N-(4-(2-chloro-5-methylpyrimidin-4-yl)phenyl)-N-(3-chlorobenzyl)-2,4-dihydroxybenzamide

ID: ALA3729164

PubChem CID: 127037315

Max Phase: Preclinical

Molecular Formula: C25H19Cl2N3O3

Molecular Weight: 480.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cnc(Cl)nc1-c1ccc(N(Cc2cccc(Cl)c2)C(=O)c2ccc(O)cc2O)cc1

Standard InChI:  InChI=1S/C25H19Cl2N3O3/c1-15-13-28-25(27)29-23(15)17-5-7-19(8-6-17)30(14-16-3-2-4-18(26)11-16)24(33)21-10-9-20(31)12-22(21)32/h2-13,31-32H,14H2,1H3

Standard InChI Key:  KUUZLDUCOUHSFK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024    2.6977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8964   -0.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1931   -1.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1885   -3.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8871   -3.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5904   -3.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -1.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8007    1.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0971    0.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0919   -0.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7903   -1.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4939   -0.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8824   -5.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5799   -6.0002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5728   -7.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8683   -8.2562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1709   -7.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1779   -6.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5308   -8.0953    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.2200   -5.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1384    1.3283    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
  1  7  1  0
  3  8  1  0
  4  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 13 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
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 24 13  1  0
 17 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 27 31  1  0
 30 32  1  0
 21 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3729164

   ---

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: 480.35

Molecular Weight (Monoisotopic): 479.0803

AlogP: 6.02

#Rotatable Bonds: 5

Polar Surface Area: 86.55

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.83

CX Basic pKa: 0.29

CX LogP: 6.18

CX LogD: 6.04

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.34

Np Likeness Score: -1.23

References

1.  (2015)  Resorcinol n-aryl amide compounds, for use as pyruvate dehydrogenase kinase inhibitors, 

2. Morrell, J A JA and 5 more authors.  2003-12  AZD7545 is a selective inhibitor of pyruvate dehydrogenase kinase 2.  [PMID:14641019]

3. Meng, Tao T and 10 more authors.  2014-12-11  Discovery and optimization of 4,5-diarylisoxazoles as potent dual inhibitors of pyruvate dehydrogenase kinase and heat shock protein 90.  [PMID:25383915]

4. Moore, Jonathan D and 12 more authors.  2014-12-30  VER-246608, a novel pan-isoform ATP competitive inhibitor of pyruvate dehydrogenase kinase, disrupts Warburg metabolism and induces context-dependent cytostasis in cancer cells.  [PMID:25404640]

5. Narayan, Satya S and 7 more authors.  2019-01-01  ASR352, A potent anticancer agent: Synthesis, preliminary SAR, and biological activities against colorectal cancer bulk, 5-fluorouracil/oxaliplatin resistant and stem cells.  [PMID:30384048]

Source

Source(1):

• Patent Bioactivity Data