(1Z,2E)-2-{[(3-Methylbenzofuran-2-yl)carbonyl]hydrazono}-N-(4-bromophenyl)propanehydrazonoyl chloride

ID: ALA1079861

PubChem CID: 44613711

Max Phase: Preclinical

Molecular Formula: C19H16BrClN4O2

Molecular Weight: 447.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=N\NC(=O)c1oc2ccccc2c1C)/C(Cl)=N/Nc1ccc(Br)cc1

Standard InChI:  InChI=1S/C19H16BrClN4O2/c1-11-15-5-3-4-6-16(15)27-17(11)19(26)25-22-12(2)18(21)24-23-14-9-7-13(20)8-10-14/h3-10,23H,1-2H3,(H,25,26)/b22-12+,24-18-

Standard InChI Key:  JWFKMPCDGMGALP-SZQFWKLMSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -5.9946   -7.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6107   -8.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7859   -8.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5564   -6.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7328   -6.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3460   -7.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5269   -7.5833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4075   -6.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1528   -6.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2924   -5.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6773   -6.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9797   -6.8171    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6448   -5.5524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2495   -6.4331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5518   -6.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1783   -6.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5843   -7.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8760   -6.9297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2108   -5.6650    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6062   -6.5457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3038   -6.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2669   -7.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637   -8.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6948   -7.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7249   -7.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0273   -6.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3931   -8.3058    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
 11 13  2  0
  3  6  2  0
 12 14  1  0
  1  2  2  0
 14 15  2  0
  5  4  2  0
 15 16  1  0
  6  7  1  0
 15 17  1  0
  7  8  1  0
 16 18  2  0
  8  9  2  0
 16 19  1  0
  9  5  1  0
 18 20  1  0
  4  1  1  0
 20 21  1  0
  9 10  1  0
 21 22  2  0
  5  6  1  0
 22 23  1  0
  8 11  1  0
 23 24  2  0
 24 25  1  0
 11 12  1  0
 25 26  2  0
 26 21  1  0
  2  3  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1079861

   (1Z,2E)-N-(4-bromophenyl)-2-[(3-methyl-1-benzofuran-2-carbonyl)hydrazinylidene]propanehydrazonoyl chloride

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: 447.72

Molecular Weight (Monoisotopic): 446.0145

AlogP: 5.27

#Rotatable Bonds: 5

Polar Surface Area: 78.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.34

CX Basic pKa: 0.91

CX LogP: 5.35

CX LogD: 5.35

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.41

Np Likeness Score: -1.01

References

1. Abdel-Aziz HA, Mekawey AA..  (2009)  Stereoselective synthesis and antimicrobial activity of benzofuran-based (1E)-1-(piperidin-1-yl)-N2-arylamidrazones.,  44  (12): [PMID:19782439] [10.1016/j.ejmech.2009.09.002]

Source

Source(1):

• Scientific Literature