Pub Date : 2024-10-20DOI: 10.1080/10406638.2023.2276251
Research on synthetic methods for the preparation of oxazoles is an important issue among synthetic chemists because oxazole derivatives are structural subunits of various natural active products and are valuable synthetic and pharmaceutical precursors. In this research work, we constructed CuBr supported on surface of magnetic Fe3O4 nanoparticles modified with 6-(aminomethyl)nicotinic acid [Fe3O4@AMNA-CuBr nanocomposite] and evaluated its catalytic activity for the preparation of highly substituted oxazoles through one-pot three-component reactions of diphenylacetylene derivatives with aryl nitriles and water in PEG as the solvent. The results shown that the Fe3O4@AMNA-CuBr catalyst was used 8 times without significant decrease in catalytic activity. XRD and TEM analysis confirmed that the structure and morphology that the Fe3O4@AMNA-CuBr catalyst did not change after 8 runs.
{"title":"Fabrication of Fe3O4@AMNA-CuBr Nanocomposite as a Highly Efficient and Reusable Heterogenous Catalyst for Synthesis of Highly Substituted Oxazoles","authors":"","doi":"10.1080/10406638.2023.2276251","DOIUrl":"10.1080/10406638.2023.2276251","url":null,"abstract":"<div><div>Research on synthetic methods for the preparation of oxazoles is an important issue among synthetic chemists because oxazole derivatives are structural subunits of various natural active products and are valuable synthetic and pharmaceutical precursors. In this research work, we constructed CuBr supported on surface of magnetic Fe<sub>3</sub>O<sub>4</sub> nanoparticles modified with 6-(aminomethyl)nicotinic acid [Fe<sub>3</sub>O<sub>4</sub>@AMNA-CuBr nanocomposite] and evaluated its catalytic activity for the preparation of highly substituted oxazoles through one-pot three-component reactions of diphenylacetylene derivatives with aryl nitriles and water in PEG as the solvent. The results shown that the Fe<sub>3</sub>O<sub>4</sub>@AMNA-CuBr catalyst was used 8 times without significant decrease in catalytic activity. XRD and TEM analysis confirmed that the structure and morphology that the Fe<sub>3</sub>O<sub>4</sub>@AMNA-CuBr catalyst did not change after 8 runs.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135480599","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: 10.1080/10406638.2023.2276248
The compound 1,3-diphenyl-1H-pyrazole-4-carbaldehyde (1) was utilized as a fundamental component in the synthesis of novel N-phenyl pyrazole derivatives. Substituted N-phenyl pyrazole compounds including 2-cyano-3-(1,3-diphenyl-1H-pyrazol-4-yl)-N-Substituted-acrylamide derivatives (4a–h), 4-(hydrazineylidenemethyl)-1,3-diphenyl-1H-pyrazole (6) and 2-cyano-N'-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)-acetohydrazide (11) were obtained in moderate yields through the reaction of 1 with 2-cyano-N-substituted acetamide derivatives 3a–h, hydrazine hydrate, and cyanoacetohydrazide under basic-catalyzed conditions, respectively. Moreover, hydrazinyl-pyarzole 6 reacted with 4,5,6,7-tetrabromoisobenzofuran-1,3-dione (7) to afford 4,5,6,7-tetrabromo-2-(((1,3-diphenyl-1H-pyrazol-4-yl)methylene)amino)- isoindoline-1,3-dione (8). Furthermore, pyrazoloacetohydrazide 11 is condensed with salicylaldehyde derivatives 12a–e to give pyrazolochromene carbohydrazide derivatives 13a–e. Also, acetohydrazide 11 refluxed with N, N-dimethylformamide dimethyl acetal to produce 2-cyano-3-(dimethylamino)-N'-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)acrylohydrazide (15), which upon exposure to acidic conditions underwent cyclization to form 4-((dimethylamino)methylene)-6-(1,3-diphenyl-1H-pyrazol-4-yl)pyridazine-3,5(4H,6H)-dione (16). The newly synthesized compounds were identified and confirmed using elemental and spectral data analyses as IR, MS, 1H NMR, 13C NMR, and 2D NMR analysis (H-H COSY, HSQC, HMBC, and NOSEY), Also, DFT studies were done to prove the geometrical optimization and spatial distributions orbitals of compounds 4a and 11. The toxicity of N-phenylpyrazole compounds was tested against the corn leaf aphid (Rhopalosiphum maidis) and the mealy plum aphid (Hyalopterus pruni). Compounds 4c, 13c, and 13d were found to be the most potent to control the two insects compared with acetamiprid 20% SP recommended by the Ministry of Agriculture. The biochemical investigation of insects was studied to the most effective compounds on insects as well, and the toxicity of compounds 4c, 13c, and 13d was studied on the predators (Hippodamia variegata, Cydonia vicina isis, Cydonia vicina nilotica, and 4th instar larvae H. variegata) under laboratory conditions.
{"title":"Synthesis and Insecticidal Assessment of Some Innovative Heterocycles Incorporating a Pyrazole Moiety","authors":"","doi":"10.1080/10406638.2023.2276248","DOIUrl":"10.1080/10406638.2023.2276248","url":null,"abstract":"<div><div>The compound 1,3-diphenyl-1<em>H</em>-pyrazole-4-carbaldehyde (<strong>1</strong>) was utilized as a fundamental component in the synthesis of novel <em>N</em>-phenyl pyrazole derivatives. Substituted <em>N</em>-phenyl pyrazole compounds including 2-cyano-3-(1,3-diphenyl-1<em>H</em>-pyrazol-4-yl)-<em>N</em>-Substituted-acrylamide derivatives (<strong>4a</strong>–<strong>h</strong>), 4-(hydrazineylidenemethyl)-1,3-diphenyl-1<em>H</em>-pyrazole (<strong>6</strong>) and 2-cyano-<em>N'</em>-((1,3-diphenyl-1<em>H</em>-pyrazol-4-yl)methylene)-acetohydrazide (<strong>11</strong>) were obtained in moderate yields through the reaction of <strong>1</strong> with 2-cyano-<em>N</em>-substituted acetamide derivatives <strong>3a</strong>–<strong>h,</strong> hydrazine hydrate, and cyanoacetohydrazide under basic-catalyzed conditions, respectively. Moreover, hydrazinyl-pyarzole <strong>6</strong> reacted with 4,5,6,7-tetrabromoisobenzofuran-1,3-dione <strong>(7)</strong> to afford 4,5,6,7-tetrabromo-2-(((1,3-diphenyl-1<em>H</em>-pyrazol-4-yl)methylene)amino)- isoindoline-1,3-dione <strong>(8).</strong> Furthermore, pyrazoloacetohydrazide <strong>11</strong> is condensed with salicylaldehyde derivatives <strong>12a</strong>–<strong>e</strong> to give pyrazolochromene carbohydrazide derivatives <strong>13a</strong>–<strong>e</strong>. Also, acetohydrazide <strong>11</strong> refluxed with <em>N, N</em>-dimethylformamide dimethyl acetal to produce 2-cyano-3-(dimethylamino)-<em>N'</em>-((1,3-diphenyl-1<em>H</em>-pyrazol-4-yl)methylene)acrylohydrazide (<strong>15</strong>), which upon exposure to acidic conditions underwent cyclization to form 4-((dimethylamino)methylene)-6-(1,3-diphenyl-1<em>H</em>-pyrazol-4-yl)pyridazine-3,5(4<em>H</em>,6<em>H</em>)-dione (<strong>16</strong>). The newly synthesized compounds were identified and confirmed using elemental and spectral data analyses as IR, MS, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and 2D NMR analysis (H-H COSY, HSQC, HMBC, and NOSEY), Also, DFT studies were done to prove the geometrical optimization and spatial distributions orbitals of compounds <strong>4a</strong> and <strong>11</strong>. The toxicity of <em>N</em>-phenylpyrazole compounds was tested against the corn leaf aphid (<em>Rhopalosiphum maidis</em>) and the mealy plum aphid (<em>Hyalopterus pruni</em>). Compounds <strong>4c, 13c,</strong> and <strong>13d</strong> were found to be the most potent to control the two insects compared with acetamiprid 20% SP recommended by the Ministry of Agriculture. The biochemical investigation of insects was studied to the most effective compounds on insects as well, and the toxicity of compounds <strong>4c, 13c,</strong> and <strong>13d</strong> was studied on the predators (<em>Hippodamia variegata, Cydonia vicina isis, Cydonia vicina nilotica, and 4<sup>th</sup> instar larvae H. variegata</em>) under laboratory conditions.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135480602","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: 10.1080/10406638.2023.2270126
An efficient, facile, and catalyst-free one-pot multicomponent green strategy under neat or aqueous conditions has been developed to synthesize a series of spiro compounds that contain two biologically active pharmacophores, benzochromenes/thio-chromenes and indan-1,3-dione, in a single molecular framework. The desired Spiroindene-1,3dione-benzochromene/thio-chromene derivatives were yielded through a one-pot, three-component reaction between ninhydrin, substituted 1,3-dicarbonyls, and 2-naphthol/2-naphthalene thiol via the Knoevenagel–Michael cascade. The advances of this strategy include high product yields (94–82%), the formation of a new asymmetric center, cost-effectiveness, atom economy, and a straightforward workup procedure that does not require any additional purification steps.
{"title":"A Catalyst-Free One-Pot Multicomponent Green Strategy for the Synthesis of Spiroindene-1,3dione-Benzochromene/ Thio-Chromene Derivatives under Neat/Aqueous Conditions","authors":"","doi":"10.1080/10406638.2023.2270126","DOIUrl":"10.1080/10406638.2023.2270126","url":null,"abstract":"<div><div>An efficient, facile, and catalyst-free one-pot multicomponent green strategy under neat or aqueous conditions has been developed to synthesize a series of spiro compounds that contain two biologically active pharmacophores, benzochromenes/thio-chromenes and indan-1,3-dione, in a single molecular framework. The desired Spiroindene-1,3dione-benzochromene/thio-chromene derivatives were yielded through a one-pot, three-component reaction between ninhydrin, substituted 1,3-dicarbonyls, and 2-naphthol/2-naphthalene thiol <em>via</em> the Knoevenagel–Michael cascade. The advances of this strategy include high product yields (94–82%), the formation of a new asymmetric center, cost-effectiveness, atom economy, and a straightforward workup procedure that does not require any additional purification steps.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135869248","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: 10.1080/10406638.2023.2274476
The fullerene derivative hexagonal system is obtained from fullerene Cn and hexagonal system sticked by a common edge. The Merrifield–Simmons index of a graph G is defined as the total number of the independent sets of G. In this paper, we give the lower and larger bound of Merrifield–Simmons index of the fullerene derivative hexagonal system. Furthermore, we give two formulas of the Merrifield–Simmons index of the fullerene derivative hexagonal system C20 ⊗ l(n) and C20 ⊗ (l(n1), l(n2)).
{"title":"The Merrifield–Simmons Index of the Fullerene Derivative Hexagonal System","authors":"","doi":"10.1080/10406638.2023.2274476","DOIUrl":"10.1080/10406638.2023.2274476","url":null,"abstract":"<div><div>The fullerene derivative hexagonal system is obtained from fullerene <em>C<sub>n</sub></em> and hexagonal system sticked by a common edge. The Merrifield–Simmons index of a graph <em>G</em> is defined as the total number of the independent sets of <em>G</em>. In this paper, we give the lower and larger bound of Merrifield–Simmons index of the fullerene derivative hexagonal system. Furthermore, we give two formulas of the Merrifield–Simmons index of the fullerene derivative hexagonal system <em>C</em><sub>20</sub> ⊗ <em>l</em>(<em>n</em>) and <em>C</em><sub>20</sub> ⊗ (<em>l</em>(<em>n</em><sub>1</sub>), <em>l</em>(<em>n</em><sub>2</sub>)).</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135933109","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: 10.1080/10406638.2023.2270116
Bioactive molecules have been significantly known for therapeutic potential. One such molecule, garcinol, is a naturally occurring benzophenone derived from medicinally applicable many species of garcinia family, more specifically Garcinia indica. Diverse therapeutic applications of garcinol and Garcinia indica have been studied and documented in the literature. This review covers our previous study on garcinol and its analogs as target-specific potential anti-cancer and anti-inflammatory agents. Also, it accomplishes recent reports on the medicinal significance and challenges of garcinol and its analogs to develop as therapeutics.
{"title":"Anticancer and anti-Inflammatory Activities of Garcinol and Its Analogs","authors":"","doi":"10.1080/10406638.2023.2270116","DOIUrl":"10.1080/10406638.2023.2270116","url":null,"abstract":"<div><div>Bioactive molecules have been significantly known for therapeutic potential. One such molecule, garcinol, is a naturally occurring benzophenone derived from medicinally applicable many species of garcinia family, more specifically <em>Garcinia indica</em>. Diverse therapeutic applications of garcinol and <em>Garcinia indica</em> have been studied and documented in the literature. This review covers our previous study on garcinol and its analogs as target-specific potential anti-cancer and anti-inflammatory agents. Also, it accomplishes recent reports on the medicinal significance and challenges of garcinol and its analogs to develop as therapeutics.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136078739","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: 10.1080/10406638.2023.2272012
In view of the extremely important biological and medicinal properties of napthofurans, the synthesis of these heterocycles has fascinated the interest of medicinal and organic chemists. Keeping this in mind, we herein report the synthesis and antimicrobial evaluation of 4-N-aryl-naphtho[2,1-b]furo[3,2-d] pyrimidines 5 (a–l). Structures of these synthesized compounds were confirmed by spectral analysis like IR, NMR, and Mass spectrometry. The in vitro antimicrobial activities were reported for all the compounds 5 (a–l). The compounds 5e and 5f exhibited excellent antibacterial, antifungal, and antidermatophytic activities against tested pathogens at MIC 3.125, and 3.125 µg/mL, respectively. Furthermore, molecular docking studies of these compounds against S. aureus tyrosyl-tRNA synthetase (PDB ID: 1JIJ), S. aureus Gyrase (PDB ID: 2XCT), and SARS-CoV-2 Omicron (PDB ID: 7TOB), revealed the potential binding mode of the ligands to the site of the appropriate targets. Finally, drug-likeness and structure-activity relationship studies were also disclosed.
鉴于萘呋喃具有极其重要的生物和药用特性，这些杂环的合成引起了医药和有机化学家的兴趣。有鉴于此，我们在此报告 4-N-芳基萘并[2,1-b]呋喃并[3,2-d]嘧啶 5（a-l）的合成和抗菌评价。通过红外光谱、核磁共振和质谱等光谱分析确认了这些合成化合物的结构。报告了所有化合物 5（a-l）的体外抗菌活性。化合物 5e 和 5f 在 MIC 值分别为 3.125 微克/毫升和 3.125 微克/毫升的情况下，对测试病原体表现出卓越的抗菌、抗真菌和抗皮肤癣菌活性。此外，这些化合物针对金黄色葡萄球菌酪氨酰-tRNA 合成酶（PDB ID：1JIJ）、金黄色葡萄球菌回旋酶（PDB ID：2XCT）和 SARS-CoV-2 Omicron（PDB ID：7TOB）的分子对接研究揭示了配体与相应靶点的潜在结合模式。最后，还披露了药物相似性和结构-活性关系研究。
{"title":"Design, Synthesis, Spectral Analysis, Drug Likeness Prediction, and Molecular Docking Investigations of New Naphtho[2,1-b]Furan Encompassing Pyrimidines as Potential Antimicrobial Agents","authors":"","doi":"10.1080/10406638.2023.2272012","DOIUrl":"10.1080/10406638.2023.2272012","url":null,"abstract":"<div><div>In view of the extremely important biological and medicinal properties of napthofurans, the synthesis of these heterocycles has fascinated the interest of medicinal and organic chemists. Keeping this in mind, we herein report the synthesis and antimicrobial evaluation of 4-<em>N</em>-aryl-naphtho[2,1-<em>b</em>]furo[3,2-<em>d</em>] pyrimidines <strong>5 (a–l)</strong>. Structures of these synthesized compounds were confirmed by spectral analysis like IR, NMR, and Mass spectrometry. The <em>in vitro</em> antimicrobial activities were reported for all the compounds <strong>5 (a–l)</strong>. The compounds <strong>5e</strong> and <strong>5f</strong> exhibited excellent antibacterial, antifungal, and antidermatophytic activities against tested pathogens at MIC 3.125, and 3.125 µg/mL, respectively. Furthermore, molecular docking studies of these compounds against <em>S. aureus</em> tyrosyl-tRNA synthetase (<strong>PDB ID: 1JIJ</strong>), <em>S. aureus Gyrase</em> (<strong>PDB ID: 2XCT</strong>), and SARS-CoV-2 Omicron (<strong>PDB ID: 7TOB</strong>), revealed the potential binding mode of the ligands to the site of the appropriate targets. Finally, drug-likeness and structure-activity relationship studies were also disclosed.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136157106","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: 10.1080/10406638.2023.2270767
A series of benzoquinoline-based heterocycles was synthesized using 2-((3-chlorobenzo[f]quinolin-2-yl)methylene)hydrazine-1-carbothioamide as a key material via condensation of 3-chlorobenzo[f]quinoline-2-carbaldehyde with thiosemicarbazide. The titled thiosemicarbazone scaffold was conducted with some carbon electrophilic reagents such as acetic anhydride, chloroacetyl chloride, chloroacetic acid, 2-bromo-1-(3-nitrophenyl)ethan-1-one, 2-chloro-N-phenylacetamide, and dimethyl but-2-ynedioate to obtain triazole thione, imidazolone, thiazolidinone, and thiazole derivatives. On the other hand, hydrazinolysis of thiosemicarbazone did not proceed as expected but it gave the azine derivative. The in vitro antitumor and antioxidant activity of the synthesized compounds were screened and revealed that triazole thione and thiazole derivatives were the most potent.
{"title":"Synthesis, Cytotoxic, and Antioxidant Activity of Some Benzoquinoline-Based Heterocycles","authors":"","doi":"10.1080/10406638.2023.2270767","DOIUrl":"10.1080/10406638.2023.2270767","url":null,"abstract":"<div><div>A series of benzoquinoline-based heterocycles was synthesized using 2-((3-chlorobenzo[<em>f</em>]quinolin-2-yl)methylene)hydrazine-1-carbothioamide as a key material <em>via</em> condensation of 3-chlorobenzo[<em>f</em>]quinoline-2-carbaldehyde with thiosemicarbazide. The titled thiosemicarbazone scaffold was conducted with some carbon electrophilic reagents such as acetic anhydride, chloroacetyl chloride, chloroacetic acid, 2-bromo-1-(3-nitrophenyl)ethan-1-one, 2-chloro-<em>N</em>-phenylacetamide, and dimethyl but-2-ynedioate to obtain triazole thione, imidazolone, thiazolidinone, and thiazole derivatives. On the other hand, hydrazinolysis of thiosemicarbazone did not proceed as expected but it gave the azine derivative. The <em>in vitro</em> antitumor and antioxidant activity of the synthesized compounds were screened and revealed that triazole thione and thiazole derivatives were the most potent.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136234152","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: 10.1080/10406638.2023.2271112
Cancer is one of the leading causes of death. Quinoline is well known as one of the most potent pharmaceutically active scaffolds with remarkable pharmacological properties. So, in this article, we focused our efforts on the utility of the key scaffold N′-(1-(4-((7-chloroquinolin-4-yl)amino)phenyl)ethylidene)-2-cyanoacetohydrazide (5) in the synthesis of their novel heterocyclic compounds with potential as anticancer agents. Based on these preliminary screening results against four different human cancer cell lines (HepG2, MCF-7, HCT-116, and PC-3). Gratifyingly, compounds 9 and 16 showed the highest anticancer activity. Adenosine A2B receptor (A2BAR) was found to be the probable cellular target for both promising candidate compounds 9 and 16. The docking study of tested compounds 9 and 16 revealed that they bind more strongly to the A2BAR as compared to that of its co-crystalized ligand, suggesting that the anticancer activities of the tested compounds may be related to their ability to block the A2BAR receptor signaling in cancer cells, leading to cell death. Computational studies and countersurfaces of the novel compounds helped us clarify and interpret the compounds that have high and low anticancer activity. Noteworthy, the results of these studies are approximately compatible with what was done in vitro.
{"title":"Synthesis, Anti-Proliferative Activity, DFT and Docking Studies of Some Novel Chloroquinoline-Based Heterocycles","authors":"","doi":"10.1080/10406638.2023.2271112","DOIUrl":"10.1080/10406638.2023.2271112","url":null,"abstract":"<div><div>Cancer is one of the leading causes of death. Quinoline is well known as one of the most potent pharmaceutically active scaffolds with remarkable pharmacological properties. So, in this article, we focused our efforts on the utility of the key scaffold <em>N</em>′-(1-(4-((7-chloroquinolin-4-yl)amino)phenyl)ethylidene)-2-cyanoacetohydrazide (<strong>5</strong>) in the synthesis of their novel heterocyclic compounds with potential as anticancer agents. Based on these preliminary screening results against four different human cancer cell lines (HepG2, MCF-7, HCT-116, and PC-3). Gratifyingly, compounds <strong>9</strong> and <strong>16</strong> showed the highest anticancer activity. Adenosine A2B receptor (A2BAR) was found to be the probable cellular target for both promising candidate compounds <strong>9</strong> and <strong>16</strong>. The docking study of tested compounds <strong>9</strong> and <strong>16</strong> revealed that they bind more strongly to the A2BAR as compared to that of its co-crystalized ligand, suggesting that the anticancer activities of the tested compounds may be related to their ability to block the A2BAR receptor signaling in cancer cells, leading to cell death. Computational studies and countersurfaces of the novel compounds helped us clarify and interpret the compounds that have high and low anticancer activity. Noteworthy, the results of these studies are approximately compatible with what was done <em>in vitro</em>.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134909692","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: 10.1080/10406638.2023.2270123
The present study deals with the application of ab initio method using density functional theory (DFT) at M06-2X/6-311++G(d,p) to characterize the considered molecule completely. Though the anti-bacterial activity of the 3-(amino thiazolyl)quinolone derivatives was studied, the effects of intermolecular hydrogen bonding on chemical and biological processes remain unexplored or have not been thoroughly investigated so far. Investigations into non-covalent interactions were carried out using the reduced density gradient methodology and the quantum theory of atoms in molecules. An electron localization function was used to investigate the electronic vicinity of each atom in a molecule. Natural bond orbital analysis was used to determine the correlated stabilization energies for the intermolecular hydrogen bonds (H-bonds) that are responsible for the molecular stability of the dimer structure. The electrophilic and nucleophilic sites were predicted using the molecular electrostatic potential. The density of states and partial density of states were also used to represent the frontier molecular orbitals. The inhibitory activities of the compound with different classes of bacteria were also investigated using molecular docking simulation.
本研究采用 M06-2X/6-311++G(d,p)密度泛函理论 (DFT) 的 ab initio 方法，对所研究的分子进行了全面的表征。虽然对 3-(氨基噻唑基)喹诺酮衍生物的抗菌活性进行了研究，但分子间氢键对化学和生物过程的影响仍有待探索，或者说迄今为止尚未进行深入研究。对非共价相互作用的研究采用了还原密度梯度法和分子中原子的量子理论。利用电子定位功能研究了分子中每个原子的电子邻域。自然键轨道分析用于确定分子间氢键（H 键）的相关稳定能量，这些氢键是二聚体结构分子稳定性的原因。利用分子静电位预测了亲电和亲核位点。此外，还使用了状态密度和部分状态密度来表示前沿分子轨道。此外，还利用分子对接模拟研究了该化合物对不同种类细菌的抑制活性。
{"title":"Computational Analysis on Molecular Stability and Binding Affinity of 3-(Aminothiazolyl)Quinolone Derivative as Multitargeting Antibacterial Agents through Ab Initio Methods and Molecular Docking","authors":"","doi":"10.1080/10406638.2023.2270123","DOIUrl":"10.1080/10406638.2023.2270123","url":null,"abstract":"<div><div>The present study deals with the application of <em>ab initio</em> method using density functional theory (DFT) at M06-2X/6-311++G(d,p) to characterize the considered molecule completely. Though the anti-bacterial activity of the 3-(amino thiazolyl)quinolone derivatives was studied, the effects of intermolecular hydrogen bonding on chemical and biological processes remain unexplored or have not been thoroughly investigated so far. Investigations into non-covalent interactions were carried out using the reduced density gradient methodology and the quantum theory of atoms in molecules. An electron localization function was used to investigate the electronic vicinity of each atom in a molecule. Natural bond orbital analysis was used to determine the correlated stabilization energies for the intermolecular hydrogen bonds (H-bonds) that are responsible for the molecular stability of the dimer structure. The electrophilic and nucleophilic sites were predicted using the molecular electrostatic potential. The density of states and partial density of states were also used to represent the frontier molecular orbitals. The inhibitory activities of the compound with different classes of bacteria were also investigated using molecular docking simulation.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135218206","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: 10.1080/10406638.2023.2270119
The principle approach of the present study is directed to find an appropriate technique to create a new category of multi-fused compounds including furo[3,2-g]chromenes. The novel 2-acetyl-3-amino-6,10-dimethoxy-4-oxo-4H-difuro[3,2-c:3′,2′-g]chromene (3) was efficiently synthesized and utilized as a key intermediate to build a new class of multi-fused compounds namely furo[3′′,2′′:6′,7′]chromeno[3′,4′:4,5]furo[3,2-b]pyridines. Reaction of precursor 3 with active methylene nitriles yielded 2-amino-3-substituted furo[3′′,2′′:6′,7′]chromeno[3′,4′:4,5]furo[3,2-b]pyridines 4–9. Also, Friedländer's reaction of precursor 3 with active methylene ketones produced hetero-annulated furochromenofuropyridines 10–13. The synthesized compounds showed high inhibition action when tested in vitro against fungal strains, whereas compounds 3 and 8 showed good inhibitory effects against all types of tested microorganisms. The structures of the novel annulated compounds were inferred using spectral and analytical results.
{"title":"Design, Characterization and Antimicrobial Efficiency of Novel Annulated Furo[3'',2'':6',7']Chromeno[3',4':4,5]Furo [3,2-b]Pyridines","authors":"","doi":"10.1080/10406638.2023.2270119","DOIUrl":"10.1080/10406638.2023.2270119","url":null,"abstract":"<div><div>The principle approach of the present study is directed to find an appropriate technique to create a new category of multi-fused compounds including furo[3,2-<em>g</em>]chromenes. The novel 2-acetyl-3-amino-6,10-dimethoxy-4-oxo-4<em>H</em>-difuro[3,2-<em>c</em>:3′,2′-<em>g</em>]chromene (<strong>3</strong>) was efficiently synthesized and utilized as a key intermediate to build a new class of multi-fused compounds namely furo[3′′,2′′:6′,7′]chromeno[3′,4′:4,5]furo[3,2-<em>b</em>]pyridines. Reaction of precursor <strong>3</strong> with active methylene nitriles yielded 2-amino-3-substituted furo[3′′,2′′:6′,7′]chromeno[3′,4′:4,5]furo[3,2-<em>b</em>]pyridines <strong>4</strong>–<strong>9</strong>. Also, Friedländer's reaction of precursor <strong>3</strong> with active methylene ketones produced hetero-annulated furochromenofuropyridines <strong>10</strong>–<strong>13</strong>. The synthesized compounds showed high inhibition action when tested <em>in vitro</em> against fungal strains, whereas compounds <strong>3</strong> and <strong>8</strong> showed good inhibitory effects against all types of tested microorganisms. The structures of the novel annulated compounds were inferred using spectral and analytical results.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135778414","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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