{"title":"具有治疗潜力和催化作用的 1,10-菲罗啉基四氮杂大环配体及其镍配合物的合成、表征和抗氧化筛选","authors":"Emmanuel C. Ohaekenyem, Ikenna Onyido","doi":"10.1515/pac-2024-0212","DOIUrl":null,"url":null,"abstract":"In this study, we present a synthetic route for the preparation of a novel 1,10- phenanthroline-based tetraza-macrocyclic ligand, 5,12,25,28-tetraazaheptacyclo [14.8.4.2⁴,⁷.2<jats:sup>10</jats:sup>,<jats:sup>13</jats:sup>.0⁶,<jats:sup>11</jats:sup>.0<jats:sup>19</jats:sup>,<jats:sup>27</jats:sup>.0<jats:sup>22</jats:sup>,<jats:sup>26</jats:sup>]dotriaconta-1 (25),4,6,8,10,12,16(28),17,19(27),20,22(26),23,29, 31-tetradecaene, 3 and its corresponding nickel complex, (28Z)-1,3,6,31-tetraaza-2-nickelaoctacyclo [17.9.3.2⁷,<jats:sup>28</jats:sup>.0³,<jats:sup>16</jats:sup>.0⁴,<jats:sup>13</jats:sup>.0⁵, <jats:sup>10</jats:sup>.0<jats:sup>22</jats:sup>,<jats:sup>30</jats:sup>.0<jats:sup>25</jats:sup>,<jats:sup>29</jats:sup>]tritriaconta-4(13),5(10),6,8,11,14,16,19(31),20,22(30), 23,25(29),26,28(32)-tetradecaene, 8. The ligand was synthesized via a condensation reaction involving 2,9-dimethyl-1,10-phenanthroline and 2,9-dicarbaldehyde-1,10 phenanthroline, followed by nickel metal complexation. Fourier-transformed infrared (FT-IR) spectroscopy, gas chromatography-mass spectrometry (GC-MS), 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, and thermal analyses were employed to characterize the ligand and its Ni complex. Their ADMET parameters and potential macromolecular targets calculations showed they have therapeutic potentials. The antioxidant assay shows that Ni-complex is approximately 9 times more potent than the ligand with IC<jats:sub>50</jats:sub> values of 0.045 mg/ml and 0.404 mg/ml, respectively. Their microspecies distribution which was predicted using ChemAxon Predictor revealed their catalytic potentials The reaction mechanisms involved are discussed. The 1,10-phenanthroline-based macrocyclic ligand and its nickel complex significantly expand the structural diversity within the tetraza-macrocyclic ligand system and serve as base ligands for the development of possible derivatives, with concomitant applicability in drug development and catalysis.","PeriodicalId":20911,"journal":{"name":"Pure and Applied Chemistry","volume":null,"pages":null},"PeriodicalIF":2.0000,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis, characterization and antioxidant screening of a 1,10-phenanthroline-based tetraza-macrocyclic ligand and its nickel complex with therapeutic potential and catalytic significance\",\"authors\":\"Emmanuel C. Ohaekenyem, Ikenna Onyido\",\"doi\":\"10.1515/pac-2024-0212\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"In this study, we present a synthetic route for the preparation of a novel 1,10- phenanthroline-based tetraza-macrocyclic ligand, 5,12,25,28-tetraazaheptacyclo [14.8.4.2⁴,⁷.2<jats:sup>10</jats:sup>,<jats:sup>13</jats:sup>.0⁶,<jats:sup>11</jats:sup>.0<jats:sup>19</jats:sup>,<jats:sup>27</jats:sup>.0<jats:sup>22</jats:sup>,<jats:sup>26</jats:sup>]dotriaconta-1 (25),4,6,8,10,12,16(28),17,19(27),20,22(26),23,29, 31-tetradecaene, 3 and its corresponding nickel complex, (28Z)-1,3,6,31-tetraaza-2-nickelaoctacyclo [17.9.3.2⁷,<jats:sup>28</jats:sup>.0³,<jats:sup>16</jats:sup>.0⁴,<jats:sup>13</jats:sup>.0⁵, <jats:sup>10</jats:sup>.0<jats:sup>22</jats:sup>,<jats:sup>30</jats:sup>.0<jats:sup>25</jats:sup>,<jats:sup>29</jats:sup>]tritriaconta-4(13),5(10),6,8,11,14,16,19(31),20,22(30), 23,25(29),26,28(32)-tetradecaene, 8. The ligand was synthesized via a condensation reaction involving 2,9-dimethyl-1,10-phenanthroline and 2,9-dicarbaldehyde-1,10 phenanthroline, followed by nickel metal complexation. Fourier-transformed infrared (FT-IR) spectroscopy, gas chromatography-mass spectrometry (GC-MS), 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, and thermal analyses were employed to characterize the ligand and its Ni complex. Their ADMET parameters and potential macromolecular targets calculations showed they have therapeutic potentials. The antioxidant assay shows that Ni-complex is approximately 9 times more potent than the ligand with IC<jats:sub>50</jats:sub> values of 0.045 mg/ml and 0.404 mg/ml, respectively. Their microspecies distribution which was predicted using ChemAxon Predictor revealed their catalytic potentials The reaction mechanisms involved are discussed. The 1,10-phenanthroline-based macrocyclic ligand and its nickel complex significantly expand the structural diversity within the tetraza-macrocyclic ligand system and serve as base ligands for the development of possible derivatives, with concomitant applicability in drug development and catalysis.\",\"PeriodicalId\":20911,\"journal\":{\"name\":\"Pure and Applied Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.0000,\"publicationDate\":\"2024-07-17\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Pure and Applied Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1515/pac-2024-0212\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Pure and Applied Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1515/pac-2024-0212","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Synthesis, characterization and antioxidant screening of a 1,10-phenanthroline-based tetraza-macrocyclic ligand and its nickel complex with therapeutic potential and catalytic significance
In this study, we present a synthetic route for the preparation of a novel 1,10- phenanthroline-based tetraza-macrocyclic ligand, 5,12,25,28-tetraazaheptacyclo [14.8.4.2⁴,⁷.210,13.0⁶,11.019,27.022,26]dotriaconta-1 (25),4,6,8,10,12,16(28),17,19(27),20,22(26),23,29, 31-tetradecaene, 3 and its corresponding nickel complex, (28Z)-1,3,6,31-tetraaza-2-nickelaoctacyclo [17.9.3.2⁷,28.0³,16.0⁴,13.0⁵, 10.022,30.025,29]tritriaconta-4(13),5(10),6,8,11,14,16,19(31),20,22(30), 23,25(29),26,28(32)-tetradecaene, 8. The ligand was synthesized via a condensation reaction involving 2,9-dimethyl-1,10-phenanthroline and 2,9-dicarbaldehyde-1,10 phenanthroline, followed by nickel metal complexation. Fourier-transformed infrared (FT-IR) spectroscopy, gas chromatography-mass spectrometry (GC-MS), 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, and thermal analyses were employed to characterize the ligand and its Ni complex. Their ADMET parameters and potential macromolecular targets calculations showed they have therapeutic potentials. The antioxidant assay shows that Ni-complex is approximately 9 times more potent than the ligand with IC50 values of 0.045 mg/ml and 0.404 mg/ml, respectively. Their microspecies distribution which was predicted using ChemAxon Predictor revealed their catalytic potentials The reaction mechanisms involved are discussed. The 1,10-phenanthroline-based macrocyclic ligand and its nickel complex significantly expand the structural diversity within the tetraza-macrocyclic ligand system and serve as base ligands for the development of possible derivatives, with concomitant applicability in drug development and catalysis.
期刊介绍:
Pure and Applied Chemistry is the official monthly Journal of IUPAC, with responsibility for publishing works arising from those international scientific events and projects that are sponsored and undertaken by the Union. The policy is to publish highly topical and credible works at the forefront of all aspects of pure and applied chemistry, and the attendant goal is to promote widespread acceptance of the Journal as an authoritative and indispensable holding in academic and institutional libraries.