N-(2-Hydroxy-2-methyl-1-(4-(trifluoromethoxy)phenyl)propyl)-2-oxo-2,3-dihydropyrido[2,3-b]pyrazine-4(1H)-carboxamide

ID: ALA4068452

Chembl Id: CHEMBL4068452

PubChem CID: 117949072

Max Phase: Preclinical

Molecular Formula: C19H19F3N4O4

Molecular Weight: 424.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(O)C(NC(=O)N1CC(=O)Nc2cccnc21)c1ccc(OC(F)(F)F)cc1

Standard InChI:  InChI=1S/C19H19F3N4O4/c1-18(2,29)15(11-5-7-12(8-6-11)30-19(20,21)22)25-17(28)26-10-14(27)24-13-4-3-9-23-16(13)26/h3-9,15,29H,10H2,1-2H3,(H,24,27)(H,25,28)

Standard InChI Key:  MQPYMNITEROIMR-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA4068452

   N-[2-hydroxy-2-methyl-1-[4-(trifluoromethoxy)phenyl]propyl]-2-oxo-1,3-dihydropyrido[2,3-b]pyrazine-4-carboxamide

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: 424.38

Molecular Weight (Monoisotopic): 424.1358

AlogP: 2.96

#Rotatable Bonds: 4

Polar Surface Area: 103.79

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.16

CX Basic pKa: 1.74

CX LogP: 2.50

CX LogD: 2.50

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.70

Np Likeness Score: -0.91

References

1. Mikami S, Nakamura S, Ashizawa T, Nomura I, Kawasaki M, Sasaki S, Oki H, Kokubo H, Hoffman ID, Zou H, Uchiyama N, Nakashima K, Kamiguchi N, Imada H, Suzuki N, Iwashita H, Taniguchi T..  (2017)  Discovery of Clinical Candidate N-((1S)-1-(3-Fluoro-4-(trifluoromethoxy)phenyl)-2-methoxyethyl)-7-methoxy-2-oxo-2,3-dihydropyrido[2,3-b]pyrazine-4(1H)-carboxamide (TAK-915): A Highly Potent, Selective, and Brain-Penetrating Phosphodiesterase 2A Inhibitor for the Treatment of Cognitive Disorders.,  60  (18): [PMID:28796496] [10.1021/acs.jmedchem.7b00807]

2. Nadur NF, de Azevedo LL, Caruso L, Graebin CS, Lacerda RB, Kümmerle AE..  (2021)  The long and winding road of designing phosphodiesterase inhibitors for the treatment of heart failure.,  212  [PMID:33412421] [10.1016/j.ejmech.2020.113123]

Source

Source(1):

• Scientific Literature