3,4-dihydroxy-N-[5-(4-nitrobenzyl)-4-phenylthiazol-2-yl]-benzamide

ID: ALA4442912

PubChem CID: 57991609

Max Phase: Preclinical

Molecular Formula: C23H17N3O5S

Molecular Weight: 447.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1nc(-c2ccccc2)c(Cc2ccc([N+](=O)[O-])cc2)s1)c1ccc(O)c(O)c1

Standard InChI:  InChI=1S/C23H17N3O5S/c27-18-11-8-16(13-19(18)28)22(29)25-23-24-21(15-4-2-1-3-5-15)20(32-23)12-14-6-9-17(10-7-14)26(30)31/h1-11,13,27-28H,12H2,(H,24,25,29)

Standard InChI Key:  IBFSEYHSISBJMX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    6.0092  -17.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8264  -17.2849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0808  -16.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4178  -16.0260    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7591  -16.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8583  -16.2567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5286  -17.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7150  -17.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2340  -18.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5653  -19.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3824  -19.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8598  -18.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9818  -16.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8115  -15.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4204  -14.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2507  -14.1119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4727  -13.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8642  -14.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0371  -15.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0293  -15.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8069  -15.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4228  -14.9100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4117  -15.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1886  -15.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3603  -14.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7488  -14.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9743  -14.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9170  -13.3562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1375  -14.4519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2997  -13.0626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220  -12.8114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9060  -12.5147    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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  1  7  1  0
  5 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  6 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 21  1  0
 26 28  1  0
 25 29  1  0
 30 31  2  0
 30 32  1  0
 17 30  1  0
M  CHG  2  30   1  32  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4442912

   3,4-dihydroxy-N-[5-(4-nitro-benzyl)-4-phenyl-thiazol-2-yl]-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: 447.47

Molecular Weight (Monoisotopic): 447.0889

AlogP: 4.97

#Rotatable Bonds: 6

Polar Surface Area: 125.59

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.50

CX Basic pKa: ┄

CX LogP: 6.00

CX LogD: 5.97

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.22

Np Likeness Score: -1.20

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