3-bromo-6-(cyclopropylmethyl)-10-methyl-9H-benzo[f]imidazo[1,5-a][1,2,4]triazolo[1,5-d][1,4]diazepine

ID: ALA1080398

PubChem CID: 46882400

Max Phase: Preclinical

Molecular Formula: C17H16BrN5

Molecular Weight: 370.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ncn2c1Cn1nc(CC3CC3)nc1-c1cc(Br)ccc1-2

Standard InChI:  InChI=1S/C17H16BrN5/c1-10-15-8-23-17(20-16(21-23)6-11-2-3-11)13-7-12(18)4-5-14(13)22(15)9-19-10/h4-5,7,9,11H,2-3,6,8H2,1H3

Standard InChI Key:  LHDPGSHJSSZMRH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 27  0  0  0  0  0  0  0  0999 V2000
    1.5401   -5.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5389   -5.8461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295   -6.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2277   -4.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7834   -5.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9175   -5.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9195   -5.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5668   -4.5194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789   -4.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7680   -3.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1963   -3.3424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4541   -3.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4273   -6.2054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6046   -6.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5314   -7.2371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3088   -7.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -6.9289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5573   -3.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8485   -6.2441    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.3052   -8.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0346   -8.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4544   -9.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8799   -8.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 13 14  1  0
  3  6  2  0
  5  9  1  0
  5 13  1  0
 14  6  1  0
  6  7  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
  7  8  1  0
 10 18  1  0
  8  9  1  0
  2 19  1  0
  1  2  2  0
 16 20  1  0
  7  4  2  0
 20 21  1  0
 22 21  1  0
 23 22  1  0
 21 23  1  0
  4  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1080398

   15-Bromo-10-(cyclopropylmethyl)-5-methyl-2,4,8,9,11-pentazatetracyclo[11.4.0.02,6.08,12]heptadeca-1(13),3,5,9,11,14,16-heptaene

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 370.25

Molecular Weight (Monoisotopic): 369.0589

AlogP: 3.52

#Rotatable Bonds: 2

Polar Surface Area: 48.53

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.48

CX Basic pKa: 4.71

CX LogP: 3.45

CX LogD: 3.45

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.54

Np Likeness Score: -0.85

References

1. Buettelmann B, Ballard TM, Gasser R, Fischer H, Hernandez MC, Knoflach F, Knust H, Stadler H, Thomas AW, Trube G..  (2009)  Imidazo[1,5-a][1,2,4]-triazolo[1,5-d][1,4]benzodiazepines as potent and highly selective GABAA alpha5 inverse agonists with potential for the treatment of cognitive dysfunction.,  19  (20): [PMID:19740657] [10.1016/j.bmcl.2009.08.027]

Source

Source(1):

• Scientific Literature