Molbank

Open AccessFeature PaperShort 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 January 2019

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

Open AccessFeature PaperShort 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 - 9 January 2019

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

Open AccessEditorial

Acknowledgement to Reviewers of Molbankin 2018

by Molbank Editorial Office

Molbank 2019, 2019(1), M1044; https://doi.org/10.3390/M1044 - 9 January 2019

Abstract

Rigorous peer-review is the corner-stone of high-quality academic publishing[...] Full article

Open AccessCommunication

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 December 2018

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

► Figures

Graphical abstract

Open AccessShort 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 December 2018

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

Open AccessCommunication

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 December 2018

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

Open AccessShort 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 December 2018

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

Open AccessShort 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 December 2018

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

► Figures

Graphical abstract

Open AccessShort Note

5-(4-Bromophenyl)-7-(2,4-dimethoxyphenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine

by Kautsar Ul Haq, Mareta Dewi Liawati, Abdulloh Abdulloh and Hery Suwito

Molbank 2018, 2018(4), M1037; https://doi.org/10.3390/M1037 - 17 December 2018

Abstract

A derivative of dihydrotetrazolopyrimidine has been successfully synthesized through a cyclocondensation reaction between a chalcone derivative with 5-aminotetrazole. The molecular structure of the title compound was established based on Fourier transform infrared spectra (FTIR), high-resolution mass spectrometry (HRMS), 1D and 2D nuclear magnetic [...] Read more.

A derivative of dihydrotetrazolopyrimidine has been successfully synthesized through a cyclocondensation reaction between a chalcone derivative with 5-aminotetrazole. The molecular structure of the title compound was established based on Fourier transform infrared spectra (FTIR), high-resolution mass spectrometry (HRMS), 1D and 2D nuclear magnetic resonance (NMR) spectrum. Full article

► Figures

Graphical abstract

Open AccessShort Note

Tetrahydro-1,4-thiazine-3,5-dione

by R. Alan Aitken, Alexandra M. Z. Slawin and Pei-pei Yeh

Molbank 2018, 2018(4), M1036; https://doi.org/10.3390/M1036 - 13 December 2018

Abstract

The X-ray structure of the title compound contains eight molecules in the unit cell which form the basis of a herringbone arrangement of hydrogen bonded ribbons. Full article

► Figures

Graphical abstract

Open AccessShort Note

1-(2-Hydroxyethyl)imidazolidine-2-thione

by See Mun Lee, Ainnul Hamidah Syahadah Azizan and Edward R. T. Tiekink

Molbank 2018, 2018(4), M1035; https://doi.org/10.3390/M1035 - 3 December 2018

Abstract

1-(2-Hydroxyethyl)imidazolidine-2-thione (1) was obtained as a product from an in situ reaction between N-(2-hydroxyethyl)ethylenediamine, carbon disulfide, potassium hydroxide, and di(4-fluorobenzyl)tin dichloride. Compound 1 was characterized by IR, UV, ¹H, ¹³C{¹H}, and 2D (COSY, NOESY, HSQC, and [...] Read more.

1-(2-Hydroxyethyl)imidazolidine-2-thione (1) was obtained as a product from an in situ reaction between N-(2-hydroxyethyl)ethylenediamine, carbon disulfide, potassium hydroxide, and di(4-fluorobenzyl)tin dichloride. Compound 1 was characterized by IR, UV, ¹H, ¹³C{¹H}, and 2D (COSY, NOESY, HSQC, and HMBC) NMR spectroscopies. The cyclic molecular structure was confirmed by single crystal X-ray crystallography which showed the five-membered ring to be non-planar and the π-electron density to be localized over the CN₂S chromophore. In the crystal, thioamide–N–H^…O(hydroxy) and hydroxy–O–H^…S(thione) hydrogen bonds lead to supramolecular layers in the bc-plane. Full article

Open AccessShort Note

Synthesis and Structure Elucidation of N′-(4-Methoxybenzylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide

by Mohammad Hayal Alotaibi, Hanan A. Mohamed, Bakr F. Abdel-Wahab, Amany S. Hegazy, Benson M. Kariuki and Gamal A. El-Hiti

Molbank 2018, 2018(4), M1034; https://doi.org/10.3390/M1034 - 2 December 2018

Abstract

N′-(4-Methoxybenzylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide (3) was synthesized in a yield of 88% from an acid-catalyzed reaction of 5-methyl-1-phenyl-1H-1,2,3- triazole-4-carbohydrazide and 4-methoxybenzaldehyde in ethanol under reflux for 2.5 h. The structure of 3 was confirmed by the data obtained from [...] Read more.

N′-(4-Methoxybenzylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide (3) was synthesized in a yield of 88% from an acid-catalyzed reaction of 5-methyl-1-phenyl-1H-1,2,3- triazole-4-carbohydrazide and 4-methoxybenzaldehyde in ethanol under reflux for 2.5 h. The structure of 3 was confirmed by the data obtained from infrared, nuclear magnetic resonance, mass spectroscopy, single crystal X-ray diffraction, and microanalysis. Full article

► Figures

Graphical abstract

Open AccessCommunication

Ureido Derivatives of Neoabietic Acid

by Xinyu Gao, Niping Feng, Yuhan Zi, Jianguo Cao and Guozheng Huang

Molbank 2018, 2018(4), M1033; https://doi.org/10.3390/M1033 - 29 November 2018

Abstract

A series of ureido derivatives of neoabietic acid were synthesized by application of Curtius rearrangement reaction to neoabietic acid and amines. Structure characterization of these compounds was done by ¹H-NMR, ¹³C-NMR and HRMS spectral analysis. Full article

► Figures

Graphical abstract

Open AccessCommunication

4′-(5-Methylfuran-2-yl)-2,2′:6′,2″-terpyridine: A New Ligand Obtained from a Biomass-Derived Aldehyde with Potential Application in Metal-Catalyzed Reactions

by Jérôme Husson and Laurent Guyard

Molbank 2018, 2018(4), M1032; https://doi.org/10.3390/M1032 - 24 November 2018

Abstract

The new ligand 4′-(5-methylfuran-2-yl)-2,2′:6′,2″-terpyridine (1) was prepared in one step from 2-acetylpyridine and 5-methylfurfural. The latter is an aldehyde that can be readily obtained from biomass. The new terpyridine molecule was characterized by ¹H and ¹³C-NMR spectroscopy as well [...] Read more.

The new ligand 4′-(5-methylfuran-2-yl)-2,2′:6′,2″-terpyridine (1) was prepared in one step from 2-acetylpyridine and 5-methylfurfural. The latter is an aldehyde that can be readily obtained from biomass. The new terpyridine molecule was characterized by ¹H and ¹³C-NMR spectroscopy as well as by elemental analyses and HR-MS. Owing to its chelating properties, this new terpyridine molecule was tested as a ligand in a metal-catalyzed reaction: The Ni-catalyzed dimerization of benzyl bromide. Full article

► Figures

Graphical abstract

Open AccessShort Note

N-[2-(1H-Indol-3-yl)ethyl]-2-(4-isobutylphenyl)propanamide

by Stanimir Manolov, Iliyan Ivanov and Yulian Voynikov

Molbank 2018, 2018(4), M1031; https://doi.org/10.3390/M1031 - 22 November 2018

Abstract

The compound in the title was prepared by reaction between tryptamine and ibuprofen using N,N′-dicyclohexylcarbodiimide as a “dehydrating” reagent. The structure of the newly synthesized compound was determined by nuclear magnetic resonance (NMR) (¹H-NMR and ¹³C-NMR), UV, IR, and mass spectral data. Full article

► Figures

Graphical abstract

Open AccessShort Note

N-[4-(1-Methyl-1H-imidazol-2-yl)-2,4′-bipyridin-2′-yl]benzene-1,4-diamine

by Dhafer S. Zinad, Dunya L. AL-Duhaidahaw, Ahmed Al-Amiery and Abdul Amir H. Kadhum

Molbank 2018, 2018(4), M1030; https://doi.org/10.3390/M1030 - 16 November 2018

Abstract

N-[4-(1-Methyl-1H-imidazol-2-yl)-2,4′-bipyridin-2′-yl]benzene-1,4-diamine was synthesized with a good yield by the reaction of 2′-chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine with 4-phenylenediamine. The functionalization of the pyridine was accomplished by a nucleophilic aromatic substitution (SNAr) reaction that afforded the target compound. The synthesized compound was characterized [...] Read more.

N-[4-(1-Methyl-1H-imidazol-2-yl)-2,4′-bipyridin-2′-yl]benzene-1,4-diamine was synthesized with a good yield by the reaction of 2′-chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine with 4-phenylenediamine. The functionalization of the pyridine was accomplished by a nucleophilic aromatic substitution (SNAr) reaction that afforded the target compound. The synthesized compound was characterized by chemical analysis, which includes nuclear magnetic resonance (NMR) (¹H-NMR and ¹³C-NMR), Thin Layer Chromatography-Mass Spectrometry (TLC-MS), high- performance liquid chromatography (HPLC), Gas Chromatography-Mass Spectrometry (GC-MS), and elemental analysis. Full article

Open AccessShort Note

Ethyl 4-(2-fluorophenyl)-6-methyl-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate

by Itamar Luís Gonçalves, Luciano Porto Kagami, Gustavo Machado das Neves, Liliana Rockenbach, Leonardo Davi, Alceu Felipe Soares, Solange Cristina Garcia and Vera Lucia Eifler-Lima

Molbank 2018, 2018(4), M1029; https://doi.org/10.3390/M1029 - 13 November 2018

Abstract

The Biginelli reaction is a highly versatile reaction that leads to dihydropyrimidinones/thiones. This scaffold is reported as being a privileged structure due to its ability to interact with biological targets. Synthesis of ethyl 4-(2-fluorophenyl)-6-methyl-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate was achieved through the Biginelli reaction using [...] Read more.

The Biginelli reaction is a highly versatile reaction that leads to dihydropyrimidinones/thiones. This scaffold is reported as being a privileged structure due to its ability to interact with biological targets. Synthesis of ethyl 4-(2-fluorophenyl)-6-methyl-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate was achieved through the Biginelli reaction using a functionalized thiourea. In silico studies demonstrated that the compound title showed good potential for interacting with ecto-5’-nucleotidase, which has been considered as a target in designs for anti-cancer drugs. Full article

► Figures

Graphical abstract

Open AccessShort Note

[O-Isopropyl-N-(4-nitrophenyl)thiocarbamato-κS]-(tri-4-tolylphosphine-κP)gold(I)

by Chien Ing Yeo and Edward R. T. Tiekink

Molbank 2018, 2018(4), M1028; https://doi.org/10.3390/M1028 - 5 November 2018

Abstract

The synthesis, spectroscopic characterization and X-ray crystal structure of the title compound, (4-tolyl)₃PAu[SC(O-i-Pr)=NC₆H₄NO₂-4] (1) are described. Spectroscopy exhibited the expected features confirming the formation of the compound. The molecular structure of [...] Read more.

The synthesis, spectroscopic characterization and X-ray crystal structure of the title compound, (4-tolyl)₃PAu[SC(O-i-Pr)=NC₆H₄NO₂-4] (1) are described. Spectroscopy exhibited the expected features confirming the formation of the compound. The molecular structure of 1 confirms the expected linear P–Au–S coordination geometry defined by thiolate-S and phosphane-P atoms. The nearly 7° deviation from linearity is ascribed to the close approach of the imine-bound phenyl group, indicative of a semi-localized Au^…π(arene) interaction. The three-dimensional molecular packing is consolidated by methyl- and tolyl-C–H^…O(nitro) and tolyl-C–H^…π(tolyl) interactions. Full article

► Figures

Graphical abstract

Open AccessShort Note

(E)-3-[3-(4-Morpholinophenyl)acryloyl]-2H-chromen-2-one

by Hery Suwito, Helda Dwi Hardiyanti, Kautsar Ul Haq, Alfinda Novi Kristanti and Miratul Khasanah

Molbank 2018, 2018(4), M1027; https://doi.org/10.3390/M1027 - 29 October 2018

Abstract

A new compound (E)-3-[3-(4-morpholinophenyl)acryloyl]-2H-chromen-2-one, a coumarin based chalcone derivative, has been successfully synthesized employing a molecular hybridization method through the reaction between 3-acetylcoumarin and 4-morpholinobenzaldehyde using a Claisen–Schmidt reaction using pTSA as a catalyst. The structure of the [...] Read more.

A new compound (E)-3-[3-(4-morpholinophenyl)acryloyl]-2H-chromen-2-one, a coumarin based chalcone derivative, has been successfully synthesized employing a molecular hybridization method through the reaction between 3-acetylcoumarin and 4-morpholinobenzaldehyde using a Claisen–Schmidt reaction using pTSA as a catalyst. The structure of the title compound was established using spectroscopic data FTIR, HRESI-MS, ¹H- and ¹³C-NMR. The anticancer activity against breast cancer cells line T47D and cervix cancer cells line HeLa was determined using an MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Full article

Journal Menu

E-Mail Alert

Journal Browser

Highly Accessed

Latest Books

Molbank — Open Access Journal

Latest Articles

News

Conferences

Special Issues

Jobs in Research