N-(2-(4-Ethylphenylamino)benzo[d]oxazol-5-yl)-3-(chloromethyl)benzamide

ID: ALA4077563

PubChem CID: 54765632

Max Phase: Preclinical

Molecular Formula: C23H20ClN3O2

Molecular Weight: 405.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc(Nc2nc3cc(NC(=O)c4cccc(CCl)c4)ccc3o2)cc1

Standard InChI:  InChI=1S/C23H20ClN3O2/c1-2-15-6-8-18(9-7-15)26-23-27-20-13-19(10-11-21(20)29-23)25-22(28)17-5-3-4-16(12-17)14-24/h3-13H,2,14H2,1H3,(H,25,28)(H,26,27)

Standard InChI Key:  CSZBIDMQTBGDDO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   27.9440  -13.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9429  -14.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6509  -14.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6492  -12.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3578  -13.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3626  -14.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1426  -14.3201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6200  -13.6550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1349  -12.9956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4371  -13.6501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.8416  -12.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6586  -12.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0630  -12.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6502  -11.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8288  -11.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4281  -12.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0536  -10.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6400  -10.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2362  -12.8482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2360  -12.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5282  -11.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9437  -11.6222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5333  -10.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8264  -10.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1178  -10.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1206  -11.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8281  -12.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4144  -12.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7052  -11.6318    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 14 17  1  0
 17 18  1  0
  1 19  1  0
 19 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
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4077563

   3-(chloromethyl)-N-[2-(4-ethylanilino)-1,3-benzoxazol-5-yl]benzamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 405.89

Molecular Weight (Monoisotopic): 405.1244

AlogP: 6.12

#Rotatable Bonds: 6

Polar Surface Area: 67.16

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.30

CX Basic pKa: ┄

CX LogP: 6.08

CX LogD: 6.08

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.38

Np Likeness Score: -1.54

References

1. Kim D, Won HY, Hwang ES, Kim YK, Choo HP..  (2017)  Synthesis of benzoxazole derivatives as interleukin-6 antagonists.,  25  (12): [PMID:28442260] [10.1016/j.bmc.2017.03.072]

Source

Source(1):

• Scientific Literature