Hissana Ather, Aysha A. Ali Theban, Fareeaa Ashar, Boshra Yahya A. Mohammad Essa, Yomna Ali A. Albarqi, Ghadah Saad A. Alshehri, and Renad Abdulhadi M. Almodawi
Two different series of azomethine derivatives of 1,3-substitued pyrazoles were synthesized from the intermediates 3-(4-chlorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde (3a) and 3-(furan-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde (3b) by the condensation of various substituted anilines. The intermediates were obtained from the appropriate phenylhydrazones via Vilsmeier–Haack reaction. The synthesized compounds were characterized by IR, 1H NMR and MASS spectral studies. Molecular docking studies results revealed that 4a7 and 4a8 showed highest binding affinity against fungal target secreted aspartic proteinase (Sap) 1 (2QZW) and compounds 4a8 and 4a5 showed highest binding affinity against bacterial target glucosamine-6-phosphate synthase (2VF5). In vitro antimicrobial activity of corresponding azomethine derivatives were assessed on Gram-positive and Gram-negative bacteria. Antifungal activity was assessed on Candida albicans. The results revealed that six out of fifteen compounds screened have shown good antimicrobial activity. Among them, 4a1, 4a4, 4a6 and 4a7 shown good inhibition against Candida albicans.
{"title":"Synthesis, Characterization, Molecular Docking Studies and Antimicrobial Activity of Azomethine Derivatives of 1,3-Substituted Pyrazoles","authors":"Hissana Ather, Aysha A. Ali Theban, Fareeaa Ashar, Boshra Yahya A. Mohammad Essa, Yomna Ali A. Albarqi, Ghadah Saad A. Alshehri, and Renad Abdulhadi M. Almodawi","doi":"10.3987/com-23-14877","DOIUrl":"https://doi.org/10.3987/com-23-14877","url":null,"abstract":"<span>Two different series of azomethine derivatives of 1,3-substitued pyrazoles were synthesized from the intermediates 3-(4-chlorophenyl)-1-phenyl-1</span><span>H</span><span>-pyrazole-4-carbaldehyde (</span><span>3a</span><span>) and 3-(furan-2-yl)-1-phenyl-1</span><span>H</span><span>-pyrazole-4-carbaldehyde (</span><span>3b</span><span>) by the condensation of various substituted anilines. The intermediates were obtained from the appropriate phenylhydrazones via Vilsmeier–Haack reaction. The synthesized compounds were characterized by IR, </span><span>1</span><span>H NMR and MASS spectral studies. Molecular docking studies results revealed that </span><span>4a7</span><span> and </span><span>4a8</span><span> showed highest binding affinity against fungal target secreted aspartic proteinase (Sap) 1 (</span><span>2QZW</span><span>) and compounds </span><span>4a8</span><span> and </span><span>4a5</span><span> showed highest binding affinity against bacterial target glucosamine-6-phosphate synthase </span><span>(2VF5</span><span>). </span><span>In vitro</span><span> antimicrobial activity of corresponding azomethine derivatives were assessed on Gram-positive and Gram-negative bacteria. Antifungal activity was assessed on </span><span>Candida albicans</span><span>. The results revealed that six out of fifteen compounds screened have shown good antimicrobial activity. Among them, </span><span>4a1</span><span>,</span><span> 4a4</span><span>,</span><span> 4a6 </span><span>and</span><span> 4a7</span><span> shown good inhibition against </span><span>Candida albicans</span><span>.</span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":"17 1","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138542650","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}
Tetra-N-allylation of glycoluril reactions followed by ring-closing metathesis has been used to generate new concave-shaped glycoluril derivatives. The advantages of this method are mild conditions, single-product formation and good yield.
{"title":"Synthesis of New Glycoluril Derivatives via Ring-Closing Metathesis","authors":"Sambasivarao Kotha and Deepshikha Singh","doi":"10.3987/com-23-14912","DOIUrl":"https://doi.org/10.3987/com-23-14912","url":null,"abstract":"<span>Tetra-</span><span>N</span><span>-allylation of glycoluril reactions followed by ring-closing metathesis has been used to generate new concave-shaped glycoluril derivatives. The advantages of this method are mild conditions, single-product formation and good yield.<br/></span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":"137 2","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138495427","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 highly diastereoselective one-pot synthesis generating a variety of 9,9-dimethyl-2,8-dioxabicyclo[3.3.1]nonane derivatives up to dr >19:1 has been established by the reaction of a 2’-methoxylchalcone with isobutyraldehyde via a spontaneous sequential one-pot Michael addition/aldol reaction/demethylative bicyclization in the presence of molecular iodine.
{"title":"Diastereoselective Synthesis of 2,8-Dioxabicyclo[3.3.1]Nonane Derivatives via I","authors":"-Mediated Cascade Reactions","doi":"10.3987/com-23-14891","DOIUrl":"https://doi.org/10.3987/com-23-14891","url":null,"abstract":"<span>The highly diastereoselective one-pot synthesis generating a variety of 9,9-dimethyl-2,8-dioxabicyclo[3.3.1]nonane derivatives up to </span><span>dr</span><span> >19:1 has been established by the reaction of a 2’-methoxylchalcone with isobutyraldehyde via a spontaneous sequential one-pot Michael addition/aldol reaction/demethylative bicyclization in the presence of molecular iodine. </span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":"137 3","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138495426","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}
A new chlorine-containing briarane-type diterpenoid, briastecholide N (1) was isolated from cultured octocoral Briareum stecheivia chemical screening. The structure of 1 was corroborated by 2D NMR experiments and confirmed backed by single-crystal X-ray diffraction analysis. The study found that 1 is capable of increasing the release of alkaline phosphatse (ALP) at 10 μM.
{"title":"Briastecholide N: a New Chlorine-Containing Briarane Diterpenoid Deriving from Cultured","authors":"You-Ying Chen, Yueh-Wen Liu, Su-Ying Chien, Yu-Cheng Chen, Fu-Ching Chiu, Po-Wei Huang, I-Li Su, Zhi-Hong Wen, Hung-Tsung Lee, and Ping-Jyun Sung","doi":"10.3987/com-23-14911","DOIUrl":"https://doi.org/10.3987/com-23-14911","url":null,"abstract":"<span>A new chlorine-containing briarane-type diterpenoid, briastecholide N (</span><span>1</span><span>) was isolated from cultured octocoral </span><span>Briareum stechei</span><span> </span><span>via</span><span> chemical screening. The structure of </span><span>1</span><span> was corroborated by 2D NMR experiments and confirmed backed by single-crystal X-ray diffraction analysis. The study found that </span><span>1</span><span> is capable of increasing the release of alkaline phosphatse (ALP) at </span><span>10 μM.</span><span><br/></span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":"137 4","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138495425","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}
11-O-Debenzoyltashironin is a highly oxygenated allo-cedrane sesquiterpenoid with seven contiguous chiral centers in a compact fused ring, and shows remarkable neurite extension activity. Total syntheses of the title and related compounds are reviewed.
{"title":"Synthetic Studies toward 11-","authors":"-Debenzoyltashironin","doi":"10.3987/rev-23-1018","DOIUrl":"https://doi.org/10.3987/rev-23-1018","url":null,"abstract":"<span>11-</span><span>O</span><span>-Debenzoyltashironin is a highly oxygenated </span><span>allo</span><span>-cedrane sesquiterpenoid with seven contiguous chiral centers in a compact fused ring, and shows remarkable neurite extension activity. Total syntheses of the title and related compounds are reviewed.</span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":"137 5","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138495424","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}
In the present investigation, a simple and flexible synthesis of a series of novel (E)-diethyl 2-styrylquinoline-3,4-dicarboxylates 3a-q has been achieved for the first time in good yields, involving one-pot sequential Arbuzov/Horner–Emmons reaction sequence using the newly-synthesized diethyl 2-(bromomethyl)quinoline-3,4-dicarboxylate as the substrate. The latter was obtained by NBS-mediated radical bromination reaction of the readily available diethyl 2-methylquinoline-3,4-dicarboxylate. A primary in vitro evaluation for their antiproliferative activity against human cancer cell lines (A549, HT29 and T24) revealed that the compound 3k with 3,4,5-trimethoxystyryl moiety represented the most active molecule against the tested A549 cell lines in this round of effort with the IC50 values of 2.38 µmol•L-1, being higher than the reference cisplatin.
{"title":"A Facile Synthesis and Anticancer Activity of (","authors":")-Diethyl 2-Styrylquinoline-3,4-dicarboxylates","doi":"10.3987/com-23-14909","DOIUrl":"https://doi.org/10.3987/com-23-14909","url":null,"abstract":"<span>In the present investigation, a simple and flexible synthesis of a series of novel (</span><span>E</span><span>)-diethyl 2-styrylquinoline-3,4-dicarboxylates </span><span>3a-q</span><span> has been achieved for the first time in good yields, involving one-pot sequential Arbuzov/Horner–Emmons reaction sequence using the newly-synthesized diethyl 2-(bromomethyl)quinoline-3,4-dicarboxylate as the substrate. The latter was obtained by NBS-mediated radical bromination reaction of the readily available diethyl 2-methylquinoline-3,4-dicarboxylate. A primary </span><span>in vitro </span><span>evaluation for their antiproliferative activity against human cancer cell lines (A549, HT29 and T24) revealed that the compound </span><span>3k</span><span> with 3,4,5-trimethoxystyryl moiety represented the most active molecule against the tested A549 cell lines in this round of effort with the IC</span><span>50</span><span> values of 2.38 µmol•L</span><span>-1</span><span>, being higher than the reference cisplatin.</span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":"138 1","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138495423","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}
– -Formyl- -nitroenamine reacts with phenylhydrazine to afford 1,1'-diphenyl-4,4'-bipyrazole. The unusual C–C bond formation was found to proceed in an ionic mechanism initiated by excess amount of hydrazine. This reaction is interesting from a viewpoint of synthetic chemistry because it simultaneously involves the construction of a pyrazole ring and the formation of a C–C bond under neutral conditions. -Formyl-
-b -甲酰基-b -硝基胺与苯肼反应生成1,1'-二苯基-4,4'-联吡唑。发现异常的C-C键形成是在过量的联氨引发的离子机制下进行的。从合成化学的角度来看，这个反应很有趣，因为在中性条件下，它同时涉及吡唑环的构造和C-C键的形成。b -甲酰基- b -硝基胺(1)具有多种功能，如a, b -不饱和醛，硝基烯和烯胺。推挽性质产生高度电子偏置的C-C双键，该双键可与亲核试剂或亲电试剂反应，形成多功能杂环框架
{"title":"Simultaneous Denitrative C–C Bond Formation and Construction of Pyrazole Ring Leading to 1,1'-Diphenyl-4,4'-bipyrazole","authors":"N. Nishiwaki, Kento Iwai, Nana Hatayama","doi":"10.3987/com-22-14772","DOIUrl":"https://doi.org/10.3987/com-22-14772","url":null,"abstract":"– -Formyl- -nitroenamine reacts with phenylhydrazine to afford 1,1'-diphenyl-4,4'-bipyrazole. The unusual C–C bond formation was found to proceed in an ionic mechanism initiated by excess amount of hydrazine. This reaction is interesting from a viewpoint of synthetic chemistry because it simultaneously involves the construction of a pyrazole ring and the formation of a C–C bond under neutral conditions. -Formyl-","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":"1 1","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"70398879","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}
Lei Yu, Haifeng Wang, Yuqing Sun, Ying Xu, Bing Liu, Ning Chen, Yingjie Liu, Dongxue Wang
{"title":"A New Compound Embeloside A with Hypoglycemic Potential from the Fruits of Embelia Oblongifolia Hemsl.","authors":"Lei Yu, Haifeng Wang, Yuqing Sun, Ying Xu, Bing Liu, Ning Chen, Yingjie Liu, Dongxue Wang","doi":"10.3987/com-22-14799","DOIUrl":"https://doi.org/10.3987/com-22-14799","url":null,"abstract":"","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":"1 1","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"70399215","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":"Organic Base-Catalyzed Cascade Reaction of Electron-Deficient Cyclopentadienone with Prop-2-yn-1-ols: Formation of 3-Methylenetetrahydrofuran Ring Condensed with Cyclopentenone","authors":"K. Yamaguchi","doi":"10.3987/com-23-14811","DOIUrl":"https://doi.org/10.3987/com-23-14811","url":null,"abstract":"procedure, bicyclic compounds","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":"1 1","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"70400838","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}
Longjia Yan, Yaqing Zuo, Kehui Chen, Ying Xu, Y. Le
{"title":"Synthesis and Biological Evaluation of 5-Methylpyrimidine Derivatives as Dual Inhibitors of EGFR and Src for Cancer Treatment","authors":"Longjia Yan, Yaqing Zuo, Kehui Chen, Ying Xu, Y. Le","doi":"10.3987/com-23-14824","DOIUrl":"https://doi.org/10.3987/com-23-14824","url":null,"abstract":"","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":"1 1","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"70401116","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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