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

ID: ALA4457165

PubChem CID: 57991625

Max Phase: Preclinical

Molecular Formula: C23H18N2O4S

Molecular Weight: 418.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1nc(-c2ccc(O)cc2)c(Cc2ccccc2)s1)c1ccc(O)c(O)c1

Standard InChI:  InChI=1S/C23H18N2O4S/c26-17-9-6-15(7-10-17)21-20(12-14-4-2-1-3-5-14)30-23(24-21)25-22(29)16-8-11-18(27)19(28)13-16/h1-11,13,26-28H,12H2,(H,24,25,29)

Standard InChI Key:  JQFVOJJYNKKRCP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   16.7648   -5.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5820   -5.5883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8363   -4.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1734   -4.3295    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.5146   -4.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6139   -4.5601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2204   -5.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9980   -4.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0494   -5.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6004   -5.4061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3773   -5.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5489   -4.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9375   -3.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1629   -4.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2841   -6.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4706   -6.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9895   -6.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3209   -7.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1380   -7.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6154   -6.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7373   -4.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5671   -3.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1760   -3.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0062   -2.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2282   -2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6198   -2.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7927   -3.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8406   -8.2266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3262   -4.1028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9836   -5.7031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  8  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 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
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 18 28  1  0
 12 29  1  0
 11 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4457165

   N-[5-benzyl-4-(4-hydroxyphenyl)-1,3-thiazol-2-yl]-3,4-dihydroxybenzamide

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: 418.47

Molecular Weight (Monoisotopic): 418.0987

AlogP: 4.77

#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: 5.75

CX LogD: 5.72

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.35

Np Likeness Score: -0.79

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