Lorenzo Suigo, Valentina Straniero, Ermanno Valoti
In this work, we report the unexpected conversion of a pyridine derivative into the corresponding N-benzylated pyridinium salt due to the presence of unreacted benzyl bromide in the crude product. This transformation was observed at room temperature in a solvent-free environment and without any stirring. These interesting data show how pyridinium salts can be formed in mild conditions, avoiding high temperatures that could promote the degradation of the desired product.
{"title":"2-(1-Methoxycarbonyl-2-phenyleth-1-yl)-1-benzylpyridin-1-ium Bromide","authors":"Lorenzo Suigo, Valentina Straniero, Ermanno Valoti","doi":"10.3390/m1738","DOIUrl":"https://doi.org/10.3390/m1738","url":null,"abstract":"In this work, we report the unexpected conversion of a pyridine derivative into the corresponding N-benzylated pyridinium salt due to the presence of unreacted benzyl bromide in the crude product. This transformation was observed at room temperature in a solvent-free environment and without any stirring. These interesting data show how pyridinium salts can be formed in mild conditions, avoiding high temperatures that could promote the degradation of the desired product.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"4 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136113472","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
As part of our ongoing research into the antileishmanial properties of amidoxime derivatives, we report a preliminary assessment of the antiparasitic properties of a novel compound, diethyl (5-benzyl-2-(4-(N′-hydroxycarbamimidoyl)phenyl)-5-methyl-4,5-dihydrofuran-3-yl)phosphonate. This compound was evaluated in vitro for the first time against the promastigote form of Leishmania amazonensis. Compounds containing both amidoxime and phosphonyl functional groups in dihydrofuran scaffolds are relatively rare, despite the extensive study of this heterocycle in various biological applications. Therefore, this work makes a valuable contribution to the fight against Leishmania spp. as a neglected disease. The cyclized 4,5-dihydrofuran intermediate scaffold was obtained via a three-step synthetic route that had previously been developed for accessing other derivatives, including the sulfone moiety. This synthesis was performed using a manganese-based free radical oxidative method under microwave irradiation. The intermediary 4,5-dihydrofuran, which included a nitrile group, tolerated the subsequent reaction with hydroxylamine hydrochloride, resulting in the formation of the target product. The target compound showed moderate activity in vitro against the promastigote form of L. amazonensis (IC50 = 91.1 µM).
{"title":"Diethyl (5-Benzyl-2-(4-(N′-hydroxycarbamimidoyl)phenyl)-5-methyl-4,5-dihydrofuran-3-yl)phosphonate","authors":"Oscar Leonardo Avendaño Leon, Christophe Curti, Fabiana Maia Santos Urbancg Moncorvo, Youssef Kabri, Sébastien Redon, Eduardo Caio Torres-Santos, Romain Paoli-Lombardo, Patrice Vanelle","doi":"10.3390/m1736","DOIUrl":"https://doi.org/10.3390/m1736","url":null,"abstract":"As part of our ongoing research into the antileishmanial properties of amidoxime derivatives, we report a preliminary assessment of the antiparasitic properties of a novel compound, diethyl (5-benzyl-2-(4-(N′-hydroxycarbamimidoyl)phenyl)-5-methyl-4,5-dihydrofuran-3-yl)phosphonate. This compound was evaluated in vitro for the first time against the promastigote form of Leishmania amazonensis. Compounds containing both amidoxime and phosphonyl functional groups in dihydrofuran scaffolds are relatively rare, despite the extensive study of this heterocycle in various biological applications. Therefore, this work makes a valuable contribution to the fight against Leishmania spp. as a neglected disease. The cyclized 4,5-dihydrofuran intermediate scaffold was obtained via a three-step synthetic route that had previously been developed for accessing other derivatives, including the sulfone moiety. This synthesis was performed using a manganese-based free radical oxidative method under microwave irradiation. The intermediary 4,5-dihydrofuran, which included a nitrile group, tolerated the subsequent reaction with hydroxylamine hydrochloride, resulting in the formation of the target product. The target compound showed moderate activity in vitro against the promastigote form of L. amazonensis (IC50 = 91.1 µM).","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"42 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135857373","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Camille Blouet, Stéphanie Letast, Thomas Robert, Stéphane Bach, Noël Pinaud, Nicolas Joubert, Marie-Claude Viaud-Massuard, Jean Guillon, Cédric Logé, Caroline Denevault-Sabourin
Potassium 6-oxo-7,13,16,22-tetraazatetracyclo[12.6.2.18,12.017,21]tricosa-1(20),8(23),9,11,14,16,18,21-octaen-2-yne-15-carboxylate was synthesized through a multi-step pathway, starting from commercially available 3-iodo-1,2-phenylenediamine. Structure characterization of this new substituted macrocyclic quinoxaline compound was achieved using 1H NMR, 13C NMR, and HRMS spectral analysis. This new macrocyclic derivative demonstrated submicromolar potency on both Pim-1 and Pim-2 isoforms, with an interesting selectivity profile against a selected panel of human kinases.
{"title":"Potassium 6-Oxo-7,13,16,22-tetraazatetracyclo[12.6.2.18,12.017,21]tricosa-1(20),8(23),9,11,14,16,18,21-octaen-2-yne-15-carboxylate","authors":"Camille Blouet, Stéphanie Letast, Thomas Robert, Stéphane Bach, Noël Pinaud, Nicolas Joubert, Marie-Claude Viaud-Massuard, Jean Guillon, Cédric Logé, Caroline Denevault-Sabourin","doi":"10.3390/m1735","DOIUrl":"https://doi.org/10.3390/m1735","url":null,"abstract":"Potassium 6-oxo-7,13,16,22-tetraazatetracyclo[12.6.2.18,12.017,21]tricosa-1(20),8(23),9,11,14,16,18,21-octaen-2-yne-15-carboxylate was synthesized through a multi-step pathway, starting from commercially available 3-iodo-1,2-phenylenediamine. Structure characterization of this new substituted macrocyclic quinoxaline compound was achieved using 1H NMR, 13C NMR, and HRMS spectral analysis. This new macrocyclic derivative demonstrated submicromolar potency on both Pim-1 and Pim-2 isoforms, with an interesting selectivity profile against a selected panel of human kinases.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"1 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135093876","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Irina V. Ilyina, Nikolai S. Li-Zhulanov, Yuri V. Gatilov, Konstantin P. Volcho, Alexander Yu. Sidorenko, Vladimir E. Agabekov, Nariman F. Salakhutdinov
The development of highly efficient methods for the synthesis of chemical products by using renewable raw materials is one of the topical areas of medicinal chemistry. The paper presents the synthesis of (2aR,2a1S,5aR,9bR)-4-isopropyl-7,8-dimethoxy-2a1-methyl-2,2a,2a1,3,5a,9b-hexahydrofluoreno[9,1-bc]furan. The title compound was obtained through Prins–Friedel–Crafts cascade reactions of trans-4-hydroxymethyl-2-carene, which was synthesized from 3-carene, one of the main components of gum turpentine. The product yield after purification was 48%. The compound’s structure was confirmed by X-ray diffraction analysis.
{"title":"(2aR,2a1S,5aR,9bR)-4-Isopropyl-7,8-dimethoxy-2a1-methyl-2,2a,2a1,3,5a,9b-hexahydrofluoreno[9,1-bc]furan","authors":"Irina V. Ilyina, Nikolai S. Li-Zhulanov, Yuri V. Gatilov, Konstantin P. Volcho, Alexander Yu. Sidorenko, Vladimir E. Agabekov, Nariman F. Salakhutdinov","doi":"10.3390/m1734","DOIUrl":"https://doi.org/10.3390/m1734","url":null,"abstract":"The development of highly efficient methods for the synthesis of chemical products by using renewable raw materials is one of the topical areas of medicinal chemistry. The paper presents the synthesis of (2aR,2a1S,5aR,9bR)-4-isopropyl-7,8-dimethoxy-2a1-methyl-2,2a,2a1,3,5a,9b-hexahydrofluoreno[9,1-bc]furan. The title compound was obtained through Prins–Friedel–Crafts cascade reactions of trans-4-hydroxymethyl-2-carene, which was synthesized from 3-carene, one of the main components of gum turpentine. The product yield after purification was 48%. The compound’s structure was confirmed by X-ray diffraction analysis.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"117 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135094278","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Lorenza Romagnoli, Andrea D’Annibale, Alessandro Latini
Viologens are a highly advantageous class of compounds for the synthesis of functional materials. Owing to their versatile structure, they can embed additional conjugated moieties, thus representing a convenient platform, for example for organic semiconductors and other energy-related uses. A straightforward synthesis of an extended viologen containing a bithiophene is described here, together with its UV-visible absorption and fluorescence spectroscopy, showing multiple absorption and emission bands. Thanks to its ease of synthesis and optical properties, this organic salt appears to be of potential interest for various optoelectronic applications.
{"title":"4,4′-([2,2′-Bithiophene]-5,5′-diylbis(ethyne-2,1-diyl))bis(1-methylpyridin-1-ium) Iodide","authors":"Lorenza Romagnoli, Andrea D’Annibale, Alessandro Latini","doi":"10.3390/m1733","DOIUrl":"https://doi.org/10.3390/m1733","url":null,"abstract":"Viologens are a highly advantageous class of compounds for the synthesis of functional materials. Owing to their versatile structure, they can embed additional conjugated moieties, thus representing a convenient platform, for example for organic semiconductors and other energy-related uses. A straightforward synthesis of an extended viologen containing a bithiophene is described here, together with its UV-visible absorption and fluorescence spectroscopy, showing multiple absorption and emission bands. Thanks to its ease of synthesis and optical properties, this organic salt appears to be of potential interest for various optoelectronic applications.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"21 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135739386","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A novel single crystal of (3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl)methyl benzenesulfonate has been synthetized via a one-pot sequential strategy under sonication. The single crystal has been investigated using X-ray diffraction analysis. Hydrogen bonding between C–H···O and C–H···N produces a layer structure in the crystal. According to a Hirshfeld surface analysis, interactions H···H (28.9%), H···O/O···H (26.7%) and H···C/C···H (15.8%) make the largest contributions to crystal packing. The optimized structure and the solid-state structure that was obtained through experiments are compared using density functional theory at the B3LYP/6-311 G + (d,p) level. The computed energy difference between the lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO) is 4.6548 eV.
在超声作用下，采用一锅连续策略合成了一种新型的(3-(4-氯苯基)-4,5-二氢异恶唑-5-基)甲基苯磺酸盐单晶。用x射线衍射分析对单晶进行了研究。C-H·O和C-H·N之间的氢键在晶体中形成层状结构。Hirshfeld表面分析表明，相互作用H··H(28.9%)、H··O/O··H(26.7%)和H··C/C··H(15.8%)对晶体堆积的贡献最大。利用密度泛函理论在B3LYP/6-311 G + (d,p)水平上对优化后的结构与实验得到的固态结构进行了比较。计算出最低未占据分子轨道(LUMO)和最高已占据分子轨道(HOMO)之间的能量差为4.6548 eV。
{"title":"(3-(4-Chlorophenyl)-4,5-dihydroisoxazol-5-yl)methyl Benzenesulfonate","authors":"Loubna Mokhi, Karim Chkirate, Xiaodong Zhang, Mohsine Driowya, Khalid Bougrin","doi":"10.3390/m1732","DOIUrl":"https://doi.org/10.3390/m1732","url":null,"abstract":"A novel single crystal of (3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl)methyl benzenesulfonate has been synthetized via a one-pot sequential strategy under sonication. The single crystal has been investigated using X-ray diffraction analysis. Hydrogen bonding between C–H···O and C–H···N produces a layer structure in the crystal. According to a Hirshfeld surface analysis, interactions H···H (28.9%), H···O/O···H (26.7%) and H···C/C···H (15.8%) make the largest contributions to crystal packing. The optimized structure and the solid-state structure that was obtained through experiments are compared using density functional theory at the B3LYP/6-311 G + (d,p) level. The computed energy difference between the lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO) is 4.6548 eV.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"29 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136062237","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
R. Alan Aitken, Alexandra H. Campbell, Chloé E. Fletcher, Alexandra M. Z. Slawin
The X-ray structure of the title compound, formed at low conversion in the reaction of thiosalicylic acid with thionyl chloride, has been determined. The acid chloride groups are oriented to permit an attractive non-bonding O…S interaction. Mechanisms are suggested for the formation of this unexpected product. 1H and 13C NMR data are also reported for the first time for the major reaction product, 2-mercaptobenzoyl chloride.
{"title":"2,2′-Trisulfanediyldibenzoyl Chloride","authors":"R. Alan Aitken, Alexandra H. Campbell, Chloé E. Fletcher, Alexandra M. Z. Slawin","doi":"10.3390/m1731","DOIUrl":"https://doi.org/10.3390/m1731","url":null,"abstract":"The X-ray structure of the title compound, formed at low conversion in the reaction of thiosalicylic acid with thionyl chloride, has been determined. The acid chloride groups are oriented to permit an attractive non-bonding O…S interaction. Mechanisms are suggested for the formation of this unexpected product. 1H and 13C NMR data are also reported for the first time for the major reaction product, 2-mercaptobenzoyl chloride.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"8 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136237653","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
R. Alan Aitken, David B. Cordes, An Jie Ler, Aidan P. McKay
The title dibromodisalicylaldehyde, obtained as a by-product in the m-chloroperoxybenzoic acid oxidation of 5-bromo-2-(methoxymethoxy)benzaldehyde, has been characterised by IR and NMR spectroscopy and X-ray diffraction. The structure features two independent molecules with a π–π stacking interaction between them.
{"title":"2,8-Dibromo-6H,12H-6,12-epoxydibenzo[b,f][1,5]dioxocine","authors":"R. Alan Aitken, David B. Cordes, An Jie Ler, Aidan P. McKay","doi":"10.3390/m1729","DOIUrl":"https://doi.org/10.3390/m1729","url":null,"abstract":"The title dibromodisalicylaldehyde, obtained as a by-product in the m-chloroperoxybenzoic acid oxidation of 5-bromo-2-(methoxymethoxy)benzaldehyde, has been characterised by IR and NMR spectroscopy and X-ray diffraction. The structure features two independent molecules with a π–π stacking interaction between them.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"4 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135060284","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Tiffany H. Li, Lucas C. Messer, Nathan J. Weeks, Timothy J. Fuhrer, Scott T. Iacono
The title compound was synthesized in near quantitative yields via initial nucleophilic aromatic substitution of pentafluoropyridine (PFP) with 4-(2-bromoethyl)phenol as a versatile precursor for ionic liquids (ILs). The purity and structure were determined using 1H, 13C, and 19F NMR and GC-EIMS.
{"title":"4-(4-(2-Bromoethyl)phenoxy)-2,3,5,6-tetrafluoropyridine","authors":"Tiffany H. Li, Lucas C. Messer, Nathan J. Weeks, Timothy J. Fuhrer, Scott T. Iacono","doi":"10.3390/m1730","DOIUrl":"https://doi.org/10.3390/m1730","url":null,"abstract":"The title compound was synthesized in near quantitative yields via initial nucleophilic aromatic substitution of pentafluoropyridine (PFP) with 4-(2-bromoethyl)phenol as a versatile precursor for ionic liquids (ILs). The purity and structure were determined using 1H, 13C, and 19F NMR and GC-EIMS.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"42 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135063555","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Aleksey A. Vasilev, Meglena I. Kandinska, Anton Kostadinov, Laura Dietz, Stanislav Baluschev
The development of new selective fluorogenic probes for monitoring microbiological objects and cellular compartments may help to determine the mechanism of pathogenesis of new pathogens in living cells. The easy and reliable synthetic strategy for the direct preparation of chemically pure styryl dye (E)-3-heptyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium iodide is described. The photophysical properties in different solvents and in water medium neat and in the presence of the dsDNA and RNA of the dye is demonstrated and compared with that of the known structure analogue. The cellular uptake and the ability to bind cell organelles is determined. The introduction of a heptyl substituent attached to the quaternary nitrogen atom of the benzothiazole ring leads to an improvement in the photophysical properties of the dye.
{"title":"(E)-3-Heptyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium Iodide as Solvatochromic and Fluorogenic Dye for Spectroscopy Applications","authors":"Aleksey A. Vasilev, Meglena I. Kandinska, Anton Kostadinov, Laura Dietz, Stanislav Baluschev","doi":"10.3390/m1727","DOIUrl":"https://doi.org/10.3390/m1727","url":null,"abstract":"The development of new selective fluorogenic probes for monitoring microbiological objects and cellular compartments may help to determine the mechanism of pathogenesis of new pathogens in living cells. The easy and reliable synthetic strategy for the direct preparation of chemically pure styryl dye (E)-3-heptyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium iodide is described. The photophysical properties in different solvents and in water medium neat and in the presence of the dsDNA and RNA of the dye is demonstrated and compared with that of the known structure analogue. The cellular uptake and the ability to bind cell organelles is determined. The introduction of a heptyl substituent attached to the quaternary nitrogen atom of the benzothiazole ring leads to an improvement in the photophysical properties of the dye.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"215 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135203370","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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