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

ID: ALA520693

PubChem CID: 44582927

Max Phase: Preclinical

Molecular Formula: C31H23N5O2S2

Molecular Weight: 561.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(/C=C2/CCCc3c2nc2nc4s/c(=C\c5cccs5)c(=O)n4c(=O)c2c3-c2ccc(N)cc2)cc1

Standard InChI:  InChI=1S/C31H23N5O2S2/c32-20-10-6-17(7-11-20)15-19-3-1-5-23-25(18-8-12-21(33)13-9-18)26-28(34-27(19)23)35-31-36(30(26)38)29(37)24(40-31)16-22-4-2-14-39-22/h2,4,6-16H,1,3,5,32-33H2/b19-15-,24-16-

Standard InChI Key:  LHMUSPSSMCIFLX-NBJFAONASA-N

Molfile:  

     RDKit          2D

 40 46  0  0  0  0  0  0  0  0999 V2000
   -5.1591  -17.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1591  -18.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4398  -18.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4398  -17.3163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7288  -17.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7319  -18.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178  -18.9649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0199  -17.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3012  -17.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3047  -18.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5909  -18.9670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8777  -18.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8742  -17.7305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5924  -17.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0179  -16.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3016  -16.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0187  -14.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7286  -15.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3019  -15.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7301  -16.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5900  -16.4957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0917  -18.8068    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4401  -19.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7307  -20.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7302  -21.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2994  -21.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2977  -20.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0188  -21.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0154  -19.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957  -17.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3890  -18.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1585  -16.6909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2128  -18.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6237  -18.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0192  -14.0140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5871  -21.4446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2854  -19.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8974  -20.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6117  -19.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4385  -18.9460    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 15 20  1  0
 16 19  1  0
 19 17  2  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
 17 35  1  0
 17 18  1  0
 26 36  1  0
 37 38  1  0
  6  7  1  0
  7 10  2  0
  9  8  2  0
  9 10  1  0
 34 37  2  0
 38 39  2  0
 39 40  1  0
 40 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA520693

   (4Z,14Z)-9-(4-aminophenyl)-4-[(4-aminophenyl)methylidene]-14-(thiophen-2-ylmethylidene)-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: 561.69

Molecular Weight (Monoisotopic): 561.1293

AlogP: 4.98

#Rotatable Bonds: 3

Polar Surface Area: 116.37

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.08

CX LogP: 6.72

CX LogD: 6.72

Aromatic Rings: 6

Heavy Atoms: 40

QED Weighted: 0.29

Np Likeness Score: -1.05

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