N-[5-(4-fluorobenzyl)-4-(4-hydroxyphenyl)thiazol-2-yl]-3,4-dihydroxybenzamide

ID: ALA4458409

PubChem CID: 57991643

Max Phase: Preclinical

Molecular Formula: C23H17FN2O4S

Molecular Weight: 436.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1nc(-c2ccc(O)cc2)c(Cc2ccc(F)cc2)s1)c1ccc(O)c(O)c1

Standard InChI:  InChI=1S/C23H17FN2O4S/c24-16-6-1-13(2-7-16)11-20-21(14-3-8-17(27)9-4-14)25-23(31-20)26-22(30)15-5-10-18(28)19(29)12-15/h1-10,12,27-29H,11H2,(H,25,26,30)

Standard InChI Key:  VYDVDARLGOKJIO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   16.8226  -16.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6397  -16.0756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8941  -15.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2311  -14.8168    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.5724  -15.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6717  -15.0474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2782  -15.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0557  -15.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1072  -16.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6582  -15.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4351  -15.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6067  -14.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9953  -14.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2207  -14.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3419  -16.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5283  -16.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0473  -17.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3787  -18.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1958  -18.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6732  -17.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7951  -15.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6248  -14.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2338  -13.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0640  -12.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2860  -12.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6776  -13.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8505  -13.9982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8984  -18.7139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3839  -14.5901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0414  -16.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1147  -11.8507    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
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  8 10  2  0
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 12 13  1  0
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 15 16  2  0
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 18 19  1  0
 19 20  2  0
 20 15  1  0
  1 15  1  0
  5 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
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 25 26  1  0
 26 27  2  0
 27 22  1  0
 18 28  1  0
 12 29  1  0
 11 30  1  0
 25 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4458409

   N-[5-(4-fluoro-benzyl)-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3,4-dihydroxy-benzamide

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: 436.46

Molecular Weight (Monoisotopic): 436.0893

AlogP: 4.91

#Rotatable Bonds: 5

Polar Surface Area: 102.68

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.45

CX Basic pKa: ┄

CX LogP: 5.90

CX LogD: 5.86

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.33

Np Likeness Score: -1.00

References

1.  (2014)  2,4,5-trisubstituted thiazole compounds,preparation methods,pharmaceutical compositions and medical uses thereof, 

2.  (2016)  2,4,5-trisubstituted thiazole compounds,preparation methods,pharmaceutical compositions and medical uses thereof, 

3. Brückner, David D and 6 more authors.  2005-08-01  Dibenzodioxocinones--a new class of CETP inhibitors.  [PMID:15975789]

4. Castilho, Marcelo S MS, Guido, Rafael V C RV and Andricopulo, Adriano D AD.  2007-09-15  2D Quantitative structure-activity relationship studies on a series of cholesteryl ester transfer protein inhibitors.  [PMID:17604633]

5. Rano, Thomas A TA and 5 more authors.  2009-05-01  Design and synthesis of potent inhibitors of cholesteryl ester transfer protein (CETP) exploiting a 1,2,3,4-tetrahydroquinoline platform.  [PMID:19339179]

6. Thompson, Christopher F CF and 12 more authors.  2011-06-09  Discovery of substituted biphenyl oxazolidinone inhibitors of cholesteryl ester transfer protein.  [PMID:24900324]

7. Liu, Chunchi C and 8 more authors.  2016-11-10  Design, synthesis and biological evaluation of novel cholesteryl ester transfer protein inhibitors bearing a cycloalkene scaffold.  [PMID:27490022]

8. Chang, Yongzhi Y and 7 more authors.  2017-01-27  Fragment-based discovery of novel pentacyclic triterpenoid derivatives as cholesteryl ester transfer protein inhibitors.  [PMID:27750148]

9. Chen, Dongyin D and 12 more authors.  2017-10-20  Discovery of pentacyclic triterpene 3β-ester derivatives as a new class of cholesterol ester transfer protein inhibitors.  [PMID:28802120]

10. Liu, Jian and 12 more authors.  2021-01-15  Cholesteryl ester transfer protein (CETP) inhibitors based on cyclic urea, bicyclic urea and bicyclic sulfamide cores.  [PMID:33161125]

Source

Source(1):

• Patent Bioactivity Data