4,4'-(ethane-1,2-diyl)bis(N-(4-chlorobenzylidene)aniline)

ID: ALA2268783

PubChem CID: 11305634

Max Phase: Preclinical

Molecular Formula: C28H22Cl2N2

Molecular Weight: 457.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Clc1ccc(/C=N/c2ccc(CCc3ccc(/N=C/c4ccc(Cl)cc4)cc3)cc2)cc1

Standard InChI:  InChI=1S/C28H22Cl2N2/c29-25-11-3-23(4-12-25)19-31-27-15-7-21(8-16-27)1-2-22-9-17-28(18-10-22)32-20-24-5-13-26(30)14-6-24/h3-20H,1-2H2/b31-19+,32-20+

Standard InChI Key:  AJHAWLCKFWDRND-GKTLAHRSSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    8.3447   -9.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7606   -9.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5769   -9.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9740   -9.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5488   -8.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7338   -8.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7910   -9.0630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1863   -8.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0034   -8.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4233   -9.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2396   -9.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6358   -8.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.3947   -7.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6722   -8.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0751   -9.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8964   -7.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1188   -8.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8550   -8.3882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4509   -7.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6338   -7.6727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2286   -6.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122   -6.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9993   -7.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4067   -8.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2218   -8.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5262   -9.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1821   -7.6581    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.4528   -8.2873    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
  4  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
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 13 14  2  0
 14  9  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 19 21  1  0
 16 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 21 30  1  0
 30  1  1  0
 27 31  1  0
 12 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2268783

   1-(4-chlorophenyl)-N-[4-[2-[4-[(4-chlorophenyl)methylideneamino]phenyl]ethyl]phenyl]methanimine

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: 457.40

Molecular Weight (Monoisotopic): 456.1160

AlogP: 8.28

#Rotatable Bonds: 7

Polar Surface Area: 24.72

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.17

CX LogP: 9.47

CX LogD: 9.47

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.25

Np Likeness Score: -0.64

References

1. Siddiqui IR, Singh PK, Singh J, Singh J..  (2003)  Synthesis and fungicidal activity of novel 4,4'-bis(2' '-aryl-5' '-methyl/unsubstituted-4' '-oxo-thiazolidin-3' '-yl) bibenzyl.,  51  (24): [PMID:14611172] [10.1021/jf0342324]

Source

Source(1):

• Scientific Literature