1-((3-bromo-10-methyl-9H-benzo[f]imidazo[1,5-a][1,2,4]triazolo[1,5-d][1,4]diazepin-6-yl)methyl)pyrrolidin-2-one

ID: ALA1080575

PubChem CID: 44610734

Max Phase: Preclinical

Molecular Formula: C18H17BrN6O

Molecular Weight: 413.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ncn2c1Cn1nc(CN3CCCC3=O)nc1-c1cc(Br)ccc1-2

Standard InChI:  InChI=1S/C18H17BrN6O/c1-11-15-8-25-18(21-16(22-25)9-23-6-2-3-17(23)26)13-7-12(19)4-5-14(13)24(15)10-20-11/h4-5,7,10H,2-3,6,8-9H2,1H3

Standard InChI Key:  VYEPAZHUFFXYDH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
    7.6620   -4.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6609   -4.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3514   -5.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3497   -3.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9055   -4.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0395   -4.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0415   -4.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6888   -3.5858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5009   -3.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8900   -3.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3184   -2.4089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5761   -2.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5493   -5.2719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7266   -5.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6534   -6.3037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4309   -6.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9846   -5.9955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6794   -2.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9704   -5.3105    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   10.4272   -7.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1567   -7.9038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2442   -8.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0696   -8.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4951   -8.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9326   -7.5590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1103   -6.7334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 21 22  1  0
  4  1  1  0
  2  3  1  0
  9 10  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
 10 11  1  0
 25 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1080575

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

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: 413.28

Molecular Weight (Monoisotopic): 412.0647

AlogP: 2.69

#Rotatable Bonds: 2

Polar Surface Area: 68.84

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.35

CX Basic pKa: 4.68

CX LogP: 1.93

CX LogD: 1.93

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.51

Np Likeness Score: -1.10

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