5,6-Dichloro-N-((5-(1,3-dimethylpyrazol-4-y1)-4-methyl-2-pyridyl)methyl)-1H-benzimidazol-2-amine

ID: ALA4877932

PubChem CID: 164628551

Max Phase: Preclinical

Molecular Formula: C19H18Cl2N6

Molecular Weight: 401.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(CNc2nc3cc(Cl)c(Cl)cc3[nH]2)ncc1-c1cn(C)nc1C

Standard InChI:  InChI=1S/C19H18Cl2N6/c1-10-4-12(22-8-13(10)14-9-27(3)26-11(14)2)7-23-19-24-17-5-15(20)16(21)6-18(17)25-19/h4-6,8-9H,7H2,1-3H3,(H2,23,24,25)

Standard InChI Key:  BEURPPOYQYVMBZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   13.6886   -8.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6875   -9.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3955  -10.1887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1052   -9.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1023   -8.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3937   -8.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3913   -7.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9808   -8.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8951   -7.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0957   -7.5701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6873   -8.2780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2343   -8.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8746   -8.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5022   -7.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8135  -10.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5206   -9.7770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2289  -10.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3183  -10.9947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9776   -9.8486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5254  -10.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1167  -11.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5243  -11.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3403  -11.8663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7471  -11.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3372  -10.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7504  -12.5731    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.5642  -11.1515    0.0000 Cl  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
  6  7  1  0
  1  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12  8  2  0
 11 13  1  0
  9 14  1  0
  4 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 21  1  0
 20 19  1  0
 19 17  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4877932

   ---

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: 401.30

Molecular Weight (Monoisotopic): 400.0970

AlogP: 4.89

#Rotatable Bonds: 4

Polar Surface Area: 71.42

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.07

CX Basic pKa: 6.81

CX LogP: 3.93

CX LogD: 3.84

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -1.51

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