β-Lactamase inhibition profile of new amidine-substituted diazabicyclooctanes
The diazabicyclooctane (DBO) scaffold is the backbone of non-β-lactam-based second generation β-lactamase inhibitors. As part of our efforts, we have synthesized a series of DBO derivatives A1–23 containing amidine substituents at the C2 position of the bicyclic ring. These compounds, alone and in c...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2021-03-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.17.60 |
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| author | Zafar Iqbal Lijuan Zhai Yuanyu Gao Dong Tang Xueqin Ma Jinbo Ji Jian Sun Jingwen Ji Yuanbai Liu Rui Jiang Yangxiu Mu Lili He Haikang Yang Zhixiang Yang |
| author_facet | Zafar Iqbal Lijuan Zhai Yuanyu Gao Dong Tang Xueqin Ma Jinbo Ji Jian Sun Jingwen Ji Yuanbai Liu Rui Jiang Yangxiu Mu Lili He Haikang Yang Zhixiang Yang |
| author_sort | Zafar Iqbal |
| collection | DOAJ |
| description | The diazabicyclooctane (DBO) scaffold is the backbone of non-β-lactam-based second generation β-lactamase inhibitors. As part of our efforts, we have synthesized a series of DBO derivatives A1–23 containing amidine substituents at the C2 position of the bicyclic ring. These compounds, alone and in combination with meropenem, were tested against ten bacterial strains for their antibacterial activity in vitro. All compounds did not show antibacterial activity when tested alone (MIC >64 mg/L), however, they exhibited a moderate inhibition activity in the presence of meropenem by lowering its MIC values. The compound A12 proved most potent among the other counterparts against all bacterial species with MIC from <0.125 mg/L to 2 mg/L, and is comparable to avibactam against both E. coli strains with a MIC value of <0.125 mg/L. |
| first_indexed | 2024-12-19T12:12:45Z |
| format | Article |
| id | doaj.art-a15cc7d620484f53aae7a5e3d9970587 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-19T12:12:45Z |
| publishDate | 2021-03-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-a15cc7d620484f53aae7a5e3d99705872022-12-21T20:22:08ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-03-0117171171810.3762/bjoc.17.601860-5397-17-60β-Lactamase inhibition profile of new amidine-substituted diazabicyclooctanesZafar Iqbal0Lijuan Zhai1Yuanyu Gao2Dong Tang3Xueqin Ma4Jinbo Ji5Jian Sun6Jingwen Ji7Yuanbai Liu8Rui Jiang9Yangxiu Mu10Lili He11Haikang Yang12Zhixiang Yang13Ningxia Centre of Organic Synthesis and Engineering Technology, Ningxia Academy of Agriculture and Forestry Sciences, No. 590, Huanghe East Road, Jinfeng District, Yinchuan, Ningxia 750002, P.R. ChinaNingxia Centre of Organic Synthesis and Engineering Technology, Ningxia Academy of Agriculture and Forestry Sciences, No. 590, Huanghe East Road, Jinfeng District, Yinchuan, Ningxia 750002, P.R. ChinaNingxia Centre of Organic Synthesis and Engineering Technology, Ningxia Academy of Agriculture and Forestry Sciences, No. 590, Huanghe East Road, Jinfeng District, Yinchuan, Ningxia 750002, P.R. ChinaNingxia Centre of Organic Synthesis and Engineering Technology, Ningxia Academy of Agriculture and Forestry Sciences, No. 590, Huanghe East Road, Jinfeng District, Yinchuan, Ningxia 750002, P.R. ChinaCollege of Pharmacy, Ningxia Medical University, Shengli Street, Xingqing District, Yinchuan, Ningxia 750004, P.R. ChinaNingxia Centre of Organic Synthesis and Engineering Technology, Ningxia Academy of Agriculture and Forestry Sciences, No. 590, Huanghe East Road, Jinfeng District, Yinchuan, Ningxia 750002, P.R. ChinaNingxia Centre of Organic Synthesis and Engineering Technology, Ningxia Academy of Agriculture and Forestry Sciences, No. 590, Huanghe East Road, Jinfeng District, Yinchuan, Ningxia 750002, P.R. ChinaNingxia Centre of Organic Synthesis and Engineering Technology, Ningxia Academy of Agriculture and Forestry Sciences, No. 590, Huanghe East Road, Jinfeng District, Yinchuan, Ningxia 750002, P.R. ChinaNingxia Centre of Organic Synthesis and Engineering Technology, Ningxia Academy of Agriculture and Forestry Sciences, No. 590, Huanghe East Road, Jinfeng District, Yinchuan, Ningxia 750002, P.R. ChinaNingxia Centre of Organic Synthesis and Engineering Technology, Ningxia Academy of Agriculture and Forestry Sciences, No. 590, Huanghe East Road, Jinfeng District, Yinchuan, Ningxia 750002, P.R. ChinaNingxia Centre of Organic Synthesis and Engineering Technology, Ningxia Academy of Agriculture and Forestry Sciences, No. 590, Huanghe East Road, Jinfeng District, Yinchuan, Ningxia 750002, P.R. ChinaNingxia Centre of Organic Synthesis and Engineering Technology, Ningxia Academy of Agriculture and Forestry Sciences, No. 590, Huanghe East Road, Jinfeng District, Yinchuan, Ningxia 750002, P.R. ChinaNingxia Centre of Organic Synthesis and Engineering Technology, Ningxia Academy of Agriculture and Forestry Sciences, No. 590, Huanghe East Road, Jinfeng District, Yinchuan, Ningxia 750002, P.R. ChinaNingxia Centre of Organic Synthesis and Engineering Technology, Ningxia Academy of Agriculture and Forestry Sciences, No. 590, Huanghe East Road, Jinfeng District, Yinchuan, Ningxia 750002, P.R. ChinaThe diazabicyclooctane (DBO) scaffold is the backbone of non-β-lactam-based second generation β-lactamase inhibitors. As part of our efforts, we have synthesized a series of DBO derivatives A1–23 containing amidine substituents at the C2 position of the bicyclic ring. These compounds, alone and in combination with meropenem, were tested against ten bacterial strains for their antibacterial activity in vitro. All compounds did not show antibacterial activity when tested alone (MIC >64 mg/L), however, they exhibited a moderate inhibition activity in the presence of meropenem by lowering its MIC values. The compound A12 proved most potent among the other counterparts against all bacterial species with MIC from <0.125 mg/L to 2 mg/L, and is comparable to avibactam against both E. coli strains with a MIC value of <0.125 mg/L.https://doi.org/10.3762/bjoc.17.60amidineantibacterial activityβ-lactamase inhibitorsdiazabicyclooctanesynthesis |
| spellingShingle | Zafar Iqbal Lijuan Zhai Yuanyu Gao Dong Tang Xueqin Ma Jinbo Ji Jian Sun Jingwen Ji Yuanbai Liu Rui Jiang Yangxiu Mu Lili He Haikang Yang Zhixiang Yang β-Lactamase inhibition profile of new amidine-substituted diazabicyclooctanes Beilstein Journal of Organic Chemistry amidine antibacterial activity β-lactamase inhibitors diazabicyclooctane synthesis |
| title | β-Lactamase inhibition profile of new amidine-substituted diazabicyclooctanes |
| title_full | β-Lactamase inhibition profile of new amidine-substituted diazabicyclooctanes |
| title_fullStr | β-Lactamase inhibition profile of new amidine-substituted diazabicyclooctanes |
| title_full_unstemmed | β-Lactamase inhibition profile of new amidine-substituted diazabicyclooctanes |
| title_short | β-Lactamase inhibition profile of new amidine-substituted diazabicyclooctanes |
| title_sort | β lactamase inhibition profile of new amidine substituted diazabicyclooctanes |
| topic | amidine antibacterial activity β-lactamase inhibitors diazabicyclooctane synthesis |
| url | https://doi.org/10.3762/bjoc.17.60 |
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