Drug combination therapies have been a promising strategy to overcome drug resistance. However, unexpected Drug-Drug interaction may cause adverse reactions, which puts patients in danger. Keeping this in mind, the interactions between pain killers, paracetamol (PCM) and ibuprofen sodium (IBU) with caffeine (CAF) have been studied. Apparent molar volumes (V2,ϕ) and apparent molar isentropic compression (Ks,2,ϕ)for analgesic drugs in aqueous (1, 2, 5 and 10 mmol·kg-1) caffeine (CAF) solutions have been determined from measured densities, ρ and speeds of sound, u, respectively at T = (288.15 to 318.15) K and at pressure p = 101.3 kPa. The results have also been interpreted in terms of various interactions occurring in the mixed solution. Calorimetrically determined negative values of ΔtrΔdilH0, indicate the exothermicity and thus the occurrence of energetically more favorable process. The hyperchromic shift (UV-absorption) in the spectra of PCM in aqueous solution of CAF suggest the dominance of solute-cosolute interactions through the hydrophobic-hydrophobic/hydrophilic groups (1H NMR) of PCM + CAF system.
{"title":"Interactional Behaviour of analgesic drugs in Aqueous Solution of Caffeine at different temperatures using multi-technique Approach","authors":"Aashima Beri, R. Kant, T. S. Banipal","doi":"10.1139/cjc-2023-0097","DOIUrl":"https://doi.org/10.1139/cjc-2023-0097","url":null,"abstract":"Drug combination therapies have been a promising strategy to overcome drug resistance. However, unexpected Drug-Drug interaction may cause adverse reactions, which puts patients in danger. Keeping this in mind, the interactions between pain killers, paracetamol (PCM) and ibuprofen sodium (IBU) with caffeine (CAF) have been studied. Apparent molar volumes (V2,ϕ) and apparent molar isentropic compression (Ks,2,ϕ)for analgesic drugs in aqueous (1, 2, 5 and 10 mmol·kg-1) caffeine (CAF) solutions have been determined from measured densities, ρ and speeds of sound, u, respectively at T = (288.15 to 318.15) K and at pressure p = 101.3 kPa. The results have also been interpreted in terms of various interactions occurring in the mixed solution. Calorimetrically determined negative values of ΔtrΔdilH0, indicate the exothermicity and thus the occurrence of energetically more favorable process. The hyperchromic shift (UV-absorption) in the spectra of PCM in aqueous solution of CAF suggest the dominance of solute-cosolute interactions through the hydrophobic-hydrophobic/hydrophilic groups (1H NMR) of PCM + CAF system.","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"66 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2023-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139255427","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Here, we report an efficient synthesis of L-(+)-quinic acid from the natural product D-(–)-quinic acid in a twelve-step sequence. The key steps involve the kinetic controlled selective protection of a lactone intermediate and the inversion of two stereocentres: the C-3 and C-5 hydroxyl of the quinic acid core using optimized oxidation-reduction conditions.
{"title":"A synthesis of L-(+)-quinic acid from D-(–)-quinic acid","authors":"Johnny Nguyen, Sandeep Bhosale, Andrew J. Bennet","doi":"10.1139/cjc-2023-0139","DOIUrl":"https://doi.org/10.1139/cjc-2023-0139","url":null,"abstract":"Here, we report an efficient synthesis of L-(+)-quinic acid from the natural product D-(–)-quinic acid in a twelve-step sequence. The key steps involve the kinetic controlled selective protection of a lactone intermediate and the inversion of two stereocentres: the C-3 and C-5 hydroxyl of the quinic acid core using optimized oxidation-reduction conditions.","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"14 5","pages":""},"PeriodicalIF":1.1,"publicationDate":"2023-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139263197","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Urban grime refers to films made of a complex chemical mixture of organics and inorganics deposited on outdoor surfaces. The specific chemical composition of such films can vary considerably due to geographic and seasonal influences. We compared the seasonal change of grime’s water-soluble inorganic ion content in a rural (Thamesford), suburban (Oshawa), and urban city (Toronto) in southern Ontario, Canada. Sodium, calcium, chloride, nitrate and sulphate amounts in grime was collected and quantified over four seasons in Oshawa, ON and Thamesford, ON and compared with results from a previous study in Toronto to elucidate differences. We found that all three regions displayed a clear seasonality in sodium and chloride consistent with winter road salt inputs and chloride loss in summer. Mole fractions of sulphate were consistently the lowest of the measured ions and NO3-/SO42- ratios showed a winter-spring minimum and summer-fall maximum. Urban – rural differences in the seasonal changes of ionic mole ratios suggests that additional chloride displacement by nitrate occurs within grime in Toronto that is not present in the two other rural/suburban cities in the same region.
{"title":"Comparison of Seasonality of Urban Grime in Three Southern Ontario Cities","authors":"Yao Yan Huang, Emma M. McLay, James Donaldson","doi":"10.1139/cjc-2023-0143","DOIUrl":"https://doi.org/10.1139/cjc-2023-0143","url":null,"abstract":"Urban grime refers to films made of a complex chemical mixture of organics and inorganics deposited on outdoor surfaces. The specific chemical composition of such films can vary considerably due to geographic and seasonal influences. We compared the seasonal change of grime’s water-soluble inorganic ion content in a rural (Thamesford), suburban (Oshawa), and urban city (Toronto) in southern Ontario, Canada. Sodium, calcium, chloride, nitrate and sulphate amounts in grime was collected and quantified over four seasons in Oshawa, ON and Thamesford, ON and compared with results from a previous study in Toronto to elucidate differences. We found that all three regions displayed a clear seasonality in sodium and chloride consistent with winter road salt inputs and chloride loss in summer. Mole fractions of sulphate were consistently the lowest of the measured ions and NO3-/SO42- ratios showed a winter-spring minimum and summer-fall maximum. Urban – rural differences in the seasonal changes of ionic mole ratios suggests that additional chloride displacement by nitrate occurs within grime in Toronto that is not present in the two other rural/suburban cities in the same region.","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"30 6","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134957424","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Ruonan Chen, Hongbing Yang, Qiuchen Huang, Mengyi Ba, Wen Li, Yanli Song, Zhiqiang Cai, Tao Sun, Qiaoqiao Feng, Shuai Li
In this work, an innovative ionic liquid functionalized star-shape-polymer is synthesized by coupling star-polycaprolactone with benzimidazolium (star-PCL-Bim), and statically coated into a capillary column for gas chromatographic (GC) separations. The fabricated star-PCL-Bim capillary column with moderate-polar nature reveals a high column efficiency of 3598 plates/m for n-dodecane at 120°C, and advantageous distinguishing ability (R > 1.5) for 9 aromatic isomer mixtures and 12 cis-/trans-isomers. Its excellent resolving capacity can be credit to the architecture of star-PCL-Bim, the PCL arms and π-electron-rich benzimidazolium cations, and it results in a quite different retention behavior of star-PCL-Bim from that of star-PCL and commercial HP-35 columns, with “dual-nature” selectivity in separating a mixture including 29 compounds. These favorable chromatographic characteristics demonstrate the great application potential of this material in GC, and provide a prospective strategy to obtain high-performance stationary phases.
{"title":"Benzimidazolium Ionic Liquid Functionalized Star-polycaprolactone Stationary Phase for Capillary Gas Chromatography","authors":"Ruonan Chen, Hongbing Yang, Qiuchen Huang, Mengyi Ba, Wen Li, Yanli Song, Zhiqiang Cai, Tao Sun, Qiaoqiao Feng, Shuai Li","doi":"10.1139/cjc-2023-0068","DOIUrl":"https://doi.org/10.1139/cjc-2023-0068","url":null,"abstract":"In this work, an innovative ionic liquid functionalized star-shape-polymer is synthesized by coupling star-polycaprolactone with benzimidazolium (star-PCL-Bim), and statically coated into a capillary column for gas chromatographic (GC) separations. The fabricated star-PCL-Bim capillary column with moderate-polar nature reveals a high column efficiency of 3598 plates/m for n-dodecane at 120°C, and advantageous distinguishing ability (R > 1.5) for 9 aromatic isomer mixtures and 12 cis-/trans-isomers. Its excellent resolving capacity can be credit to the architecture of star-PCL-Bim, the PCL arms and π-electron-rich benzimidazolium cations, and it results in a quite different retention behavior of star-PCL-Bim from that of star-PCL and commercial HP-35 columns, with “dual-nature” selectivity in separating a mixture including 29 compounds. These favorable chromatographic characteristics demonstrate the great application potential of this material in GC, and provide a prospective strategy to obtain high-performance stationary phases.
","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"13 s4","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135341162","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Sydney Reiber, Bennett Templeman-Vivian, Michelle Mills, Chris Tremblay, David Leitch, Erin Chernick
We report the synthesis of three triphenylamine-based verdazyl radicals. These include a mono, bis, and tris(verdazyl) at the 4-position(s) of the N–Ar groups, containing one, two, and three unpaired electrons, respectively. Each of these compounds is air stable, and fully characterized using EPR spectroscopy, high-resolution mass spectrometry, infrared spectroscopy, UV/Vis spectroscopy, and cyclic voltammetry. From the UV/Vis absorbance data, the optical absorbance energy gaps were found to be ~2.35 eV for all three verdazyl-containing compounds. Cyclic voltammetry was used to estimate the energy levels of the singly occupied molecular orbitals (SOMOs), which are -4.91 eV, -5.12 eV, and -4.98 eV for mono, bis, and tris(verdazyl) compounds respectively. Spin-spin exchange interactions were observed in the EPR spectra of both the bis and tris(verdazyl)s, leading to additional hyperfine coupling patterns and assignment of the ground states as triplet and quartet, respectively.
{"title":"Multiple Verdazyl Radicals Appended to a Triarylamine Scaffold","authors":"Sydney Reiber, Bennett Templeman-Vivian, Michelle Mills, Chris Tremblay, David Leitch, Erin Chernick","doi":"10.1139/cjc-2023-0148","DOIUrl":"https://doi.org/10.1139/cjc-2023-0148","url":null,"abstract":"We report the synthesis of three triphenylamine-based verdazyl radicals. These include a mono, bis, and tris(verdazyl) at the 4-position(s) of the N–Ar groups, containing one, two, and three unpaired electrons, respectively. Each of these compounds is air stable, and fully characterized using EPR spectroscopy, high-resolution mass spectrometry, infrared spectroscopy, UV/Vis spectroscopy, and cyclic voltammetry. From the UV/Vis absorbance data, the optical absorbance energy gaps were found to be ~2.35 eV for all three verdazyl-containing compounds. Cyclic voltammetry was used to estimate the energy levels of the singly occupied molecular orbitals (SOMOs), which are -4.91 eV, -5.12 eV, and -4.98 eV for mono, bis, and tris(verdazyl) compounds respectively. Spin-spin exchange interactions were observed in the EPR spectra of both the bis and tris(verdazyl)s, leading to additional hyperfine coupling patterns and assignment of the ground states as triplet and quartet, respectively.","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"18 ","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135872034","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Micromechanism of crystal growth has received considerable attention as a fundamental subject. However, in situ observation of the crystal growth process remains challenging. In this study, high-temperature Raman spectroscopy has been utilized to investigate the growth pattern of Bi2ZnOB2O6 crystals via in situ exploration of the starting solution structure near the crystal-solution interface. The experimental results show that the solution primarily consists of ZO4 and BO3 units corresponding to 370, 539, 664, and 1293 cm-1 vibration frequencies. These units connect with each other forming longer chains in the area close to the crystal, and they are related to the presence of low-wavenumber vibrations in the Raman spectrum. Furthermore, a loose embryonic structure of the Bi2ZnOB2O6 crystal is observed near the crystal-solution interface owing to the formation of Bi-O bonds. Therefore, this study successfully provides a clear understanding of the formation mechanism of Bi2ZnOB2O6 crystals.
{"title":"High temperature Raman spectroscopic analysis of the crystal growth of Bi2ZnOB2O6","authors":"Ji Zhang, Daojun Liu","doi":"10.1139/cjc-2023-0098","DOIUrl":"https://doi.org/10.1139/cjc-2023-0098","url":null,"abstract":"Micromechanism of crystal growth has received considerable attention as a fundamental subject. However, in situ observation of the crystal growth process remains challenging. In this study, high-temperature Raman spectroscopy has been utilized to investigate the growth pattern of Bi2ZnOB2O6 crystals via in situ exploration of the starting solution structure near the crystal-solution interface. The experimental results show that the solution primarily consists of ZO4 and BO3 units corresponding to 370, 539, 664, and 1293 cm-1 vibration frequencies. These units connect with each other forming longer chains in the area close to the crystal, and they are related to the presence of low-wavenumber vibrations in the Raman spectrum. Furthermore, a loose embryonic structure of the Bi2ZnOB2O6 crystal is observed near the crystal-solution interface owing to the formation of Bi-O bonds. Therefore, this study successfully provides a clear understanding of the formation mechanism of Bi2ZnOB2O6 crystals.
","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"17 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135808267","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Daniel Hrabowyj, Liam A. Wittenberg, Erin M. Donahue-Boyle, Yang Chen, Michael A. Brook
Increasing demand for fully recyclable polymers has prompted an interest in materials crosslinked via non-covalent interactions. Aggressive depolymerization can cleave backbone SiO bonds to generate linear oils or cyclic monomers from silicone rubbers, but one would rather recover the starting material oils simply by selectively breaking crosslinks. We demonstrate that ligand binding to metals can be used to reversibly crosslink silicone chains. Aminopropylsilicones were crosslinked via complexation with copper (II) acetate to form blue silicone oils. These oils slowly cured in air at room temperature to form soft, green elastomers over a month, or overnight at 50-55 °C in air to give robust, hard red elastomers. Potential explanations for the observed color changes are discussed. Elastomers prepared by either pathway underwent ready degradation by removal of the copper ions via competitive ligand binding using ethylenediamine, allowing for recovery of the unmodified silicone oil; the recovered amine could be reused with more copper to form a (softer) elastomer. This process provides a method for the synthesis of stable elastomeric silicones that are degradable on demand.
{"title":"Copper crosslinked silicone elastomers in RGB colors: Degradable on Demand","authors":"Daniel Hrabowyj, Liam A. Wittenberg, Erin M. Donahue-Boyle, Yang Chen, Michael A. Brook","doi":"10.1139/cjc-2023-0118","DOIUrl":"https://doi.org/10.1139/cjc-2023-0118","url":null,"abstract":"Increasing demand for fully recyclable polymers has prompted an interest in materials crosslinked via non-covalent interactions. Aggressive depolymerization can cleave backbone SiO bonds to generate linear oils or cyclic monomers from silicone rubbers, but one would rather recover the starting material oils simply by selectively breaking crosslinks. We demonstrate that ligand binding to metals can be used to reversibly crosslink silicone chains. Aminopropylsilicones were crosslinked via complexation with copper (II) acetate to form blue silicone oils. These oils slowly cured in air at room temperature to form soft, green elastomers over a month, or overnight at 50-55 °C in air to give robust, hard red elastomers. Potential explanations for the observed color changes are discussed. Elastomers prepared by either pathway underwent ready degradation by removal of the copper ions via competitive ligand binding using ethylenediamine, allowing for recovery of the unmodified silicone oil; the recovered amine could be reused with more copper to form a (softer) elastomer. This process provides a method for the synthesis of stable elastomeric silicones that are degradable on demand. 
","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"1 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":"136078833","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Nicholas Morehouse, Kelsie Graham, Samantha Cox, John Johnson, Christopher Gray
A new phenalenone derivative, 2,4,6,9-tetrahydroxy-7-methyl-2-prenyl-1H-phenalene-1,3(2H)-dione (1), was isolated from the ethyl acetate extract of a marine derived Penicillium sp. fungus that exhibited a unique antimicrobial activity profile. The planar structure of 1 was determined through a combination of 1D and 2D NMR experiments, and circular dichroism and polarimetry indicated that it was isolated as a racemic mixture of enantiomers. The antimicrobial activity of 1 was assessed against a panel of Gram-positive and Gram-negative bacteria and fungal strains and it was found to selectively inhibit the growth of Staphylococcus aureus and Mycobacterium tuberculosis.
{"title":"Isolation of an antimicrobial racemic phenalenone derivative from a marine-derived Penicillium sp. fungus","authors":"Nicholas Morehouse, Kelsie Graham, Samantha Cox, John Johnson, Christopher Gray","doi":"10.1139/cjc-2023-0100","DOIUrl":"https://doi.org/10.1139/cjc-2023-0100","url":null,"abstract":"A new phenalenone derivative, 2,4,6,9-tetrahydroxy-7-methyl-2-prenyl-1H-phenalene-1,3(2H)-dione (1), was isolated from the ethyl acetate extract of a marine derived Penicillium sp. fungus that exhibited a unique antimicrobial activity profile. The planar structure of 1 was determined through a combination of 1D and 2D NMR experiments, and circular dichroism and polarimetry indicated that it was isolated as a racemic mixture of enantiomers. The antimicrobial activity of 1 was assessed against a panel of Gram-positive and Gram-negative bacteria and fungal strains and it was found to selectively inhibit the growth of Staphylococcus aureus and Mycobacterium tuberculosis.
","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"60 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135193622","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Ricardo Alfredo Luna Mora, Francisco Barrera-Téllez, Karina Martínez-Mayorga, José Guadalupe Rosas-Jiménez, Alejandro Martínez-Zaldívar, Adrián Ricardo Hipólito-Nájera, Javier Pérez-Flores, Hulme Ríos-Guerra
We examined the near-infrared (NIR) light-induced assembly efficiency to obtain light-sensitive 3,3′-(9H-fluorene-9,9-diyl) bis(1H-indole) derivatives using natural clay as metal-free Brønsted–Löwry catalyst (bentonitic Tonsil–Actisil FF (TAFF) clay) and an adduct of aluminum (III) chloride with 9-fluorenone. Their mixtures in solventless and aprotic solvent conditions were also explored. Among all the modified reactions tested, the combined effects of TAFF natural clay with NIR light, specifically in the λ 1.1 µm spectral region, result especially efficient to achieve the formation of C–Cπ bonds between π-excessive azaheteroaromatic reagents and functionalized polycyclic aromatic hydrocarbon to give the title compound in good yields within reasonable reaction times. The reaction coordinate was obtained using quantum chemical calculations. All the reactants, products, intermediates, and transition states were obtained for four systems. Natural orbital analysis allowed us to rationalize the transformations. Overall, this approach represents a greener and equally efficient alternative for conducting C–Cπ bond construction reactions in organic chemistry, and it is especially useful for protecting photosensitive compounds from abrupt decomposition.
{"title":"Synthesis of <i>bis</i>indolyl diphenylene from its ketone derivatives by infrared irradiation supported on a natural clay","authors":"Ricardo Alfredo Luna Mora, Francisco Barrera-Téllez, Karina Martínez-Mayorga, José Guadalupe Rosas-Jiménez, Alejandro Martínez-Zaldívar, Adrián Ricardo Hipólito-Nájera, Javier Pérez-Flores, Hulme Ríos-Guerra","doi":"10.1139/cjc-2021-0288","DOIUrl":"https://doi.org/10.1139/cjc-2021-0288","url":null,"abstract":"We examined the near-infrared (NIR) light-induced assembly efficiency to obtain light-sensitive 3,3′-(9H-fluorene-9,9-diyl) bis(1H-indole) derivatives using natural clay as metal-free Brønsted–Löwry catalyst (bentonitic Tonsil–Actisil FF (TAFF) clay) and an adduct of aluminum (III) chloride with 9-fluorenone. Their mixtures in solventless and aprotic solvent conditions were also explored. Among all the modified reactions tested, the combined effects of TAFF natural clay with NIR light, specifically in the λ 1.1 µm spectral region, result especially efficient to achieve the formation of C–Cπ bonds between π-excessive azaheteroaromatic reagents and functionalized polycyclic aromatic hydrocarbon to give the title compound in good yields within reasonable reaction times. The reaction coordinate was obtained using quantum chemical calculations. All the reactants, products, intermediates, and transition states were obtained for four systems. Natural orbital analysis allowed us to rationalize the transformations. Overall, this approach represents a greener and equally efficient alternative for conducting C–Cπ bond construction reactions in organic chemistry, and it is especially useful for protecting photosensitive compounds from abrupt decomposition.","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"16 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136309260","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The synthesis and characterization of a series of new 3-substituted chloroquine (CQ) derivatives is reported along with their anti-malarial activity against CQ sensitive, 3D7, and CQ resistant, Dd2, strains of Plasmodium falciparum. The new CQ derivatives stem from the aroylation of 3-aminochloroquine which in turn is prepared in four efficient steps from 4,7-dichloroquinoline. Variation of the aroylation substituents and ring substitution patterns reveal that 4-substitution with electron-withdrawing moieties results in the lowest IC50 values, both in the same order of magnitude as CQ itself for the 3D7 strain. Given its activity against the resistant Dd2 strain, the 4-chlorobenzamido-CQ derivative is chosen as the lead compound for potential use in combination therapy.
{"title":"Synthesis and Antimalarial Activity of Novel 3-Substituted Chloroquine Derivatives","authors":"Benita Kapuku, Fadi Baakdah, E. Georges, D. Bohle","doi":"10.1139/cjc-2023-0062","DOIUrl":"https://doi.org/10.1139/cjc-2023-0062","url":null,"abstract":"The synthesis and characterization of a series of new 3-substituted chloroquine (CQ) derivatives is reported along with their anti-malarial activity against CQ sensitive, 3D7, and CQ resistant, Dd2, strains of Plasmodium falciparum. The new CQ derivatives stem from the aroylation of 3-aminochloroquine which in turn is prepared in four efficient steps from 4,7-dichloroquinoline. Variation of the aroylation substituents and ring substitution patterns reveal that 4-substitution with electron-withdrawing moieties results in the lowest IC50 values, both in the same order of magnitude as CQ itself for the 3D7 strain. Given its activity against the resistant Dd2 strain, the 4-chlorobenzamido-CQ derivative is chosen as the lead compound for potential use in combination therapy.","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"57 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2023-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87108525","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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