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Design, Synthesis, and Biological Evaluation of Peptidomimetic Tetrahydropyrrole Spirodihydroindolones as SARS-CoV-2 3CL Protease Inhibitors 拟肽四氢吡咯螺二氢吲哚酮作为sars - cov - 23cl蛋白酶抑制剂的设计、合成及生物学评价
IF 3.5 3区 医学
ACS Medicinal Chemistry Letters Pub Date : 2025-04-14 DOI: 10.1021/acsmedchemlett.4c0063710.1021/acsmedchemlett.4c00637
Liuyan Hu, Zhi Zhao, Shujing Zhang, Lei Yang, Wenjie Cui, Tianwen Hu, Jin Suo, Haiguo Sun, Qiumeng Zhang, Leike Zhang, Weiliang Zhu, Zhijian Xu*, Yumin Zhang*, Xiangrui Jiang*, Yan Zhang* and Jingshan Shen, 
{"title":"Design, Synthesis, and Biological Evaluation of Peptidomimetic Tetrahydropyrrole Spirodihydroindolones as SARS-CoV-2 3CL Protease Inhibitors","authors":"Liuyan Hu,&nbsp;Zhi Zhao,&nbsp;Shujing Zhang,&nbsp;Lei Yang,&nbsp;Wenjie Cui,&nbsp;Tianwen Hu,&nbsp;Jin Suo,&nbsp;Haiguo Sun,&nbsp;Qiumeng Zhang,&nbsp;Leike Zhang,&nbsp;Weiliang Zhu,&nbsp;Zhijian Xu*,&nbsp;Yumin Zhang*,&nbsp;Xiangrui Jiang*,&nbsp;Yan Zhang* and Jingshan Shen,&nbsp;","doi":"10.1021/acsmedchemlett.4c0063710.1021/acsmedchemlett.4c00637","DOIUrl":"https://doi.org/10.1021/acsmedchemlett.4c00637https://doi.org/10.1021/acsmedchemlett.4c00637","url":null,"abstract":"<p >The 3CL protease (3CL<sup>pro</sup>) of SARS-CoV-2 is a key enzyme that plays an essential role in mediating viral replication and transcription. In this study, we synthesized and evaluated a series of peptidomimetic compounds containing a tetrahydropyrrole spirodihydroindolone moiety. Among the target compounds, <b>13c</b> and <b>17d</b> exhibited obvious 3CL<sup>pro</sup> inhibitory activities with IC<sub>50</sub> = 3.71 and 6.21 nM, respectively. In metabolic stability testing of liver microsomes, compound <b>13c</b> showed improved stability in human liver microsomes. In addition, <b>13c</b> displayed significant anti-SARS-CoV-2 activity and high safety in Vero E6 cells (EC<sub>50</sub> = 19.26 nM, SI &gt; 400). Further investigations indicated that <b>13c</b> showed potent activity against HCoV-OC43 and favorable safety in Huh7 cells (EC<sub>50</sub> = 61 nM, SI &gt; 100). These findings suggest that compound <b>13c</b> is a promising lead compound in the development of novel 3CL<sup>pro</sup> inhibitors.</p>","PeriodicalId":20,"journal":{"name":"ACS Medicinal Chemistry Letters","volume":"16 5","pages":"790–796 790–796"},"PeriodicalIF":3.5,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143917026","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Design, Synthesis, and Biological Evaluation of Peptidomimetic Tetrahydropyrrole Spirodihydroindolones as SARS-CoV-2 3CL Protease Inhibitors. 拟肽四氢吡咯螺二氢吲哚酮作为sars - cov - 23cl蛋白酶抑制剂的设计、合成及生物学评价
IF 3.5 3区 医学
ACS Medicinal Chemistry Letters Pub Date : 2025-04-14 eCollection Date: 2025-05-08 DOI: 10.1021/acsmedchemlett.4c00637
Liuyan Hu, Zhi Zhao, Shujing Zhang, Lei Yang, Wenjie Cui, Tianwen Hu, Jin Suo, Haiguo Sun, Qiumeng Zhang, Leike Zhang, Weiliang Zhu, Zhijian Xu, Yumin Zhang, Xiangrui Jiang, Yan Zhang, Jingshan Shen
{"title":"Design, Synthesis, and Biological Evaluation of Peptidomimetic Tetrahydropyrrole Spirodihydroindolones as SARS-CoV-2 3CL Protease Inhibitors.","authors":"Liuyan Hu, Zhi Zhao, Shujing Zhang, Lei Yang, Wenjie Cui, Tianwen Hu, Jin Suo, Haiguo Sun, Qiumeng Zhang, Leike Zhang, Weiliang Zhu, Zhijian Xu, Yumin Zhang, Xiangrui Jiang, Yan Zhang, Jingshan Shen","doi":"10.1021/acsmedchemlett.4c00637","DOIUrl":"10.1021/acsmedchemlett.4c00637","url":null,"abstract":"<p><p>The 3CL protease (3CL<sup>pro</sup>) of SARS-CoV-2 is a key enzyme that plays an essential role in mediating viral replication and transcription. In this study, we synthesized and evaluated a series of peptidomimetic compounds containing a tetrahydropyrrole spirodihydroindolone moiety. Among the target compounds, <b>13c</b> and <b>17d</b> exhibited obvious 3CL<sup>pro</sup> inhibitory activities with IC<sub>50</sub> = 3.71 and 6.21 nM, respectively. In metabolic stability testing of liver microsomes, compound <b>13c</b> showed improved stability in human liver microsomes. In addition, <b>13c</b> displayed significant anti-SARS-CoV-2 activity and high safety in Vero E6 cells (EC<sub>50</sub> = 19.26 nM, SI > 400). Further investigations indicated that <b>13c</b> showed potent activity against HCoV-OC43 and favorable safety in Huh7 cells (EC<sub>50</sub> = 61 nM, SI > 100). These findings suggest that compound <b>13c</b> is a promising lead compound in the development of novel 3CL<sup>pro</sup> inhibitors.</p>","PeriodicalId":20,"journal":{"name":"ACS Medicinal Chemistry Letters","volume":"16 5","pages":"790-796"},"PeriodicalIF":3.5,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12067102/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143951713","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
The Discovery of Bridged Benzoazepine Amides as Selective Allosteric Modulators of RIPK1 桥接苯氮卓类酰胺作为RIPK1选择性变构调节剂的发现
IF 3.5 3区 医学
ACS Medicinal Chemistry Letters Pub Date : 2025-04-14 DOI: 10.1021/acsmedchemlett.5c0006310.1021/acsmedchemlett.5c00063
Joanna L. Chen*, Joey L. Methot, Matthew J. Mitcheltree, Andrew Musacchio, Emily B. Corcoran, Guo Feng, Alfred Lammens, Klaus Maskos, Rachel L. Palte, Meredith M. Rickard, Karin M. Otte, My S. Mansueto, Sriraman Venkat, Christopher Sondey, Maren Thomsen, Charles A. Lesburg, Xavier Fradera, Matthew J. Fell, Erin F. DiMauro and Phieng Siliphaivanh, 
{"title":"The Discovery of Bridged Benzoazepine Amides as Selective Allosteric Modulators of RIPK1","authors":"Joanna L. Chen*,&nbsp;Joey L. Methot,&nbsp;Matthew J. Mitcheltree,&nbsp;Andrew Musacchio,&nbsp;Emily B. Corcoran,&nbsp;Guo Feng,&nbsp;Alfred Lammens,&nbsp;Klaus Maskos,&nbsp;Rachel L. Palte,&nbsp;Meredith M. Rickard,&nbsp;Karin M. Otte,&nbsp;My S. Mansueto,&nbsp;Sriraman Venkat,&nbsp;Christopher Sondey,&nbsp;Maren Thomsen,&nbsp;Charles A. Lesburg,&nbsp;Xavier Fradera,&nbsp;Matthew J. Fell,&nbsp;Erin F. DiMauro and Phieng Siliphaivanh,&nbsp;","doi":"10.1021/acsmedchemlett.5c0006310.1021/acsmedchemlett.5c00063","DOIUrl":"https://doi.org/10.1021/acsmedchemlett.5c00063https://doi.org/10.1021/acsmedchemlett.5c00063","url":null,"abstract":"<p >Receptor-interacting protein kinase 1 (RIPK1) plays an essential role in necroptosis, a form of inflammatory, caspase-independent, programmed cell death. Allosteric inhibitors of RIPK1 have been shown to block necroptotic cell death and thus may offer potential therapeutic opportunities across a range of infectious, autoimmune, and neurodegenerative diseases. We report the structure-informed discovery of a novel series of bridged benzoazepine amides as part of our efforts to develop a CNS-penetrant small-molecule inhibitor of RIPK1 with a low projected oral human dose.</p>","PeriodicalId":20,"journal":{"name":"ACS Medicinal Chemistry Letters","volume":"16 5","pages":"811–818 811–818"},"PeriodicalIF":3.5,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143917030","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
The Discovery of Bridged Benzoazepine Amides as Selective Allosteric Modulators of RIPK1. 桥接苯氮卓类酰胺作为RIPK1选择性变构调节剂的发现。
IF 3.5 3区 医学
ACS Medicinal Chemistry Letters Pub Date : 2025-04-14 eCollection Date: 2025-05-08 DOI: 10.1021/acsmedchemlett.5c00063
Joanna L Chen, Joey L Methot, Matthew J Mitcheltree, Andrew Musacchio, Emily B Corcoran, Guo Feng, Alfred Lammens, Klaus Maskos, Rachel L Palte, Meredith M Rickard, Karin M Otte, My S Mansueto, Sriraman Venkat, Christopher Sondey, Maren Thomsen, Charles A Lesburg, Xavier Fradera, Matthew J Fell, Erin F DiMauro, Phieng Siliphaivanh
{"title":"The Discovery of Bridged Benzoazepine Amides as Selective Allosteric Modulators of RIPK1.","authors":"Joanna L Chen, Joey L Methot, Matthew J Mitcheltree, Andrew Musacchio, Emily B Corcoran, Guo Feng, Alfred Lammens, Klaus Maskos, Rachel L Palte, Meredith M Rickard, Karin M Otte, My S Mansueto, Sriraman Venkat, Christopher Sondey, Maren Thomsen, Charles A Lesburg, Xavier Fradera, Matthew J Fell, Erin F DiMauro, Phieng Siliphaivanh","doi":"10.1021/acsmedchemlett.5c00063","DOIUrl":"10.1021/acsmedchemlett.5c00063","url":null,"abstract":"<p><p>Receptor-interacting protein kinase 1 (RIPK1) plays an essential role in necroptosis, a form of inflammatory, caspase-independent, programmed cell death. Allosteric inhibitors of RIPK1 have been shown to block necroptotic cell death and thus may offer potential therapeutic opportunities across a range of infectious, autoimmune, and neurodegenerative diseases. We report the structure-informed discovery of a novel series of bridged benzoazepine amides as part of our efforts to develop a CNS-penetrant small-molecule inhibitor of RIPK1 with a low projected oral human dose.</p>","PeriodicalId":20,"journal":{"name":"ACS Medicinal Chemistry Letters","volume":"16 5","pages":"811-818"},"PeriodicalIF":3.5,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12067136/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143952318","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Novel Piperidinylpyridinylcarbonitrile Derivatives as QPCT and QPCTL Inhibitors for Treating Cancer 新型哌啶基吡啶基碳腈衍生物作为QPCT和QPCTL抑制剂治疗癌症
IF 3.5 3区 医学
ACS Medicinal Chemistry Letters Pub Date : 2025-04-14 DOI: 10.1021/acsmedchemlett.5c0019810.1021/acsmedchemlett.5c00198
Ram W. Sabnis*, 
{"title":"Novel Piperidinylpyridinylcarbonitrile Derivatives as QPCT and QPCTL Inhibitors for Treating Cancer","authors":"Ram W. Sabnis*,&nbsp;","doi":"10.1021/acsmedchemlett.5c0019810.1021/acsmedchemlett.5c00198","DOIUrl":"https://doi.org/10.1021/acsmedchemlett.5c00198https://doi.org/10.1021/acsmedchemlett.5c00198","url":null,"abstract":"<p >Provided herein are novel piperidinylpyridinylcarbonitrile derivatives as QPCT and QPCTL inhibitors, pharmaceutical compositions, use of such compounds in treating cancer, and processes for preparing such compounds.</p>","PeriodicalId":20,"journal":{"name":"ACS Medicinal Chemistry Letters","volume":"16 5","pages":"758–759 758–759"},"PeriodicalIF":3.5,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143917029","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Novel Piperidinylpyridinylcarbonitrile Derivatives as QPCT and QPCTL Inhibitors for Treating Cancer. 新型哌啶基吡啶基碳腈衍生物作为QPCT和QPCTL抑制剂治疗癌症。
IF 3.5 3区 医学
ACS Medicinal Chemistry Letters Pub Date : 2025-04-14 eCollection Date: 2025-05-08 DOI: 10.1021/acsmedchemlett.5c00198
Ram W Sabnis
{"title":"Novel Piperidinylpyridinylcarbonitrile Derivatives as QPCT and QPCTL Inhibitors for Treating Cancer.","authors":"Ram W Sabnis","doi":"10.1021/acsmedchemlett.5c00198","DOIUrl":"10.1021/acsmedchemlett.5c00198","url":null,"abstract":"<p><p>Provided herein are novel piperidinylpyridinylcarbonitrile derivatives as QPCT and QPCTL inhibitors, pharmaceutical compositions, use of such compounds in treating cancer, and processes for preparing such compounds.</p>","PeriodicalId":20,"journal":{"name":"ACS Medicinal Chemistry Letters","volume":"16 5","pages":"758-759"},"PeriodicalIF":3.5,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12067109/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143951144","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Pharmaceutical Research - Academic Collaborations: An Insider's Perspective. 药物研究-学术合作：内部人士的观点。
IF 3.5 3区 医学
ACS Medicinal Chemistry Letters Pub Date : 2025-04-11 eCollection Date: 2025-05-08 DOI: 10.1021/acsmedchemlett.5c00083
Stevan W Djuric
{"title":"Pharmaceutical Research - Academic Collaborations: An Insider's Perspective.","authors":"Stevan W Djuric","doi":"10.1021/acsmedchemlett.5c00083","DOIUrl":"10.1021/acsmedchemlett.5c00083","url":null,"abstract":"<p><p>A constant pressure on the pharmaceutical industry is the need to develop new therapeutics in a more cost-effective and timely manner. In this letter, I describe the potential that the development and implementation of enabling chemistry technology has for reducing cycle time and cost of goods. Several of these innovations were produced through industry and academic collaborations in which complementary areas of expertise were brought to the table.</p>","PeriodicalId":20,"journal":{"name":"ACS Medicinal Chemistry Letters","volume":"16 5","pages":"851-855"},"PeriodicalIF":3.5,"publicationDate":"2025-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12067122/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143952525","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Pharmaceutical Research - Academic Collaborations: An Insider’s Perspective 药物研究-学术合作：内部人士的观点
IF 3.5 3区 医学
ACS Medicinal Chemistry Letters Pub Date : 2025-04-11 DOI: 10.1021/acsmedchemlett.5c0008310.1021/acsmedchemlett.5c00083
Stevan W Djuric*, 
{"title":"Pharmaceutical Research - Academic Collaborations: An Insider’s Perspective","authors":"Stevan W Djuric*,&nbsp;","doi":"10.1021/acsmedchemlett.5c0008310.1021/acsmedchemlett.5c00083","DOIUrl":"https://doi.org/10.1021/acsmedchemlett.5c00083https://doi.org/10.1021/acsmedchemlett.5c00083","url":null,"abstract":"<p >A constant pressure on the pharmaceutical industry is the need to develop new therapeutics in a more cost-effective and timely manner. In this letter, I describe the potential that the development and implementation of enabling chemistry technology has for reducing cycle time and cost of goods. Several of these innovations were produced through industry and academic collaborations in which complementary areas of expertise were brought to the table.</p>","PeriodicalId":20,"journal":{"name":"ACS Medicinal Chemistry Letters","volume":"16 5","pages":"851–855 851–855"},"PeriodicalIF":3.5,"publicationDate":"2025-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsmedchemlett.5c00083","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143917024","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Novel Substituted Cyclic Compounds as SLC6A19 Inhibitors for Treating Phenylketonuria and Other Amino Acidurias. 新型取代环化合物作为SLC6A19抑制剂治疗苯丙酮尿症和其他氨基酸尿症。
IF 3.5 3区 医学
ACS Medicinal Chemistry Letters Pub Date : 2025-04-11 eCollection Date: 2025-05-08 DOI: 10.1021/acsmedchemlett.5c00177
Ram W Sabnis
{"title":"Novel Substituted Cyclic Compounds as SLC6A19 Inhibitors for Treating Phenylketonuria and Other Amino Acidurias.","authors":"Ram W Sabnis","doi":"10.1021/acsmedchemlett.5c00177","DOIUrl":"10.1021/acsmedchemlett.5c00177","url":null,"abstract":"<p><p>Provided herein are novel substituted cyclic compounds as SLC6A19 inhibitors, pharmaceutical compositions, use of such compounds in treating phenylketonuria, and other amino acidurias and processes for preparing such compounds.</p>","PeriodicalId":20,"journal":{"name":"ACS Medicinal Chemistry Letters","volume":"16 5","pages":"734-735"},"PeriodicalIF":3.5,"publicationDate":"2025-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12067105/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143950780","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Genetic Variation in Drug Targets: Are We Ready for the Era of Precision Medicinal Chemistry? 药物靶点的遗传变异：我们准备好进入精准药物化学时代了吗？
IF 3.5 3区 医学
ACS Medicinal Chemistry Letters Pub Date : 2025-04-11 eCollection Date: 2025-05-08 DOI: 10.1021/acsmedchemlett.5c00153
Clinton G L Veale, Adrienne L Edkins
{"title":"Genetic Variation in Drug Targets: Are We Ready for the Era of Precision Medicinal Chemistry?","authors":"Clinton G L Veale, Adrienne L Edkins","doi":"10.1021/acsmedchemlett.5c00153","DOIUrl":"10.1021/acsmedchemlett.5c00153","url":null,"abstract":"<p><p>Natural genetic variations profoundly impact drug target interactions causing variations in in vitro biological data. The overall occurrence or \"rare genetic variation\" is common and enriched within population groups. Incorporating population-level genetic information earlier into the drug discovery pipeline would allow medicinal chemists to contribute to the precision medicine movement, designing drugs with more population relevance.</p>","PeriodicalId":20,"journal":{"name":"ACS Medicinal Chemistry Letters","volume":"16 5","pages":"706-710"},"PeriodicalIF":3.5,"publicationDate":"2025-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12067103/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143952276","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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