(3-Chlorophenylamino)-acetic acid [1-pyridin-4-yl-meth-(E)-ylidene]-hydrazide

ID: ALA3728445

PubChem CID: 9661728

Max Phase: Preclinical

Molecular Formula: C14H13ClN4O

Molecular Weight: 288.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CNc1cccc(Cl)c1)N/N=C/c1ccncc1

Standard InChI:  InChI=1S/C14H13ClN4O/c15-12-2-1-3-13(8-12)17-10-14(20)19-18-9-11-4-6-16-7-5-11/h1-9,17H,10H2,(H,19,20)/b18-9+

Standard InChI Key:  CWUZHXXAZSEESR-GIJQJNRQSA-N

Molfile:  

     RDKit          2D

 20 21  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 N   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
   -2.5972   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -3.7570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8509   -5.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1872   -7.5117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4854   -8.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4855   -9.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7845  -10.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0836   -9.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0836   -8.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7846   -7.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7845  -11.7149    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
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 16 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3728445

   2-(3-chloroanilino)-N'-[(E)-1-(4-pyridyl)methylidene]acetohydrazide

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: 288.74

Molecular Weight (Monoisotopic): 288.0778

AlogP: 2.30

#Rotatable Bonds: 5

Polar Surface Area: 66.38

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.70

CX Basic pKa: 4.26

CX LogP: 1.64

CX LogD: 1.64

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.66

Np Likeness Score: -2.46

References

1.  (2007)  Hydrazide compounds, 

2. Okawa T, Aramaki Y, Yamamoto M, Kobayashi T, Fukumoto S, Toyoda Y, Henta T, Hata A, Ikeda S, Kaneko M, Hoffman ID, Sang BC, Zou H, Kawamoto T..  (2017)  Design, Synthesis, and Evaluation of the Highly Selective and Potent G-Protein-Coupled Receptor Kinase 2 (GRK2) Inhibitor for the Potential Treatment of Heart Failure.,  60  (16): [PMID:28699740] [10.1021/acs.jmedchem.7b00443]

3. Cho, Sung Yun SY and 9 more authors.  2013-12-15  Design and synthesis of novel 3-(benzo[d]oxazol-2-yl)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine derivatives as selective G-protein-coupled receptor kinase-2 and -5 inhibitors.  [PMID:24210504]

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data