1-(2,6-Dichloro-4-pyridyl)-3-((5-(dimethylamino)-4-methyl-2-pyridyl)amino)urea

ID: ALA4871414

PubChem CID: 164621155

Max Phase: Preclinical

Molecular Formula: C14H16Cl2N6O

Molecular Weight: 355.23

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(NNC(=O)Nc2cc(Cl)nc(Cl)c2)ncc1N(C)C

Standard InChI:  InChI=1S/C14H16Cl2N6O/c1-8-4-13(17-7-10(8)22(2)3)20-21-14(23)18-9-5-11(15)19-12(16)6-9/h4-7H,1-3H3,(H,17,20)(H2,18,19,21,23)

Standard InChI Key:  XUVLLHQXENRQMM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    3.2508   -2.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2497   -2.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9577   -3.2756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -2.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6646   -2.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9559   -1.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3757   -3.2736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0828   -2.8639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7912   -3.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4982   -2.8617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7924   -4.0886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9535   -0.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2066   -3.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2035   -4.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9110   -4.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6190   -4.0847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6151   -3.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9070   -2.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3207   -2.8511    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.9119   -5.3116    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5430   -1.6386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5428   -0.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8354   -2.0474    0.0000 C   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
  1 21  1  0
 21 22  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4871414

   ---

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: 355.23

Molecular Weight (Monoisotopic): 354.0763

AlogP: 3.31

#Rotatable Bonds: 4

Polar Surface Area: 82.18

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.88

CX Basic pKa: 6.43

CX LogP: 3.41

CX LogD: 3.37

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.58

Np Likeness Score: -1.87

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