N-[6-[2-[(5-Bromo-2-pyrimidinyl)oxy]ethoxy]-5-(2-methoxyphenoxy)-4-pyrimidinyl]-N'-(phenylmethyl)-sulfamide

ID: ALA2165328

Chembl Id: CHEMBL2165328

PubChem CID: 21979601

Max Phase: Preclinical

Molecular Formula: C24H23BrN6O6S

Molecular Weight: 603.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1Oc1c(NS(=O)(=O)NCc2ccccc2)ncnc1OCCOc1ncc(Br)cn1

Standard InChI:  InChI=1S/C24H23BrN6O6S/c1-34-19-9-5-6-10-20(19)37-21-22(31-38(32,33)30-13-17-7-3-2-4-8-17)28-16-29-23(21)35-11-12-36-24-26-14-18(25)15-27-24/h2-10,14-16,30H,11-13H2,1H3,(H,28,29,31)

Standard InChI Key:  LSQXFROVPNDBMN-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2165328

   N-(benzylsulfamoyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(2-methoxyphenoxy)pyrimidin-4-amine

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: 603.46

Molecular Weight (Monoisotopic): 602.0583

AlogP: 3.73

#Rotatable Bonds: 13

Polar Surface Area: 146.68

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.24

CX Basic pKa: 3.11

CX LogP: 3.46

CX LogD: 3.13

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.22

Np Likeness Score: -1.00

References

1. Bolli MH, Boss C, Binkert C, Buchmann S, Bur D, Hess P, Iglarz M, Meyer S, Rein J, Rey M, Treiber A, Clozel M, Fischli W, Weller T..  (2012)  The discovery of N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propylsulfamide (Macitentan), an orally active, potent dual endothelin receptor antagonist.,  55  (17): [PMID:22862294] [10.1021/jm3009103]

2. Boss C, Bolli MH, Gatfield J..  (2016)  From bosentan (Tracleer®) to macitentan (Opsumit®): The medicinal chemistry perspective.,  26  (15): [PMID:27321813] [10.1016/j.bmcl.2016.06.014]

Source

Source(1):

• Scientific Literature