016, 2016(4), M912; doi:10.3390/M912 -
Abstract Benzyl 2-((E)-tosyliminomethyl)penylcarbamate was prepared in good yield and characterized by the condensation reaction of benzyl 2-formylphenylcarbamate with p-toluenesulfonyl amine. The structure of the newly synthesized compound was determined using 1H, 13C-NMR, IR and mass spectral data. Full article
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Open AccessShort Note
(E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one
Molbank 2016, 2016(4), M911; doi:10.3390/M911 -
Abstract
The title chalcone (E)-1-(2-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one was prepared with an excellent yield from a Claisen–Schmidt condensation reaction between o-aminoacetophenone and p-chlorobenzaldehyde. This product will be used as a key precursor for the development of an alternative route for the total synthesis
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The title chalcone (E)-1-(2-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one was prepared with an excellent yield from a Claisen–Schmidt condensation reaction between o-aminoacetophenone and p-chlorobenzaldehyde. This product will be used as a key precursor for the development of an alternative route for the total synthesis of dubamine and graveoline alkaloids. Single crystals of the title compound suitable for X-ray diffraction were grown via slow evaporation in ethanol at room temperature. A complete crystallographic study was performed in depth to unequivocally confirm its structure and determine some interesting supramolecular properties. The crystal structure of the title o-aminochalcone, C15H12ClNO, shows two molecules per asymmetric unit (Z′ = 2) and adopts an E configuration about the C=C double bond. In the title compound, the mean plane of the non-H atoms of the central chalcone fragment C—C(O)—C—C—C is as follows: [r.m.s. deviation = 0.0130 Å for A-B and 0.0043 for C-D molecules]. In the crystal, molecules are linked by N—H...N and C—H...O, hydrogen bonds forming edge-fused R66(46) rings parallel to (100). Additionally, N—H...O hydrogen bonds generate a three-dimensional network. Full article
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Figure 1

Open AccessShort Note
5-[(3-Fluorophenyl)(2-hydroxy-6-oxocyclohex-1-en-1-yl)methyl]-6-hydroxy-1,3-dimethylpyrimidine-2,4(1H,3H)-dione
Molbank 2016, 2016(4), M910; doi:10.3390/M910 -
Abstract
5-[(3-Fluorophenyl)(2-hydroxy-6-oxocyclohex-1-en-1-yl)-methyl]-6-hydroxy-1,3-di-methylpyrimidine-2,4(1H,3H)-dione 3 was synthesized via a multicomponent reaction. The Aldol–Michael addition reactions of N,N-dimethylbarbituric acid, cyclohexane-1,3-dione, and 3-fluorobenzaldehyde in aqueous solution gave the product in high yield. The molecular structure of the compound was confirmed by
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5-[(3-Fluorophenyl)(2-hydroxy-6-oxocyclohex-1-en-1-yl)-methyl]-6-hydroxy-1,3-di-methylpyrimidine-2,4(1H,3H)-dione 3 was synthesized via a multicomponent reaction. The Aldol–Michael addition reactions of N,N-dimethylbarbituric acid, cyclohexane-1,3-dione, and 3-fluorobenzaldehyde in aqueous solution gave the product in high yield. The molecular structure of the compound was confirmed by spectroscopic methods and X-ray crystallography. The title compound (C19H19FN2O5·H2O) crystallizes in the Monoclinic form, P21/c, a = 7.8630 (5) Å, b = 20.0308 (13) Å, c = 11.3987 (8) Å, β = 104.274 (3)°, V = 1739.9 (2)° Å3, Z = 4, Rint = 0.117, wR(F2) = 0.124, T = 100 K. Full article
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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 crossed
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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 and
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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 good
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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 yield.
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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, 1
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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(1H
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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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