Nicholas Morehouse, Kelsie Graham, Samantha Cox, John Johnson, Christopher Gray
{"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
{"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}
{"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}
Cheng Yang, Jinren Yan, Jiang Wu, Rujie Li, Qingju Liu
{"title":"Photocatalytic splitting of water on g-C3N4-based single-atom Pt catalysts with stable “sandwich” structure: A combined first principles and semiempirical investigation","authors":"Cheng Yang, Jinren Yan, Jiang Wu, Rujie Li, Qingju Liu","doi":"10.1139/cjc-2023-0066","DOIUrl":"https://doi.org/10.1139/cjc-2023-0066","url":null,"abstract":"Solar-to-hydrogen energy conversion is a promising strategy to solve environmental pollution and energy crisis by utilizing photocatalytic water splitting. In this work, a “sandwich” structure of g-C3N4-based single-atom Pt catalyst for photocatalytic water splitting is proposed and investigated using a combined first principles and semiempirical study method. The calculation results indicate that, without any cocatalyst, the photogenerated holes in the valence band of BL-g-C3N4 cannot oxidize H2O to O2, and its OER performance is not better than that of the pristine monolayer g-C3N4. Significantly, the photogenerated holes in the valence band of the \"sandwich\" structured photocatalyst g-C3N4-Pt1-g-C3N4 can oxidize H2O to O2 without any cocatalyst. That is, the OER performance of g-C3N4-Pt1-g-C3N4 is better than that of the pristine g-C3N4 and the pristine BL-g-C3N4. However, it can be found that the introduction of single Pt atom confinement in the BL-g-C3N4 cannot effectively reduce HER energy barrier or improve the hydrogen evolution kinetics of BL-g-C3N4. In other words, the introduction of the confined single Pt atom in the BL-g-C3N4 not only fails to improve HER performance of BL-g-C3N4, but deteriorates HER catalytic performance of BL-g-C3N4. These findings provide some theoretical insights for engineers to prepare photocatalysts with higher activity and stability.","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"7 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2023-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84021803","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}
{"title":"Characterization and swelling behavior of hydrogels from N-isopropylacrylamide, N,N′-diethylacrylamide, acrylic acid, and its use for drug release","authors":"Huynh Nguyen Anh Tuan, H. Phuong","doi":"10.1139/cjc-2023-0019","DOIUrl":"https://doi.org/10.1139/cjc-2023-0019","url":null,"abstract":"Here, a series of semi-interpenetrating polymer network (semi-IPN) hydrogels were synthesized and investigated by combining three materials such as N-isopropylacrylamide (NIPAM), N,N′-diethylacrylamide (DEA), and acrylic acid (AAc). The linear copolymer p(NIPAM-co-AAc) was introduced into DEA solution in the presence of N,N′-methylenebisacrylamide to synthesize p(NIPAM-co-AAc)/pDEA semi-IPN hydrogels using free radical polymerization. Scanning electron microscope images demonstrated the porous morphology of hydrogels with pore sizes in the range of 220–969 µm. The physicochemical properties of polymers were evaluated by various characterization techniques, including gel permeation chromatography, dynamic light scattering, differential scanning calorimetry, rheological measurement, mechanical properties, and swelling behaviors. The results indicated that the introduction of linear copolymers into conventional hydrogels has significantly improved the properties of the hydrogels. Besides, the use of NIPAM has significantly improved the thermal sensitivity of the polymers in this work. Finally, a selected semi-IPN hydrogel was evaluated for its potential for the drug release of paracetamol. The sorption of paracetamol was an exothermic process that obeyed the Freundlich isotherms, with the highest sorption of 119.57 mg/g. The paracetamol release followed the Korsmeyer–Peppas model and was consistent with the Fickian diffusion mechanism.","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"145 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2023-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86643214","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}
Yunju Zhang, Yong-guo Liu, Meilian Zhao, Yuxi Sun, Shuxin Liu
{"title":"The influence of monomolecular water and bimolecular water on BrO + CH2O reaction","authors":"Yunju Zhang, Yong-guo Liu, Meilian Zhao, Yuxi Sun, Shuxin Liu","doi":"10.1139/cjc-2022-0237","DOIUrl":"https://doi.org/10.1139/cjc-2022-0237","url":null,"abstract":"The catalytic influence of water molecules on BrO + CH2O reaction was discussed through the investigation of mechanism and kinetics. The potential energy surfaces and dynamic properties of the BrO + CH2O reaction were investigated at the CCSD(T)/aug-cc-pVTZ//B3LYP/cc-pVTZ level. The reaction generates four different products, respectively, through four pathways without water and nine pathways with water. The results have shown that the generation of HCO + HOBr occupied the entire reaction without water. The rate constants were obtained by employing the KisThelP program based on the Transition State Theory with Wigner tunneling correction. This rate constants of the naked reaction are lower than that in the presence of monomolecular water and are higher than that in the presence of bimolecular water. The current calculations indicated that monomolecular water could accelerate the BrO + CH2O reaction, while bimolecular water could not accelerate the BrO + CH2O reaction. The effective rate constants (in the presence of monomolecular water and bimolecular water) are much lower than that of the naked reaction.","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"41 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2023-07-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85555184","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}
Mélanie Sollin, S. Hosseininasab, J. Malenfant, Mohamed EL-akhrass, Amaia Lopez de Arbina, Alicia Montulet, M. Frenette
{"title":"Oxidation of Secondary Hydroperoxides via αC-H Abstraction to Form Ketones and Hydroxyl Radicals: Fluorene Autoxidation as a Model System","authors":"Mélanie Sollin, S. Hosseininasab, J. Malenfant, Mohamed EL-akhrass, Amaia Lopez de Arbina, Alicia Montulet, M. Frenette","doi":"10.1139/cjc-2022-0089","DOIUrl":"https://doi.org/10.1139/cjc-2022-0089","url":null,"abstract":"Organic and biological molecules with relatively weak C-H bonds can react with O2 via a free-radical reaction called autoxidation. The primary products of these peroxyl-radical-driven reactions are hydroperoxides, R2CHOOH. If autoxidation continues, the secondary oxidation of hydroperoxides is known to form ketones, R2C=O, but this mechanism is not well characterized. Importantly, we find that ketone formation produces a highly reactive hydroxyl radical, HO•. We can trap HO• using benzene as a solvent to form quantifiable amounts of phenol. Fluorene was chosen as a model system to study this secondary oxidation in great detail. Kinetic modeling allowed the measurement of rate constants for the primary and secondary autoxidation reactions as 11.3 M-1s-1 and 25 M-1s-1, respectively. DFT modeling likewise predicts a faster oxidation for the secondary autoxidation. This type of kinetic measurement and modeling approach could be useful to study the autoxidation of plastics, petrochemicals, and lipids.","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"11 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2023-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88573389","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}
{"title":"Arrayed and Entangled Silicon Nanowires Using Au Nanoparticle Catalysts Prepared by Pulsed Laser-induced Dewetting","authors":"Alison Joy Fulton, Yujun Shi","doi":"10.1139/cjc-2023-0047","DOIUrl":"https://doi.org/10.1139/cjc-2023-0047","url":null,"abstract":"The use of pulsed laser-induced dewetting (PLiD) is reported as a novel approach in the fabrication of Au nanoparticle (NP) catalytic arrays for the growth of Si nanowires (NWs) by chemical vapor deposition using SiCl4in the presence of H2. On polished Si substrates, PLiD generates Au NP catalysts with long-range order and narrow size distributions. It has been shown that the monodispersed distribution of Au NPs provides consistent diameter control of the as-grown Si NWs. A systematic exploration of the Si NW synthesis time, temperature and gas flow rates illustrates a level of tunability in terms of morphology, be it arrayed or entangled Si NWs, with varying experimental parameters. An investigation of the effect of growth temperature also showed that Si NWs can be synthesized at temperatures as low as 700 ⁰C when using SiCl4 as the precursor. The use of porous Si substrates enabled direct observation of the diameter-dependent growth due to the simultaneous presence of three Au NP size distributions. Growth from the small- and medium-size Au NP catalysts occurred first, followed by that from the large-size Au NPs, which was only observed at extended times or high SiCl4 flow rates. The delayed onset of growth from the large-size Au NPs is due to the longer time to achieve Si super-saturation of larger catalyst NPs. The morphology and diameter control of the as-grown Si NWs reported in this work makes this approach potentially useful towards applications such as nanoelectronics, sensors, and LIB electrodes depending on the desired morphology.","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"35 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2023-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77078559","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}
{"title":"Introduction to the WATOC Special Issue","authors":"R. J. Boyd, Alex Brown, G. DiLabio, S. Wetmore","doi":"10.1139/cjc-2023-0078","DOIUrl":"https://doi.org/10.1139/cjc-2023-0078","url":null,"abstract":"","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"9 2 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2023-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78329761","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}
Khandra Barrett, Matthew Dupuis, Anna Crossman, SunMin Park, T. George, C. Vogels, Jillian Rourke, Jason D. Masuda, S. Westcott
{"title":"Synthesis, characterization, and anticancer properties of iminopyridine platinum(II) complexes containing long aliphatic chains‡","authors":"Khandra Barrett, Matthew Dupuis, Anna Crossman, SunMin Park, T. George, C. Vogels, Jillian Rourke, Jason D. Masuda, S. Westcott","doi":"10.1139/cjc-2023-0031","DOIUrl":"https://doi.org/10.1139/cjc-2023-0031","url":null,"abstract":"A series of iminopyridine ligands were prepared from the condensation reaction of 6-methylpyridine-2-carboxaldehyde and long chain aliphatic primary amines. Square planar platinum(II) complexes were synthesized from the reaction of [PtCl2(η2-coe)]2 (coe = cis-cyclooctene) with two equivalents of ligand. The synthesis of the platinum compounds appears to go through a 5-coordinate trigonal pyramidal species where coe remains coordinated initially but eventually dissociates to afford the 4-coordinate complexes. Ligands and platinum complexes were characterized using multi-nuclear NMR and FT-IR spectroscopies as well as an X-ray diffraction study for the platinum complex derived from n-hexylamine. The cytotoxic properties of the platinum complexes against the ovarian cancer cell line SKOV-3 using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric method were examined. Relative cytotoxicities of the platinum complexes follow a trend of greater potency with increasing chain length against the SKOV-3 cell line, with the longest aliphatic hydrocarbon chain (C16) exhibiting anticancer effects comparable to that of cisplatin.","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"550 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2023-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77202532","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}