6-(4-chlorophenyl)-10-(4-chlorophenylmethylene)-2-(4-N,N-dimethyl-aminophenylmethylene)-7,8,9,10-tetrahydrothiazolo[3',2':1,2]pyrimido[4,5-b]quinoline-3,5-dione

ID: ALA451648

PubChem CID: 44582928

Max Phase: Preclinical

Molecular Formula: C35H26Cl2N4O2S

Molecular Weight: 637.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc(/C=c2\sc3nc4nc5c(c(-c6ccc(Cl)cc6)c4c(=O)n3c2=O)CCC/C5=C/c2ccc(Cl)cc2)cc1

Standard InChI:  InChI=1S/C35H26Cl2N4O2S/c1-40(2)26-16-8-21(9-17-26)19-28-33(42)41-34(43)30-29(22-10-14-25(37)15-11-22)27-5-3-4-23(18-20-6-12-24(36)13-7-20)31(27)38-32(30)39-35(41)44-28/h6-19H,3-5H2,1-2H3/b23-18-,28-19-

Standard InChI Key:  QNQCCTAURFGNHD-MZYWVZRRSA-N

Molfile:  

     RDKit          2D

 44 50  0  0  0  0  0  0  0  0999 V2000
    3.4212  -17.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212  -18.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1408  -19.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1408  -17.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8521  -17.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8490  -18.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5634  -19.1174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5613  -17.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2802  -17.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2768  -18.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9906  -19.1194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7042  -18.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7077  -17.8826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9892  -17.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5632  -16.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2798  -16.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625  -14.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8523  -15.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2796  -15.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8508  -16.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9915  -16.6473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4905  -18.9593    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1405  -19.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8502  -20.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8507  -21.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2821  -21.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2838  -20.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5624  -21.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658  -19.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4864  -17.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9712  -18.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7408  -16.8425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7953  -18.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2065  -19.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7898  -19.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2003  -20.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0252  -20.4398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4380  -19.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0251  -19.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5620  -14.1648    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.9945  -21.5980    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.4374  -21.1534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0253  -21.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2615  -21.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  1  0
 14 21  2  0
  5  4  1  0
 12 22  1  0
  5  6  2  0
  3 23  2  0
 23 24  1  0
 24 25  2  0
  1  2  1  0
 26 27  1  0
  1  4  1  0
  9 14  1  0
 10 11  1  0
 11 12  2  0
 24 29  1  0
 25 28  1  0
 28 26  2  0
 27 29  2  0
 12 13  1  0
 13 30  1  0
 22 31  1  0
 13 14  1  0
 30 31  1  0
  2  3  1  0
 30 32  2  0
  8 15  1  0
 31 33  2  0
 15 16  2  0
 33 34  1  0
  5  8  1  0
 34 35  2  0
 17 18  1  0
 35 36  1  0
  6  7  1  0
 36 37  2  0
  7 10  2  0
 37 38  1  0
  9  8  2  0
 38 39  2  0
 39 34  1  0
  9 10  1  0
 17 40  1  0
 15 20  1  0
 26 41  1  0
 16 19  1  0
 37 42  1  0
 19 17  2  0
 42 43  1  0
 18 20  2  0
 42 44  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA451648

   (4Z,14Z)-9-(4-chlorophenyl)-4-[(4-chlorophenyl)methylidene]-14-[[4-(dimethylamino)phenyl]methylidene]-15-thia-2,12,17-triazatetracyclo[8.7.0.03,8.012,16]heptadeca-1(10),2,8,16-tetraene-11,13-dione

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: 637.59

Molecular Weight (Monoisotopic): 636.1154

AlogP: 7.13

#Rotatable Bonds: 4

Polar Surface Area: 67.57

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 4.55

CX LogP: 9.79

CX LogD: 9.78

Aromatic Rings: 6

Heavy Atoms: 44

QED Weighted: 0.21

Np Likeness Score: -0.95

References

1. El-Gazzar AB, Youssef MM, Youssef AM, Abu-Hashem AA, Badria FA..  (2009)  Design and synthesis of azolopyrimidoquinolines, pyrimidoquinazolines as anti-oxidant, anti-inflammatory and analgesic activities.,  44  (2): [PMID:18462840] [10.1016/j.ejmech.2008.03.022]

Source

Source(1):

• Scientific Literature