6-chloro-2-(4-methoxybenzylthio)-3-(2-methoxyphenyl)quinazolin-4(3H)-one

ID: ALA3945396

PubChem CID: 134146256

Max Phase: Preclinical

Molecular Formula: C23H19ClN2O3S

Molecular Weight: 438.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CSc2nc3ccc(Cl)cc3c(=O)n2-c2ccccc2OC)cc1

Standard InChI:  InChI=1S/C23H19ClN2O3S/c1-28-17-10-7-15(8-11-17)14-30-23-25-19-12-9-16(24)13-18(19)22(27)26(23)20-5-3-4-6-21(20)29-2/h3-13H,14H2,1-2H3

Standard InChI Key:  RAECKEPGPWCPGE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   47.6915  -15.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.6904  -15.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.4052  -16.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.4034  -14.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.1188  -15.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.1196  -15.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.8349  -16.2592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   50.5499  -15.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   50.5451  -15.0144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   49.8292  -14.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   51.2540  -14.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   51.9713  -15.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   52.6828  -14.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   52.6782  -13.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   51.9562  -13.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   51.2477  -13.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   51.2660  -16.2541    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   51.2692  -17.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   51.9852  -17.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   51.9851  -18.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   52.7003  -18.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   53.4142  -18.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   53.4083  -17.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   52.6925  -17.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.8249  -13.7822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   54.1308  -18.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   54.8431  -18.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.9770  -14.6127    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   50.5296  -13.3716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   50.5223  -12.5466    0.0000 C   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  1  0
 10  5  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  9 11  1  0
  8 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 10 25  2  0
 22 26  1  0
 26 27  1  0
  1 28  1  0
 16 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3945396

   ---

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: 438.94

Molecular Weight (Monoisotopic): 438.0805

AlogP: 5.35

#Rotatable Bonds: 6

Polar Surface Area: 53.35

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.94

CX LogD: 5.94

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.30

Np Likeness Score: -1.62

References

1. El-Messery SM, Hassan GS, Nagi MN, Habib EE, Al-Rashood ST, El-Subbagh HI..  (2016)  Synthesis, biological evaluation and molecular modeling study of some new methoxylated 2-benzylthio-quinazoline-4(3H)-ones as nonclassical antifolates.,  26  (19): [PMID:27554444] [10.1016/j.bmcl.2016.08.022]

Source

Source(1):

• Scientific Literature