1-(2,6-Dichloro-4-pyridyl)-3-((6-(4-fluoropheny1)-4-methyl-2-pyridyl)amino)urea

ID: ALA4873481

PubChem CID: 164622072

Max Phase: Preclinical

Molecular Formula: C18H14Cl2FN5O

Molecular Weight: 406.25

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(NNC(=O)Nc2cc(Cl)nc(Cl)c2)nc(-c2ccc(F)cc2)c1

Standard InChI:  InChI=1S/C18H14Cl2FN5O/c1-10-6-14(11-2-4-12(21)5-3-11)23-17(7-10)25-26-18(27)22-13-8-15(19)24-16(20)9-13/h2-9H,1H3,(H,23,25)(H2,22,24,26,27)

Standard InChI Key:  ZIRKUBSFZITPEM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   15.7935  -28.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7923  -29.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5004  -29.5867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2100  -29.1772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2072  -28.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4986  -27.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9184  -29.5847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6255  -29.1750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3338  -29.5825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0409  -29.1728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3351  -30.3997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4962  -27.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7492  -29.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7461  -30.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4536  -30.8055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1617  -30.3958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1578  -29.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4497  -29.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8634  -29.1621    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.4545  -31.6227    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.0843  -29.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3785  -29.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6710  -29.5825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6699  -30.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3823  -30.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0869  -30.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9624  -30.8095    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  6 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 17 19  1  0
 15 20  1  0
  2 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4873481

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 406.25

Molecular Weight (Monoisotopic): 405.0559

AlogP: 5.05

#Rotatable Bonds: 4

Polar Surface Area: 78.94

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.88

CX Basic pKa: 5.80

CX LogP: 5.48

CX LogD: 5.47

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.42

Np Likeness Score: -1.78

References

1. Mammoliti O, Palisse A, Joannesse C, El Bkassiny S, Allart B, Jaunet A, Menet C, Coornaert B, Sonck K, Duys I, Clément-Lacroix P, Oste L, Borgonovi M, Wakselman E, Christophe T, Houvenaghel N, Jans M, Heckmann B, Sanière L, Brys R..  (2021)  Discovery of the S1P2 Antagonist GLPG2938 (1-[2-Ethoxy-6-(trifluoromethyl)-4-pyridyl]-3-[[5-methyl-6-[1-methyl-3-(trifluoromethyl)pyrazol-4-yl]pyridazin-3-yl]methyl]urea), a Preclinical Candidate for the Treatment of Idiopathic Pulmonary Fibrosis.,  64  (9.0): [PMID:33939425] [10.1021/acs.jmedchem.1c00138]

2. Osada, Makoto M, Yatomi, Yutaka Y, Ohmori, Tsukasa T, Ikeda, Hitoshi H and Ozaki, Yukio Y.  2002-12-06  Enhancement of sphingosine 1-phosphate-induced migration of vascular endothelial cells and smooth muscle cells by an EDG-5 antagonist.  [PMID:12445827]

3. Sanna, M Germana MG and 10 more authors.  2004-04-02  Sphingosine 1-phosphate (S1P) receptor subtypes S1P1 and S1P3, respectively, regulate lymphocyte recirculation and heart rate.  [PMID:14732717]

4. Deng, Hongfeng H and 6 more authors.  2013-10-10  Discovery of Clinical Candidate GSK1842799 As a Selective S1P1 Receptor Agonist (Prodrug) for Multiple Sclerosis.  [PMID:24900589]

5. Demont, Emmanuel H EH and 22 more authors.  2016-02-11  Discovery of Tetrahydropyrazolopyridine as Sphingosine 1-Phosphate Receptor 3 (S1P3)-Sparing S1P1 Agonists Active at Low Oral Doses.  [PMID:26751273]

6. Scott, F L FL and 12 more authors.  2016-06  Ozanimod (RPC1063) is a potent sphingosine-1-phosphate receptor-1 (S1P1 ) and receptor-5 (S1P5 ) agonist with autoimmune disease-modifying activity.  [PMID:26990079]

Source

Source(1):

• Scientific Literature