4-(4'-(benzyloxy)biphenyl-4-yl)-2-methyloxazole

ID: ALA4758988

PubChem CID: 162657968

Max Phase: Preclinical

Molecular Formula: C23H19NO2

Molecular Weight: 341.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1nc(-c2ccc(-c3ccc(OCc4ccccc4)cc3)cc2)co1

Standard InChI:  InChI=1S/C23H19NO2/c1-17-24-23(16-25-17)21-9-7-19(8-10-21)20-11-13-22(14-12-20)26-15-18-5-3-2-4-6-18/h2-14,16H,15H2,1H3

Standard InChI Key:  SKGSMZJQJAPEFO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   23.4751   -7.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0515   -7.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4539   -8.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2844   -8.6529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7044   -7.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5261   -7.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9292   -8.6723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7534   -8.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1754   -7.9727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7671   -7.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9443   -7.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.7509   -7.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9625   -7.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9498   -8.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7304   -8.5651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2750   -8.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0003   -7.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4050   -8.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4625   -7.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6375   -7.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2250   -8.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6375   -9.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4625   -9.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8750   -8.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  3 13  1  0
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 21 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4758988

   ---

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: 341.41

Molecular Weight (Monoisotopic): 341.1416

AlogP: 5.90

#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: 0.41

CX LogP: 5.29

CX LogD: 5.29

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.45

Np Likeness Score: -0.57

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