(E)-1-(2-(1-(4-nitrophenyl)ethylidene)hydrazyl)-4-chlorophthalazine

ID: ALA4099014

PubChem CID: 9619213

Max Phase: Preclinical

Molecular Formula: C16H12ClN5O2

Molecular Weight: 341.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=N\Nc1nnc(Cl)c2ccccc12)c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C16H12ClN5O2/c1-10(11-6-8-12(9-7-11)22(23)24)18-20-16-14-5-3-2-4-13(14)15(17)19-21-16/h2-9H,1H3,(H,20,21)/b18-10+

Standard InChI Key:  GKXRTVIPCADKKD-VCHYOVAHSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   10.6124   -7.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6080   -7.8561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8909   -8.2643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8865   -9.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6035   -9.5083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5992  -10.3366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8820  -10.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1649  -10.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4518  -10.7415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7349  -10.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7392   -9.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4564   -9.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1692   -9.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8776  -11.5730    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.3282   -6.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9008   -6.6120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0379   -7.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7531   -6.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7580   -5.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0414   -5.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3291   -5.7984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4742   -5.3938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4774   -4.5697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1862   -5.8086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  4 13  1  0
  8 13  1  0
  7 14  1  0
  1 15  1  0
  1 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 15  1  0
 22 23  2  0
 22 24  1  0
 19 22  1  0
M  CHG  2  22   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4099014

   1-(4-Nitrophenyl)ethanone (4-chloro-1-phthalazinyl)hydrazone

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: 341.76

Molecular Weight (Monoisotopic): 341.0680

AlogP: 4.03

#Rotatable Bonds: 4

Polar Surface Area: 93.31

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.90

CX Basic pKa: 3.16

CX LogP: 3.80

CX LogD: 3.80

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.44

Np Likeness Score: -1.55

References

1. Romero AH, Medina R, Alcala A, García-Marchan Y, Núñez-Duran J, Leañez J, Mijoba A, Ciangherotti C, Serrano-Martín X, López SE..  (2017)  Design, synthesis, structure-activity relationship and mechanism of action studies of a series of 4-chloro-1-phthalazinyl hydrazones as a potent agent against Leishmania braziliensis.,  127  [PMID:28119201] [10.1016/j.ejmech.2017.01.022]

Source

Source(1):

• Scientific Literature