(E)-6-Chloro-2-(4-nitrostyryl)-4-(2-dimethylaminoethyl)aminoquinazoline

ID: ALA4756911

PubChem CID: 162657374

Max Phase: Preclinical

Molecular Formula: C20H20ClN5O2

Molecular Weight: 397.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(C)CCNc1nc(/C=C/c2ccc([N+](=O)[O-])cc2)nc2ccc(Cl)cc12

Standard InChI:  InChI=1S/C20H20ClN5O2/c1-25(2)12-11-22-20-17-13-15(21)6-9-18(17)23-19(24-20)10-5-14-3-7-16(8-4-14)26(27)28/h3-10,13H,11-12H2,1-2H3,(H,22,23,24)/b10-5+

Standard InChI Key:  RVCSNLSTCGFWSG-BJMVGYQFSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    1.9879   -4.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9868   -5.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6948   -5.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6930   -4.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4016   -4.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4024   -5.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1109   -5.7046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8192   -5.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8145   -4.4717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1054   -4.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5285   -5.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2346   -5.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9439   -5.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9424   -6.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6509   -6.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3580   -6.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3521   -5.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6431   -5.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1010   -3.2511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8066   -2.8388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5164   -3.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2219   -2.8313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9318   -3.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2176   -2.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0681   -6.9088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7736   -6.4965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0723   -7.7260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2801   -4.0737    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 24  1  0
 25 26  2  0
 25 27  1  0
 16 25  1  0
  1 28  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4756911

   ---

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: 397.87

Molecular Weight (Monoisotopic): 397.1306

AlogP: 4.34

#Rotatable Bonds: 7

Polar Surface Area: 84.19

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.75

CX LogP: 5.25

CX LogD: 3.89

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: -1.40

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