A Convenient One-Pot Synthesis of Novel Benzimidazole–Thiazinone Derivatives and Their Antimicrobial Activity
<b>Background:</b> The increasing prevalence of antimicrobial resistant highlights the urgent need for the new therapeutic agents. This study aimed to design and synthesize fused tricyclic benzimidazole–thiazinone derivatives (<b>CS1</b>–<b>CS10</b>) through a con...
Saved in:
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2024-12-01
|
| Series: | Antibiotics |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2079-6382/13/12/1155 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1850036645475123200 |
|---|---|
| author | Sabahat Samreen Asghar Ali Saiema Ahmedi Mohammad Raghib Anzarul Haque Nikhat Manzoor Afzal Hussain Mohammad Abid Afreen Inam |
| author_facet | Sabahat Samreen Asghar Ali Saiema Ahmedi Mohammad Raghib Anzarul Haque Nikhat Manzoor Afzal Hussain Mohammad Abid Afreen Inam |
| author_sort | Sabahat Samreen |
| collection | DOAJ |
| description | <b>Background:</b> The increasing prevalence of antimicrobial resistant highlights the urgent need for the new therapeutic agents. This study aimed to design and synthesize fused tricyclic benzimidazole–thiazinone derivatives (<b>CS1</b>–<b>CS10</b>) through a convenient method and evaluate their antimicrobial activity against various microorganisms. <b>Methods:</b> A series of fused tricyclic benzimidazole–thiazinone derivatives was rationally designed and synthesized in one pot by the reaction between trans substituted acrylic acids and 1<i>H</i>-benzo[d]imidazole-2-thiol using coupling reagent TBTU (2-(1<i>H</i>-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate). The structure of these compounds was confirmed through various spectroscopic techniques like IR, <sup>1</sup>H and <sup>13</sup>C NMR, the DEPT and 2D-HMQC NMR techniques were also performed to confirm the relation of both carbon and proton. Further, the compounds were in vitro evaluated for their effectiveness against the <i>Candida</i> species and a panel of standard bacterial isolates. <b>Results:</b> The synthesized compounds showed moderate antimicrobial activity. Among all of the compounds, <b>CS4</b> exhibited potent inhibition against <i>Pseudomonas aeruginosa</i> and <i>Escherichia coli</i> at 256 and 512 μg/mL concentrations, respectively. Additional research indicated that compound <b>CS4</b> demonstrated a synergistic effect after combining with the standard antibacterial drug ciprofloxacin. <b>Conclusions:</b> These results suggest that <b>CS4</b> is the best-synthesized antibacterial agent particularly in combination therapies. These findings highlight its promise for further development as a novel antibacterial agent. |
| format | Article |
| id | doaj-art-d1c0ca9f015744cdbb5d6658fb9e6ee2 |
| institution | DOAJ |
| issn | 2079-6382 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Antibiotics |
| spelling | doaj-art-d1c0ca9f015744cdbb5d6658fb9e6ee22025-08-20T02:57:05ZengMDPI AGAntibiotics2079-63822024-12-011312115510.3390/antibiotics13121155A Convenient One-Pot Synthesis of Novel Benzimidazole–Thiazinone Derivatives and Their Antimicrobial ActivitySabahat Samreen0Asghar Ali1Saiema Ahmedi2Mohammad Raghib3Anzarul Haque4Nikhat Manzoor5Afzal Hussain6Mohammad Abid7Afreen Inam8Medicinal Chemistry Laboratory, Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, IndiaDepartment of Biochemistry, School of Chemical and Life Sciences (SCLS), Jamia Hamdard, New Delhi 110062, IndiaDepartment of Biosciences, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, IndiaMedicinal Chemistry Laboratory, Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, IndiaCentral Laboratories Unit, Qatar University, Doha 2713, QatarDepartment of Biosciences, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, IndiaDepartment of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh 11451, Saudi ArabiaDepartment of Biosciences, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, IndiaMedicinal Chemistry Laboratory, Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, India<b>Background:</b> The increasing prevalence of antimicrobial resistant highlights the urgent need for the new therapeutic agents. This study aimed to design and synthesize fused tricyclic benzimidazole–thiazinone derivatives (<b>CS1</b>–<b>CS10</b>) through a convenient method and evaluate their antimicrobial activity against various microorganisms. <b>Methods:</b> A series of fused tricyclic benzimidazole–thiazinone derivatives was rationally designed and synthesized in one pot by the reaction between trans substituted acrylic acids and 1<i>H</i>-benzo[d]imidazole-2-thiol using coupling reagent TBTU (2-(1<i>H</i>-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate). The structure of these compounds was confirmed through various spectroscopic techniques like IR, <sup>1</sup>H and <sup>13</sup>C NMR, the DEPT and 2D-HMQC NMR techniques were also performed to confirm the relation of both carbon and proton. Further, the compounds were in vitro evaluated for their effectiveness against the <i>Candida</i> species and a panel of standard bacterial isolates. <b>Results:</b> The synthesized compounds showed moderate antimicrobial activity. Among all of the compounds, <b>CS4</b> exhibited potent inhibition against <i>Pseudomonas aeruginosa</i> and <i>Escherichia coli</i> at 256 and 512 μg/mL concentrations, respectively. Additional research indicated that compound <b>CS4</b> demonstrated a synergistic effect after combining with the standard antibacterial drug ciprofloxacin. <b>Conclusions:</b> These results suggest that <b>CS4</b> is the best-synthesized antibacterial agent particularly in combination therapies. These findings highlight its promise for further development as a novel antibacterial agent.https://www.mdpi.com/2079-6382/13/12/1155thiazinoneTBTUantibacterialantifungal<i>Candida</i> speciessynergetic effect |
| spellingShingle | Sabahat Samreen Asghar Ali Saiema Ahmedi Mohammad Raghib Anzarul Haque Nikhat Manzoor Afzal Hussain Mohammad Abid Afreen Inam A Convenient One-Pot Synthesis of Novel Benzimidazole–Thiazinone Derivatives and Their Antimicrobial Activity Antibiotics thiazinone TBTU antibacterial antifungal <i>Candida</i> species synergetic effect |
| title | A Convenient One-Pot Synthesis of Novel Benzimidazole–Thiazinone Derivatives and Their Antimicrobial Activity |
| title_full | A Convenient One-Pot Synthesis of Novel Benzimidazole–Thiazinone Derivatives and Their Antimicrobial Activity |
| title_fullStr | A Convenient One-Pot Synthesis of Novel Benzimidazole–Thiazinone Derivatives and Their Antimicrobial Activity |
| title_full_unstemmed | A Convenient One-Pot Synthesis of Novel Benzimidazole–Thiazinone Derivatives and Their Antimicrobial Activity |
| title_short | A Convenient One-Pot Synthesis of Novel Benzimidazole–Thiazinone Derivatives and Their Antimicrobial Activity |
| title_sort | convenient one pot synthesis of novel benzimidazole thiazinone derivatives and their antimicrobial activity |
| topic | thiazinone TBTU antibacterial antifungal <i>Candida</i> species synergetic effect |
| url | https://www.mdpi.com/2079-6382/13/12/1155 |
| work_keys_str_mv | AT sabahatsamreen aconvenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity AT asgharali aconvenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity AT saiemaahmedi aconvenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity AT mohammadraghib aconvenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity AT anzarulhaque aconvenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity AT nikhatmanzoor aconvenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity AT afzalhussain aconvenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity AT mohammadabid aconvenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity AT afreeninam aconvenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity AT sabahatsamreen convenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity AT asgharali convenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity AT saiemaahmedi convenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity AT mohammadraghib convenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity AT anzarulhaque convenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity AT nikhatmanzoor convenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity AT afzalhussain convenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity AT mohammadabid convenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity AT afreeninam convenientonepotsynthesisofnovelbenzimidazolethiazinonederivativesandtheirantimicrobialactivity |