Arkadiusz Sokal, Roman Wrzalik, J. Klimontko, E. Chrobak, E. Bębenek, Monika Kadela-Tomanek
Quinoline and isoquinoline moieties occur in many natural and synthetic compounds exhibiting high biological activity. The purpose of this study was to analyze the chemical structures of 5,8-quinolinedione and 5,8-isoquinoline derivatives using FT-IR spectroscopy supplemented with theoretical DFT calculations. Spectroscopic measurements were conducted using the attenuated total reflection (ATR) mode in the frequency range of 4000–400 cm−1. An analysis of FT-IR spectra was carried out, assigning the characteristic vibration frequencies of various functional groups to individual peaks. It was found that the experimental and calculated FT-IR spectra showed a good correlation for all the compounds under study. The most significant difference in the spectra occurred in the region of carbonyl bands. For compounds with the 5,8-quinolinedione moiety, two separated C=O vibration peaks were observed, while for compounds with the 5,8-isoquinolinedione moiety, the carbonyl vibrations created only one peak. This difference makes it possible to distinguish between the 5,8-quinolinedione and 5,8-isoquinolinedione derivatives.
{"title":"5,8-Quinolinedione Attached to Quinone Derivatives: XRD Diffraction, Fourier Transform Infrared Spectra and Computational Analysis","authors":"Arkadiusz Sokal, Roman Wrzalik, J. Klimontko, E. Chrobak, E. Bębenek, Monika Kadela-Tomanek","doi":"10.3390/m1747","DOIUrl":"https://doi.org/10.3390/m1747","url":null,"abstract":"Quinoline and isoquinoline moieties occur in many natural and synthetic compounds exhibiting high biological activity. The purpose of this study was to analyze the chemical structures of 5,8-quinolinedione and 5,8-isoquinoline derivatives using FT-IR spectroscopy supplemented with theoretical DFT calculations. Spectroscopic measurements were conducted using the attenuated total reflection (ATR) mode in the frequency range of 4000–400 cm−1. An analysis of FT-IR spectra was carried out, assigning the characteristic vibration frequencies of various functional groups to individual peaks. It was found that the experimental and calculated FT-IR spectra showed a good correlation for all the compounds under study. The most significant difference in the spectra occurred in the region of carbonyl bands. For compounds with the 5,8-quinolinedione moiety, two separated C=O vibration peaks were observed, while for compounds with the 5,8-isoquinolinedione moiety, the carbonyl vibrations created only one peak. This difference makes it possible to distinguish between the 5,8-quinolinedione and 5,8-isoquinolinedione derivatives.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"23 1","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139226692","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}
Wilson Castrillón-López, Andrés F. Yepes, Wilson Cardona-Galeano
A series of 5-FU-ASA hybrids were synthesized with good yields using click chemistry as the key step. The structures of these compounds were elucidated by spectroscopic analysis. Finally, an optimal pharmacokinetic profile was also estimated for each synthetized hybrid. Taken together, hybrids 4a–h could be used as starting points for further pharmacological studies concerning therapeutic cancer intervention.
{"title":"Synthesis and In Silico Drug-Likeness Modeling of 5-FU/ASA Hybrids","authors":"Wilson Castrillón-López, Andrés F. Yepes, Wilson Cardona-Galeano","doi":"10.3390/m1745","DOIUrl":"https://doi.org/10.3390/m1745","url":null,"abstract":"A series of 5-FU-ASA hybrids were synthesized with good yields using click chemistry as the key step. The structures of these compounds were elucidated by spectroscopic analysis. Finally, an optimal pharmacokinetic profile was also estimated for each synthetized hybrid. Taken together, hybrids 4a–h could be used as starting points for further pharmacological studies concerning therapeutic cancer intervention.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"3 1","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139233327","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}
N. Danilenko, Mariia O. Lutsuk, Svetlana E. Patlasova, Elena I. Korotkova, A. Khlebnikov
New 2-(4-(fluorosulfonyloxy)phenyl)benzoxazole (2) was synthesized through the SuFEx click reaction in a two-chamber reactor. The effect of silylation on the yield of the target compound was investigated. The fluorescent properties of compound 2 were determined using experimental and computational methods.
{"title":"2-(4-(Fluorosulfonyloxy)phenyl)benzoxazole","authors":"N. Danilenko, Mariia O. Lutsuk, Svetlana E. Patlasova, Elena I. Korotkova, A. Khlebnikov","doi":"10.3390/m1746","DOIUrl":"https://doi.org/10.3390/m1746","url":null,"abstract":"New 2-(4-(fluorosulfonyloxy)phenyl)benzoxazole (2) was synthesized through the SuFEx click reaction in a two-chamber reactor. The effect of silylation on the yield of the target compound was investigated. The fluorescent properties of compound 2 were determined using experimental and computational methods.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"13 1","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139234243","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}
T. M. Syeda, Muadh R. Al-Shaidi, Ibtihal Basri, M. Merzouk, F. Aldabbagh
Treatment of the non-purified mixture of dinitro isomers obtained from the nitration of 1,4-dimethoxybenzene with piperidine led to the isolation of novel but minor adduct, 1-(2,5-dimethoxy-4-nitrophenyl)piperidine (2b) in 15% yield. Yields of nucleophilic aromatic substitution adducts are high when using purified 1,4-dimethoxy-2,5-dinitrobenzene (1b) with piperidine and pyrrolidine to give (2b) and 1-(2,5-dimethoxy-4-nitrophenyl)pyrrolidine (3b) in 76% and 82% yield, respectively.
{"title":"1-(2,5-Dimethoxy-4-nitrophenyl)piperidine","authors":"T. M. Syeda, Muadh R. Al-Shaidi, Ibtihal Basri, M. Merzouk, F. Aldabbagh","doi":"10.3390/m1744","DOIUrl":"https://doi.org/10.3390/m1744","url":null,"abstract":"Treatment of the non-purified mixture of dinitro isomers obtained from the nitration of 1,4-dimethoxybenzene with piperidine led to the isolation of novel but minor adduct, 1-(2,5-dimethoxy-4-nitrophenyl)piperidine (2b) in 15% yield. Yields of nucleophilic aromatic substitution adducts are high when using purified 1,4-dimethoxy-2,5-dinitrobenzene (1b) with piperidine and pyrrolidine to give (2b) and 1-(2,5-dimethoxy-4-nitrophenyl)pyrrolidine (3b) in 76% and 82% yield, respectively.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"13 1","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139227922","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}
Kseniya S. Kovaleva, Olga I. Yarovaya, Irina A. Chernyshova, Alexandra L. Zakharenko, Sergey V. Cheresiz, Amirhossein Azimirad, Andrey G. Pokrovsky, Olga I. Lavrik, Nariman F. Salakhutdinov
New imidazolidine-2,4,5-triones with norabietic, nordehydroabietic, and adamantane substituents were synthesized by reacting oxalyl chloride and the corresponding ureas, providing good yields. Bioisosteric replacement of the ureide group with a parabanic acid fragment made it possible to increase the solubility of compounds and conduct biological studies. The compounds inhibit the DNA repair enzyme tyrosyl-DNA phosphodiesterase 1 in submicromolar concentrations. Cytotoxic concentrations were also studied on the glioblastoma cell line SNB19.
{"title":"Synthesis of Norabietyl and Nordehydroabietyl Imidazolidine-2,4,5-Triones and Their Activity against Tyrosyl-DNA Phosphodiesterase 1","authors":"Kseniya S. Kovaleva, Olga I. Yarovaya, Irina A. Chernyshova, Alexandra L. Zakharenko, Sergey V. Cheresiz, Amirhossein Azimirad, Andrey G. Pokrovsky, Olga I. Lavrik, Nariman F. Salakhutdinov","doi":"10.3390/m1743","DOIUrl":"https://doi.org/10.3390/m1743","url":null,"abstract":"New imidazolidine-2,4,5-triones with norabietic, nordehydroabietic, and adamantane substituents were synthesized by reacting oxalyl chloride and the corresponding ureas, providing good yields. Bioisosteric replacement of the ureide group with a parabanic acid fragment made it possible to increase the solubility of compounds and conduct biological studies. The compounds inhibit the DNA repair enzyme tyrosyl-DNA phosphodiesterase 1 in submicromolar concentrations. Cytotoxic concentrations were also studied on the glioblastoma cell line SNB19.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" 38","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135241785","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
Despite having been known for a long time, quaternary 4,4′-bipyridinium salts, or viologens, are still a highly inspiring class of compounds, thanks to their peculiar redox and charge transfer properties. However, more complex structures containing multiple pyridinium rings, also interspaced by conjugated moieties, allow an even wider synthetic variability and tunability of their characteristics. The compound described herein is a star-shaped, fully conjugated molecule with three methylated pyridinium rings connected by a triple bond spacer to a central benzene core, which was synthesized from readily available building blocks, representing a quite simple model of multi-pyridyl extended viologen; its UV–visible absorption and fluorescence spectra have also been investigated.
{"title":"4,4′,4″-(Benzene-1,3,5-triyltris(ethyne-2,1-diyl))tris(1-methylpyridin-1-ium) Iodide","authors":"Lorenza Romagnoli, Andrea D’Annibale, Alessandro Latini","doi":"10.3390/m1742","DOIUrl":"https://doi.org/10.3390/m1742","url":null,"abstract":"Despite having been known for a long time, quaternary 4,4′-bipyridinium salts, or viologens, are still a highly inspiring class of compounds, thanks to their peculiar redox and charge transfer properties. However, more complex structures containing multiple pyridinium rings, also interspaced by conjugated moieties, allow an even wider synthetic variability and tunability of their characteristics. The compound described herein is a star-shaped, fully conjugated molecule with three methylated pyridinium rings connected by a triple bond spacer to a central benzene core, which was synthesized from readily available building blocks, representing a quite simple model of multi-pyridyl extended viologen; its UV–visible absorption and fluorescence spectra have also been investigated.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"52 10","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135429828","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}
New derivative of 28-acetylbetulin containing a phenylpropynoyl moiety at the C-3 position was obtained by Steglich method. The chemical structure of this compound has been determined through 1H NMR, 13C NMR, IR, EI MS and HRMS. The antiproliferative effects of 28-O-acetyl-3-O’-(phenylpropynoyl)betulin were evaluated against three human cancer cell lines: T47D (breast cancer), CCRF/CEM (leukemia), SW707 (colorectal adenocarcinoma) and murine cell line P388 (leukemia). The synthesized compound exhibited moderate antiproliferative activity against P388 cells (IC50 = 35.51 µM). The in silico analysis showed that the title compound meets the criteria of Veber’s rule.
用Steglich法合成了含有C-3位苯基丙基的28-乙酰白桦林衍生物。该化合物的化学结构通过1H NMR、13C NMR、IR、EI MS和HRMS进行了表征。研究了28- o -乙酰基-3- o ' -(苯丙基)白桦林对3种人类癌细胞系T47D(乳腺癌)、CCRF/CEM(白血病)、SW707(结直肠癌)和小鼠P388(白血病)的抗增殖作用。合成的化合物对P388细胞具有中等的抗增殖活性(IC50 = 35.51µM)。结果表明，标题化合物符合Veber规则。
{"title":"28-O-Acetyl-3-O’-(Phenylpropynoyl)Betulin","authors":"Ewa Bębenek, Monika Kadela-Tomanek, Beata Filip-Psurska, Elwira Chrobak","doi":"10.3390/m1741","DOIUrl":"https://doi.org/10.3390/m1741","url":null,"abstract":"New derivative of 28-acetylbetulin containing a phenylpropynoyl moiety at the C-3 position was obtained by Steglich method. The chemical structure of this compound has been determined through 1H NMR, 13C NMR, IR, EI MS and HRMS. The antiproliferative effects of 28-O-acetyl-3-O’-(phenylpropynoyl)betulin were evaluated against three human cancer cell lines: T47D (breast cancer), CCRF/CEM (leukemia), SW707 (colorectal adenocarcinoma) and murine cell line P388 (leukemia). The synthesized compound exhibited moderate antiproliferative activity against P388 cells (IC50 = 35.51 µM). The in silico analysis showed that the title compound meets the criteria of Veber’s rule.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"18 2","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135266067","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}
This Special Issue, “Molecules from Side Reactions II”, belongs to the section Organic Synthesis of the journal Molbank and was launched in 2021, after the first edition, “Molecules from Side Reactions” [...]
本特刊 "Molecules from Side Reactions II "属于《Molbank》杂志的有机合成栏目，在第一期 "Molecules from Side Reactions" [...] 之后，于 2021 年推出。
{"title":"Editorial: Special Issue “Molecules from Side Reactions II”","authors":"S. D’Errico, Annalisa Guaragna","doi":"10.3390/m1740","DOIUrl":"https://doi.org/10.3390/m1740","url":null,"abstract":"This Special Issue, “Molecules from Side Reactions II”, belongs to the section Organic Synthesis of the journal Molbank and was launched in 2021, after the first edition, “Molecules from Side Reactions” [...]","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"7 1","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139316122","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}
Anastasiya V. Petrova, Irina V. Zueva, Konstantin A. Petrov
In this study, the synthesis and biological activities of previously and newly synthesized oleanolic acid derivatives containing seven-membered cyclic amines at the C28 position were described. The obtained compounds were fully characterized via 1H and 13C NMR spectroscopy, and the bioactivity was evaluated by Ellman’s method. Among the tested compounds, 2,3-indolo-oleanolic acid was found to be the most active compound with an IC50 value of 0.78 µM against acetylcholinesterase. These results are significant due to the fact that research on the inhibition of acetylcholinesterase and butyrylcholinesterase enzymes by oleanolic acid, in particular indoloderivatives, is limited.
{"title":"Synthesis and Cholinesterase Inhibitory Potency of 2,3-Indolo-oleanolic Acid and Some Related Derivatives","authors":"Anastasiya V. Petrova, Irina V. Zueva, Konstantin A. Petrov","doi":"10.3390/m1739","DOIUrl":"https://doi.org/10.3390/m1739","url":null,"abstract":"In this study, the synthesis and biological activities of previously and newly synthesized oleanolic acid derivatives containing seven-membered cyclic amines at the C28 position were described. The obtained compounds were fully characterized via 1H and 13C NMR spectroscopy, and the bioactivity was evaluated by Ellman’s method. Among the tested compounds, 2,3-indolo-oleanolic acid was found to be the most active compound with an IC50 value of 0.78 µM against acetylcholinesterase. These results are significant due to the fact that research on the inhibition of acetylcholinesterase and butyrylcholinesterase enzymes by oleanolic acid, in particular indoloderivatives, is limited.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"8 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135883393","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}
Paul R. Palme, Richard Goddard, Markus Leutzsch, Adrian Richter, Peter Imming, Rüdiger W. Seidel
Betaines of squaric acid have gained research interest because of their structural and spectral properties. We elucidated the crystal and molecular structure of the triethylammonium betaine of squaric acid (1) by X-ray crystallography, IR, and NMR spectroscopy augmented by Hirshfeld surface analysis and DFT calculations. The crystal structure determination using Hirshfeld atom refinement reveals that the resonance hybrid structure with partial enolate character of the two lateral squaric acid C=O groups describes 1 best. The solid-state supramolecular structure features weak intermolecular C−H···O hydrogen bonds. The number of C=O bands in the IR spectrum in the solid-state is consistent with local C2v symmetry of the squaric acid residue in 1. The 13C NMR signals of this group in solution were assigned based on 2D NMR experiments and computational prediction using the Gauge-Independent Atom Orbital (GIAO) method. The present study provides the first structural characterization of a betaine of squaric acid containing a four-coordinate nitrogen atom directly attached to the four-membered ring.
{"title":"Structural Elucidation of the Triethylammonium Betaine of Squaric Acid","authors":"Paul R. Palme, Richard Goddard, Markus Leutzsch, Adrian Richter, Peter Imming, Rüdiger W. Seidel","doi":"10.3390/m1737","DOIUrl":"https://doi.org/10.3390/m1737","url":null,"abstract":"Betaines of squaric acid have gained research interest because of their structural and spectral properties. We elucidated the crystal and molecular structure of the triethylammonium betaine of squaric acid (1) by X-ray crystallography, IR, and NMR spectroscopy augmented by Hirshfeld surface analysis and DFT calculations. The crystal structure determination using Hirshfeld atom refinement reveals that the resonance hybrid structure with partial enolate character of the two lateral squaric acid C=O groups describes 1 best. The solid-state supramolecular structure features weak intermolecular C−H···O hydrogen bonds. The number of C=O bands in the IR spectrum in the solid-state is consistent with local C2v symmetry of the squaric acid residue in 1. The 13C NMR signals of this group in solution were assigned based on 2D NMR experiments and computational prediction using the Gauge-Independent Atom Orbital (GIAO) method. The present study provides the first structural characterization of a betaine of squaric acid containing a four-coordinate nitrogen atom directly attached to the four-membered ring.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"34 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":"136113445","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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