2-{6-[2-(3,5-Dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy}-N-propylacetamide

ID: ALA3315088

Chembl Id: CHEMBL3315088

Cas Number: 1035572-38-3

PubChem CID: 66829720

Max Phase: Preclinical

Molecular Formula: C20H22Cl2N2O5

Molecular Weight: 441.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCNC(=O)COc1c(C(=O)Cc2c(Cl)cncc2Cl)ccc(OC)c1OC

Standard InChI:  InChI=1S/C20H22Cl2N2O5/c1-4-7-24-18(26)11-29-19-12(5-6-17(27-2)20(19)28-3)16(25)8-13-14(21)9-23-10-15(13)22/h5-6,9-10H,4,7-8,11H2,1-3H3,(H,24,26)

Standard InChI Key:  HOKIHKLKOZWCRY-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3315088

   N-Propyl-2-(2-((3,5-dichloro-4-pyridyl)acetyl)-5,6-dimethoxyphenoxy)acetamide

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: 441.31

Molecular Weight (Monoisotopic): 440.0906

AlogP: 3.74

#Rotatable Bonds: 10

Polar Surface Area: 86.75

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.10

CX Basic pKa: 1.42

CX LogP: 2.66

CX LogD: 2.66

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.57

Np Likeness Score: -0.78

References

1. Felding J, Sørensen MD, Poulsen TD, Larsen J, Andersson C, Refer P, Engell K, Ladefoged LG, Thormann T, Vinggaard AM, Hegardt P, Søhoel A, Nielsen SF..  (2014)  Discovery and early clinical development of 2-{6-[2-(3,5-dichloro-4-pyridyl)acetyl]-2,3-dimethoxyphenoxy}-N-propylacetamide (LEO 29102), a soft-drug inhibitor of phosphodiesterase 4 for topical treatment of atopic dermatitis.,  57  (14): [PMID:24984230] [10.1021/jm500378a]

2. Larsen J,Lambert M,Pettersson H,Vifian T,Larsen M,Ollerstam A,Hegardt P,Eskilsson C,Laursen S,Soehoel A,Skak-Nielsen T,Hansen LM,Knudsen NØ,Eirefelt S,Sørensen MD,Stilou TG,Nielsen SF.  (2020)  Discovery and Early Clinical Development of Isobutyl 1-[8-Methoxy-5-(1-oxo-3H-isobenzofuran-5-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxylate (LEO 39652), a Novel "Dual-Soft" PDE4 Inhibitor for Topical Treatment of Atopic Dermatitis.,  63  (23): [PMID:33054196] [10.1021/acs.jmedchem.0c00797]

Source

Source(1):

• Scientific Literature