5-(4-chlorophenyl)-9-(chlorophenylmethylene)-4-(4-methoxyphenyl-amino)-2-methylthio-6,7,8,9-tetrahydropyrimido[4,5-b]quinoline

ID: ALA472845

PubChem CID: 44582600

Max Phase: Preclinical

Molecular Formula: C32H28Cl2N4OS

Molecular Weight: 587.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(NC2NC(SC)=Nc3nc4c(c(-c5ccc(Cl)cc5)c32)CCC/C4=C/c2ccc(Cl)cc2)cc1

Standard InChI:  InChI=1S/C32H28Cl2N4OS/c1-39-25-16-14-24(15-17-25)35-30-28-27(20-8-12-23(34)13-9-20)26-5-3-4-21(18-19-6-10-22(33)11-7-19)29(26)36-31(28)38-32(37-30)40-2/h6-18,30,35H,3-5H2,1-2H3,(H,36,37,38)/b21-18-

Standard InChI Key:  OIQADDAKUUEPPE-UZYVYHOESA-N

Molfile:  

     RDKit          2D

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   11.9715   -1.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6913   -1.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6913   -0.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4028   -0.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3997   -1.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1145   -1.8873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   15.5425   -1.8893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2564   -1.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2598   -0.6519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   14.1137    2.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4030    1.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8311    1.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4016    1.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6911   -2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4010   -3.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4014   -3.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8336   -3.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8352   -3.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1136   -4.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1169   -2.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1132    3.0676    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.5588   -4.3690    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.9701   -1.8867    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.9697   -2.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2534    1.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9640    0.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6770    0.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6764    1.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9568    2.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2468    1.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3893    2.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1044    1.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 16 21  1  0
 17 20  1  0
 20 18  2  0
 19 21  2  0
 15  1  1  0
  4  7  1  0
  4 22  2  0
  6  5  1  0
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  6  7  2  0
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  2  3  1  0
  2  5  1  0
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 11 12  1  0
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 12 13  2  0
 25 30  1  0
 13 14  1  0
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 31 32  1  0
  3  4  1  0
  1 33  1  0
  9 16  1  0
 33 34  2  0
 16 17  2  0
 34 35  1  0
  6  9  1  0
 35 36  2  0
 18 19  1  0
 36 37  1  0
  7  8  1  0
 37 38  2  0
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  8 11  2  0
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 39 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA472845

   (9Z)-5-(4-chlorophenyl)-9-[(4-chlorophenyl)methylidene]-N-(4-methoxyphenyl)-2-methylsulfanyl-4,6,7,8-tetrahydro-1H-pyrimido[4,5-b]quinolin-4-amine

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: 587.58

Molecular Weight (Monoisotopic): 586.1361

AlogP: 9.01

#Rotatable Bonds: 5

Polar Surface Area: 58.54

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 2.76

CX LogP: 9.69

CX LogD: 9.69

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.24

Np Likeness Score: -0.52

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