N-benzyl-5-chloro-N-(4-(2-chloro-5-methoxypyrimidin-4-yl)phenyl)-2,4-dihydroxybenzamide

ID: ALA3732115

PubChem CID: 117972551

Max Phase: Preclinical

Molecular Formula: C25H19Cl2N3O4

Molecular Weight: 496.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cnc(Cl)nc1-c1ccc(N(Cc2ccccc2)C(=O)c2cc(Cl)c(O)cc2O)cc1

Standard InChI:  InChI=1S/C25H19Cl2N3O4/c1-34-22-13-28-25(27)29-23(22)16-7-9-17(10-8-16)30(14-15-5-3-2-4-6-15)24(33)18-11-19(26)21(32)12-20(18)31/h2-13,31-32H,14H2,1H3

Standard InChI Key:  LLGHHTDOUJTEOP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -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
    0.0000   -2.7000    0.0000 Cl  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
   -6.4828   -5.2708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0
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  6 31  1  0
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M  END

Alternative Forms

1. Parent:

   

   ALA3732115

   N-benzyl-5-chloro-N-[4-(2-chloro-5-methoxypyrimidin-4-yl)phenyl]-2,4-dihydroxybenzamide

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: 496.35

Molecular Weight (Monoisotopic): 495.0753

AlogP: 5.72

#Rotatable Bonds: 6

Polar Surface Area: 95.78

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.99

CX Basic pKa: 0.29

CX LogP: 5.51

CX LogD: 4.92

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.33

Np Likeness Score: -0.97

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