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

ID: ALA503337

PubChem CID: 44582926

Max Phase: Preclinical

Molecular Formula: C34H23Cl2N3O3S

Molecular Weight: 624.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=c2\sc3nc4nc5c(c(-c6ccc(Cl)cc6)c4c(=O)n3c2=O)CCC/C5=C/c2ccc(Cl)cc2)cc1

Standard InChI:  InChI=1S/C34H23Cl2N3O3S/c1-42-25-15-7-20(8-16-25)18-27-32(40)39-33(41)29-28(21-9-13-24(36)14-10-21)26-4-2-3-22(17-19-5-11-23(35)12-6-19)30(26)37-31(29)38-34(39)43-27/h5-18H,2-4H2,1H3/b22-17-,27-18-

Standard InChI Key:  QEBOKYBIRASKQL-ABWJXVKVSA-N

Molfile:  

     RDKit          2D

 43 49  0  0  0  0  0  0  0  0999 V2000
   11.0669   -8.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0669   -8.9443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7864   -9.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7864   -7.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4976   -8.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4945   -8.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2089   -9.3572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2068   -7.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9258   -8.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9223   -8.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6362   -9.3593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3498   -8.9443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3532   -8.1224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6348   -7.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2088   -6.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9254   -6.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2081   -5.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4978   -5.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9252   -5.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4964   -6.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6371   -6.8872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1361   -9.1991    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.7862  -10.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4958  -10.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4962  -11.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9276  -11.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9293  -10.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2080  -11.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2113  -10.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1321   -7.8663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6168   -8.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3864   -7.0824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4409   -8.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8520   -9.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4353   -9.9644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8459  -10.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6708  -10.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0836   -9.9613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6707   -9.2506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2076   -4.4046    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.6401  -11.8378    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.0829  -11.3932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6709  -12.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 18 20  2  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
M  END

Alternative Forms

1. Parent:

   

   ALA503337

   (4Z,14Z)-9-(4-chlorophenyl)-4-[(4-chlorophenyl)methylidene]-14-[(4-methoxyphenyl)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: 624.55

Molecular Weight (Monoisotopic): 623.0837

AlogP: 7.07

#Rotatable Bonds: 4

Polar Surface Area: 73.56

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 1.04

CX LogP: 9.52

CX LogD: 9.52

Aromatic Rings: 6

Heavy Atoms: 43

QED Weighted: 0.21

Np Likeness Score: -0.81

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