Design, synthesis, and structure-activity relationship of new isobenzofuranone ligands of protein kinase C

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 11, 2004, Pages 2963-2967

  Baba, Yoshiyasu ^a,b   Ogoshi, Yosuke ^a   Hirai, Go ^a   Yanagisawa, Takeshi ^b   Nagamatsu, Kumiko ^b,d   Mayumi, Satoshi ^c   Hashimoto, Yuichi ^c   Sodeoka, Mikiko ^a,b,c,d  

^a TOHOKU UNIVERSITY   (Japan)

^b SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

^d JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; DIACYLGLYCEROL; FURANONE DERIVATIVE; ISOBENZOFURAN DERIVATIVE; ISOBENZOFURANONE; LIGAND; PROTEIN KINASE C; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG SYNTHESIS; EVALUATION; HYDROGEN BOND; LIGAND BINDING; PROTEIN DOMAIN; PROTEIN PROTEIN INTERACTION; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION;

BENZOFURANS; BINDING SITES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; HYDROGEN BONDING; LIGANDS; MOLECULAR STRUCTURE; PROTEIN BINDING; PROTEIN KINASE C; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 2342518915     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.02.097     Document Type: Article

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39. 3) was used instead of 1f. The docking model was constructed in the Affinity module of the INSIGHT II molecular program developed by MSI (now succeeded by Accelrys, San Diego). The first binding placement of isobenzofuranone within the PKCδ C1B domain was made by superimposing the molecule on the critical functional groups of phorbol 13-acetate. We constructed a 'grid', which is partitioned into bulk (nonflexible) and movable atoms of the ligand/receptor system; interactions among bulk atoms are approximated by using the accurate and efficient molecular mechanical/grid (MM/Grid) method, while interactions among movable atoms are treated using a full force field representation. The grid was defined by the amino acid residues within 6 Å around the isobenzofuranone. The binding model was made using a Monte Carlo type procedure to search both conformational and Cartesian space