2-(2-ethoxyphenyl)-4-(4'-methylbiphenyl-4-yl)oxazole

ID: ALA4761471

PubChem CID: 162660392

Max Phase: Preclinical

Molecular Formula: C24H21NO2

Molecular Weight: 355.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1ccccc1-c1nc(-c2ccc(-c3ccc(C)cc3)cc2)co1

Standard InChI:  InChI=1S/C24H21NO2/c1-3-26-23-7-5-4-6-21(23)24-25-22(16-27-24)20-14-12-19(13-15-20)18-10-8-17(2)9-11-18/h4-16H,3H2,1-2H3

Standard InChI Key:  NORGTHMMGPAEPQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   35.1582  -19.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3388  -19.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9191  -19.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3178  -20.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1404  -20.4904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5563  -19.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3702  -19.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7695  -20.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5859  -20.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0039  -19.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5996  -19.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7845  -19.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1010  -19.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6308  -19.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8498  -19.3220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8373  -20.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6105  -20.4035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.1689  -20.6093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4278  -20.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7598  -20.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8324  -21.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5787  -21.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2436  -21.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8210  -19.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3544  -19.4532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6128  -19.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9447  -19.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  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
  6  7  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
  3 13  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 10 24  1  0
 19 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4761471

   ---

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: 355.44

Molecular Weight (Monoisotopic): 355.1572

AlogP: 6.38

#Rotatable Bonds: 5

Polar Surface Area: 35.26

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.33

CX LogD: 6.33

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.42

Np Likeness Score: -0.86

References

1. Ahmad H,Ullah S,Rahman F,Saeed A,Pelletier J,Sévigny J,Hassan A,Iqbal J.  (2020)  Synthesis of biphenyl oxazole derivatives via Suzuki coupling and biological evaluations as nucleotide pyrophosphatase/phosphodiesterase-1 and -3 inhibitors.,  208  [PMID:32883636] [10.1016/j.ejmech.2020.112759]

2. Nadel, Yael Y and 11 more authors.  2014-06-12  Highly potent and selective ectonucleotide pyrophosphatase/phosphodiesterase I inhibitors based on an adenosine 5'-(α or γ)-thio-(α,β- or β,γ)-methylenetriphosphate scaffold.  [PMID:24846781]

3. Lee, Sang-Yong SY and 5 more authors.  2016-07-15  Thiazolo[3,2-a]benzimidazol-3(2H)-one derivatives: Structure-activity relationships of selective nucleotide pyrophosphatase/phosphodiesterase1 (NPP1) inhibitors.  [PMID:27265686]

4. Zelikman, Vadim V and 8 more authors.  2018-05-10  Highly Selective and Potent Ectonucleotide Pyrophosphatase-1 (NPP1) Inhibitors Based on Uridine 5'-Pα,α-Dithiophosphate Analogues.  [PMID:29681152]

5. Nassir, Molhm and 8 more authors.  2019-12-15  Structure-activity relationship study of NPP1 inhibitors based on uracil-N1-(methoxy)ethyl-β-phosphate scaffold.  [PMID:31610377]

6. Ahmad, Haseen and 7 more authors.  2020-12-15  Synthesis of biphenyl oxazole derivatives via Suzuki coupling and biological evaluations as nucleotide pyrophosphatase/phosphodiesterase-1 and -3 inhibitors.  [PMID:32883636]

Source

Source(1):

• Scientific Literature