2-(4-(2-(5-(2-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)ethoxy)benzylidene)malononitrile

ID: ALA2296208

PubChem CID: 76309422

Max Phase: Preclinical

Molecular Formula: C20H13ClN4O2S

Molecular Weight: 408.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CC(C#N)=Cc1ccc(OCCSc2nnc(-c3ccccc3Cl)o2)cc1

Standard InChI:  InChI=1S/C20H13ClN4O2S/c21-18-4-2-1-3-17(18)19-24-25-20(27-19)28-10-9-26-16-7-5-14(6-8-16)11-15(12-22)13-23/h1-8,11H,9-10H2

Standard InChI Key:  UHHNGUJLUYHWMP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   17.7388   -9.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5542   -9.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9611   -8.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5537   -7.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7352   -7.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3320   -8.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7783   -8.5763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2577   -9.2347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0359   -8.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0348   -8.1639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2559   -7.9134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7516   -9.3764    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.4512   -8.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4351   -8.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1346   -7.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8502   -8.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8609   -8.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5757   -9.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2762   -8.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2574   -8.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5422   -7.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9923   -9.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6913   -8.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4074   -9.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6742   -8.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6603   -7.2367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1202   -9.6537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9612   -7.1616    0.0000 Cl  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
  3  7  1  0
  8  9  1  0
  7  8  1  0
  9 10  2  0
 10 11  1  0
 11  7  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  3  0
 24 27  3  0
  4 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2296208

   2-[[4-[2-[[5-(2-Chlorophenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]ethoxy]phenyl]methylidene]propanedinitrile

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: 408.87

Molecular Weight (Monoisotopic): 408.0448

AlogP: 4.99

#Rotatable Bonds: 7

Polar Surface Area: 95.73

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.48

CX LogD: 4.48

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.31

Np Likeness Score: -1.95

References

1. Deora GS, Karthikeyan C, Moorthy NSHN, Rathore V, Rawat AK, Tamrakar AK, Srivastava AK, Trivedi P.  (2013)  Design, synthesis and biological evaluation of novel arylidine-malononitrile derivatives as non-carboxylic inhibitors of protein tyrosine phosphatase 1B,  22  (11): [10.1007/s00044-013-0528-1]

Source

Source(1):

• Scientific Literature