Unraveling the synthetic strategy, structure activity relationship of azetidinones: Insights into their multidrug and toxin extrusion protein (MATE transporter) inhibition facilitating drug development against MDR
[Display omitted] •Chemistry of β-lactams/Azetidinones.•Aspects of different reactions viz., Staudinger’s, Gilman-Speeter, Kinugasa, Ugi-MCR etc. for synthesis of azetidinones.•Schematic representations of various reported azetidinones exploring anticancer and antimicrobial activities.•Structure act...
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| Published in | Bioorganic chemistry Vol. 156; p. 108194 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
Elsevier Inc
01.03.2025
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| Subjects | |
| Online Access | Get full text |
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| Abstract | [Display omitted]
•Chemistry of β-lactams/Azetidinones.•Aspects of different reactions viz., Staudinger’s, Gilman-Speeter, Kinugasa, Ugi-MCR etc. for synthesis of azetidinones.•Schematic representations of various reported azetidinones exploring anticancer and antimicrobial activities.•Structure activity relationship of the azetidinone bearing compounds with different molecular targets.
Heterocyclic chemistry gathered a wide audience due to their presence in potential drug candidates and being attractive synthons initiating several retro-syntheses the organic as well as in medicinal chemistry fields. Among them, azetidinones have been a subject of discussion due to their serendipity, curiosity, versatility by Penicillin and Cephalosporins as β-lactam antibiotics. Despite possessing a large margin of biological activities, azetidinones mainly work as antimicrobial, interfering with bacterial cell-wall synthesis blocking transpeptidase. The structure and synthetic strategy of the azetidinone arouse its research interest in drug discovery pipeline. However, the extensive use of antibiotics in the modern era contributes to drug resistance that could only be counterbalanced involving hybridization approach. To explore the potency of the azetidinones, potent compounds found from literatures, have been screened through molecular docking against MATE transporter, targeting for prevailing multidrug resistance. The present review makes a sincere effort to compile the synthetic information and orientations involving hybridization of azetidinones with biologically active scaffolds emphasizing on antimicrobial and anticancer efficacies along with their MATE inhibition, keeping an eye upon the structure activity relationship in a systematic way. The study could motivate the researchers for developing a wide array of β-lactam derivatives more prominently targeting newer pathways to fight MDR. |
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| AbstractList | [Display omitted]
•Chemistry of β-lactams/Azetidinones.•Aspects of different reactions viz., Staudinger’s, Gilman-Speeter, Kinugasa, Ugi-MCR etc. for synthesis of azetidinones.•Schematic representations of various reported azetidinones exploring anticancer and antimicrobial activities.•Structure activity relationship of the azetidinone bearing compounds with different molecular targets.
Heterocyclic chemistry gathered a wide audience due to their presence in potential drug candidates and being attractive synthons initiating several retro-syntheses the organic as well as in medicinal chemistry fields. Among them, azetidinones have been a subject of discussion due to their serendipity, curiosity, versatility by Penicillin and Cephalosporins as β-lactam antibiotics. Despite possessing a large margin of biological activities, azetidinones mainly work as antimicrobial, interfering with bacterial cell-wall synthesis blocking transpeptidase. The structure and synthetic strategy of the azetidinone arouse its research interest in drug discovery pipeline. However, the extensive use of antibiotics in the modern era contributes to drug resistance that could only be counterbalanced involving hybridization approach. To explore the potency of the azetidinones, potent compounds found from literatures, have been screened through molecular docking against MATE transporter, targeting for prevailing multidrug resistance. The present review makes a sincere effort to compile the synthetic information and orientations involving hybridization of azetidinones with biologically active scaffolds emphasizing on antimicrobial and anticancer efficacies along with their MATE inhibition, keeping an eye upon the structure activity relationship in a systematic way. The study could motivate the researchers for developing a wide array of β-lactam derivatives more prominently targeting newer pathways to fight MDR. Heterocyclic chemistry gathered a wide audience due to their presence in potential drug candidates and being attractive synthons initiating several retro-syntheses the organic as well as in medicinal chemistry fields. Among them, azetidinones have been a subject of discussion due to their serendipity, curiosity, versatility by Penicillin and Cephalosporins as β-lactam antibiotics. Despite possessing a large margin of biological activities, azetidinones mainly work as antimicrobial, interfering with bacterial cell-wall synthesis blocking transpeptidase. The structure and synthetic strategy of the azetidinone arouse its research interest in drug discovery pipeline. However, the extensive use of antibiotics in the modern era contributes to drug resistance that could only be counterbalanced involving hybridization approach. To explore the potency of the azetidinones, potent compounds found from literatures, have been screened through molecular docking against MATE transporter, targeting for prevailing multidrug resistance. The present review makes a sincere effort to compile the synthetic information and orientations involving hybridization of azetidinones with biologically active scaffolds emphasizing on antimicrobial and anticancer efficacies along with their MATE inhibition, keeping an eye upon the structure activity relationship in a systematic way. The study could motivate the researchers for developing a wide array of β-lactam derivatives more prominently targeting newer pathways to fight MDR.Heterocyclic chemistry gathered a wide audience due to their presence in potential drug candidates and being attractive synthons initiating several retro-syntheses the organic as well as in medicinal chemistry fields. Among them, azetidinones have been a subject of discussion due to their serendipity, curiosity, versatility by Penicillin and Cephalosporins as β-lactam antibiotics. Despite possessing a large margin of biological activities, azetidinones mainly work as antimicrobial, interfering with bacterial cell-wall synthesis blocking transpeptidase. The structure and synthetic strategy of the azetidinone arouse its research interest in drug discovery pipeline. However, the extensive use of antibiotics in the modern era contributes to drug resistance that could only be counterbalanced involving hybridization approach. To explore the potency of the azetidinones, potent compounds found from literatures, have been screened through molecular docking against MATE transporter, targeting for prevailing multidrug resistance. The present review makes a sincere effort to compile the synthetic information and orientations involving hybridization of azetidinones with biologically active scaffolds emphasizing on antimicrobial and anticancer efficacies along with their MATE inhibition, keeping an eye upon the structure activity relationship in a systematic way. The study could motivate the researchers for developing a wide array of β-lactam derivatives more prominently targeting newer pathways to fight MDR. Heterocyclic chemistry gathered a wide audience due to their presence in potential drug candidates and being attractive synthons initiating several retro-syntheses the organic as well as in medicinal chemistry fields. Among them, azetidinones have been a subject of discussion due to their serendipity, curiosity, versatility by Penicillin and Cephalosporins as β-lactam antibiotics. Despite possessing a large margin of biological activities, azetidinones mainly work as antimicrobial, interfering with bacterial cell-wall synthesis blocking transpeptidase. The structure and synthetic strategy of the azetidinone arouse its research interest in drug discovery pipeline. However, the extensive use of antibiotics in the modern era contributes to drug resistance that could only be counterbalanced involving hybridization approach. To explore the potency of the azetidinones, potent compounds found from literatures, have been screened through molecular docking against MATE transporter, targeting for prevailing multidrug resistance. The present review makes a sincere effort to compile the synthetic information and orientations involving hybridization of azetidinones with biologically active scaffolds emphasizing on antimicrobial and anticancer efficacies along with their MATE inhibition, keeping an eye upon the structure activity relationship in a systematic way. The study could motivate the researchers for developing a wide array of β-lactam derivatives more prominently targeting newer pathways to fight MDR. |
| ArticleNumber | 108194 |
| Author | Roy, Partha Sahoo, Jyotirmaya Panda, Preetesh Kumar Mal, Suvadeep Mahapatra, Monalisa Pakeeraiah, Kakarla Paidesetty, Sudhir Kumar |
| Author_xml | – sequence: 1 givenname: Suvadeep surname: Mal fullname: Mal, Suvadeep organization: Medicinal Chemistry Research Laboratory, School of Pharmaceutical Sciences, Siksha ‘O’ Anusandhan (Deemed to be University), Campus-2, Ghatikia, Kalinga Nagar, Bhubaneswar, Odisha 751003, India – sequence: 2 givenname: Monalisa surname: Mahapatra fullname: Mahapatra, Monalisa organization: Medicinal Chemistry Research Laboratory, School of Pharmaceutical Sciences, Siksha ‘O’ Anusandhan (Deemed to be University), Campus-2, Ghatikia, Kalinga Nagar, Bhubaneswar, Odisha 751003, India – sequence: 3 givenname: Kakarla surname: Pakeeraiah fullname: Pakeeraiah, Kakarla organization: Medicinal Chemistry Research Laboratory, School of Pharmaceutical Sciences, Siksha ‘O’ Anusandhan (Deemed to be University), Campus-2, Ghatikia, Kalinga Nagar, Bhubaneswar, Odisha 751003, India – sequence: 4 givenname: Preetesh Kumar surname: Panda fullname: Panda, Preetesh Kumar organization: Medicinal Chemistry Research Laboratory, School of Pharmaceutical Sciences, Siksha ‘O’ Anusandhan (Deemed to be University), Campus-2, Ghatikia, Kalinga Nagar, Bhubaneswar, Odisha 751003, India – sequence: 5 givenname: Jyotirmaya surname: Sahoo fullname: Sahoo, Jyotirmaya organization: School of Pharmacy, Arka Jain University, Jameshedpur, Jharkand 832108, India – sequence: 6 givenname: Partha surname: Roy fullname: Roy, Partha email: partharoy2502@gmail.com organization: GITAM School of Pharmacy, GITAM (Deemed to be University), Vishakhapatnam 530045, India – sequence: 7 givenname: Sudhir Kumar surname: Paidesetty fullname: Paidesetty, Sudhir Kumar email: sairampaidesetty@gmail.com organization: Medicinal Chemistry Research Laboratory, School of Pharmaceutical Sciences, Siksha ‘O’ Anusandhan (Deemed to be University), Campus-2, Ghatikia, Kalinga Nagar, Bhubaneswar, Odisha 751003, India |
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| Keywords | MAT AcOH SAR HOMO LUMO DABCO ADMET EGFR THF Rh IC50 Ph DMAP EC50 CA-4 Microbial DMF MATE transporter inhibitor HPLC nM CuBr AcONa DILI DCC MIC Multidrug resistance DIPEA POCl3 LiHMDS β-lactam DCM Naph LD50 TEA LC50 ZOI CuI ROS µM AMPK Azetidinone CuCl IPA Cancer |
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•Chemistry of β-lactams/Azetidinones.•Aspects of different reactions viz., Staudinger’s, Gilman-Speeter, Kinugasa, Ugi-MCR etc. for synthesis... Heterocyclic chemistry gathered a wide audience due to their presence in potential drug candidates and being attractive synthons initiating several... |
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| SubjectTerms | Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Azetidines - chemical synthesis Azetidines - chemistry Azetidines - pharmacology Azetidinone Cancer Drug Development Drug Resistance, Multiple, Bacterial - drug effects Humans MATE transporter inhibitor Microbial Microbial Sensitivity Tests Molecular Docking Simulation Molecular Structure Multidrug resistance SAR Structure-Activity Relationship β-lactam |
| Title | Unraveling the synthetic strategy, structure activity relationship of azetidinones: Insights into their multidrug and toxin extrusion protein (MATE transporter) inhibition facilitating drug development against MDR |
| URI | https://dx.doi.org/10.1016/j.bioorg.2025.108194 https://www.ncbi.nlm.nih.gov/pubmed/39848168 https://www.proquest.com/docview/3159439426 |
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