4-(4'-methoxybiphenyl-4-yl)-2-phenyloxazole

ID: ALA4759734

PubChem CID: 162657475

Max Phase: Preclinical

Molecular Formula: C22H17NO2

Molecular Weight: 327.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2ccc(-c3coc(-c4ccccc4)n3)cc2)cc1

Standard InChI:  InChI=1S/C22H17NO2/c1-24-20-13-11-17(12-14-20)16-7-9-18(10-8-16)21-15-25-22(23-21)19-5-3-2-4-6-19/h2-15H,1H3

Standard InChI Key:  KZEPXJXUGJXBDB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    2.2023  -19.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3828  -19.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9632  -19.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3618  -20.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1844  -20.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6004  -19.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4143  -19.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136  -20.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6300  -20.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0480  -19.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6437  -19.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8286  -19.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1450  -19.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3270  -19.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1061  -19.3302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1266  -20.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3480  -20.4117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7871  -20.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8651  -19.8338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2660  -20.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5319  -20.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2011  -20.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1251  -21.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3774  -21.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7133  -21.4313    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
 10 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4759734

   ---

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: 327.38

Molecular Weight (Monoisotopic): 327.1259

AlogP: 5.68

#Rotatable Bonds: 4

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: 5.46

CX LogD: 5.46

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.48

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