{"title":"含苯甲醛肟的二茂铁羧酸酯的合成、结构表征及对癌细胞的初步细胞毒性研究。","authors":"Zhipeng Ruan, Jianping Yong, Le Li, Canzhong Lu, Olagoke Zacchaeus Olatunde","doi":"10.2174/0113816128391868250430081054","DOIUrl":null,"url":null,"abstract":"<p><strong>Aim: </strong>This study aimed to design and synthesize new ferrocene derivatives for the development of potent anticancer drugs.</p><p><strong>Background: </strong>Cancer is a major cause of death globally. Some small-molecule anticancer drugs have been used in clinics for the treatment of cancer, and several candidates are in different phases of clinical trials. However, cancer chemotherapy is still highly inadequate due to the side effects of the clinical drugs. Thus, developing novel anticancer drugs is essential.</p><p><strong>Methods: </strong>Firstly, we synthesized the R-substituted benzaldoxime intermediates (2a-2s) using R-substituted benzaldehyde (1a-1s) and hydroxylamine hydrochloride. Then, the target compounds (3a-3s) were synthesized using ferrocene carboxylic acid and R-substituted benzaldoxime intermediates (2a-2s) using DCC and DMAP as catalysts. The purity of the target compounds was determined by HPLC, and their structures were characterized using NMR, SC-XRD, and HR-ESIMS. Subsequently, the preliminary in vitro cytotoxicity against HeLa, A549, and A2780 cell lines was evaluated using MTT assay.</p><p><strong>Results: </strong>The results showed compound 3a to exhibit cytotoxicity against both HeLa and A549 cancer cell lines with IC50 values of 0.691 and 0.876 mM, respectively. Compound 3k showed potent cytotoxicity against HeLa cell lines with an IC50 value of 0.097 mM, compounds 3n and 3o exhibited potent cytotoxicity against three cancer cell lines, compound 3q showed potent cytotoxicity against HeLa cell lines with an IC50 value of 0.175 mM, while compound 3s exhibited potent cytotoxicity against HeLa and A549 cell lines with IC50 values of 0.470 and 0.298 mM, respectively.</p><p><strong>Conclusion: </strong>In this work, 19 new ferrocene derivatives containing R-substituted benzaldoxime moieties (3a- 3s) were synthesized and their structures were confirmed. Their cytotoxicity against HeLa, A549, and A2780 cell lines was tested, and the results showed that several compounds exhibited potent cytotoxicity against the tested cancer cell lines. This work developed a variety of ferrocene compounds, providing lead compounds based on ferrocene pharmacophore for the development of anticancer drugs.</p>","PeriodicalId":10845,"journal":{"name":"Current pharmaceutical design","volume":" ","pages":""},"PeriodicalIF":2.6000,"publicationDate":"2025-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis and Structural Characterization of Ferrocenyl Carboxylate Containing Benzaldoxime Moieties and Preliminary Cytotoxicity against Cancer Cell Lines.\",\"authors\":\"Zhipeng Ruan, Jianping Yong, Le Li, Canzhong Lu, Olagoke Zacchaeus Olatunde\",\"doi\":\"10.2174/0113816128391868250430081054\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><strong>Aim: </strong>This study aimed to design and synthesize new ferrocene derivatives for the development of potent anticancer drugs.</p><p><strong>Background: </strong>Cancer is a major cause of death globally. Some small-molecule anticancer drugs have been used in clinics for the treatment of cancer, and several candidates are in different phases of clinical trials. However, cancer chemotherapy is still highly inadequate due to the side effects of the clinical drugs. Thus, developing novel anticancer drugs is essential.</p><p><strong>Methods: </strong>Firstly, we synthesized the R-substituted benzaldoxime intermediates (2a-2s) using R-substituted benzaldehyde (1a-1s) and hydroxylamine hydrochloride. Then, the target compounds (3a-3s) were synthesized using ferrocene carboxylic acid and R-substituted benzaldoxime intermediates (2a-2s) using DCC and DMAP as catalysts. The purity of the target compounds was determined by HPLC, and their structures were characterized using NMR, SC-XRD, and HR-ESIMS. Subsequently, the preliminary in vitro cytotoxicity against HeLa, A549, and A2780 cell lines was evaluated using MTT assay.</p><p><strong>Results: </strong>The results showed compound 3a to exhibit cytotoxicity against both HeLa and A549 cancer cell lines with IC50 values of 0.691 and 0.876 mM, respectively. Compound 3k showed potent cytotoxicity against HeLa cell lines with an IC50 value of 0.097 mM, compounds 3n and 3o exhibited potent cytotoxicity against three cancer cell lines, compound 3q showed potent cytotoxicity against HeLa cell lines with an IC50 value of 0.175 mM, while compound 3s exhibited potent cytotoxicity against HeLa and A549 cell lines with IC50 values of 0.470 and 0.298 mM, respectively.</p><p><strong>Conclusion: </strong>In this work, 19 new ferrocene derivatives containing R-substituted benzaldoxime moieties (3a- 3s) were synthesized and their structures were confirmed. Their cytotoxicity against HeLa, A549, and A2780 cell lines was tested, and the results showed that several compounds exhibited potent cytotoxicity against the tested cancer cell lines. This work developed a variety of ferrocene compounds, providing lead compounds based on ferrocene pharmacophore for the development of anticancer drugs.</p>\",\"PeriodicalId\":10845,\"journal\":{\"name\":\"Current pharmaceutical design\",\"volume\":\" \",\"pages\":\"\"},\"PeriodicalIF\":2.6000,\"publicationDate\":\"2025-05-08\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Current pharmaceutical design\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://doi.org/10.2174/0113816128391868250430081054\",\"RegionNum\":4,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"PHARMACOLOGY & PHARMACY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current pharmaceutical design","FirstCategoryId":"3","ListUrlMain":"https://doi.org/10.2174/0113816128391868250430081054","RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"PHARMACOLOGY & PHARMACY","Score":null,"Total":0}
Synthesis and Structural Characterization of Ferrocenyl Carboxylate Containing Benzaldoxime Moieties and Preliminary Cytotoxicity against Cancer Cell Lines.
Aim: This study aimed to design and synthesize new ferrocene derivatives for the development of potent anticancer drugs.
Background: Cancer is a major cause of death globally. Some small-molecule anticancer drugs have been used in clinics for the treatment of cancer, and several candidates are in different phases of clinical trials. However, cancer chemotherapy is still highly inadequate due to the side effects of the clinical drugs. Thus, developing novel anticancer drugs is essential.
Methods: Firstly, we synthesized the R-substituted benzaldoxime intermediates (2a-2s) using R-substituted benzaldehyde (1a-1s) and hydroxylamine hydrochloride. Then, the target compounds (3a-3s) were synthesized using ferrocene carboxylic acid and R-substituted benzaldoxime intermediates (2a-2s) using DCC and DMAP as catalysts. The purity of the target compounds was determined by HPLC, and their structures were characterized using NMR, SC-XRD, and HR-ESIMS. Subsequently, the preliminary in vitro cytotoxicity against HeLa, A549, and A2780 cell lines was evaluated using MTT assay.
Results: The results showed compound 3a to exhibit cytotoxicity against both HeLa and A549 cancer cell lines with IC50 values of 0.691 and 0.876 mM, respectively. Compound 3k showed potent cytotoxicity against HeLa cell lines with an IC50 value of 0.097 mM, compounds 3n and 3o exhibited potent cytotoxicity against three cancer cell lines, compound 3q showed potent cytotoxicity against HeLa cell lines with an IC50 value of 0.175 mM, while compound 3s exhibited potent cytotoxicity against HeLa and A549 cell lines with IC50 values of 0.470 and 0.298 mM, respectively.
Conclusion: In this work, 19 new ferrocene derivatives containing R-substituted benzaldoxime moieties (3a- 3s) were synthesized and their structures were confirmed. Their cytotoxicity against HeLa, A549, and A2780 cell lines was tested, and the results showed that several compounds exhibited potent cytotoxicity against the tested cancer cell lines. This work developed a variety of ferrocene compounds, providing lead compounds based on ferrocene pharmacophore for the development of anticancer drugs.
期刊介绍：
Current Pharmaceutical Design publishes timely in-depth reviews and research articles from leading pharmaceutical researchers in the field, covering all aspects of current research in rational drug design. Each issue is devoted to a single major therapeutic area guest edited by an acknowledged authority in the field.
Each thematic issue of Current Pharmaceutical Design covers all subject areas of major importance to modern drug design including: medicinal chemistry, pharmacology, drug targets and disease mechanism.
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