Rita M.A. Borik, Ashraf H. F. Abd El-Wahab, Hany M. M. Hamed, Khatib S. Ismail
{"title":"香豆素的异芳香化第二部分:新型吡啶并[2,3-d]嘧啶衍生物的合成、反应和抗菌活性","authors":"Rita M.A. Borik, Ashraf H. F. Abd El-Wahab, Hany M. M. Hamed, Khatib S. Ismail","doi":"10.2174/0115701794290718240322054346","DOIUrl":null,"url":null,"abstract":"Background: Condensation of 3-acetyl-2H-chromen-2-one (1) with 2‐(4-methoxybenzylidene) malononitrile (2) in ammonium acetate/acetic acid or absolute ethanol/piperidine affords pyridine (3) and chromen-2-one (4) derivatives, respectively. background: Synthesis of a novel series of chromen-3-yl-pyridine derivatives were elucidated using spectroscopic techniques and elemental analysis. antimicrobial activities of compounds were then evaluated in vitro. Compound (E)-3-(3-(4-methoxyphenyl)acryloyl)-2H-chromen-2-one (4), was more effective against all five microorganisms and nicotinonitrile derivative 3 and 1,8-naphthyridin-2-yl)-2H-chromen-2-one derivative 14, while compounds 9, 10a-c, 11, 12 and 13 were moderate activity for antimicrobial activities. Methods: In this study, the reaction of 3 with an electrophilic reagent, namely, formic acid, acetic anhydride and formamide afforded the pyridopyrimidinone and pyridine derivatives (6- 9). Also, treatment of 3 with different aromatic aldehydes, carbon disulfide, NaN3/NH4Cl, 2- (4-methoxybenzylidene)malononitrile and acetophenone afforded pyridopyrimidinone, carbamodithioic acid, tetrazol-5-yl-chromen-2-one, 2H-chromen-2-one, and pyridine derivatives (10-14), respectively. Results: This study synthesized coumarins with antimicrobial activity and verified the structure and purity of the synthesized compounds using spectral data. Conclusion: The new compounds were evaluated in vitro for their antimicrobial activity against gram-positive bacteria (Staphylococcus aureus, Methicillin-resistant Staphylococcus aureus) and gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), in addition to fungus (Candida albicans). The investigated substances 3 and 14 presented good activity against MRSA, E. coli, P. aeruginosa and C. albicans, while compounds 9, 10a-c, 11, 12 and 13 exhibited good to moderate activity.","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2024-04-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Heteroaromatization of Coumarin Part II: Synthesis, Reactions, Antimicrobial Activities of Novel Pyrido[2,3-d]pyrimidine Derivatives\",\"authors\":\"Rita M.A. Borik, Ashraf H. F. Abd El-Wahab, Hany M. M. Hamed, Khatib S. Ismail\",\"doi\":\"10.2174/0115701794290718240322054346\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Background: Condensation of 3-acetyl-2H-chromen-2-one (1) with 2‐(4-methoxybenzylidene) malononitrile (2) in ammonium acetate/acetic acid or absolute ethanol/piperidine affords pyridine (3) and chromen-2-one (4) derivatives, respectively. background: Synthesis of a novel series of chromen-3-yl-pyridine derivatives were elucidated using spectroscopic techniques and elemental analysis. antimicrobial activities of compounds were then evaluated in vitro. Compound (E)-3-(3-(4-methoxyphenyl)acryloyl)-2H-chromen-2-one (4), was more effective against all five microorganisms and nicotinonitrile derivative 3 and 1,8-naphthyridin-2-yl)-2H-chromen-2-one derivative 14, while compounds 9, 10a-c, 11, 12 and 13 were moderate activity for antimicrobial activities. Methods: In this study, the reaction of 3 with an electrophilic reagent, namely, formic acid, acetic anhydride and formamide afforded the pyridopyrimidinone and pyridine derivatives (6- 9). Also, treatment of 3 with different aromatic aldehydes, carbon disulfide, NaN3/NH4Cl, 2- (4-methoxybenzylidene)malononitrile and acetophenone afforded pyridopyrimidinone, carbamodithioic acid, tetrazol-5-yl-chromen-2-one, 2H-chromen-2-one, and pyridine derivatives (10-14), respectively. Results: This study synthesized coumarins with antimicrobial activity and verified the structure and purity of the synthesized compounds using spectral data. Conclusion: The new compounds were evaluated in vitro for their antimicrobial activity against gram-positive bacteria (Staphylococcus aureus, Methicillin-resistant Staphylococcus aureus) and gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), in addition to fungus (Candida albicans). The investigated substances 3 and 14 presented good activity against MRSA, E. coli, P. aeruginosa and C. albicans, while compounds 9, 10a-c, 11, 12 and 13 exhibited good to moderate activity.\",\"PeriodicalId\":11101,\"journal\":{\"name\":\"Current organic synthesis\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2024-04-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Current organic synthesis\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.2174/0115701794290718240322054346\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current organic synthesis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.2174/0115701794290718240322054346","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Heteroaromatization of Coumarin Part II: Synthesis, Reactions, Antimicrobial Activities of Novel Pyrido[2,3-d]pyrimidine Derivatives
Background: Condensation of 3-acetyl-2H-chromen-2-one (1) with 2‐(4-methoxybenzylidene) malononitrile (2) in ammonium acetate/acetic acid or absolute ethanol/piperidine affords pyridine (3) and chromen-2-one (4) derivatives, respectively. background: Synthesis of a novel series of chromen-3-yl-pyridine derivatives were elucidated using spectroscopic techniques and elemental analysis. antimicrobial activities of compounds were then evaluated in vitro. Compound (E)-3-(3-(4-methoxyphenyl)acryloyl)-2H-chromen-2-one (4), was more effective against all five microorganisms and nicotinonitrile derivative 3 and 1,8-naphthyridin-2-yl)-2H-chromen-2-one derivative 14, while compounds 9, 10a-c, 11, 12 and 13 were moderate activity for antimicrobial activities. Methods: In this study, the reaction of 3 with an electrophilic reagent, namely, formic acid, acetic anhydride and formamide afforded the pyridopyrimidinone and pyridine derivatives (6- 9). Also, treatment of 3 with different aromatic aldehydes, carbon disulfide, NaN3/NH4Cl, 2- (4-methoxybenzylidene)malononitrile and acetophenone afforded pyridopyrimidinone, carbamodithioic acid, tetrazol-5-yl-chromen-2-one, 2H-chromen-2-one, and pyridine derivatives (10-14), respectively. Results: This study synthesized coumarins with antimicrobial activity and verified the structure and purity of the synthesized compounds using spectral data. Conclusion: The new compounds were evaluated in vitro for their antimicrobial activity against gram-positive bacteria (Staphylococcus aureus, Methicillin-resistant Staphylococcus aureus) and gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), in addition to fungus (Candida albicans). The investigated substances 3 and 14 presented good activity against MRSA, E. coli, P. aeruginosa and C. albicans, while compounds 9, 10a-c, 11, 12 and 13 exhibited good to moderate activity.
期刊介绍:
Current Organic Synthesis publishes in-depth reviews, original research articles and letter/short communications on all areas of synthetic organic chemistry i.e. asymmetric synthesis, organometallic chemistry, novel synthetic approaches to complex organic molecules, carbohydrates, polymers, protein chemistry, DNA chemistry, supramolecular chemistry, molecular recognition and new synthetic methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by experts who are internationally known for their eminent research contributions. The journal is essential reading to all synthetic organic chemists. Current Organic Synthesis should prove to be of great interest to synthetic chemists in academia and industry who wish to keep abreast with recent developments in key fields of organic synthesis.