2-Acetyl-10-[(3-chloro-4-methoxybenzyl)amino]-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridine-8-carbonitrile

ID: ALA4062273

Chembl Id: CHEMBL4062273

Cas Number: 1448419-13-3

PubChem CID: 89706867

Max Phase: Preclinical

Molecular Formula: C23H21ClN4O2

Molecular Weight: 420.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CNc2c3c(nc4ccc(C#N)cc24)CCN(C(C)=O)C3)cc1Cl

Standard InChI:  InChI=1S/C23H21ClN4O2/c1-14(29)28-8-7-21-18(13-28)23(17-9-15(11-25)3-5-20(17)27-21)26-12-16-4-6-22(30-2)19(24)10-16/h3-6,9-10H,7-8,12-13H2,1-2H3,(H,26,27)

Standard InChI Key:  YLBRHUHHQIYMSH-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA4062273

   PDE5-IN-6c

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: 420.90

Molecular Weight (Monoisotopic): 420.1353

AlogP: 4.29

#Rotatable Bonds: 4

Polar Surface Area: 78.25

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.06

CX LogP: 2.87

CX LogD: 2.71

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.68

Np Likeness Score: -1.56

References

1. Fiorito J, Vendome J, Saeed F, Staniszewski A, Zhang H, Yan S, Deng SX, Arancio O, Landry DW..  (2017)  Identification of a Novel 1,2,3,4-Tetrahydrobenzo[b][1,6]naphthyridine Analogue as a Potent Phosphodiesterase 5 Inhibitor with Improved Aqueous Solubility for the Treatment of Alzheimer's Disease.,  60  (21): [PMID:28985058] [10.1021/acs.jmedchem.7b00979]

2. Das B, Baidya ATK, Mathew AT, Yadav AK, Kumar R..  (2022)  Structural modification aimed for improving solubility of lead compounds in early phase drug discovery.,  56  [PMID:35033884] [10.1016/j.bmc.2022.116614]

Source

Source(1):

• Scientific Literature