2-(5-tert-Butylisoxazol-3-yl)-N'-(3,5-dichlorophenyl)-2-oxoacetohydrazonoyl Cyanide

ID: ALA3593329

PubChem CID: 71711999

Max Phase: Preclinical

Molecular Formula: C16H14Cl2N4O2

Molecular Weight: 365.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(C(=O)/C(C#N)=N/Nc2cc(Cl)cc(Cl)c2)no1

Standard InChI:  InChI=1S/C16H14Cl2N4O2/c1-16(2,3)14-7-12(22-24-14)15(23)13(8-19)21-20-11-5-9(17)4-10(18)6-11/h4-7,20H,1-3H3/b21-13+

Standard InChI Key:  XCBFEZRMLYPSFY-FYJGNVAPSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031   -3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -3.7494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070   -5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6078   -5.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0086   -6.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296   -6.6047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6109   -7.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6460   -5.3970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8244   -8.3594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3609   -9.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8609   -9.7860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3974   -8.3594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2416  -10.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4351  -10.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7532  -12.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9465  -11.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383    1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  3  0
 10 13  1  0
 10 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 13  2  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
  2 23  1  0
  4 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3593329

   (1E)-2-(5-tert-butyl-1,2-oxazol-3-yl)-N-(3,5-dichloroanilino)-2-oxoethanimidoyl cyanide

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: 365.22

Molecular Weight (Monoisotopic): 364.0494

AlogP: 4.45

#Rotatable Bonds: 4

Polar Surface Area: 91.28

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.41

CX Basic pKa: ┄

CX LogP: 5.54

CX LogD: 3.82

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.49

Np Likeness Score: -1.49

References

1. Ye N, Zhu Y, Chen H, Liu Z, Mei FC, Wild C, Chen H, Cheng X, Zhou J..  (2015)  Structure-Activity Relationship Studies of Substituted 2-(Isoxazol-3-yl)-2-oxo-N'-phenyl-acetohydrazonoyl Cyanide Analogues: Identification of Potent Exchange Proteins Directly Activated by cAMP (EPAC) Antagonists.,  58  (15): [PMID:26151319] [10.1021/acs.jmedchem.5b00635]

2. Wang P, Liu Z, Chen H, Ye N, Cheng X, Zhou J..  (2017)  Exchange proteins directly activated by cAMP (EPACs): Emerging therapeutic targets.,  27  (8): [PMID:28283242] [10.1016/j.bmcl.2017.02.065]

Source

Source(1):

• Scientific Literature