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

ID: ALA4457626

PubChem CID: 57991599

Max Phase: Preclinical

Molecular Formula: C23H24N2O4S

Molecular Weight: 424.52

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/C23H24N2O4S/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/h6-11,13-14,26-28H,1-5,12H2,(H,24,25,29)

Standard InChI Key:  JYDBFJWEKLXWEZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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  122.9398  -15.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  122.8107  -14.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  122.0405  -14.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  121.9114  -13.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  122.5526  -13.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  123.3228  -13.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  123.4518  -14.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  123.7100  -16.0123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  122.2986  -16.2358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  122.4235  -12.4573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  121.1412  -13.4957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  121.3734  -15.0933    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  121.5449  -15.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  120.8305  -16.3128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  120.2174  -15.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  120.5529  -15.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  119.4104  -15.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  119.1555  -16.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  118.3485  -16.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  117.7965  -16.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  118.0514  -15.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  118.8584  -15.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  116.9895  -16.4469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  120.0167  -14.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  119.1917  -14.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  118.7792  -13.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  117.9542  -13.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  117.5417  -14.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  117.9542  -14.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  118.7792  -14.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  2  7  2  0
  1  8  2  0
  1  9  1  0
  5 10  1  0
  4 11  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 12 16  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 20 23  1  0
 15 17  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 25 30  1  0
 24 25  1  0
 16 24  1  0
  9 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4457626

   N-[5-cyclohexylmethyl-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: 424.52

Molecular Weight (Monoisotopic): 424.1457

AlogP: 5.30

#Rotatable Bonds: 5

Polar Surface Area: 102.68

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.45

CX Basic pKa: ┄

CX LogP: 6.22

CX LogD: 6.19

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.42

Np Likeness Score: -0.65

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