Molbank

5 pages, 561 KB

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^*

Department of Chemistry, Faculty of Science and Technology, Airlangga University, Surabaya 60115, Indonesia

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

Viewed by 2374

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

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Graphical abstract

5 pages, 1685 KB

Open AccessShort Note

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

by R. Alan Aitken^*

, Alexandra M. Z. Slawin

and Pei-pei Yeh

EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews Fife KY16 9ST, UK

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

Cited by 3 | Viewed by 2544

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

(This article belongs to the Section Structure Determination)

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Graphical abstract

7 pages, 801 KB

Open AccessShort Note

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

by See Mun Lee

, Ainnul Hamidah Syahadah Azizan and Edward R. T. Tiekink^*

Research Centre for Crystalline Materials, School of Science and Technology, Sunway University, Bandar Sunway 47500, Malaysia

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

Cited by 3 | Viewed by 3353

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

(This article belongs to the Section Structure Determination)

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Figure 1

5 pages, 1694 KB

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 Alotaibi¹

, Hanan A. Mohamed^2,3, Bakr F. Abdel-Wahab^2,3

, Amany S. Hegazy⁴, Benson M. Kariuki^4,* and Gamal A. El-Hiti^5,*

¹ National Center for Petrochemicals Technology, King Abdulaziz City for Science and Technology, P.O. Box 6086, Riyadh 11442, Saudi Arabia

² Department of Chemistry, College of Science and Humanities, Shaqra University, P.O. Box 33, Duwadimi 11911, Saudi Arabia

³ Applied Organic Chemistry Department, National Research Centre, Dokki, Giza 12622, Egypt

⁴ School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK

⁵ Department of Optometry, College of Applied Medical Sciences, King Saud University, P.O. Box 10219, Riyadh 11433, Saudi Arabia

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

Cited by 3 | Viewed by 2726

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

(This article belongs to the Section Structure Determination)

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Graphical abstract

6 pages, 840 KB

Open AccessCommunication

Ureido Derivatives of Neoabietic Acid

by Xinyu Gao^1,2, Niping Feng¹, Yuhan Zi¹, Jianguo Cao^1,* and Guozheng Huang^1,3,*

¹ College of Life and Environmental Sciences, Shanghai Normal University, Shanghai 201418, China

² College of Mathematics, Physics and Information Engineering, Zhejiang Normal University, Jinhua 321004, China

³ Key Laboratory of Plant Resources and Chemistry of Arid Zone, State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China

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

Viewed by 3200

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

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Graphical abstract

4 pages, 704 KB

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

Institut UTINAM UMR CNRS 6213, UFR Sciences et Techniques, Université de Bourgogne-Franche-Comté, 16 Route de Gray, 25030 Besançon cedex, France

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

Cited by 8 | Viewed by 3151

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

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Graphical abstract

4 pages, 279 KB

Open AccessShort Note

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

by Stanimir Manolov¹

, Iliyan Ivanov^1,2,*

and Yulian Voynikov³

¹ Department of Organic Chemistry, Faculty of Chemistry, University of Plovdiv, 24 Tzar Assen str., 4000 Plovdiv, Bulgaria

² Department of Natural-Mathematical and Business Sciences, University of Plovdiv, Branch Smolyan, 32 “Dicho Petrov” Str., 4700 Smolyan, Bulgaria

³ Faculty of Pharmacy, Medical University of Sofia, 2 Dunav Str., 1000 Sofia, Bulgaria

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

Cited by 2 | Viewed by 3604

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

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Graphical abstract

4 pages, 380 KB

Open AccessShort Note

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

by Dhafer S. Zinad^1,*

, Dunya L. AL-Duhaidahaw², Ahmed Al-Amiery^3,*

and Abdul Amir H. Kadhum⁴

¹ Applied Science Department, University of Technology, Baghdad 10001, Iraq

² Pharmaceutical Chemistry Department, College of Pharmacy, University of Kufa, AL-Najaf 31001, Iraq

³ Energy and Renewable Energies Technology Center, University of Technology, Baghdad 10001, Iraq

⁴ Department of Chemical & Process Engineering, Faculty of Engineering & Built Environment, Universiti Kebangsaan Malaysia, Bangi, Selangor 43600, Malaysia

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

Cited by 2 | Viewed by 2676

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

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Scheme 1

4 pages, 348 KB

Open AccessShort Note

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

by Itamar Luís Gonçalves¹

, Luciano Porto Kagami¹

, Gustavo Machado das Neves¹

, Liliana Rockenbach¹, Leonardo Davi¹, Alceu Felipe Soares¹, Solange Cristina Garcia² and Vera Lucia Eifler-Lima^1,*

¹ Laboratório de Síntese Orgânica Medicinal/LaSOM, Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul/UFRGS, Av. Ipiranga 2752, Porto Alegre-RS 90610-000, Brazil

² Laboratório de Toxicologia / LATOX. Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul/UFRGS, Av. Ipiranga 2752, Porto Alegre-RS 90610-000, Brazil

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

Cited by 1 | Viewed by 3752

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

(This article belongs to the Special Issue Molecules from Multicomponent Reactions)

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Graphical abstract

6 pages, 829 KB

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^*

Research Centre for Crystalline Materials, School of Science and Technology, Sunway University, No. 5 Jalan Universiti, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia

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

Viewed by 2407

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

(This article belongs to the Section Structure Determination)

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Graphical abstract

5 pages, 478 KB

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

Department of Chemistry, Faculty of Science and Technology, Airlangga University, Surabaya 60115, Indonesia

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

Cited by 9 | Viewed by 3449

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

(This article belongs to the Collection Molecules from Catalytic Processes)

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Figure 1

3 pages, 586 KB

Open AccessFeature PaperShort Note

2,3,4-Trioxo-1-(1H-pyrrolo[2,3-b]pyridin-7-ium-7yl)-cyclobutan-1-ide

by Duc Hoàng Lande, Conrad Kunick

and Johann Grünefeld^*

Institut für Medizinische und Pharmazeutische Chemie, Technische Universität Braunschweig, Beethovenstraße 55, 38106 Braunschweig, Germany

Molbank 2018, 2018(4), M1026; https://doi.org/10.3390/M1026 - 12 Oct 2018

Cited by 1 | Viewed by 2545

Abstract

2,3,4-Trioxo-1-(1H-pyrrolo[2,3-b]pyridin-7-ium-7-yl)-cyclobutan-1-ide was obtained by reaction of squaric acid with 7-azaindole in acetic anhydride. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Scheme 1

7 pages, 1207 KB

Open AccessShort Note

Dichlorido(η⁶-p-cymene)[tris(2-cyanoethyl)phosphine]ruthenium(II)

by William Henderson^1,*

, Ashwin Gopalan Nair¹, Nathan R. Halcovich²

and Edward R. T. Tiekink^3,*

¹ Chemistry, School of Science, University of Waikato, Private Bag 3105, Hamilton 3240, New Zealand

² Department of Chemistry, Lancaster University, Lancaster LA1 4YB, UK

³ Research Centre for Crystalline Materials, School of Science and Technology, Sunway University, No. 5 Jalan Universiti, Bandar Sunway 47500, Selangor Darul Ehsan, Malaysia

Molbank 2018, 2018(4), M1025; https://doi.org/10.3390/M1025 - 12 Oct 2018

Cited by 3 | Viewed by 3797

Abstract

The tris(2-cyanoethyl)phosphine (tcep) complex [RuCl₂{P(CH₂CH₂CN)₃}(η⁶-p-cymene)] (p-cymene = p-CH₃C₆H₄ⁱPr) was synthesised by the bridge-splitting reaction of the chlorido-dimer [RuCl₂( [...] Read more.

The tris(2-cyanoethyl)phosphine (tcep) complex [RuCl₂{P(CH₂CH₂CN)₃}(η⁶-p-cymene)] (p-cymene = p-CH₃C₆H₄ⁱPr) was synthesised by the bridge-splitting reaction of the chlorido-dimer [RuCl₂(η⁶-p-cymene)]₂ with tcep. The complex was characterised by a single-crystal X-ray structure determination as well as NMR spectroscopy, ESI mass spectrometry, and microelemental analysis. X-ray crystallography shows the ruthenium atom is coordinated by p-cymene in a η⁶-fashion, two chlorides and the phosphorus atom of the tcep ligand with the donor set defining a distorted octahedral geometry. The ESI mass spectrometry study reveals that the complex readily forms negative ions [M + Cl]⁻ and [2M + Cl]⁻ by association with a chloride ion. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

7 pages, 3381 KB

Open AccessCommunication

Purine-Furan and Purine-Thiophene Conjugates

by Zigfrīds Kapilinskis, Irina Novosjolova^*

and Māris Turks

Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, Latvia

Molbank 2018, 2018(4), M1024; https://doi.org/10.3390/M1024 - 8 Oct 2018

Cited by 2 | Viewed by 3240

Abstract

Furyl and thienyl moieties were introduced into a purine structure to elevate its fluorescence properties, while a trityl group was used to increase the amorphous properties of the purine compounds. The title compounds were prepared by a sequence involving a Mitsunobu, a S [...] Read more.

Furyl and thienyl moieties were introduced into a purine structure to elevate its fluorescence properties, while a trityl group was used to increase the amorphous properties of the purine compounds. The title compounds were prepared by a sequence involving a Mitsunobu, a S_NAr and a Suzuki–Miyaura reaction and their photophysical properties were studied. Quantum yields in the solution reached up to 88% but only up to 5% in the thin layer. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Graphical abstract

6 pages, 576 KB

Open AccessCommunication

1-Methyl-3-{4-[(4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl)benzyl]}-2-phenylindole

by Jean Guillon^1,*

, Solène Savrimoutou¹, Sandra Rubio¹ and Vanessa Desplat²

¹ Laboratoire ARNA, INSERM U1212 / UMR CNRS 5320, UFR des Sciences Pharmaceutiques, Univ. Bordeaux, 146 rue Léo Saignat, CEDEX, F-33076 Bordeaux, France

² Cellules souches hématopoïétiques normales et leucémiques, INSERM U1035, UFR des Sciences Pharmaceutiques, Univ. Bordeaux, CEDEX, F-33076 Bordeaux, France

Molbank 2018, 2018(4), M1023; https://doi.org/10.3390/M1023 - 4 Oct 2018

Cited by 4 | Viewed by 3059

Abstract

The 1-methyl-3-{4-[(4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl)benzyl]}-2-phenylindole compound has been successfully synthesized via a multistep pathway starting from 2-phenylindole. Structure characterization of this new indole derivative was done by FTIR, ¹H-NMR, ¹³C-NMR, and HRMS spectral analysis. The title compound showed high cytotoxic potential against [...] Read more.

The 1-methyl-3-{4-[(4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl)benzyl]}-2-phenylindole compound has been successfully synthesized via a multistep pathway starting from 2-phenylindole. Structure characterization of this new indole derivative was done by FTIR, ¹H-NMR, ¹³C-NMR, and HRMS spectral analysis. The title compound showed high cytotoxic potential against five leukemia cell lines (K562, HL60, U937, U266, and Jurkat cell lines). Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Graphical abstract

7 pages, 3190 KB

Open AccessCommunication

Synthesis of 4-(2H-[1,2,4]-Triazol-5-ylsulfanyl)-1,2-dihydropyrazol-3-one via Ring-Switching Hydrazinolysis of 5-Ethoxymethylidenethiazolo [3,2-b][1,2,4]triazol-6-one

by Serhii Holota^1,2

, Yaroslav Shylych¹, Halyna Derkach³, Olexandr Karpenko⁴, Andrzej Gzella⁵ and Roman Lesyk^1,*

¹ Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, Ukraine

² Department of Organic Chemistry and Pharmacy, Lesya Ukrainka Eastern European National University, Volya Avenue 13, 43025 Lutsk, Ukraine

³ Department of Chemistry, Ivano-Frankivsk National Medical University, Halytska 2, 76018 Ivano-Frankivsk, Ukraine

⁴ Enamine Ltd., 23 Alexandra Matrosova, 01103 Kyiv, Ukraine

⁵ Department of Organic Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznan, Poland

Molbank 2018, 2018(4), M1022; https://doi.org/10.3390/M1022 - 1 Oct 2018

Cited by 7 | Viewed by 3714

Abstract

4-(1H-[1,2,4]-Triazol-5-ylsulfanyl)-1,2-dihydropyrazol-3-one (4) was synthesized with a yield of 55% via ring-switching hydrazinolysis of 5-ethoxymethylidenethiazolo[3,2-b][1,2,4] triazol-6-one (3) in ethanol medium. The initial 1H-[1,2,4]-triazole-3-thiol (1) was modified via a two-step reaction: S-alkylation [...] Read more.

4-(1H-[1,2,4]-Triazol-5-ylsulfanyl)-1,2-dihydropyrazol-3-one (4) was synthesized with a yield of 55% via ring-switching hydrazinolysis of 5-ethoxymethylidenethiazolo[3,2-b][1,2,4] triazol-6-one (3) in ethanol medium. The initial 1H-[1,2,4]-triazole-3-thiol (1) was modified via a two-step reaction: S-alkylation with chloroacetic acid under Williamson reaction conditions, and further one-pot cyclization–condensation with triethylorthoformate in the acetic anhydride medium, yielding compound 3. The structures of compounds 3 and 4 were confirmed by LC-MS, NMR spectra and a single X-ray diffraction analysis (for compound 4). Full article

(This article belongs to the Section Structure Determination)

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Figure 1

3 pages, 371 KB

Open AccessShort Note

6-[1-Acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-3-yl]-2(3H)-benzoxazolone

by Yordanka Ivanova^1,*, Antonya Todorova¹, Christo Chanev² and Ognyan Petrov²

¹ Department of Plant Pathology and Chemistry, Faculty of Ecology and Landscape Architecture, University of Forestry, 10 Kliment Ohridsky Blvd., 1756 Sofia, Bulgaria

² Department of Pharmaceutical and Applied Organic Chemistry, Faculty of Chemistry and Pharmacy, Sofia University St. Kliment Ohridski, 1 James Bourchier Blvd., 1164 Sofia, Bulgaria

Molbank 2018, 2018(4), M1021; https://doi.org/10.3390/M1021 - 30 Sep 2018

Viewed by 2533

Abstract

The title compound, 6-[1-acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]-2(3H)-benzoxazolone, was synthesized by condensation of 6-[3-(4-methoxyphenyl)-2-propenoyl]-2(3H)-benzoxazolone (1) and hydrazine hydrate in acetic acid in 84% yield. The structure of the target compound was confirmed using ¹H-NMR, ¹³C-NMR, IR, MS, and elemental analysis. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Scheme 1

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Molbank, Volume 2018, Issue 4 (December 2018) – 17 articles

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