Pub Date : 2024-10-20DOI: 10.1080/10406638.2023.2276238
Sulfamic acid-functionalized Zr-MOF-NH2 was used as an active acidic metal-organic framework catalyst for the synthesis of new 6-amino-5-(4-amino-2-oxo-2H-chromen) (AAOC) analogs via a one-step reaction between 2-hydroxy-5-(aryldiazenyl)benzaldehyde, 4-aminocumarin, and 6-amino-1,3-dimethyluracil or 6-amino-uracil in EtOH under reflux conditions. The resulting UiO-66-NHSO3H was characterized by employing different types of spectroscopic techniques such as XRD, BET, FESEM, EDS, FT-IR, and TGA. In addition, ease of procedure, short reaction time, and recycling of the catalyst without much change in the catalytic activity are the advantages of this method.
{"title":"Sulfamic Acid Supported Zr-MOF: An Effective Catalyst for One-Step Synthesis of Novel 6-Amino-5-(4-Amino-2-Oxo-2H-Chromen) Analogs","authors":"","doi":"10.1080/10406638.2023.2276238","DOIUrl":"10.1080/10406638.2023.2276238","url":null,"abstract":"<div><div>Sulfamic acid-functionalized Zr-MOF-NH<sub>2</sub> was used as an active acidic metal-organic framework catalyst for the synthesis of new 6-amino-5-(4-amino-2-oxo-2<em>H</em>-chromen) (AAOC) analogs <em>via</em> a one-step reaction between 2-hydroxy-5-(aryldiazenyl)benzaldehyde, 4-aminocumarin, and 6-amino-1,3-dimethyluracil or 6-amino-uracil in EtOH under reflux conditions. The resulting UiO-66-NHSO<sub>3</sub>H was characterized by employing different types of spectroscopic techniques such as XRD, BET, FESEM, EDS, FT-IR, and TGA. In addition, ease of procedure, short reaction time, and recycling of the catalyst without much change in the catalytic activity are the advantages of this method.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 9","pages":"Pages 6213-6231"},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135873905","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-20DOI: 10.1080/10406638.2023.2273884
The peculiar one-pot reaction involving Carbaldehydes, malononitrile, and indane 1,3-dione was used to explain the alternative synthesis of indeno-pyridine and indeno-pyran derivatives. The synthesis of indeno-pyridine or indeno-pyran derivatives has been examined based on an effective modification in the Michael addition of indane 1,3-dione or malononitrile on Knoevenagel product throughout the reaction process. The reaction required up to 30 min to complete utilizing CuO nanoparticles (NPs) in water at room temperature, making the approach innovative and environmentally benign. All of the produced compounds have been validated using spectroscopic data. And they were then tested for their antimicrobial activities. All tested compounds showing greater efficacy against Sertaconazol and Chloramphenicol.
{"title":"Synthesis and Biological Activity of Indeno-Pyridine and Indeno-Pyran Derivatives in One-Pot Reaction","authors":"","doi":"10.1080/10406638.2023.2273884","DOIUrl":"10.1080/10406638.2023.2273884","url":null,"abstract":"<div><div>The peculiar one-pot reaction involving Carbaldehydes, malononitrile, and indane 1,3-dione was used to explain the alternative synthesis of indeno-pyridine and indeno-pyran derivatives. The synthesis of indeno-pyridine or indeno-pyran derivatives has been examined based on an effective modification in the Michael addition of indane 1,3-dione or malononitrile on Knoevenagel product throughout the reaction process. The reaction required up to 30 min to complete utilizing CuO nanoparticles (NPs) in water at room temperature, making the approach innovative and environmentally benign. All of the produced compounds have been validated using spectroscopic data. And they were then tested for their antimicrobial activities. All tested compounds showing greater efficacy against Sertaconazol and Chloramphenicol.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 9","pages":"Pages 6115-6124"},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135475279","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-20DOI: 10.1080/10406638.2023.2270124
Developing multicomponent reactions in a cascade manner is a long-standing interest to chemists to access valuable organic materials more economically. Herein, we described a simple, economically viable method for synthesizing 11H-benzo[b]fluoren-11-one, a dual-state organic fluorophore, starting from ortho phthalaldehyde (OPA) in DMSO solvent. Simple and rapid product isolation, high atom economy, short reaction time, and scalability are the attractive features of the method. During the optimization of the reaction condition, we observed that DMSO, DMF, and acetone served one carbon to form the said compound besides their role as solvents. A plausible mechanism has been proposed based on the evidence obtained from LCMS analysis of the incomplete reaction mixture.
{"title":"Synthesis of 11H-Benzo[b]Fluoren-11-One via an Unprecedented Cascade Reaction of O-Phthaladehyde","authors":"","doi":"10.1080/10406638.2023.2270124","DOIUrl":"10.1080/10406638.2023.2270124","url":null,"abstract":"<div><div>Developing multicomponent reactions in a cascade manner is a long-standing interest to chemists to access valuable organic materials more economically. Herein, we described a simple, economically viable method for synthesizing 11H-benzo[<em>b</em>]fluoren-11-one, a dual-state organic fluorophore, starting from ortho phthalaldehyde (OPA) in DMSO solvent. Simple and rapid product isolation, high atom economy, short reaction time, and scalability are the attractive features of the method. During the optimization of the reaction condition, we observed that DMSO, DMF, and acetone served one carbon to form the said compound besides their role as solvents. A plausible mechanism has been proposed based on the evidence obtained from LCMS analysis of the incomplete reaction mixture.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 9","pages":"Pages 5851-5858"},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135618616","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-20DOI: 10.1080/10406638.2023.2270117
The study aimed to design a novel nanocatalyst, 1,3-Benzothiazole-2,5-diamine supported on nanocellulose (BTDA@CNC), which was characterized using various analytical techniques such as FT-IR, XRD, TGA, SEM, TEM, and CHN. The nanocatalyst was utilized for the synthesis of 1,2,4-triazole derivatives through a simple and efficient three-component reaction between aldehyde derivatives, semicarbazide, and ethanol. The protocol offered advantages such as a simple procedure, high yields, short reaction time, and an environmentally benign method. The nanocatalyst could be readily separated by filter and reused without significant loss of its catalytic efficiency. The synthesized compounds showed moderate activity against both Gram-positive and Gram-negative bacteria, and the antifungal properties of the candida albicans synthesized derivatives were also investigated.
{"title":"Synthesis of 1,2,4-Triazole Derivatives via 1,3-Benzothiazole-2,5-Diamine Supported on Nanocellulose as Novel Recyclable Nano Catalyst","authors":"","doi":"10.1080/10406638.2023.2270117","DOIUrl":"10.1080/10406638.2023.2270117","url":null,"abstract":"<div><div>The study aimed to design a novel nanocatalyst, 1,3-Benzothiazole-2,5-diamine supported on nanocellulose (BTDA@CNC), which was characterized using various analytical techniques such as FT-IR, XRD, TGA, SEM, TEM, and CHN. The nanocatalyst was utilized for the synthesis of 1,2,4-triazole derivatives through a simple and efficient three-component reaction between aldehyde derivatives, semicarbazide, and ethanol. The protocol offered advantages such as a simple procedure, high yields, short reaction time, and an environmentally benign method. The nanocatalyst could be readily separated by filter and reused without significant loss of its catalytic efficiency. The synthesized compounds showed moderate activity against both Gram-positive and Gram-negative bacteria, and the antifungal properties of the candida albicans synthesized derivatives were also investigated.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 9","pages":"Pages 5784-5796"},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135888457","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-20DOI: 10.1080/10406638.2023.2273885
A series of new 5-(trifluoromethyl)-benzo[d]imidazole linked N-phenylamide compounds was designed and synthesized using 1-chloro-2-nitro-4-(trifluoromethyl)benzene as raw material via five steps. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. The bioassay results indicated that some of them exhibited moderate insecticidal activity (>50% inhibition) against Mythimna separata and Nilaparvata lugens at 500 μg/mL.
{"title":"Synthesis and Insecticidal Activity of Novel Trifluoromethylbenzimidazole Linked N-Phenylamide Compounds","authors":"","doi":"10.1080/10406638.2023.2273885","DOIUrl":"10.1080/10406638.2023.2273885","url":null,"abstract":"<div><div>A series of new 5-(trifluoromethyl)-benzo[<em>d</em>]imidazole linked <em>N</em>-phenylamide compounds was designed and synthesized using 1-chloro-2-nitro-4-(trifluoromethyl)benzene as raw material <em>via</em> five steps. Their structures were confirmed by <sup>1</sup>H NMR, <sup>13</sup>C NMR and HRMS. The bioassay results indicated that some of them exhibited moderate insecticidal activity (>50% inhibition) against <em>Mythimna separata</em> and <em>Nilaparvata lugens</em> at 500 μg/mL.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 9","pages":"Pages 6125-6135"},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136377140","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-20DOI: 10.1080/10406638.2023.2270114
Herein, fluorinated thioureas with various substituents (F1-F3) were synthesized and characterized spectroscopically and analytically to investigate their properties as antibacterial agents. Prior to experimental studies, Density Functional Theory (DFT) modeling was performed at B3LYP/6-31G (d,p) to complement and offer comparative overview with the experimental findings. With regards to all theoretical analyses, the Frontier Molecular Orbital (FMO) demonstrated a desirable low HOMO-LUMO gap for all three designated derivatives, particularly F1 (1.60 eV), which is consistent with its GCRDs values, namely its high electronegativity and low hardness values that corresponds to low LUMO energy, suggesting higher bacterial activity. Agar diffusion assay was used for the preliminary screening of in-vitro antibacterial activity against pathogenic Gram-positive and Gram-negative bacteria. All three derivates successfully inhibit at least two bacterial strains (B. cereus, S. aureus), but none were able to penetrate into E. coli. The highest inhibition rate was exhibited by F3 at 33.33 ± 0.71% against S. aureus, whilst F1 only managed to gain 29.63 ± 0.00% of inhibition rate for the same bacterium. Meanwhile, the lowest penetration rate was recorded at 1.53 ± 0.35% by F2 against B. cereus.
{"title":"Computational and Experimental Investigation of Antibacterial Properties of Some Fluorinated Thioureas","authors":"","doi":"10.1080/10406638.2023.2270114","DOIUrl":"10.1080/10406638.2023.2270114","url":null,"abstract":"<div><div>Herein, fluorinated thioureas with various substituents (<strong>F1-F3</strong>) were synthesized and characterized spectroscopically and analytically to investigate their properties as antibacterial agents. Prior to experimental studies, Density Functional Theory (DFT) modeling was performed at B3LYP/6-31G (d,p) to complement and offer comparative overview with the experimental findings. With regards to all theoretical analyses, the Frontier Molecular Orbital (FMO) demonstrated a desirable low HOMO-LUMO gap for all three designated derivatives, particularly <strong>F1</strong> (1.60 eV), which is consistent with its GCRDs values, namely its high electronegativity and low hardness values that corresponds to low LUMO energy, suggesting higher bacterial activity. Agar diffusion assay was used for the preliminary screening of <em>in</em>-<em>vitro</em> antibacterial activity against pathogenic Gram-positive and Gram-negative bacteria. All three derivates successfully inhibit at least two bacterial strains (<em>B. cereus</em>, <em>S. aureus</em>), but none were able to penetrate into <em>E. coli</em>. The highest inhibition rate was exhibited by <strong>F3</strong> at 33.33 ± 0.71% against <em>S. aureus</em>, whilst <strong>F1</strong> only managed to gain 29.63 ± 0.00% of inhibition rate for the same bacterium. Meanwhile, the lowest penetration rate was recorded at 1.53 ± 0.35% by <strong>F2</strong> against <em>B. cereus</em>.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 9","pages":"Pages 5749-5767"},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134973242","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-20DOI: 10.1080/10406638.2023.2270121
This study investigated the level of polycyclic aromatic hydrocarbons (PAHs) in seafood, namely, C. sapidus (Crab), P. mollusca (Mollusc), Cambarus sp. (Crayfish), Caridea (Shrimp) from Orashi River in Omoku, Rivers State of Nigeria. The PAHs in the samples were determined by gas chromatography–mass spectrometry. There was no variation in the relative level of PAHs congeners. The mean concentrations of individual PAHs decreased in the order: D(a,h)ant > Pyr > Fluth > B(g,h,i)p > B(a)A > B(b)f > Ind (1,2, 3)pyr > B(a)pyr > Chr > B(k)flu > Ant > Flu > Phen > Aceth > Ace > Nap. Anthracene contributed the highest PAHs values, with 51.685% in Caridea. The EDI values of B(a)P, Ʃ2PAH, Ʃ4PAH, Ʃ8PAH across all the seafood were within the maximum permissible limit recommended by EFSA; this suggests that the accumulation of the PAHs in the body system are within the permitted levels. Similarly, the HI of the PAHs congeners obtained from this study were less than 1 which is the safe limit recommended by USEPA. The total Excess Cancer Risk of the PAHs congeners obtained from this study exceeded the permissible maximum limit recommended by USEPA. This study suggests that the water may be contaminated with PAHs which have the tendency to cause non-carcinogenic and carcinogenic risk because of frequent and high consumption of seafoods.
{"title":"Assessment of Polycyclic Aromatic Hydrocarbons (PAHs) in Seafood from Orashi River in Omoku, Rivers State of Nigeria and Human Health Risk Assessment","authors":"","doi":"10.1080/10406638.2023.2270121","DOIUrl":"10.1080/10406638.2023.2270121","url":null,"abstract":"<div><div>This study investigated the level of polycyclic aromatic hydrocarbons (PAHs) in seafood, namely, <em>C. sapidus</em> (Crab), <em>P. mollusca</em> (Mollusc), <em>Cambarus sp.</em> (Crayfish), <em>Caridea</em> (Shrimp) from Orashi River in Omoku, Rivers State of Nigeria. The PAHs in the samples were determined by gas chromatography–mass spectrometry. There was no variation in the relative level of PAHs congeners. The mean concentrations of individual PAHs decreased in the order: D(a,h)ant > Pyr > Fluth > B(g,h,i)p > B(a)A > B(b)f > Ind (1,2, 3)pyr > B(a)pyr > Chr > B(k)flu > Ant > Flu > Phen > Aceth > Ace > Nap. Anthracene contributed the highest PAHs values, with 51.685% in <em>Caridea</em>. The EDI values of B(a)P, Ʃ<sub>2</sub>PAH, Ʃ<sub>4</sub>PAH, Ʃ<sub>8</sub>PAH across all the seafood were within the maximum permissible limit recommended by EFSA; this suggests that the accumulation of the PAHs in the body system are within the permitted levels. Similarly, the HI of the PAHs congeners obtained from this study were less than 1 which is the safe limit recommended by USEPA. The total Excess Cancer Risk of the PAHs congeners obtained from this study exceeded the permissible maximum limit recommended by USEPA. This study suggests that the water may be contaminated with PAHs which have the tendency to cause non-carcinogenic and carcinogenic risk because of frequent and high consumption of seafoods.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 9","pages":"Pages 5811-5828"},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135169403","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-20DOI: 10.1080/10406638.2023.2273886
The one-pot four-component condensation of benzoic acid (R1), aniline (R2), benzaldehyde (R3), and 2-isocyano-2-methylpropane was investigated at the B3LYP/6-311G** level to explore the reaction mechanism as a theoretical study. All routes were studied and structure of intermediates (IM) was optimized and all of the respective transition states (TS) were found. The calculation results proved that the proposed mechanism consists of eight steps that rate determining the state is nucleophilic attack of isocyanide to benzaldehyde.
{"title":"Finding the Best Proposed Mechanism for Ugi Multi-Component Reaction by DFT Study","authors":"","doi":"10.1080/10406638.2023.2273886","DOIUrl":"10.1080/10406638.2023.2273886","url":null,"abstract":"<div><div>The one-pot four-component condensation of benzoic acid (R1), aniline (R2), benzaldehyde (R3), and 2-isocyano-2-methylpropane was investigated at the B3LYP/6-311G** level to explore the reaction mechanism as a theoretical study. All routes were studied and structure of intermediates (IM) was optimized and all of the respective transition states (TS) were found. The calculation results proved that the proposed mechanism consists of eight steps that rate determining the state is nucleophilic attack of isocyanide to benzaldehyde.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 9","pages":"Pages 6136-6151"},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135391700","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-20DOI: 10.1080/10406638.2023.2272013
A new and efficient manufacturing technology is disclosed in the present work for the preparation of benzoylphenylureas and their key intermediates. This new route significantly reduces the number of reaction steps from six to three, resulting in a streamlined process. Additionally, the overall yield is increased from 56% to over 69%. Compared to the original process route, the new manufacturing route has the advantages of fewer chemical steps, higher overall yield, less process safety hazard and environmental impact. Considering these factors, the new manufacturing route exhibits considerable potential for industrialization.
{"title":"Development of a New Manufacturing Route for Benzoylphenylureas and Their Key Intermediates","authors":"","doi":"10.1080/10406638.2023.2272013","DOIUrl":"10.1080/10406638.2023.2272013","url":null,"abstract":"<div><div>A new and efficient manufacturing technology is disclosed in the present work for the preparation of benzoylphenylureas and their key intermediates. This new route significantly reduces the number of reaction steps from six to three, resulting in a streamlined process. Additionally, the overall yield is increased from 56% to over 69%. Compared to the original process route, the new manufacturing route has the advantages of fewer chemical steps, higher overall yield, less process safety hazard and environmental impact. Considering these factors, the new manufacturing route exhibits considerable potential for industrialization.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 9","pages":"Pages 6064-6075"},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135413729","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-20DOI: 10.1080/10406638.2023.2266549
In this elucidation, we focused on the synthesis of isonicotinic heterocyclic molecules through reaction of isonicotinic acid hydrazide with phthalic anhydride, which produced an excellent yield of the equivalent N-(1,3-dioxoisoindolin-2-yl)isonicotinamide (3), and isonicotinic acid hydrazide can react easily with different aldehydes to form derivatives of Schiff bases. Furthermore, the reactivity of hydrazide with CS2 which cyclized in the presence of acid to give the corresponding 1,3,4-oxadiazole in derivative 7, and the presence of NH2NH2 produced a 1H-1,2,4-triazole derivative 9 that readily reacted with phenacyl bromide with the elimination of -HBr to produce 6-phenyl-3-(pyridine-4-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine (11). Hydrazide 1 reacts readily with many methylene compounds to produce a wide range of heterocycles. The presence of each produced heterocyclic was confirmed by spectral analysis investigation. Moreover, the synthesized compounds exhibited antimicrobial and antitumor activity against HepG2 liver tumor cells and neck squamous cell carcinoma (HNSCC) cancer cells, and the result was confirmed with different proteins through molecular docking simulation. Moreover, the optimization of the nicotinic compounds with DFT/B3LYP-631(G) basis set and determination of their physical descriptors correlated for its biological evaluation.
{"title":"Numerous Heterocyclic Compounds with an Isonicotinic Moiety have Been Studied for Their Synthesis, Antibacterial, Anticancer, Docking Simulation, and DFT Characteristics","authors":"","doi":"10.1080/10406638.2023.2266549","DOIUrl":"10.1080/10406638.2023.2266549","url":null,"abstract":"<div><div>In this elucidation, we focused on the synthesis of isonicotinic heterocyclic molecules through reaction of isonicotinic acid hydrazide with phthalic anhydride, which produced an excellent yield of the equivalent <em>N</em>-(1,3-dioxoisoindolin-2-yl)isonicotinamide (3), and isonicotinic acid hydrazide can react easily with different aldehydes to form derivatives of Schiff bases. Furthermore, the reactivity of hydrazide with CS<sub>2</sub> which cyclized in the presence of acid to give the corresponding 1,3,4-oxadiazole in derivative <strong>7</strong>, and the presence of NH<sub>2</sub>NH<sub>2</sub> produced a 1<em>H</em>-1,2,4-triazole derivative <strong>9</strong> that readily reacted with phenacyl bromide with the elimination of -HBr to produce 6-phenyl-3-(pyridine-4-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine (<strong>11</strong>). Hydrazide 1 reacts readily with many methylene compounds to produce a wide range of heterocycles. The presence of each produced heterocyclic was confirmed by spectral analysis investigation. Moreover, the synthesized compounds exhibited antimicrobial and antitumor activity against HepG2 liver tumor cells and neck squamous cell carcinoma (HNSCC) cancer cells, and the result was confirmed with different proteins through molecular docking simulation. Moreover, the optimization of the nicotinic compounds with DFT/B3LYP-631(G) basis set and determination of their physical descriptors correlated for its biological evaluation.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 9","pages":"Pages 5707-5748"},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135766624","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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