Molbank

Open AccessShort Note

Dichloro[N-[(η⁶-phenyl)methyl]-4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8tetrahydronaphthalen-2-yl)vinyl)benzamide](1,3,5-triaza-7-phosphatricyclo [3.3.1.1^3,7]decane-κP⁷)ruthenium

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Molbank 2022, 2022(4), M1506; https://doi.org/10.3390/M1506 (registering DOI) - 25 Nov 2022

Abstract

Bexarotene-tethered RuII(arene) compounds with 1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane (PTA) were prepared as an analog of RAPTA antitumor complexes in order to evaluate their in vitro antiproliferative activity against human cancer cell lines. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessCommunication

Synthesis of 6-Methyluracilpentylviologen Resorcinarene Cavitand

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Vyacheslav E. Semenov

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Igor S. Antipin

Molbank 2022, 2022(4), M1507; https://doi.org/10.3390/M1507 (registering DOI) - 25 Nov 2022

Abstract

Resorcinarenes, as macrocyclic compounds, are widely used to recognize substrates and create supramolecular assemblies. Their bowl-like form organizes functional groups at the upper and lower rims, which has a substantial impact on the molecular recognition of various substrates. As a result, resorcinarenes make [...] Read more.

Resorcinarenes, as macrocyclic compounds, are widely used to recognize substrates and create supramolecular assemblies. Their bowl-like form organizes functional groups at the upper and lower rims, which has a substantial impact on the molecular recognition of various substrates. As a result, resorcinarenes make good drug nanocarrier candidates. This paper presents the synthesis of a new resorcinarene cavitand functionalized along the upper rim with methyluracil and viologen fragments for its potential use in drug delivery. Methyluracils and viologens are well-known receptor-targeted compounds capable of facilitating the vector transfer of drugs and increasing the effectiveness of their action on cells. The paper describes the synthesis of resorcinarene modified with methyluracil and viologen groups along with its structure determined by ¹H-, ¹³C-NMR and IR spectroscopy. Full article

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Scheme 1

Open AccessCommunication

Diverse Hydrogen-Bonded Structural Motifs in 1,4-Diazabicyclo[2.2.2]octane N,N’-Dioxide Salts with Oxoanions

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Ksenia D. Abasheeva

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Pavel A. Demakov

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Vladimir P. Fedin

Molbank 2022, 2022(4), M1508; https://doi.org/10.3390/M1508 (registering DOI) - 25 Nov 2022

Abstract

Four new hybrid inorganic–organic salts of 1,4-diazabicyclo[2.2.2]octane N,N’-dioxide (odabco) with the formulae odabco·2HNO₃ (1), odabco·HClO₄ (2), odabco·H₂SO₄ (3) and odabco·2H₂SO₄ (4) were synthesized and characterized by single-crystal [...] Read more.

Four new hybrid inorganic–organic salts of 1,4-diazabicyclo[2.2.2]octane N,N’-dioxide (odabco) with the formulae odabco·2HNO₃ (1), odabco·HClO₄ (2), odabco·H₂SO₄ (3) and odabco·2H₂SO₄ (4) were synthesized and characterized by single-crystal x-ray diffraction (XRD), powder XRD and infrared spectroscopy. Compound 1 is based on the isolated (H₂odabco)²⁺ fragments, representing 0D structure. 2 is based on cationic 1D {Hodabco}_nⁿ⁺ hydrogen-bonded chains. Compound 3 comprising a strongly coordinated sulfate anion consists of two-component hydrogen-bonded {-H₂odabco-SO₄₋} fragments forming uncharged 1D helical chains. 4 contains both {-HSO₄-}_n^n– and {-HSO₄-H₂odabco-HSO₄₋} hydrogen bonding motifs, resulting in a 3D polymeric network. A comparative structural analysis of both the obtained and the previously reported cognate structures was performed to rationalize the impact of the degree of odabco protonation and the anion donor ability on the structural features and dimensionalities of odabco-based hydrogen-bonded lattices. Full article

(This article belongs to the Section Structure Determination)

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Open AccessShort Note

(E)-3-(2-(4-methylthiazol-2-yl)hydrazineylidene)chromane-2,4-dione

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Fatlinda Rahmani

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Aurélien Crochet

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Fabio Zobi

Molbank 2022, 2022(4), M1504; https://doi.org/10.3390/M1504 - 24 Nov 2022

Abstract

(E)-3-(2-(4-methylthiazol-2-yl)hydrazineylidene)chromane-2,4-dione was synthesized for the first time and the compound was characterized by ¹H and ¹³C spectroscopy, IR spectroscopy, and UV-Vis. The chemical structure and isomeric configuration of the molecule were confirmed by single-crystal X-ray diffraction. Full article

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Open AccessShort Note

2-Benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

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Ivette Morales-Salazar

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Mónica A. Rincón-Guevara

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Eduardo González-Zamora

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Alejandro Islas-Jácome

Molbank 2022, 2022(4), M1503; https://doi.org/10.3390/M1503 - 23 Nov 2022

Abstract

The new polyheterocyclic compound 2-benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (1) was synthesized via a one-pot process involving an Ugi-Zhu three-component reaction coupled to a cascade aza-Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration process, using toluene as the solvent, ytterbium (III) triflate as the [...] Read more.

The new polyheterocyclic compound 2-benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (1) was synthesized via a one-pot process involving an Ugi-Zhu three-component reaction coupled to a cascade aza-Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration process, using toluene as the solvent, ytterbium (III) triflate as the Lewis acid catalyst, and microwave-dielectric heating to increase the overall yield by up to 73%, while decreasing the reaction time to less than one hour. Product 1 was fully characterized by its physicochemical properties and using spectroscopic techniques (IR, HRMS and NMR). Full article

(This article belongs to the Collection Heterocycle Reactions)

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Graphical abstract

Open AccessShort Note

N²,N⁶-Bis(6-iodo-2-methyl-4-oxoquinazolin-3(4H)-yl)pyridine-2,6-dicarboxamide

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Maja Molnar

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Mario Komar

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Igor Jerković

Molbank 2022, 2022(4), M1500; https://doi.org/10.3390/M1500 - 21 Nov 2022

Abstract

A green chemistry method was applied in the synthesis of N²,N⁶-bis(6-iodo-2-methyl-4-oxoquinazolin-3(4H)-yl)pyridine-2,6-dicarboxamide. The desired compound was synthesized mechanochemically, using a choline chloride-based deep eutectic solvent as a catalyst. The synthesis took 20 min and the new compound was characterized using different spectral methods. Full article

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Open AccessCommunication

N⁴-(2-Amino-4-fluorophenyl)-N¹-(3-{2-[2-(3-{[2-(2,6-dioxo-3-piperidyl)-1,3-dioxoisoindolin-4-yl]amino}propoxy)ethoxy]ethoxy}propyl)terephthalamide

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Molbank 2022, 2022(4), M1501; https://doi.org/10.3390/M1501 - 21 Nov 2022

Abstract

The design of proteolysis targeting chimeras (PROTACs) has become a promising technology for modifying a protein of interest (POI) through protein degradation. Herein, we describe the synthetic pathway to develop N⁴-(2-amino-4-fluorophenyl)-N¹-(3-{2-[2-(3-{[2-(2,6-dioxo-3-piperidyl)-1,3-dioxoisoindolin-4-yl]amino}propoxy)ethoxy]ethoxy}propyl)terephthalamide, which was designed to work as a [...] Read more.

The design of proteolysis targeting chimeras (PROTACs) has become a promising technology for modifying a protein of interest (POI) through protein degradation. Herein, we describe the synthetic pathway to develop N⁴-(2-amino-4-fluorophenyl)-N¹-(3-{2-[2-(3-{[2-(2,6-dioxo-3-piperidyl)-1,3-dioxoisoindolin-4-yl]amino}propoxy)ethoxy]ethoxy}propyl)terephthalamide, which was designed to work as a selective degrader of histone deacetylase-3 (HDAC3). The newly synthesized compounds were characterized by ¹H-NMR, ¹³C-NMR, IR and HRMS. The title compound was tested in vitro against human class-I HDACs isoforms and showed IC₅₀ = 3.4 µM against HDAC3; however, it did not show degradation for the targeted HDACs. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessShort Note

(η⁴-Tetraphenylcyclobutadiene)-(η⁵-pentaphenylcyclopentadienyl)-cobalt

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Christian Klein-Heßling

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Karlheinz Sünkel

Molbank 2022, 2022(4), M1502; https://doi.org/10.3390/M1502 - 21 Nov 2022

Abstract

A one-pot reaction starting with C₅Ph₅Br, n-BuLi and [CoCl(PPh₃)₃] followed by the addition of diphenylethyne produces the title compound with 12% yield. Spectroscopic characterization involved ¹H, ¹³C-NMR, UV-Vis and mass spectrometry. A [...] Read more.

A one-pot reaction starting with C₅Ph₅Br, n-BuLi and [CoCl(PPh₃)₃] followed by the addition of diphenylethyne produces the title compound with 12% yield. Spectroscopic characterization involved ¹H, ¹³C-NMR, UV-Vis and mass spectrometry. A crystal structure determination showed that the central aromatic rings are exactly parallel with the cyclobutadiene ring further apart from the metal as usual. The pentaphenyl–cyclopentadienyl ligand shows an usual paddlewheel orientation, whereas in the tetraphenyl–cyclobutadiene ligand, two of the phenyl groups are nearly coplanar with the four-membered ring. There are also numerous C–H…C(π) interactions between the phenyl groups on the same ring, as well as between rings. Full article

(This article belongs to the Section Structure Determination)

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Open AccessCommunication

Synthesis and Crystal Structures of Halogen-Substituted 2-Aryl-N-phenylbenzimidazoles

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Anastasia G. Koptyaeva

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Alexander Y. Zakharov

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Stanislav I. Bezzubov

Molbank 2022, 2022(4), M1498; https://doi.org/10.3390/M1498 - 18 Nov 2022

Abstract

Four 2-arylbenzimidazoles (aryl = 4-Br-phenyl (1), 3-Br-phenyl (2), 4-I-phenyl (3), 3-I-phenyl (4)) were synthesized and characterized by ¹H, ¹³C{¹H} NMR, UV–Vis spectroscopy and single-crystal X-ray diffraction. Both pairs of benzimidazoles bearing [...] Read more.

Four 2-arylbenzimidazoles (aryl = 4-Br-phenyl (1), 3-Br-phenyl (2), 4-I-phenyl (3), 3-I-phenyl (4)) were synthesized and characterized by ¹H, ¹³C{¹H} NMR, UV–Vis spectroscopy and single-crystal X-ray diffraction. Both pairs of benzimidazoles bearing the halogen atom at the same position form isostructural crystals, in which para-substituted compounds 1 and 3 are assembled by weak C–H···π and π···π interactions while their meta-isomers 2 and 4 are linked via intermolecular halogen···nitrogen and C–H···π contacts. Full article

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Open AccessShort Note

19β,28-Epoxy-18α-olean-3β-ol-2-furoate from Allobetulin (19β,28-Epoxy-18α-olean-3β-ol)

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Fulgentius Nelson Lugemwa

Molbank 2022, 2022(4), M1499; https://doi.org/10.3390/M1499 - 18 Nov 2022

Abstract

The E ring of betulin rearranges and forms a cyclic ether when treated with an acid. Treatment of betulin with iodine generated hydrogen iodide in situ, which went on to promote the rearrangement at C-19 and C-20, followed by cyclization to form allobetulin. [...] Read more.

The E ring of betulin rearranges and forms a cyclic ether when treated with an acid. Treatment of betulin with iodine generated hydrogen iodide in situ, which went on to promote the rearrangement at C-19 and C-20, followed by cyclization to form allobetulin. A reaction of allobetulin with 2-furoyl chloride yielded 19β,28-Epoxy-18α-olean-3β-ol-2-furoate. Full article

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

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Scheme 1

Open AccessShort Note

4,4′-(Butane-1,4-diyl)bis(4-methyl-1,2-dioxolane-3,5-dione)

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Vera A. Vil’

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Evgenii S. Gorlov

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Alexander O. Terent’ev

Molbank 2022, 2022(4), M1497; https://doi.org/10.3390/M1497 - 17 Nov 2022

Abstract

Over the past decades, studies of cyclic diacyl peroxides have shown superior or even fundamentally new reactivity compared to their acyclic counterparts in various reactions. Previously, the scope of cyclic diacyl peroxides was limited to the mono peroxy compounds. The first doubled cyclic [...] Read more.

Over the past decades, studies of cyclic diacyl peroxides have shown superior or even fundamentally new reactivity compared to their acyclic counterparts in various reactions. Previously, the scope of cyclic diacyl peroxides was limited to the mono peroxy compounds. The first doubled cyclic diacyl peroxide is presented herein. The diperoxide was characterized by NMR spectroscopy, mass spectrometry, and IR spectroscopy. The structure of 4,4′-(butane-1,4-diyl)bis(4-methyl-1,2-dioxolane-3,5-dione) was confirmed by X-ray diffraction analysis. The novel diperoxide was prepared in a 55% overall yield in three steps from dibromobutane and diethyl methylmalonate. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessShort Note

bis[N-(4-Bromophenyl)pyridine-2-carboxamidato]palladium

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Pinky N. Mjwara

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Tshephiso R. Papo

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Siphamandla Sithebe

Molbank 2022, 2022(4), M1496; https://doi.org/10.3390/M1496 - 17 Nov 2022

Abstract

We report the crystal structure of bis[N-(4-bromophenyl)pyridine-2-carboxamidato]Palladium (C1) which was isolated from the reaction of aqueous potassium tetrachloropalladate(II) and N-(4-bromophenyl)-pyridine-2-carboxamide in dichloromethane under nitrogen flow. The structure was characterised by the following spectroscopic methods ¹H NMR, FT-IR and X-ray diffraction. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

Open AccessShort Note

(1RS,2RS,6RS)-2-(6-Amino-9H-purin-9-yl)-8-azaspiro[5.6]dodec-10-en-1-ol Dihydrochloride

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Ildar R. Iusupov

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Konstantin A. Lyssenko

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Andrea Altieri

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Alexander V. Kurkin

Molbank 2022, 2022(4), M1495; https://doi.org/10.3390/M1495 - 15 Nov 2022

Abstract

The title compound (1RS,2RS,6RS)-2-(6-Amino-9H-purin-9-yl)-8-azaspiro[5.6]dodec-10-en-1-ol dihydrochloride was synthesized for the first time in two steps, the first of which was a regioselectivity of epoxide ring-opening reaction under the action of adenine, yielding N-tert-butoxycarbonyl-((1RS,2RS [...] Read more.

The title compound (1RS,2RS,6RS)-2-(6-Amino-9H-purin-9-yl)-8-azaspiro[5.6]dodec-10-en-1-ol dihydrochloride was synthesized for the first time in two steps, the first of which was a regioselectivity of epoxide ring-opening reaction under the action of adenine, yielding N-tert-butoxycarbonyl-((1RS,2RS,6RS)-2-(6-amino-9H-purin-9-yl)-8-azaspiro[5.6]dodec-10-en-1-ol. By treating the latter with a saturated methanolic solution of hydrogen chloride, it was possible to obtain ((1RS,2RS,6RS)-2-(6-Amino-9H-purin-9-yl)-8-azaspiro[5.6]dodec-10-en-1-ol dihydrochloride. The features of the molecular and crystal structure of ((1RS,2RS,6RS)-2-(6-Amino-9H-purin-9-yl)-8-azaspiro[5.6]dodec-10-en-1-ol dihydrochloride are discussed based on X-ray diffraction studies. The product overall yield was 40% out of two steps and after purification by column chromatography and recrystallization. The product was characterized by ¹H-NMR, ¹³C-NMR, IR spectroscopy, HRMS and X-ray. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

3-Morpholino-7-[N-methyl-N-(4′-carboxyphenyl)amino]phenothiazinium Chloride

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Molbank 2022, 2022(4), M1493; https://doi.org/10.3390/M1493 - 14 Nov 2022

Abstract

The synthesis of 3-morpholino-7-[N-methyl-N-(4′-carboxyphenyl)amino]phenothiazinium chloride is reported here. Interestingly, non-symmetric phenothiazinium salt is functionalized with a carboxylic acid group that allows the easy and stable anchoring on metal oxides. In addition, the morpholine unit reduces the dye aggregation tendency; [...] Read more.

The synthesis of 3-morpholino-7-[N-methyl-N-(4′-carboxyphenyl)amino]phenothiazinium chloride is reported here. Interestingly, non-symmetric phenothiazinium salt is functionalized with a carboxylic acid group that allows the easy and stable anchoring on metal oxides. In addition, the morpholine unit reduces the dye aggregation tendency; thus, improving its potential applications in the biomedical and photo-electrocatalytic field. Full article

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Open AccessShort Note

(S)-(1-Pyrrolidin-2-ylmethyl)quinuclidin-1-ium Bromide

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Molbank 2022, 2022(4), M1494; https://doi.org/10.3390/M1494 - 14 Nov 2022

Abstract

(S)-(1-Pyrrolidin-2-ylmethyl)quinuclidine-1-ium bromide was synthesized in a six-step reaction process starting from l-proline and spectroscopically and thermally characterized. Full article

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Graphical abstract

Open AccessShort Note

4-Methyl-7-((2-((5-methyl-1,3,4-thiadiazol-2-yl)thio)ethyl)thio)-coumarin

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Vanya Kurteva

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Rusi Rusew

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Boris Shivachev

Molbank 2022, 2022(4), M1491; https://doi.org/10.3390/M1491 - 12 Nov 2022

Abstract

The novel compound 4-methyl-7-((2-((5-methyl-1,3,4-thiadiazol-2-yl)thio)ethyl)thio)-coumarin is obtained in good yield via a two-step protocol; that is, initial synthesis of the reagent 2-((2-chloroethyl)thio)-5-methyl-1,3,4-thiadiazole followed by alkylation of 7-mercapto-4-methylcoumarin. The product’s structure is assigned by 1D and 2D NMR experiments and is confirmed by single-crystal XRD. [...] Read more.

The novel compound 4-methyl-7-((2-((5-methyl-1,3,4-thiadiazol-2-yl)thio)ethyl)thio)-coumarin is obtained in good yield via a two-step protocol; that is, initial synthesis of the reagent 2-((2-chloroethyl)thio)-5-methyl-1,3,4-thiadiazole followed by alkylation of 7-mercapto-4-methylcoumarin. The product’s structure is assigned by 1D and 2D NMR experiments and is confirmed by single-crystal XRD. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Open AccessShort Note

Methyl 5-(2-Fluoro-4-nitrophenyl)furan-2-carboxylate

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Molbank 2022, 2022(4), M1492; https://doi.org/10.3390/M1492 - 12 Nov 2022

Abstract

5-Phenyl-furan-2-carboxylic acids have emerged as a new, promising class of antimycobacterial agents that have the ability to interfere with iron homeostasis. Considering the lack of structural data on these compounds, we analyzed the crystal of a fluorinated ester derivative of 5-(4-nitrophenyl)furan-2-carboxylic acid, one [...] Read more.

5-Phenyl-furan-2-carboxylic acids have emerged as a new, promising class of antimycobacterial agents that have the ability to interfere with iron homeostasis. Considering the lack of structural data on these compounds, we analyzed the crystal of a fluorinated ester derivative of 5-(4-nitrophenyl)furan-2-carboxylic acid, one of the most potent candidates in the series. Here, we describe the preparation of methyl 5-(2-fluoro-4-nitrophenyl)furan-2-carboxylate (1) and its analysis by ¹H-NMR, ¹³C-NMR, HRMS, and SC-XRD. Full article

(This article belongs to the Section Structure Determination)

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Open AccessShort Note

2-((4-(2-Ethylhexyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)methylene)malononitrile

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Nikita S. Gudim

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Ekaterina A. Knyazeva

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Konstantin P. Trainov

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Oleg A. Rakitin

Molbank 2022, 2022(4), M1490; https://doi.org/10.3390/M1490 - 11 Nov 2022

Abstract

New small acceptor–donor (A–D) molecules have been recently investigated as a component of organic solar cells. In this research, 2-((4-(2-ethylhexyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)methylene)malononitrile was prepared from 4-(2-ethylhexyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole in a two-step process via Vilsmeier–Haack formylation [...] Read more.

New small acceptor–donor (A–D) molecules have been recently investigated as a component of organic solar cells. In this research, 2-((4-(2-ethylhexyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)methylene)malononitrile was prepared from 4-(2-ethylhexyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole in a two-step process via Vilsmeier–Haack formylation and Knoevenagel reaction with malononitrile. The structures of newly synthesized compounds were established by means of elemental analysis, high-resolution mass spectrometry, ¹H, ¹³C NMR, IR and UV–Vis spectroscopy, as well as mass spectrometry. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessShort Note

5-Chloro-6-oxo-6H-xantheno[4,3-d]thiazole-2-carbonitrile

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Konstantinos Paraskevas

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Christos Iliopoulos-Tsoutsouvas

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Eleftheria A. Georgiou

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Ioannis K. Kostakis

Molbank 2022, 2022(4), M1489; https://doi.org/10.3390/M1489 - 10 Nov 2022

Abstract

Xanthones and benzothiazoles are important classes of heterocyclic compounds with versatile biological activities. Herein, we describe a straightforward and scalable synthesis of 5-chloro-6-oxo-6H-xantheno[4,3-d]thiazole-2-carbonitrile, a thiazole-fused xanthone, via a six-step approach, using Appel’s salt for the synthesis of the thiazole [...] Read more.

Xanthones and benzothiazoles are important classes of heterocyclic compounds with versatile biological activities. Herein, we describe a straightforward and scalable synthesis of 5-chloro-6-oxo-6H-xantheno[4,3-d]thiazole-2-carbonitrile, a thiazole-fused xanthone, via a six-step approach, using Appel’s salt for the synthesis of the thiazole ring. The thiazole-fused xanthone was fully characterized employing ¹H and ¹³C NMR spectra, using direct and long-range heteronuclear correlation experiments (HMBC and HMQC). Full article

(This article belongs to the Collection Heterocycle Reactions)

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