Improvement of σ1 receptor affinity by late-stage C-H-bond arylation of spirocyclic lactones

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 7, 2013, Pages 1844-1856

  Meyer, Christina ^a   Neue, Benedikt ^a   Schepmann, Dirk ^a   Yanagisawa, Shuichi ^b   Yamaguchi, Junichiro ^b   Würthwein, Ernst Ulrich ^a   Itami, Kenichiro ^b   Wünsch, Bernhard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

1 Ligands; C H bond arylation of complex thiophenes; DFT calculations; Hydrophobic pocket; Spirocyclic lactones

Indexed keywords

1 BENZYL 1' (4 METHOXYPHENYL)SPIRO[PIPERIDINE 4,4' THIENO[3,4 C]PYRAN] 6' (7'H)ONE; 1 BENZYL 1' PHENYLSPIRO[PIPERIDINE 4,4' THIENO[3,4 C]PYRAN] 6' (7'H)ONE; 1 BENZYL 2' PHENYLSPIRO [PIPERIDINE 4,7' THIENO[2,3 C]PYRAN] 5' (4'H) ONE; 1 BENZYL 3' (4 METHOXYPHENYL)SPIRO [PIPERIDINE 4,7' THIENO[2,3 C]PYRAN] 5' (4'H) ONE; 1 BENZYL 3' BROMOSPIRO[PIPERIDINE 4,4' THIENO[2,3 C]FURAN] 6' ONE; 1 BENZYL 3' PHENYLSPIRO [PIPERIDINE 4,7' THIENO[2,3 C]PYRAN] 5' (4'H) ONE; 1 BENZYL 4 [3 (2,2 DIMETHOXYETHYL)THIOPHEN 2 YL]PIPERIDIN 4 OL; 1 BENZYL 4 [4 (2,2 DIMETHOXYETHYL)THIOPHEN 3 YL]PIPERIDIN 4 OL; 1 BENZYL 4' (1,1' BIPHENYL 4 YL)SPIRO [PIPERIDINE 4,1'THIENO[3,4 C]PYRAN] 3' ONE; 1 BENZYL 4' (4 METHOXYPHENYL)SPIRO[PIPERIDINE 4,1' THIENO[3,4 C]FURAN] 3' ONE; 1 BENZYL 4' PHENYLSPIRO[PIPERIDINE 4,1' THIENO[3,4 C]FURAN] 3' ONE; 1 BENZYL 4',5' DIHYDROSPIRO[PIPERIDINE 4,7' THIENO[2,3C]PYRAN] 5' OL; 1 BENZYL 4',6' BIS(4 METHOXYPHENYL)SPIRO[PIPERIDINE 4,1' THIENO[3,4 C]FURAN] 3' ONE; 1 BENZYL 4',6' DIPHENYLSPIRO[PIPERIDINE 4,1' THIENO[3,4 C]FURAN] 3' ONE; 1 BENZYL 6' (4 METHOXYPHENYL)SPIRO[PIPERIDINE 4,1' THIENO[3,4 C]FURAN] 3' ONE; 1 BENZYL 6' PHENYLSPIRO[PIPERIDINE 4,1' THIENO[3,4 C]FURAN] 3' ONE; 1 BENZYL 6',7' DIHYDROSPIRO[PIPERIDINE 4,4' THIENO[3,4C]PYRAN] 6' OL; 1 BENZYLSPIRO[PIPERIDINE 4,1' THIENO[3,4 C]PYRAN] 3' ONE; 1 BENZYLSPIRO[PIPERIDINE 4,4' THIENO[3,4 C]PYRAN] 6'(7'H) ONE; 1 BENZYLSPIRO[PIPERIDINE 4,7' THIENO[2,3 C]PYRAN] 5'(4'H) ONE; 2,2' BIPYRIDINE; 4 (1 BENZYL 3' OXOSPIRO[PIPERIDINE 4,1' THIENO[3,4 C]FURAN] 6' YL)BENZONITRILE; 4 (1 BENZYL 6' OXO 6',7' DIHYDROSPIRO [PIPERIDINE 4,4'THIENO[3,4 C]PYRAN] 1' YL) BENZONITRILE; 4,4' (1 BENZYL 3' OXOSPIRO[PIPERIDINE 4,1' THIENO[3,4 C]FURAN] 4',6' YL)DIBENZONITRILE; CARBON; HYDROGEN; LACTONE DERIVATIVE; LEAD CHLORIDE; THIOPHENE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; ARYLATION; CALCULATION; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG STRUCTURE; QUANTUM CHEMISTRY; RECEPTOR AFFINITY; THERMODYNAMICS;

ANIMALS; GUINEA PIGS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LACTONES; PROTEIN BINDING; RATS; RECEPTORS, SIGMA; SPIRO COMPOUNDS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES;

EID: 84875212566     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.01.038     Document Type: Article

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