N-(4-(2-chloro-5-methoxypyrimidin-4-yl)phenyl)-2,4-dihydroxy-N-(isothiazol-4-ylmethyl)benzamide

ID: ALA3727595

PubChem CID: 117972706

Max Phase: Preclinical

Molecular Formula: C22H17ClN4O4S

Molecular Weight: 468.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cnc(Cl)nc1-c1ccc(N(Cc2cnsc2)C(=O)c2ccc(O)cc2O)cc1

Standard InChI:  InChI=1S/C22H17ClN4O4S/c1-31-19-10-24-22(23)26-20(19)14-2-4-15(5-3-14)27(11-13-9-25-32-12-13)21(30)17-7-6-16(28)8-18(17)29/h2-10,12,28-29H,11H2,1H3

Standard InChI Key:  ZBEYKNGCVKIDQV-UHFFFAOYSA-N

Molfile:  

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   -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
   -7.8525    1.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8524    0.2390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0978   -1.0574    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6317   -0.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA3727595

   N-[4-(2-chloro-5-methoxypyrimidin-4-yl)phenyl]-2,4-dihydroxy-N-(1,2-thiazol-4-ylmethyl)benzamide

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: 468.92

Molecular Weight (Monoisotopic): 468.0659

AlogP: 4.52

#Rotatable Bonds: 6

Polar Surface Area: 108.67

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.83

CX Basic pKa: 1.66

CX LogP: 3.88

CX LogD: 3.74

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.40

Np Likeness Score: -0.86

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