1-(2-Chloro-6-isopropyloxypyridin-4-yl)-3-(2,6-dichloropyridin-4-yl)urea

ID: ALA4874765

PubChem CID: 164627194

Max Phase: Preclinical

Molecular Formula: C14H13Cl3N4O2

Molecular Weight: 375.64

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)Oc1cc(NC(=O)Nc2cc(Cl)nc(Cl)c2)cc(Cl)n1

Standard InChI:  InChI=1S/C14H13Cl3N4O2/c1-7(2)23-13-6-9(5-12(17)21-13)19-14(22)18-8-3-10(15)20-11(16)4-8/h3-7H,1-2H3,(H2,18,19,20,21,22)

Standard InChI Key:  ADGVMQDQYGFLAQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   24.0484   -1.7418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3322   -2.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6174   -1.7396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3309   -2.9770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9013   -2.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9044   -2.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1892   -3.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4774   -2.9730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4815   -2.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1932   -1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7680   -1.7290    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   24.7632   -2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7571   -2.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4711   -3.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1881   -2.9816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1868   -2.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4722   -1.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8973   -1.7398    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.4694   -4.2209    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.1882   -4.2145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4765   -4.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4756   -5.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7615   -4.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  9 11  1  0
  1 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 16 18  1  0
 14 19  1  0
  7 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4874765

   ---

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: 375.64

Molecular Weight (Monoisotopic): 374.0104

AlogP: 4.87

#Rotatable Bonds: 4

Polar Surface Area: 76.14

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.80

CX Basic pKa: 0.44

CX LogP: 4.37

CX LogD: 4.37

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.75

Np Likeness Score: -1.22

References

1. Luo D, Zhang Y, Yang S, Tian X, Lv Y, Guo Z, Liu X, Han G, Liu S, Wang W, Cui S, Qu X, Wan S..  (2021)  Design, synthesis and biological evaluation of sphingosine-1-phosphate receptor 2 antagonists as potent 5-FU-resistance reversal agents for the treatment of colorectal cancer.,  225  [PMID:34411894] [10.1016/j.ejmech.2021.113775]

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