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5-Methyl-6-oxo-8-trimethylsilanylethynyl-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid tert-butyl ester

ID: ALA300840

Chembl Id: CHEMBL300840

PubChem CID: 10092944

Max Phase: Preclinical

Molecular Formula: C22H27N3O3Si

Molecular Weight: 409.56

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  CN1Cc2c(C(=O)OC(C)(C)C)ncn2-c2ccc(C#C[Si](C)(C)C)cc2C1=O

Standard InChI:  InChI=1S/C22H27N3O3Si/c1-22(2,3)28-21(27)19-18-13-24(4)20(26)16-12-15(10-11-29(5,6)7)8-9-17(16)25(18)14-23-19/h8-9,12,14H,13H2,1-7H3

Standard InChI Key:  NGWYCOVARFKQDW-UHFFFAOYSA-N

Associated Targets(Human)

GABRA1 Tclin GABA-A receptor; alpha-1/beta-3/gamma-2 (1565 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GABRG2 Tclin GABA-A receptor; alpha-2/beta-3/gamma-2 (949 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GABRG2 Tclin GABA-A receptor; alpha-3/beta-3/gamma-2 (1250 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GABRG2 Tclin GABA-A receptor; alpha-5/beta-3/gamma-2 (1334 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GABRG2 Tclin GABA-A receptor; alpha-6/beta-3/gamma-2 (367 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GABRG2 Tclin GABA A receptor alpha-4/beta-3/gamma-2 (109 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GABRA1 Tclin GABA-A receptor; alpha-1/beta-2/gamma-2 (1171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GABRB2 Tclin GABA A receptor alpha-2/beta-2/gamma-2 (194 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GABRB2 Tclin GABA A receptor alpha-3/beta-2/gamma-2 (101 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GABRB2 Tclin GABA A receptor alpha-6/beta-2/gamma-2 (27 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

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MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

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Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 409.56Molecular Weight (Monoisotopic): 409.1822AlogP: #Rotatable Bonds:
Polar Surface Area: Molecular Species: HBA: HBD:
#RO5 Violations: HBA (Lipinski): HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: CX LogD:
Aromatic Rings: Heavy Atoms: QED Weighted: Np Likeness Score:

References

1. Liu R, Hu RJ, Zhang P, Skolnick P, Cook JM..  (1996)  Synthesis and pharmacological properties of novel 8-substituted imidazobenzodiazepines: high-affinity, selective probes for alpha 5-containing GABAA receptors.,  39  (9): [PMID:8627617] [10.1021/jm950887n]
2. Huang Q, Liu R, Zhang P, He X, McKernan R, Gan T, Bennett DW, Cook JM..  (1998)  Predictive models for GABAA/benzodiazepine receptor subtypes: studies of quantitative structure-activity relationships for imidazobenzodiazepines at five recombinant GABAA/benzodiazepine receptor subtypes [alphaxbeta3gamma2 (x = 1-3, 5, and 6)] via comparative molecular field analysis.,  41  (21): [PMID:9767648] [10.1021/jm980317y]
3. Li X, Cao H, Zhang C, Furtmueller R, Fuchs K, Huck S, Sieghart W, Deschamps J, Cook JM..  (2003)  Synthesis, in vitro affinity, and efficacy of a bis 8-ethynyl-4H-imidazo[1,5a]- [1,4]benzodiazepine analogue, the first bivalent alpha5 subtype selective BzR/GABA(A) antagonist.,  46  (26): [PMID:14667209] [10.1021/jm034164c]
4. Huang Q, He X, Ma C, Liu R, Yu S, Dayer CA, Wenger GR, McKernan R, Cook JM..  (2000)  Pharmacophore/receptor models for GABA(A)/BzR subtypes (alpha1beta3gamma2, alpha5beta3gamma2, and alpha6beta3gamma2) via a comprehensive ligand-mapping approach.,  43  (1): [PMID:10633039] [10.1021/jm990341r]

Source