3-(5-Methyl-isoxazol-3-yl)-6-(pyridin-2-ylmethoxy)-[1,2,4]triazolo[3,4-a]phthalazine

ID: ALA68684

Chembl Id: CHEMBL68684

PubChem CID: 9885130

Max Phase: Preclinical

Molecular Formula: C19H14N6O2

Molecular Weight: 358.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(-c2nnc3c4ccccc4c(OCc4ccccn4)nn23)no1

Standard InChI:  InChI=1S/C19H14N6O2/c1-12-10-16(24-27-12)18-22-21-17-14-7-2-3-8-15(14)19(23-25(17)18)26-11-13-6-4-5-9-20-13/h2-10H,11H2,1H3

Standard InChI Key:  YTGZSWOWFGVAFH-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA68684

   5-Methyl-3-(6-(pyridin-2-ylmethoxy)-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)isoxazole

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: 358.36

Molecular Weight (Monoisotopic): 358.1178

AlogP: 3.21

#Rotatable Bonds: 4

Polar Surface Area: 91.23

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.78

CX LogP: 2.68

CX LogD: 2.68

Aromatic Rings: 5

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: -2.06

References

1. Sternfeld F, Carling RW, Jelley RA, Ladduwahetty T, Merchant KJ, Moore KW, Reeve AJ, Street LJ, O'Connor D, Sohal B, Atack JR, Cook S, Seabrook G, Wafford K, Tattersall FD, Collinson N, Dawson GR, Castro JL, MacLeod AM..  (2004)  Selective, orally active gamma-aminobutyric acidA alpha5 receptor inverse agonists as cognition enhancers.,  47  (9): [PMID:15084116] [10.1021/jm031076j]

2. Street LJ, Sternfeld F, Jelley RA, Reeve AJ, Carling RW, Moore KW, McKernan RM, Sohal B, Cook S, Pike A, Dawson GR, Bromidge FA, Wafford KA, Seabrook GR, Thompson SA, Marshall G, Pillai GV, Castro JL, Atack JR, MacLeod AM..  (2004)  Synthesis and biological evaluation of 3-heterocyclyl-7,8,9,10-tetrahydro-(7,10-ethano)-1,2,4-triazolo[3,4-a]phthalazines and analogues as subtype-selective inverse agonists for the GABA(A)alpha5 benzodiazepine binding site.,  47  (14): [PMID:15214791] [10.1021/jm0407613]

3. 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]

4. Károlyi BI, Potor A, Kapus GL, Fodor L, Bobok A, Krámos B, Magdó I, Bata I, Szabó G..  (2023)  Novel imidazo[1,5-a]quinoxaline derivatives: SAR, selectivity and modeling challenges en route to the identification of an α5-GABAA receptor NAM.,  80  [PMID:36549396] [10.1016/j.bmcl.2022.129107]

Source

Source(1):

• Scientific Literature