4-(biphenyl-4-yl)-2-phenyloxazole

ID: ALA4742029

PubChem CID: 162646256

Max Phase: Preclinical

Molecular Formula: C21H15NO

Molecular Weight: 297.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  c1ccc(-c2ccc(-c3coc(-c4ccccc4)n3)cc2)cc1

Standard InChI:  InChI=1S/C21H15NO/c1-3-7-16(8-4-1)17-11-13-18(14-12-17)20-15-23-21(22-20)19-9-5-2-6-10-19/h1-15H

Standard InChI Key:  UVNYYCUMRBFWJY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   35.6823   -7.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8629   -7.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4433   -7.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8419   -8.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6645   -8.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0805   -8.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8944   -8.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2937   -8.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1101   -8.7367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5281   -8.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1237   -7.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3087   -7.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6251   -7.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1550   -7.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3740   -7.5387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3614   -8.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1347   -8.6202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6930   -8.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9537   -8.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2857   -8.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3583   -9.7644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1046  -10.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7695   -9.6361    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
M  END

Alternative Forms

1. Parent:

   

   ALA4742029

   ---

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: 297.36

Molecular Weight (Monoisotopic): 297.1154

AlogP: 5.68

#Rotatable Bonds: 3

Polar Surface Area: 26.03

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.62

CX LogD: 5.62

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.49

Np Likeness Score: -0.66

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