2,4-dihydroxy-N-(isothiazol-4-ylmethyl)-N-(4-(3-methyl-5-(N-(thiophen-2-ylmethyl)sulfamoyl)pyridin-2-yl)phenyl)benzamide

ID: ALA3728220

PubChem CID: 127024137

Max Phase: Preclinical

Molecular Formula: C28H24N4O5S3

Molecular Weight: 592.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(S(=O)(=O)NCc2cccs2)cnc1-c1ccc(N(Cc2cnsc2)C(=O)c2ccc(O)cc2O)cc1

Standard InChI:  InChI=1S/C28H24N4O5S3/c1-18-11-24(40(36,37)31-14-23-3-2-10-38-23)15-29-27(18)20-4-6-21(7-5-20)32(16-19-13-30-39-17-19)28(35)25-9-8-22(33)12-26(25)34/h2-13,15,17,31,33-34H,14,16H2,1H3

Standard InChI Key:  FBRKPMZCQHNIJI-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3728220

   ---

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: 592.72

Molecular Weight (Monoisotopic): 592.0909

AlogP: 5.31

#Rotatable Bonds: 9

Polar Surface Area: 132.72

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.82

CX Basic pKa: 1.74

CX LogP: 4.81

CX LogD: 4.67

Aromatic Rings: 5

Heavy Atoms: 40

QED Weighted: 0.21

Np Likeness Score: -1.59

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