(E)-6-Chloro-2-(4-nitrostyryl)-4-(1-piperidinylethyl)aminoquinazoline

ID: ALA4764913

PubChem CID: 162661709

Max Phase: Preclinical

Molecular Formula: C23H24ClN5O2

Molecular Weight: 437.93

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc(/C=C/c2nc(NCCN3CCCCC3)c3cc(Cl)ccc3n2)cc1

Standard InChI:  InChI=1S/C23H24ClN5O2/c24-18-7-10-21-20(16-18)23(25-12-15-28-13-2-1-3-14-28)27-22(26-21)11-6-17-4-8-19(9-5-17)29(30)31/h4-11,16H,1-3,12-15H2,(H,25,26,27)/b11-6+

Standard InChI Key:  PPSBBIUJXBCPJK-IZZDOVSWSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   12.9540   -4.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9528   -5.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6609   -6.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6591   -4.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3677   -4.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3684   -5.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0770   -6.0389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7852   -5.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7805   -4.8060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0714   -4.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4945   -6.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2006   -5.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9099   -6.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9085   -6.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6169   -7.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3240   -6.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3182   -6.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6092   -5.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0671   -3.5854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7726   -3.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4825   -3.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1880   -3.1656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8965   -3.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5999   -3.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5998   -2.3483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8901   -1.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1805   -2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0341   -7.2431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7397   -6.8309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0384   -8.0603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2461   -4.4080    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 10 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 28 29  2  0
 28 30  1  0
 16 28  1  0
  1 31  1  0
M  CHG  2  28   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4764913

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 437.93

Molecular Weight (Monoisotopic): 437.1619

AlogP: 5.26

#Rotatable Bonds: 7

Polar Surface Area: 84.19

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.72

CX LogP: 6.04

CX LogD: 4.70

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: -1.46

References

1. Wei XW,Yuan JM,Huang WY,Chen NY,Li XJ,Pan CX,Mo DL,Su GF.  (2020)  2-Styryl-4-aminoquinazoline derivatives as potent DNA-cleavage, p53-activation and in vivo effective anticancer agents.,  186  [PMID:31761381] [10.1016/j.ejmech.2019.111851]

Source

Source(1):

• Scientific Literature