{"@context":{"@vocab":"https://cir.nii.ac.jp/schema/1.0/","rdfs":"http://www.w3.org/2000/01/rdf-schema#","dc":"http://purl.org/dc/elements/1.1/","dcterms":"http://purl.org/dc/terms/","foaf":"http://xmlns.com/foaf/0.1/","prism":"http://prismstandard.org/namespaces/basic/2.0/","cinii":"http://ci.nii.ac.jp/ns/1.0/","datacite":"https://schema.datacite.org/meta/kernel-4/","ndl":"http://ndl.go.jp/dcndl/terms/","jpcoar":"https://github.com/JPCOAR/schema/blob/master/2.0/"},"@id":"https://cir.nii.ac.jp/crid/1360004232015293184.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1016/j.bmc.2013.08.036"}},{"identifier":{"@type":"URI","@value":"https://api.elsevier.com/content/article/PII:S096808961300730X?httpAccept=text/xml"}},{"identifier":{"@type":"URI","@value":"https://api.elsevier.com/content/article/PII:S096808961300730X?httpAccept=text/plain"}},{"identifier":{"@type":"PMID","@value":"24051074"}}],"resourceType":"学術雑誌論文(journal article)","dc:title":[{"@value":"Conformational restriction approach to β-secretase (BACE1) inhibitors III: Effective investigation of the binding mode by combinational use of X-ray analysis, isothermal titration calorimetry and theoretical calculations"}],"description":[{"notation":[{"@value":"For further investigation of BACE1 inhibitors using conformational restriction with sp(3) hybridized carbon, we applied this approach to 6-substituted aminopyrimidone derivatives 3 to improve the inhibitory activity by reducing the entropic energy loss upon binding to BACE1. Among eight stereoisomers synthesized, [trans-(1'R,2'R),6S] isomer 6 exhibited the best BACE1 inhibitory activity, which was statistically superior to that of the corresponding ethylene linker compound (R)-3. Combinational examinations of the binding mode of 6 were performed, which included isothermal titration calorimetry (ITC), X-ray crystallographic structure analysis and theoretical calculations, to clarify the effect of our conformational restriction approach. From the ITC measurement, the binding entropy of 6 was found to be ∼0.5kcal larger than that of (R)-3, which is considered to be affected by conformational restriction with a cyclopropane ring."}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1380004232015293187","@type":"Researcher","foaf:name":[{"@value":"Shuji Yonezawa"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004232015293188","@type":"Researcher","foaf:name":[{"@value":"Kenichiro Fujiwara"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004232015293192","@type":"Researcher","foaf:name":[{"@value":"Takahiko Yamamoto"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004232015293185","@type":"Researcher","foaf:name":[{"@value":"Kazunari Hattori"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004232015293184","@type":"Researcher","foaf:name":[{"@value":"Hidekuni Yamakawa"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004232015293194","@type":"Researcher","foaf:name":[{"@value":"Chie Muto"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004232015293190","@type":"Researcher","foaf:name":[{"@value":"Motoko Hosono"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004232015293191","@type":"Researcher","foaf:name":[{"@value":"Yoshikazu Tanaka"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004232015293189","@type":"Researcher","foaf:name":[{"@value":"Toru Nakano"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004232015293195","@type":"Researcher","foaf:name":[{"@value":"Hiroshi Takemoto"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004232015293193","@type":"Researcher","foaf:name":[{"@value":"Mitsuhiro Arisawa"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004232015293186","@type":"Researcher","foaf:name":[{"@value":"Satoshi Shuto"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"09680896"}],"prism:publicationName":[{"@value":"Bioorganic & Medicinal Chemistry"}],"dc:publisher":[{"@value":"Elsevier 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Conformation"},{"@id":"https://cir.nii.ac.jp/all?q=Stereoisomerism","dc:title":"Stereoisomerism"},{"@id":"https://cir.nii.ac.jp/all?q=Calorimetry","dc:title":"Calorimetry"},{"@id":"https://cir.nii.ac.jp/all?q=Crystallography,%20X-Ray","dc:title":"Crystallography, X-Ray"},{"@id":"https://cir.nii.ac.jp/all?q=Amides","dc:title":"Amides"},{"@id":"https://cir.nii.ac.jp/all?q=Protein%20Structure,%20Tertiary","dc:title":"Protein Structure, Tertiary"},{"@id":"https://cir.nii.ac.jp/all?q=Structure-Activity%20Relationship","dc:title":"Structure-Activity Relationship"},{"@id":"https://cir.nii.ac.jp/all?q=Aspartic%20Acid%20Endopeptidases","dc:title":"Aspartic Acid Endopeptidases"},{"@id":"https://cir.nii.ac.jp/all?q=Humans","dc:title":"Humans"},{"@id":"https://cir.nii.ac.jp/all?q=Thermodynamics","dc:title":"Thermodynamics"},{"@id":"https://cir.nii.ac.jp/all?q=Protease%20Inhibitors","dc:title":"Protease Inhibitors"},{"@id":"https://cir.nii.ac.jp/all?q=Amyloid%20Precursor%20Protein%20Secretases","dc:title":"Amyloid Precursor Protein Secretases"},{"@id":"https://cir.nii.ac.jp/all?q=Protein%20Binding","dc:title":"Protein Binding"}],"project":[{"@id":"https://cir.nii.ac.jp/crid/1040282257176464896","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"24390023"},{"@type":"JGN","@value":"JP24390023"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-24390023/"}],"notation":[{"@language":"ja","@value":"シクロプロパンの構造特性と三次元的多様性を鍵とする分子設計に基づく創薬研究"},{"@language":"en","@value":"Medicinal chemical study by the three-dimensional structural diversity-oriented strategy based on the characteristic steric and stereoelectronic features of cyclopropane"}]}],"relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360004233223940096","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Conformational 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Enantioselective Synthesis of <i>cis-</i> and <i>trans-</i>1-Arylpiperazyl-2-phenylcyclopropanes Designed as Antidopaminergic Agents"}]},{"@id":"https://cir.nii.ac.jp/crid/1363951794722985600","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Development of Versatile <i>cis</i>- and <i>trans</i>-Dicarbon-Substituted Chiral Cyclopropane Units:  Synthesis of (1<i>S</i>,2<i>R</i>)- and (1<i>R</i>,2<i>R</i>)-2-Aminomethyl-1-(1<i>H</i>-imidazol-4-yl)cyclopropanes and Their Enantiomers as Conformationally Restricted Analogues of Histamine"}]},{"@id":"https://cir.nii.ac.jp/crid/1363951795754285312","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Thermodynamic and Structural Effects of Conformational Constraints in Protein−Ligand Interactions. Entropic Paradoxy Associated with Ligand Preorganization"}]},{"@id":"https://cir.nii.ac.jp/crid/1364233268633963264","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Design and Validation of Bicyclic Iminopyrimidinones As Beta Amyloid Cleaving Enzyme-1 (BACE1) Inhibitors: Conformational Constraint to Favor a Bioactive Conformation"}]},{"@id":"https://cir.nii.ac.jp/crid/1364233269821808640","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"The Amyloid Hypothesis of Alzheimer's Disease: Progress and Problems on the Road to Therapeutics"}]},{"@id":"https://cir.nii.ac.jp/crid/1364233271163337472","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Asymmetric Synthesis of β-Amino Acid Derivatives Incorporating a Broad Range of Substitution Patterns by Enolate Additions to<i>tert</i>-Butanesulfinyl Imines"}]},{"@id":"https://cir.nii.ac.jp/crid/1390001204162102016","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Conformational Analysis of the NMDA Receptor Antagonist (1S,2R)-1-Phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide (PPDC) Designed by a Novel Conformational Restriction Method Based on the Structural Feature of Cyclopropane Ring."}]},{"@id":"https://cir.nii.ac.jp/crid/1390282679251316736","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@language":"ja","@value":"アルツハイマー病治療薬としてのアミロイド抑制薬の研究開発状況"},{"@language":"en","@value":"Progress in the development of anti-amyloid drugs for treatment of Alzheimer’s disease"},{"@language":"ja-Kana","@value":"アルツハイマービョウ チリョウヤク ト シテ ノ アミロイド ヨクセイヤク ノ ケンキュウ カイハツ ジョウキョウ"},{"@value":"Progress in the development of anti-amyloid drugs for treatment of Alzheimer&rsquo;s disease"}]},{"@id":"https://cir.nii.ac.jp/crid/1881428067476539136","@type":"Dataset","relationType":["isSourceOf"],"jpcoar:relatedTitle":[{"@value":"BindingDB Entry 50005685: Conformational restriction approach to β-secretase (BACE1) inhibitors III: effective investigation of the binding mode by combinational use of X-ray analysis, isothermal titration calorimetry and theoretical calculations."}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1016/j.bmc.2013.08.036"},{"@type":"KAKEN","@value":"PRODUCT-14568460"},{"@type":"OPENAIRE","@value":"doi_dedup___::babb92374a1c212e0797d285d00bc12b"},{"@type":"CROSSREF","@value":"10.1002/chem.201702119_references_DOI_TM2W1yojMxun0eEgWeWvPhTGEz7"}]}