Compounds > le 404
Page last updated: 2024-08-02 20:53:44

le 404

Description

Cross-References

ID SourceID
PubMed CID11558055
CHEMBL ID201170
MeSH IDM0496170

Synonyms (7)

Synonym
CHEMBL201170 ,
le404
bdbm50180913
11-methyl-11-aza-tricyclo[12.4.0.0.3,8]octadeca-1(18),3(8),4,6,14,16-hexaen-6-ol
7-methyl-5,6,7,8,9,14-hexahydrodibenzo[d,g]azecin-3-ol
11-methyl-11-aza-tricyclo[12.4.0.03,8]octadeca-1(14),3,5,7,15,17-hexaen-6-ol
3-hydroxy-7-methyl-5,6,7,8,9,14-hexahydrodibenzo[d,g]azecine

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
D(2) dopamine receptorHomo sapiens (human)Ki0.0207AID261571; AID261576; AID305859; AID343051; AID452073
D(1A) dopamine receptorHomo sapiens (human)Ki0.0006AID261570; AID261575; AID305858; AID343050; AID452072
D(4) dopamine receptorHomo sapiens (human)Ki0.0113AID452075
D(1B) dopamine receptorHomo sapiens (human)Ki0.0015AID261573; AID261578; AID297409; AID305862; AID452076
D(3) dopamine receptorHomo sapiens (human)Ki0.0473AID261572; AID305860; AID452074

Bioassays (29)

Assay IDTitleYearJournalArticle
AID305861Binding affinity to human cloned dopamine D4.4 receptor expressed in CHO cells2007Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5
ISSN: 0960-894X		Dopamine/serotonin receptor ligands. Part 15: Oxygenation of the benz-indolo-azecine LE 300 leads to novel subnanomolar dopamine D1/D5 antagonists.
AID452079Agonist activity at human dopamine D1 receptor expressed in HEK293 cells assessed as intracellular calcium by fluorescence microplate reader2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
ISSN: 1464-3391		Dibenzazecine scaffold rebuilding--is the flexibility always essential for high dopamine receptor affinities?
AID261575Inhibition of D1 dopamine receptor in HEK 293 cells by intracellular calcium assay2006Journal of medicinal chemistry, Mar-23, Volume: 49, Issue:6
ISSN: 0022-2623		Dopamine/serotonin receptor ligands. 12(1): SAR studies on hexahydro-dibenz[d,g]azecines lead to 4-chloro-7-methyl-5,6,7,8,9,14-hexahydrodibenz[d,g]azecin-3-ol, the first picomolar D5-selective dopamine-receptor antagonist.
AID261570Displacement of [3H]SCH 23390 from D1 dopamine receptor2006Journal of medicinal chemistry, Mar-23, Volume: 49, Issue:6
ISSN: 0022-2623		Dopamine/serotonin receptor ligands. 12(1): SAR studies on hexahydro-dibenz[d,g]azecines lead to 4-chloro-7-methyl-5,6,7,8,9,14-hexahydrodibenz[d,g]azecin-3-ol, the first picomolar D5-selective dopamine-receptor antagonist.
AID452076Displacement of [3H]SCH23390 from human dopamine D5 receptor expressed in CHO cells by scintillation counting2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
ISSN: 1464-3391		Dibenzazecine scaffold rebuilding--is the flexibility always essential for high dopamine receptor affinities?
AID305864Agonist activity at human dopamine D2 receptor assessed as increase in intramolecular calcium concentration by calcium fluorescence assay2007Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5
ISSN: 0960-894X		Dopamine/serotonin receptor ligands. Part 15: Oxygenation of the benz-indolo-azecine LE 300 leads to novel subnanomolar dopamine D1/D5 antagonists.
AID261576Inhibition of D2L dopamine receptor in HEK 293 cells by intracellular calcium assay2006Journal of medicinal chemistry, Mar-23, Volume: 49, Issue:6
ISSN: 0022-2623		Dopamine/serotonin receptor ligands. 12(1): SAR studies on hexahydro-dibenz[d,g]azecines lead to 4-chloro-7-methyl-5,6,7,8,9,14-hexahydrodibenz[d,g]azecin-3-ol, the first picomolar D5-selective dopamine-receptor antagonist.
AID343051Displacement of [3H]SCH23390 from human cloned dopamine D2L receptor2008Bioorganic & medicinal chemistry letters, Jul-01, Volume: 18, Issue:13
ISSN: 1464-3405		Dopamine/serotonin receptor ligands. Part 17: a cross-target SAR approach: affinities of azecine-styled ligands for 5-HT(2A) versus D1 and D2 receptors.
AID261572Binding affinity to D3 dopamine receptor by radioligand binding assay2006Journal of medicinal chemistry, Mar-23, Volume: 49, Issue:6
ISSN: 0022-2623		Dopamine/serotonin receptor ligands. 12(1): SAR studies on hexahydro-dibenz[d,g]azecines lead to 4-chloro-7-methyl-5,6,7,8,9,14-hexahydrodibenz[d,g]azecin-3-ol, the first picomolar D5-selective dopamine-receptor antagonist.
AID261571Displacement of [3H]spiperone from D2L dopamine receptor2006Journal of medicinal chemistry, Mar-23, Volume: 49, Issue:6
ISSN: 0022-2623		Dopamine/serotonin receptor ligands. 12(1): SAR studies on hexahydro-dibenz[d,g]azecines lead to 4-chloro-7-methyl-5,6,7,8,9,14-hexahydrodibenz[d,g]azecin-3-ol, the first picomolar D5-selective dopamine-receptor antagonist.
AID305859Displacement of [3H]spiperone from human cloned dopamine D2L receptor expressed in CHO cells2007Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5
ISSN: 0960-894X		Dopamine/serotonin receptor ligands. Part 15: Oxygenation of the benz-indolo-azecine LE 300 leads to novel subnanomolar dopamine D1/D5 antagonists.
AID305865Agonist activity at human dopamine D5 receptor assessed as increase in intramolecular calcium concentration by calcium fluorescence assay2007Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5
ISSN: 0960-894X		Dopamine/serotonin receptor ligands. Part 15: Oxygenation of the benz-indolo-azecine LE 300 leads to novel subnanomolar dopamine D1/D5 antagonists.
AID343052Antagonist activity at serotonin 5HT2A receptor assessed as effect on 5HT-induced isometric contractile force in isolated rings of pig coronary artery2008Bioorganic & medicinal chemistry letters, Jul-01, Volume: 18, Issue:13
ISSN: 1464-3405		Dopamine/serotonin receptor ligands. Part 17: a cross-target SAR approach: affinities of azecine-styled ligands for 5-HT(2A) versus D1 and D2 receptors.
AID261578Inhibition of D5 dopamine receptor in HEK 293 cells by intracellular calcium assay2006Journal of medicinal chemistry, Mar-23, Volume: 49, Issue:6
ISSN: 0022-2623		Dopamine/serotonin receptor ligands. 12(1): SAR studies on hexahydro-dibenz[d,g]azecines lead to 4-chloro-7-methyl-5,6,7,8,9,14-hexahydrodibenz[d,g]azecin-3-ol, the first picomolar D5-selective dopamine-receptor antagonist.
AID452074Displacement of [3H]spiperone from human dopamine D3 receptor expressed in CHO cells by scintillation counting2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
ISSN: 1464-3391		Dibenzazecine scaffold rebuilding--is the flexibility always essential for high dopamine receptor affinities?
AID452075Displacement of [3H]spiperone from human dopamine D4 receptor expressed in CHO cells by scintillation counting2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
ISSN: 1464-3391		Dibenzazecine scaffold rebuilding--is the flexibility always essential for high dopamine receptor affinities?
AID305863Agonist activity at human dopamine D1 receptor assessed as increase in intramolecular calcium concentration by calcium fluorescence assay2007Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5
ISSN: 0960-894X		Dopamine/serotonin receptor ligands. Part 15: Oxygenation of the benz-indolo-azecine LE 300 leads to novel subnanomolar dopamine D1/D5 antagonists.
AID452072Displacement of [3H]SCH23390 from human dopamine D1 receptor expressed in CHO cells by scintillation counting2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
ISSN: 1464-3391		Dibenzazecine scaffold rebuilding--is the flexibility always essential for high dopamine receptor affinities?
AID452077Antagonist activity at human dopamine D1 receptor expressed in HEK293 cells assessed as SKF-38393-induced intracellular calcium by fluorescence microplate reader2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
ISSN: 1464-3391		Dibenzazecine scaffold rebuilding--is the flexibility always essential for high dopamine receptor affinities?
AID261577Inhibition of D3 dopamine receptor in HEK 293 cells by intracellular calcium assay2006Journal of medicinal chemistry, Mar-23, Volume: 49, Issue:6
ISSN: 0022-2623		Dopamine/serotonin receptor ligands. 12(1): SAR studies on hexahydro-dibenz[d,g]azecines lead to 4-chloro-7-methyl-5,6,7,8,9,14-hexahydrodibenz[d,g]azecin-3-ol, the first picomolar D5-selective dopamine-receptor antagonist.
AID305862Binding affinity to human cloned dopamine D5 receptor expressed in HEK 293 cells2007Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5
ISSN: 0960-894X		Dopamine/serotonin receptor ligands. Part 15: Oxygenation of the benz-indolo-azecine LE 300 leads to novel subnanomolar dopamine D1/D5 antagonists.
AID305860Binding affinity to human cloned dopamine D3 receptor expressed in CHO cells2007Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5
ISSN: 0960-894X		Dopamine/serotonin receptor ligands. Part 15: Oxygenation of the benz-indolo-azecine LE 300 leads to novel subnanomolar dopamine D1/D5 antagonists.
AID297409Displacement of [3H]SCH 23390 from human dopamine D5 receptor expressed in HEK293 cells2007Journal of medicinal chemistry, Sep-06, Volume: 50, Issue:18
ISSN: 0022-2623		Dopamine/serotonin receptor ligands. 16.(1) Expanding dibenz[d,g]azecines to 11- and 12-membered homologues. Interaction with dopamine D(1)-D(5) receptors.
AID343050Displacement of [3H]SCH23390 from human cloned dopamine D1 receptor2008Bioorganic & medicinal chemistry letters, Jul-01, Volume: 18, Issue:13
ISSN: 1464-3405		Dopamine/serotonin receptor ligands. Part 17: a cross-target SAR approach: affinities of azecine-styled ligands for 5-HT(2A) versus D1 and D2 receptors.
AID452080Agonist activity at human dopamine D2L receptor expressed in HEK293 cells assessed as intracellular calcium by fluorescence microplate reader2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
ISSN: 1464-3391		Dibenzazecine scaffold rebuilding--is the flexibility always essential for high dopamine receptor affinities?
AID305858Displacement of [3H]SCH 23390 from human cloned dopamine D1 receptor expressed in HEK 293 cells2007Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5
ISSN: 0960-894X		Dopamine/serotonin receptor ligands. Part 15: Oxygenation of the benz-indolo-azecine LE 300 leads to novel subnanomolar dopamine D1/D5 antagonists.
AID261573Binding affinity to D5 dopamine receptor by radioligand binding assay2006Journal of medicinal chemistry, Mar-23, Volume: 49, Issue:6
ISSN: 0022-2623		Dopamine/serotonin receptor ligands. 12(1): SAR studies on hexahydro-dibenz[d,g]azecines lead to 4-chloro-7-methyl-5,6,7,8,9,14-hexahydrodibenz[d,g]azecin-3-ol, the first picomolar D5-selective dopamine-receptor antagonist.
AID452078Antagonist activity at human dopamine D2L receptor expressed in HEK293 cells assessed as quinpirole-induced intracellular calcium by fluorescence microplate reader2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
ISSN: 1464-3391		Dibenzazecine scaffold rebuilding--is the flexibility always essential for high dopamine receptor affinities?
AID452073Displacement of [3H]spiperone from human dopamine D2L receptor expressed in CHO cells by scintillation counting2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
ISSN: 1464-3391		Dibenzazecine scaffold rebuilding--is the flexibility always essential for high dopamine receptor affinities?

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (100.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
ketanserin
1
aromatic ketone;
organofluorine compound;
piperidines;
quinazolines		alpha-adrenergic antagonist;
antihypertensive agent;
cardiovascular drug;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
serotonergic antagonist		2008200816.0medium000100
le 300
3
indoles2006200817.0high000300
dihydrexidine
1
phenanthridines2009200915.0medium000100
stepholidine
1
2009200915.0medium000100
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020