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Volume 2019
Issue 1
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Molbank, Volume 2019, Issue 1 (March 2019) – 18 articles

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6 pages, 1255 KiB  
Short Note
4-[(3,4-Dimethoxybenzylidene)amino]-5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
by Soukhyarani Gopal Nayak and Boja Poojary
Molbank 2019, 2019(1), M1055; https://doi.org/10.3390/M1055 - 29 Mar 2019
Viewed by 1888
Abstract
4-Amino-5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (1) upon treatment with 3,4-dimethoxybenzaldehyde in 10 mL of absolute ethanol in the presence of a catalytic amount of acetic acid produced the target compound 4-[(3,4-dimethoxybenzylidene)amino]-5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (2) in 80% yield. [...] Read more.
4-Amino-5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (1) upon treatment with 3,4-dimethoxybenzaldehyde in 10 mL of absolute ethanol in the presence of a catalytic amount of acetic acid produced the target compound 4-[(3,4-dimethoxybenzylidene)amino]-5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (2) in 80% yield. The obtained solid product was recrystallized from ethanol. The compound was characterized by elemental analyses, mass spectrometry, FT-IR, 1H and 13C-NMR spectroscopy. To study the binding interactions of the compound with receptor, it was docked with the human prostaglandin reductase (PTGR2). The docking pose and noncovalent interactions gave insights into its plausible inhibitory action. Full article
(This article belongs to the Collection Molecules from Catalytic Processes)
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Figure 1

3 pages, 318 KiB  
Short Note
1-[(1S,2S)-1,2-Bis(2-hydroxyphenyl)-2-pivaloylaminoethylamino]-2,2-dimethyl-1-propanone
by Fulgentius Nelson Lugemwa
Molbank 2019, 2019(1), M1054; https://doi.org/10.3390/M1054 - 22 Mar 2019
Viewed by 1569
Abstract
When 2-[(1S,2S)-1,2-diamino-2(2-hydroxyphenyl)ethyl]phenol (I) was reacted with 2 mole equivalents of trimethyl acetic (pivalic) anhydride in tetrahydrofuran at room temperature, 1-[(1S,2S)-1,2-bis(2-hydroxyphenyl)-2-pivaloylaminoethylamino]-2,2-dimethyl-1-propanone (II) was obtained quantitatively as the only product. The structure of [...] Read more.
When 2-[(1S,2S)-1,2-diamino-2(2-hydroxyphenyl)ethyl]phenol (I) was reacted with 2 mole equivalents of trimethyl acetic (pivalic) anhydride in tetrahydrofuran at room temperature, 1-[(1S,2S)-1,2-bis(2-hydroxyphenyl)-2-pivaloylaminoethylamino]-2,2-dimethyl-1-propanone (II) was obtained quantitatively as the only product. The structure of the product was determined using 1H- and 13C-NMR. The COSY spectrum indicated that the single –NH was coupled to the single benzylic proton, –CH. The versality of the transformation could be used to generate additional compounds for use in various research areas. Full article
(This article belongs to the Section Organic Synthesis)
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Scheme 1

4 pages, 353 KiB  
Short Note
3,6-Dibromopyridazine-4,5-diamine
by Timofey N. Chmovzh, Ekaterina A. Knyazeva, Olga O. Ustimenko and Oleg A. Rakitin
Molbank 2019, 2019(1), M1053; https://doi.org/10.3390/M1053 - 21 Mar 2019
Cited by 2 | Viewed by 1735
Abstract
Dihalogenated derivatives of 1,2,5-chalcogenadiazoles fused with benzene or heterocyclic rings are of interest as starting compounds for photovoltaic materials. The 1,2,5-chalcogenadiazole ring in these heterocycles was most commonly prepared from the corresponding ortho-diamine moiety. In this communication, 3,6-dibromopyridazine-4,5-diamine was prepared via the [...] Read more.
Dihalogenated derivatives of 1,2,5-chalcogenadiazoles fused with benzene or heterocyclic rings are of interest as starting compounds for photovoltaic materials. The 1,2,5-chalcogenadiazole ring in these heterocycles was most commonly prepared from the corresponding ortho-diamine moiety. In this communication, 3,6-dibromopyridazine-4,5-diamine was prepared via the reaction of 4,7-dibromo[1,2,5]thiadiazolo[3,4-d]pyridazine with sodium methoxide in THF by heating at reflux for four hours. The structure of the newly synthesized compound was established by means of high resolution mass-spectrometry, 1H, 13C-NMR and IR spectroscopy, and mass-spectrometry. Full article
(This article belongs to the Section Organic Synthesis)
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5 pages, 816 KiB  
Short Note
1-[N-Methyl-N-(Phenyl)amino]-3-(4-Methylphenyl)Thiourea
by Chien Ing Yeo and Edward R. T. Tiekink
Molbank 2019, 2019(1), M1052; https://doi.org/10.3390/M1052 - 11 Mar 2019
Cited by 2 | Viewed by 1745
Abstract
The title compound, 1-[N-methyl-N-(phenyl)amino]-3-(4-methylphenyl)thiourea (1), was synthesized by the reaction of 1-methyl-1-phenyl hydrazine and 4-tolyl isothiocyanate, and was characterized by spectroscopy (1H and 13C{1H} NMR, IR, and UV), elemental analysis as well [...] Read more.
The title compound, 1-[N-methyl-N-(phenyl)amino]-3-(4-methylphenyl)thiourea (1), was synthesized by the reaction of 1-methyl-1-phenyl hydrazine and 4-tolyl isothiocyanate, and was characterized by spectroscopy (1H and 13C{1H} NMR, IR, and UV), elemental analysis as well as by single crystal X-ray crystallography. In the solid state, the molecule exists as the thioamide tautomer and features an anti-disposition of the thioamide–N–H atoms; an intramolecular N–H⋯N hydrogen bond is noted. The molecular conformation resembles that of the letter L. In the molecular packing, thioamide-N1–H⋯S1(thione) hydrogen bonds lead to centrosymmetric eight-membered {⋯HNCS}2 synthons. The dimers are assembled into a supramolecular layer in the bc-plane by phenyl- and methyl-C–H⋯π(phenyl) interactions. Full article
(This article belongs to the Section Structure Determination)
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13 pages, 5409 KiB  
Short Note
Dicyclohexylammonium O,O’-Diphenyl Phosphate, [(C6H11)2NH2][(C6H5O)2P(O)(O)]: Spectroscopic Study, Crystal Structure, and Hirshfeld Surface Analysis
by Samira Nazari Moghaddam, Akbar Raissi Shabari, Fahimeh Sabbaghi, Mehrdad Pourayoubi and Abdul Ajees Abdul Salam
Molbank 2019, 2019(1), M1051; https://doi.org/10.3390/M1051 - 02 Mar 2019
Cited by 1 | Viewed by 2093
Abstract
The title salt, [(C6H11)2NH2][(C6H5O)2P(O)(O)], crystallizes in the chiral space group P212121, composed of achiral cation and anion components. The strong charge-assisted N–H…O [...] Read more.
The title salt, [(C6H11)2NH2][(C6H5O)2P(O)(O)], crystallizes in the chiral space group P212121, composed of achiral cation and anion components. The strong charge-assisted N–H…O hydrogen bonds build a linear assembly along the a axis, including a non-centrosymmetric C22(6) chain graph-set motif. The intra and intermolecular C–H…O interactions as well as the C–H…π-electron ring interactions also exist in the crystal structure. Fingerprint plots are used for a detailed investigation of intermolecular interactions participating in the crystal packing. The spectroscopic features (IR, 1H NMR, 13C{1H} NMR, 31P{1H} NMR, and mass) are studied. Full article
(This article belongs to the Section Structure Determination)
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Figure 1

4 pages, 446 KiB  
Short Note
9-Aminoquino[2',3':3,4]pyrrolo[2,1-b]quinazolin-11(13H)-one
by Eugen Schneider and Norbert Haider
Molbank 2019, 2019(1), M1050; https://doi.org/10.3390/M1050 - 01 Mar 2019
Cited by 1 | Viewed by 2035
Abstract
Chemoselective reduction of the corresponding 9-nitro precursor by catalytic transfer hydrogenation afforded the title compound, a new 9-amino derivative of the antitumor alkaloid Luotonin A, in good yield. The structure of the compound was established by means of 1D and 2D 1H-NMR [...] Read more.
Chemoselective reduction of the corresponding 9-nitro precursor by catalytic transfer hydrogenation afforded the title compound, a new 9-amino derivative of the antitumor alkaloid Luotonin A, in good yield. The structure of the compound was established by means of 1D and 2D 1H-NMR and 13C-NMR spectroscopy as well as by EI-MS and high-resolution ESI-MS. Full article
(This article belongs to the Collection Molecules from Catalytic Processes)
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Graphical abstract

4 pages, 764 KiB  
Communication
(S)-Ethyl 2-(tert-butoxycarbonylamino)-3-(2-iodo-4,5-methylenedioxyphenyl)propanoate
by Giovanni Lentini, Maria Maddalena Cavalluzzi, Leonardo Degennaro, Giuseppe Fracchiolla, Filippo Perna and Antonio Scilimati
Molbank 2019, 2019(1), M1049; https://doi.org/10.3390/M1049 - 21 Feb 2019
Viewed by 1898
Abstract
A multistep gram-scale synthesis of (S)-ethyl 2-(tert-butoxycarbonylamino)-3-(2-iodo-4,5-methylenedioxyphenyl)propanoate (2) has been developed. The title compound was prepared starting from commercially available l-DOPA which was O- and N-protected before undergoing iodination by CF3CO2 [...] Read more.
A multistep gram-scale synthesis of (S)-ethyl 2-(tert-butoxycarbonylamino)-3-(2-iodo-4,5-methylenedioxyphenyl)propanoate (2) has been developed. The title compound was prepared starting from commercially available l-DOPA which was O- and N-protected before undergoing iodination by CF3CO2Ag/I2. The structure of the target compound was confirmed using IR, 1H-NMR, 13C-NMR, 2D (COSY, HSQC) NMR spectroscopy, as well as ESI-MS and HRMS. Full article
(This article belongs to the Section Organic Synthesis)
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Graphical abstract

6 pages, 1407 KiB  
Short Note
N1-{4-[2-(Methylthio)-1H-imidazol-5-yl]pyridin-2-yl}benzene-1,4-diamine
by Ahmed El-Gokha, Francesco Ansideri, Stanislav Andreev, Dieter Schollmeyer, Stefan Laufer and Pierre Koch
Molbank 2019, 2019(1), M1048; https://doi.org/10.3390/M1048 - 20 Feb 2019
Cited by 1 | Viewed by 2066
Abstract
The title compound N1-{4-[2-(methylthio)-1H-imidazol-5-yl]pyridin-2-yl}benzene-1,4-diamine (2) was synthesized via nucleophilic aromatic substitution of 2-chloro-4-[2-(methylthio)-1H-imidazol-5-yl]pyridine (3) and p-phenylenediamine under acidic conditions. The synthesized compound 2 was characterized by 1H-NMR, 13C-NMR, MS HPLC, [...] Read more.
The title compound N1-{4-[2-(methylthio)-1H-imidazol-5-yl]pyridin-2-yl}benzene-1,4-diamine (2) was synthesized via nucleophilic aromatic substitution of 2-chloro-4-[2-(methylthio)-1H-imidazol-5-yl]pyridine (3) and p-phenylenediamine under acidic conditions. The synthesized compound 2 was characterized by 1H-NMR, 13C-NMR, MS HPLC, IR and UV-VIS. Additionally, the structure of 2 was confirmed by single crystal X-ray diffraction. Pyridinylimidazole 2 displays moderate affinity towards the c-Jun N-terminal kinase 3 and shows selectivity versus the closely related p38α mitogen-activated protein kinase. Full article
(This article belongs to the Section Structure Determination)
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Figure 1

5 pages, 1198 KiB  
Short Note
4-(4-Chlorophenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thione
by Chien Ing Yeo, Ainnul Hamidah Syahadah Azizan and Edward R.T. Tiekink
Molbank 2019, 2019(1), M1047; https://doi.org/10.3390/M1047 - 19 Feb 2019
Cited by 1 | Viewed by 1977
Abstract
The title compound, 4-(4-chlorophenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thione (1), was synthesized by a hetero-cyclization reaction of 4-chlorophenyl isothiocyanate and formic hydrazide. Compound 1 was characterized by a single-crystal X-ray structure determination as well as 1H and 13C{1H} NMR, IR, [...] Read more.
The title compound, 4-(4-chlorophenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thione (1), was synthesized by a hetero-cyclization reaction of 4-chlorophenyl isothiocyanate and formic hydrazide. Compound 1 was characterized by a single-crystal X-ray structure determination as well as 1H and 13C{1H} NMR, IR, and UV spectroscopy, and microelemental analysis. X-ray crystallography on 1 confirms the molecule exists as the thione tautomer and shows the five-membered ring to be planar and to form a dihedral angle of 82.70(5)° with the appended chlorophenyl ring, indicating an almost orthogonal relationship. In the molecular packing, supramolecular dimers are formed via thioamide-N–H⋯S(thione) hydrogen bonds and these are connected by C=S⋯π(triazolyl) and C-Cl⋯π(triazolyl) interactions, leading to a three-dimensional architecture. Full article
(This article belongs to the Section Structure Determination)
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Graphical abstract

5 pages, 886 KiB  
Short Note
(R,S)-5-(4-Chlorophenyl)-3-{(E)-2-[(R,S)-2,6,6-trimethylcyclohex-2-en-1-yl]vinyl}-4,5-dihydro-1H-pyrazole-1-carboximidamide Hydrochloride
by Michele Cristina Carvalho and Lucas Pizzuti
Molbank 2019, 2019(1), M1046; https://doi.org/10.3390/M1046 - 14 Feb 2019
Viewed by 1592
Abstract
Pyrazoline and amidine motifs are important in medicinal chemistry due to their broad spectrum of bioactivities. This work’s goal was to synthesize a new hybrid amidino pyrazoline from terpenyl chalcone. The chosen method consists of making the terpenyl chalcone react with aminoguanidine hydrochloride [...] Read more.
Pyrazoline and amidine motifs are important in medicinal chemistry due to their broad spectrum of bioactivities. This work’s goal was to synthesize a new hybrid amidino pyrazoline from terpenyl chalcone. The chosen method consists of making the terpenyl chalcone react with aminoguanidine hydrochloride in the presence of potassium hydroxide using ethanol as solvent. The reaction was carried out under ultrasonic irradiation. The resulting terpenyl amidino pyrazoline was isolated after separation in a silica-gel chromatographic column in 86% of yield. The product structure was confirmed by the analysis of the high resolution mass, 1H and 13C-NMR spectra. The data was consistent with the expected structure. In summary, the method was efficient for the synthesis of a new hybrid terpenyl amidino pyrazolines under sonochemical conditions. Full article
(This article belongs to the Section Organic Synthesis)
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Graphical abstract

5 pages, 700 KiB  
Short Note
3,5-Bis[5-(thiazol-2-yl)thien-2-yl]-4H-1,2,6-thiadiazin-4-one
by Andreas S. Kalogirou and Panayiotis A. Koutentis
Molbank 2019, 2019(1), M1045; https://doi.org/10.3390/M1045 - 15 Jan 2019
Viewed by 2133
Abstract
Stille coupling of 3,5-bis(5-bromothien-2-yl)-4H-1,2,6-thiadiazin-4-one (10) with 2-(tri-n-butylstannyl)thiazole and Pd(Ph3P)2Cl2 in PhMe, at ca. 110 °C, for 2 h, gave 3,5-bis[5-(thiazol-2-yl)thien-2-yl]-4H-1,2,6-thiadiazin-4-one (9) in 81% yield. The latter is evaluated for its electronic properties. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Figure 1

2 pages, 125 KiB  
Editorial
Acknowledgement to Reviewers of Molbank in 2018
by Molbank Editorial Office
Molbank 2019, 2019(1), M1044; https://doi.org/10.3390/M1044 - 09 Jan 2019
Viewed by 1347
Abstract
Rigorous peer-review is the corner-stone of high-quality academic publishing[...] Full article
5 pages, 691 KiB  
Short Note
3-Chloro-5-(3-n-hexylthien-2-yl)-4H-1,2,6-thiadiazin-4-one
by Andreas S. Kalogirou and Panayiotis A. Koutentis
Molbank 2019, 2019(1), M1043; https://doi.org/10.3390/M1043 - 09 Jan 2019
Viewed by 2066
Abstract
Stille coupling of 5-chloro-4-oxo-4H-1,2,6-thiadiazin-3-yl trifluoromethanesulfonate (7) with tributyl(3-n-hexylthien-2-yl)stannane and Pd(Ph3P)2Cl2 in PhMe at ca. 20 °C, for 24 h gave 3-chloro-5-(3-n-hexylthien-2-yl)-4H-1,2,6-thiadiazin-4-one (9) with a 60% yield. [...] Read more.
Stille coupling of 5-chloro-4-oxo-4H-1,2,6-thiadiazin-3-yl trifluoromethanesulfonate (7) with tributyl(3-n-hexylthien-2-yl)stannane and Pd(Ph3P)2Cl2 in PhMe at ca. 20 °C, for 24 h gave 3-chloro-5-(3-n-hexylthien-2-yl)-4H-1,2,6-thiadiazin-4-one (9) with a 60% yield. The latter is a potentially useful building block for the synthesis of oligomeric and polymeric donors for organic photovoltaics. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Figure 1

6 pages, 995 KiB  
Communication
Effective Synthesis of a Novel Tetrahydrofuran Containing Triterpenoid: 5′(Z)-Benzylidene-tetrahydrofurano[3,2-b]lup-20(29)-en-28-oate
by Rinat Gubaidullin, Darya Nedopekina, Regina Evstifeeva and Yurij Prochukhan
Molbank 2019, 2019(1), M1042; https://doi.org/10.3390/M1042 - 28 Dec 2018
Viewed by 2165
Abstract
The title compound 5′(Z)-benzylidene-tetrahydrofurano[3,2-b]lup-20(29)-en-28-oate was synthesized with high chemo-, regio-, and stereoselectivity by 5-exo-dig cycloisomerization of methyl 2α-phenylpropynyl-3-oxolup-20(29)-en-28-oate with use of KN(SiMe3)2-DME. The novel betulinic acid derivative was fully characterized by conventional analytical methods and all proton [...] Read more.
The title compound 5′(Z)-benzylidene-tetrahydrofurano[3,2-b]lup-20(29)-en-28-oate was synthesized with high chemo-, regio-, and stereoselectivity by 5-exo-dig cycloisomerization of methyl 2α-phenylpropynyl-3-oxolup-20(29)-en-28-oate with use of KN(SiMe3)2-DME. The novel betulinic acid derivative was fully characterized by conventional analytical methods and all proton and carbon signals have been completely assigned by 2D-NMR experiments. Full article
(This article belongs to the Section Organic Synthesis)
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Graphical abstract

5 pages, 885 KiB  
Short Note
5-(6-Hydroxy-6-methyl-5-oxoheptan-2-yl)-2-methyl Phenyl Acetate
by Maya Damayanti Rahayu, Susi Kusumaningrum and Hayun Hayun
Molbank 2019, 2019(1), M1041; https://doi.org/10.3390/M1041 - 26 Dec 2018
Cited by 1 | Viewed by 2415
Abstract
We synthesized a novel compound, 5-(6-hydroxy-6-methyl-5-oxoheptan-2-yl)-2-methylphenyl acetate, in a good yield by oxidation of 1-O-acetyl-xanthorrizol using potassium permanganate in acidic condition. The structure was elucidated by Fourier Transform Infrared (FTIR), 1H-Nuclear Magnetic Resonance (NMR) and 13C-NMR, two-dimensional (2D)-HSQC, Distortionless [...] Read more.
We synthesized a novel compound, 5-(6-hydroxy-6-methyl-5-oxoheptan-2-yl)-2-methylphenyl acetate, in a good yield by oxidation of 1-O-acetyl-xanthorrizol using potassium permanganate in acidic condition. The structure was elucidated by Fourier Transform Infrared (FTIR), 1H-Nuclear Magnetic Resonance (NMR) and 13C-NMR, two-dimensional (2D)-HSQC, Distortionless Enhancement by Polarization Transfer (DEPT), 2D-Heteronuclear Multiple Bond Correlation (HMBC), and High-Resolution Mass Spectra (HRMS) spectral data. Full article
(This article belongs to the Section Organic Synthesis)
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4 pages, 415 KiB  
Short Note
2′-Chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine
by Dhafer Saber Zinad, Dunya L. AL-Duhaidahaw and Ahmed Al-Amiery
Molbank 2019, 2019(1), M1040; https://doi.org/10.3390/M1040 - 22 Dec 2018
Cited by 2 | Viewed by 1925
Abstract
The compound 2′-chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine was obtained with a good yield by the reaction of 2-chloro-4-(1-methyl-1H-imidazol-2-yl)pyridine with (2-chloropyridin-4-yl)boronic acid and structurally characterized by nuclear magnetic resonance (1H-NMR and 13C-NMR), thin-layer chromatography–mass spectrometry (TLC–MS), HPLC, gas chromatography–mass spectrometry (GC–MS), [...] Read more.
The compound 2′-chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine was obtained with a good yield by the reaction of 2-chloro-4-(1-methyl-1H-imidazol-2-yl)pyridine with (2-chloropyridin-4-yl)boronic acid and structurally characterized by nuclear magnetic resonance (1H-NMR and 13C-NMR), thin-layer chromatography–mass spectrometry (TLC–MS), HPLC, gas chromatography–mass spectrometry (GC–MS), and elemental analysis. The functionalization of the pyridine was achieved by the palladium-catalyzed Suzuki–Miyaura carbon–carbon cross-coupling reaction that afforded the target compound. Full article
(This article belongs to the Special Issue Metal-Catalyzed Synthesis)
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Scheme 1

8 pages, 835 KiB  
Communication
Synthesis of Imine Congeners of Resveratrol and Evaluation of Their Anti-Platelet Activity
by Mohammad Bigdeli, Maryam Sabbaghan, Marjan Esfahanizadeh, Farzad Kobarfard, Sara Vitalini, Marcello Iriti and Javad Sharifi-Rad
Molbank 2019, 2019(1), M1039; https://doi.org/10.3390/M1039 - 22 Dec 2018
Cited by 6 | Viewed by 2421
Abstract
Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a cardioprotective phytochemical occurring in many plant products. In this study, a new series of imine congeners of resveratrol has been synthesized in which the imine moiety replaced the double bond in the structure of resveratrol. In addition, [...] Read more.
Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a cardioprotective phytochemical occurring in many plant products. In this study, a new series of imine congeners of resveratrol has been synthesized in which the imine moiety replaced the double bond in the structure of resveratrol. In addition, the in vitro antiplatelet activity of these resveratrol derivatives has been evaluated against adenosine diphosphate (ADP), arachidonic acid (AA), and collagen as platelet aggregation inducers. In general, the synthesized compounds were active as antiplatelet agents, and, therefore, the imine functional group may be considered as an effective replacement for a double bond in resveratrol for developing new and promising antiplatelet drugs. Full article
(This article belongs to the Section Natural Products)
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Figure 1

5 pages, 378 KiB  
Short Note
5-Chloro-8-{[1-(2-chlorobenzyl)-1H-1,2,3-triazol-4-yl]methoxy}quinoline
by Luz Karime Luna Parada and Vladimir V. Kouznetsov
Molbank 2019, 2019(1), M1038; https://doi.org/10.3390/M1038 - 20 Dec 2018
Cited by 4 | Viewed by 2757
Abstract
The title quinoline derivative, 5-chloro-8-{[1-(2-chlorobenzyl)-1H-1,2,3-triazol-4-yl]methoxy}quinoline, was synthesized in a common three-step procedure from 5-chloro-8-hydroxyquinoline using O-propargylation reaction/copper-catalyzed 1,3-dipolar cycloaddition sequence. The structure of the compound was fully characterized by FT-IR, 1H- and 13C-NMR, GC-MS, and elemental analysis. Its [...] Read more.
The title quinoline derivative, 5-chloro-8-{[1-(2-chlorobenzyl)-1H-1,2,3-triazol-4-yl]methoxy}quinoline, was synthesized in a common three-step procedure from 5-chloro-8-hydroxyquinoline using O-propargylation reaction/copper-catalyzed 1,3-dipolar cycloaddition sequence. The structure of the compound was fully characterized by FT-IR, 1H- and 13C-NMR, GC-MS, and elemental analysis. Its physicochemical parameters (Lipinski’s descriptors) were also calculated using the Molinspiration Cheminformatics software. The hybrid obtained could be an interesting model for antifungal bio-essays or a suitable precursor in the synthesis of more complex triazolyl-quinoline hybrids, potential pharmacological agents. Full article
(This article belongs to the Special Issue Metal-Catalyzed Synthesis)
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