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Third-Generation CD73 Inhibitors Based on a 4,6-Disubstituted-2-thiopyridine Scaffold. 基于 4,6-二取代-2-巯基吡啶支架的第三代 CD73 抑制剂。
IF 3.6 4区 医学
ChemMedChem Pub Date : 2024-12-13 DOI: 10.1002/cmdc.202400662
Félix Grosjean, Maria Shaldaeva, Emeline Cros-Perrial, Céline Rodriguez, Rayane Ghoteimi, Aurélien Lebrun, Zhan-Guo Gao, Jean-Pierre Uttaro, Christophe Mathé, Kenneth Jacobson, Lars Petter Jordheim, Christine Ménétrier-Caux, Laurent Chaloin, Suzanne Peyrottes
{"title":"Third-Generation CD73 Inhibitors Based on a 4,6-Disubstituted-2-thiopyridine Scaffold.","authors":"Félix Grosjean, Maria Shaldaeva, Emeline Cros-Perrial, Céline Rodriguez, Rayane Ghoteimi, Aurélien Lebrun, Zhan-Guo Gao, Jean-Pierre Uttaro, Christophe Mathé, Kenneth Jacobson, Lars Petter Jordheim, Christine Ménétrier-Caux, Laurent Chaloin, Suzanne Peyrottes","doi":"10.1002/cmdc.202400662","DOIUrl":"https://doi.org/10.1002/cmdc.202400662","url":null,"abstract":"<p><p>Various series of 4,6-disubstituted-2-thiopyridine derivatives were synthesized and evaluated as potential ecto-5'-nucleotidase (CD73) inhibitors. Altogether, about ninety compounds were prepared using a general synthetic pathway involving one or two steps (eventually one-pot) procedures. Variation of the nature of the substituents in positions 4 and 6 (methyl, trifluoromethyl or phenyl) of the thiopurine ring, as well as on the thiol function, was examined and led to marked differences both in term of reactivity and ability to interfere with the putative target protein. Using a functional assay on immune cells, few compounds belonging to series 4 were shown to be able to antagonize the inhibition of the T-cell proliferation at both 100µM and 10µM (completely for 4ab and partially for 4ai), that is as potent as AOPCP which entirely reversed the inhibitory impact of exogenous ATP on T cell proliferation until 62.5 µM. In addition, we have shown that both compounds (4ab and 4ai) were also capable of moderately inhibiting the hA2A receptor with Ki in the µmolar range in HEK-293 cells. Thus, with the aim to reduce the molecular size and the lipophilicity of our initial scaffold, we finally observed by serendipity a modification of the potential target of our compounds.</p>","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":" ","pages":"e202400662"},"PeriodicalIF":3.6,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142816850","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Discovery of Novel Pyrido[2,3-b]pyrazine Human Cytomegalovirus Polymerase Inhibitors with Broad Spectrum Antiherpetic Activity and Reduced hERG Inhibition.
IF 3.6 4区 医学
ChemMedChem Pub Date : 2024-12-10 DOI: 10.1002/cmdc.202400629
Bing Bai, Appan Srinivas Kandadai, Mostofa Hena, Alexandr Belovodskiy, John Shen, Michael Houghton, James A Nieman
{"title":"Discovery of Novel Pyrido[2,3-b]pyrazine Human Cytomegalovirus Polymerase Inhibitors with Broad Spectrum Antiherpetic Activity and Reduced hERG Inhibition.","authors":"Bing Bai, Appan Srinivas Kandadai, Mostofa Hena, Alexandr Belovodskiy, John Shen, Michael Houghton, James A Nieman","doi":"10.1002/cmdc.202400629","DOIUrl":"https://doi.org/10.1002/cmdc.202400629","url":null,"abstract":"<p><p>The development of non-nucleoside inhibitors targeting human cytomegalovirus (HCMV) polymerase presents a promising approach for enhancing therapeutic treatment for patients with sustained HCMV viremia. A series of non-nucleoside HCMV DNA polymerase inhibitors with various substitution groups at 2-postition of the novel pyrido[2,3-b]pyrazine core was synthesized and investigated. The study focused on optimizing HCMV polymerase inhibition while minimizing off-target inhibition of human ether-à-go-go (hERG) ion channel. Several compounds exhibited strong antiviral activity against HCMV (typical EC50 <1 µM), with favorable cytotoxicity profiles. A potent lead compound, 27, with an EC50 of 0.33 µM and improved aqueous solubility was identified. Further antiviral assessments revealed the potential of select compounds to target a broad spectrum of herpesviruses, including herpes simplex virus (HSV-1, HSV-2) and Epstein-Barr virus (EBV).</p>","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":" ","pages":"e202400629"},"PeriodicalIF":3.6,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142826810","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Isopeptidic Desferrioxamine Analogues: The Role of Hydroxamate Spacing for Chelation of Zr4.
IF 3.6 4区 医学
ChemMedChem Pub Date : 2024-12-10 DOI: 10.1002/cmdc.202400890
Lasse Outzen, Darius Ludolfs, Maximilian Irl, Susanne Kossatz, Wolfgang Maison
{"title":"Isopeptidic Desferrioxamine Analogues: The Role of Hydroxamate Spacing for Chelation of Zr4.","authors":"Lasse Outzen, Darius Ludolfs, Maximilian Irl, Susanne Kossatz, Wolfgang Maison","doi":"10.1002/cmdc.202400890","DOIUrl":"https://doi.org/10.1002/cmdc.202400890","url":null,"abstract":"<p><p>[89Zr]Zr4+ is a radionuclide of increasing clinical relevance for PET (positron emission tomography). However, an ideal chelator for stable Zr-chelation remains to be discovered. This study describes the solid-phase synthesis of octadentate Zr-chelators based on an isopeptidic (ip) scaffold derived from the natural siderophore desferrioxamine (DFOB). Several analogues with different spacers separating the chelating hydroxamates have been prepared and converted to [89Zr]Zr-complexes. The stability of these complexes was evaluated in human serum and in competition to excess of competing chelators. The assays revealed a beneficial effect of long hydroxamate spacing (9 atoms). Shorter spacing led to a decrease in complex stability. The most stable [89Zr]Zr-ipDFO complex had a high stability in challenging competition experiments with a large excess of EDTA for 72 h as determined by radio TLC and LC/MS. The straightforward synthesis, high complex stability and a modular character make ipDFO derivatives promising chelators for applications in targeted PET.</p>","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":" ","pages":"e202400890"},"PeriodicalIF":3.6,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142798735","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Inflammaging and Immunosenescence in the Post-COVID Era: Small Molecules, Big Challenges.
IF 3.6 4区 医学
ChemMedChem Pub Date : 2024-12-09 DOI: 10.1002/cmdc.202400672
Fabio Francavilla, Francesca Intranuovo, Gabriella La Spada, Enza Lacivita, Marco Catto, Elisabetta Anna Graps, Cosimo Damiano Altomare
{"title":"Inflammaging and Immunosenescence in the Post-COVID Era: Small Molecules, Big Challenges.","authors":"Fabio Francavilla, Francesca Intranuovo, Gabriella La Spada, Enza Lacivita, Marco Catto, Elisabetta Anna Graps, Cosimo Damiano Altomare","doi":"10.1002/cmdc.202400672","DOIUrl":"10.1002/cmdc.202400672","url":null,"abstract":"<p><p>Aging naturally involves a decline in biological functions, often triggering a disequilibrium of physiological processes. A common outcome is the altered response exerted by the immune system to counteract infections, known as immunosenescence, which has been recognized as a primary cause, among others, of the so-called long-COVID syndrome. Moreover, the uncontrolled immunoreaction leads to a state of subacute, chronic inflammatory state known as inflammaging, responsible in turn for the chronicization of concomitant pathologies in a self-sustaining process. Anti-inflammatory and immunosuppressant drugs are the current choice for the therapy of inflammaging in post-COVID complications, with contrasting results. The increasing knowledge of the biochemical pathways of inflammaging led to disclose new small molecules-based therapies directed toward different biological targets involved in inflammation, immunological response, and oxidative stress. Herein, paying particular attention to recent clinical data and preclinical literature, we focus on the role of endocannabinoid system in inflammaging, and the promising therapeutic option represented by the CB2R agonists, the role of novel ligands of the formyl peptide receptor 2 and ultimately the potential of newly discovered monoamine oxidase (MAO) inhibitors with neuroprotective activity in the treatment of immunosenescence.</p>","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":" ","pages":"e202400672"},"PeriodicalIF":3.6,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142798728","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Current Approaches and Strategies Applied in First-in-class Drug Discovery.
IF 3.6 4区 医学
ChemMedChem Pub Date : 2024-12-08 DOI: 10.1002/cmdc.202400639
Idrees Mohammed, Someswar Rao Sagurthi
{"title":"Current Approaches and Strategies Applied in First-in-class Drug Discovery.","authors":"Idrees Mohammed, Someswar Rao Sagurthi","doi":"10.1002/cmdc.202400639","DOIUrl":"10.1002/cmdc.202400639","url":null,"abstract":"<p><p>First-in-class drug discovery (FICDD) offers novel therapies, new biological targets and mechanisms of action (MOAs) toward targeting various diseases and provides opportunities to understand unexplored biology and to target unmet diseases. Current screening approaches followed in FICDD for discovery of hit and lead molecules can be broadly categorized and discussed under phenotypic drug discovery (PDD) and target-based drug discovery (TBDD). Each category has been further classified and described with suitable examples from the literature outlining the current trends in screening approaches applied in small molecule drug discovery (SMDD). Similarly, recent applications of functional genomics, structural biology, artificial intelligence (AI), machine learning (ML), and other such advanced approaches in FICDD have also been highlighted in the article. Further, some of the current medicinal chemistry strategies applied during discovery of hits and optimization studies such as hit-to-lead (HTL) and lead optimization (LO) have been simultaneously overviewed in this article.</p>","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":" ","pages":"e202400639"},"PeriodicalIF":3.6,"publicationDate":"2024-12-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142794016","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
4-Aza Cyclopentenone Prostaglandin Analogues: Synthesis and NF-κB Inhibitory Activities.
IF 3.6 4区 医学
ChemMedChem Pub Date : 2024-12-08 DOI: 10.1002/cmdc.202400823
William Doherty, Lorna Conway, Brian Leveau, Francesca Giulia Nacca, Lucia Chiappa, Anna Riccio, Stanley M Roberts, M Gabriella Santoro, Paul Evans
{"title":"4-Aza Cyclopentenone Prostaglandin Analogues: Synthesis and NF-κB Inhibitory Activities.","authors":"William Doherty, Lorna Conway, Brian Leveau, Francesca Giulia Nacca, Lucia Chiappa, Anna Riccio, Stanley M Roberts, M Gabriella Santoro, Paul Evans","doi":"10.1002/cmdc.202400823","DOIUrl":"10.1002/cmdc.202400823","url":null,"abstract":"<p><p>Inspired by the cyclopentenone family of prostaglandins, a series of 4-aza, cross-conjugated cyclopentenones is described. Synthesised from N-protected (4R)-aza-cyclopentenone 5, the exocyclic alkene was installed using a modified Baylis-Hillman type aldol reaction, whereby carbon-carbon bond formation is accompanied by dehydration. In this manner octanal and octenal, for example, can be introduced to mimic the ω-group present in the natural prostaglandins. Similarly, a focused range of alternative substituents were introduced using different aldehydes and ketones. The presence of the tert-butyloxycarbonyl (Boc) group on the 4-amino-cyclopentenone substituent enabled subsequent derivatisation and various electrophiles were successfully incorporated. The ability of the family of 4-amino functionalised cross-conjugated cyclopentenones to block activation of nuclear factor-kappa B (NF-κB) was studied and compared with the natural prostanoid, Δ<sup>12,14</sup>-15-deoxy-PGJ<sub>2</sub> (2). Thereafter, the synthesis of a series of thiol adducts from these compounds were prepared and similarly evaluated biologically. The adducts showed comparable and, on occasion, more potent inhibition of NF-κB than their cyclopentenone precursors and generally demonstrated diminished cytotoxicity. For example, cross-conjugated dieneone 12 inhibited the activation of NF-κB with an IC<sub>50</sub> value of 6.2 μM, whereas its endocyclic N-Boc (27) and N-acetyl (28) cysteine adducts blocked NF-κB activity with values of 1.0 and 8.0 μM respectively.</p>","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":" ","pages":"e202400823"},"PeriodicalIF":3.6,"publicationDate":"2024-12-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142794015","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Structure-Based Virtual Screening and Biological Characterization of Novel BACE-1 and Amyloid-β Aggregation Inhibitors.
IF 3.6 4区 医学
ChemMedChem Pub Date : 2024-12-07 DOI: 10.1002/cmdc.202400685
Ankita Sharma, Madhusmita Nayak, Shikha Thakur, Hemant R Jadhav, Sandip B Bharate
{"title":"Structure-Based Virtual Screening and Biological Characterization of Novel BACE-1 and Amyloid-β Aggregation Inhibitors.","authors":"Ankita Sharma, Madhusmita Nayak, Shikha Thakur, Hemant R Jadhav, Sandip B Bharate","doi":"10.1002/cmdc.202400685","DOIUrl":"10.1002/cmdc.202400685","url":null,"abstract":"<p><p>Alzheimer's disease (AD) is a complex neurodegenerative disorder having limited treatment options. The beta-site APP cleaving enzyme 1 (BACE-1) is a key target for therapeutic intervention in Alzheimer's disease. To discover new scaffolds for BACE-1 inhibitors, a ChemBridge DIVERSet library of 20,000 small molecules was employed to structure-based virtual screening. The top 45 compounds, based on docking scores and binding affinities, were tested for BACE-1 inhibitory activity using a FRET assay. Four compounds, 18 (5353320), 20 (5262831), 29 (5784196) and 32 (5794006) demonstrated more than 35 % inhibitory activity at 10 μM. Notably, pyrazole-5-carbohydrazide 29 (5784196) exhibited BACE-1 inhibition with an IC<sub>50</sub> value of 14.5 μM and a ki value of 0.25 μM. Additionally, it also inhibits the self-aggregation of β-amyloid, with IC<sub>50</sub> value of 14.87 μM. Molecular modeling and dynamics simulations provided insights into its interaction pattern and stability of the enzyme-inhibitor complex. These findings suggest that virtual screening is an efficient and cost-effective method for identifying potential leads for AD.</p>","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":" ","pages":"e202400685"},"PeriodicalIF":3.6,"publicationDate":"2024-12-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142790653","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Oligomerization of 33-mer Gliadin Peptides: Supramolecular Assemblies in Celiac Disease.
IF 3.6 4区 医学
ChemMedChem Pub Date : 2024-12-05 DOI: 10.1002/cmdc.202400789
Verónica I Dodero, María G Herrera
{"title":"Oligomerization of 33-mer Gliadin Peptides: Supramolecular Assemblies in Celiac Disease.","authors":"Verónica I Dodero, María G Herrera","doi":"10.1002/cmdc.202400789","DOIUrl":"10.1002/cmdc.202400789","url":null,"abstract":"<p><p>The 33-mer gliadin peptide and its deamidated derivative, known as 33-mer DGP, are proteolytically resistant peptides central to the pathomechanism of celiac disease (CeD), the autoimmune presentation of gluten-related disorders (GRD). Both peptides can form spontaneous oligomers in the nanomolar concentration, leading to the formation of nanostructures. In other protein-related diseases, oligomers and aggregates are central in their pathomechanism; therefore, it was hypothesized that the oligomerization of proteolytical-resistant 33-mer gliadin peptides could be an underrecognized disease trigger. This review focuses on the current understanding of 33-mer peptides and their oligomers in vitro and cellular experiments. We intend to give the necessary details that incentivize the chemistry community to get involved in the effort to understand the self-assembly of gliadin peptides and the role of their supramolecular structures in CeD and the other GRD. More research is needed to design effective and safe chemical and/or nutritional interventions beyond the gluten-free diet.</p>","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":" ","pages":"e202400789"},"PeriodicalIF":3.6,"publicationDate":"2024-12-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142783585","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
CORRIGENDUM: Correction to "Synthesis and Antitumour Evaluation of Tricyclic Indole-2-Carboxamides against Paediatric Brain Cancer Cells".
IF 3.6 4区 医学
ChemMedChem Pub Date : 2024-12-05 DOI: 10.1002/cmdc.202400911
{"title":"CORRIGENDUM: Correction to \"Synthesis and Antitumour Evaluation of Tricyclic Indole-2-Carboxamides against Paediatric Brain Cancer Cells\".","authors":"","doi":"10.1002/cmdc.202400911","DOIUrl":"https://doi.org/10.1002/cmdc.202400911","url":null,"abstract":"","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":" ","pages":"e202400911"},"PeriodicalIF":3.6,"publicationDate":"2024-12-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142783582","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Cover Feature: Zn(II)-Curcumin Complexes-Based Anticancer Agents (ChemMedChem 23/2024)
IF 3.6 4区 医学
ChemMedChem Pub Date : 2024-12-04 DOI: 10.1002/cmdc.202482302
Rajdeep Mondal, Muthukumar Keerthana, Nanjan Pandurangan, Sankarasekaran Shanmugaraju
{"title":"Cover Feature: Zn(II)-Curcumin Complexes-Based Anticancer Agents (ChemMedChem 23/2024)","authors":"Rajdeep Mondal,&nbsp;Muthukumar Keerthana,&nbsp;Nanjan Pandurangan,&nbsp;Sankarasekaran Shanmugaraju","doi":"10.1002/cmdc.202482302","DOIUrl":"https://doi.org/10.1002/cmdc.202482302","url":null,"abstract":"<p>This cover image highlights the structure and anticancer properties of Zn(II)-curcumin complexes. Curcumin whose structure is given in yellow reacts with Zn(II) ion to form the fluorescent green colored Zn(II)-curcumin complex. The two DNA double helix structures represent the DNA binding potential of Zn(II)-curcumin complexes. The cell membrane in cyan and cell organelle in blue indicate the cellular uptake and internalization of Zn(II)-curcumin complex. The white bulb highlights the light irradiation of curcumin derivatives. More details can be found in the article 10.1002/cmdc.202400558 by Sankarasekaran Shanmugaraju and co-workers.<figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":"19 23","pages":""},"PeriodicalIF":3.6,"publicationDate":"2024-12-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/cmdc.202482302","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142860063","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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