N-[4-(4-fluorophenyl)-5-(4-nitrobenzyl)thiazol-2-yl]-3,4-dihydroxybenzamide

ID: ALA4440416

PubChem CID: 57991588

Max Phase: Preclinical

Molecular Formula: C23H16FN3O5S

Molecular Weight: 465.46

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H16FN3O5S/c24-16-6-3-14(4-7-16)21-20(11-13-1-8-17(9-2-13)27(31)32)33-23(25-21)26-22(30)15-5-10-18(28)19(29)12-15/h1-10,12,28-29H,11H2,(H,25,26,30)

Standard InChI Key:  ACGZGZMXXNUVFS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
  126.4046  -16.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  126.2755  -15.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  125.5053  -15.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  125.3763  -14.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  126.0174  -13.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  126.7876  -14.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  126.9167  -15.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  127.1748  -16.6453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  125.7634  -16.8688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  125.8883  -13.0903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  124.6061  -14.1286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  124.8382  -15.7263    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  125.0098  -16.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  124.2953  -16.9458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  123.6822  -16.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  124.0178  -15.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  123.4815  -14.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  122.6565  -14.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  122.2440  -13.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  121.4190  -13.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  121.0065  -14.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  121.4190  -15.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  122.2440  -15.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  120.1815  -14.7112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  119.7690  -13.9968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  119.7690  -15.4257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  122.8752  -16.5653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  122.6203  -17.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  121.8133  -17.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  121.2613  -16.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  121.5162  -16.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  122.3232  -15.9522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  120.4543  -17.0798    0.0000 F   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  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 18 23  2  0
 24 25  2  0
 24 26  1  0
 21 24  1  0
 16 17  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 27 32  2  0
 30 33  1  0
 15 27  1  0
  9 13  1  0
M  CHG  2  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4440416

   N-[4-(4-fluoro-phenyl)-5-(4-nitro-benzyl)-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: 465.46

Molecular Weight (Monoisotopic): 465.0795

AlogP: 5.11

#Rotatable Bonds: 6

Polar Surface Area: 125.59

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.50

CX Basic pKa: ┄

CX LogP: 6.14

CX LogD: 6.11

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.21

Np Likeness Score: -1.39

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