5,7-Dichloro-3-hydroxy-1H-quinazoline-2,4-dione

ID: ALA307267

PubChem CID: 23354226

Max Phase: Preclinical

Molecular Formula: C8H4Cl2N2O3

Molecular Weight: 247.04

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c2cc(Cl)cc(Cl)c2c(=O)n1O

Standard InChI:  InChI=1S/C8H4Cl2N2O3/c9-3-1-4(10)6-5(2-3)11-8(14)12(15)7(6)13/h1-2,15H,(H,11,14)

Standard InChI Key:  MVMRFDFKPNDLQJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
    2.2042   -0.1500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792    0.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667   -0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792   -1.3917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7625   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0500    0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0500   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6625   -0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792    1.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -1.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6625   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167    0.2583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    1.0875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3833   -1.3917    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  5  1  0
  7  4  2  0
  8  6  2  0
  9  7  1  0
 10  2  2  0
 11  3  2  0
 12  8  1  0
 13  1  1  0
 14  7  1  0
 15 12  1  0
  4  6  1  0
  9 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA307267

   5,7-Dichloro-3-hydroxy-1H-quinazoline-2,4-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: 247.04

Molecular Weight (Monoisotopic): 245.9599

AlogP: 1.23

#Rotatable Bonds: ┄

Polar Surface Area: 75.09

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.26

CX Basic pKa: ┄

CX LogP: 2.60

CX LogD: 0.66

Aromatic Rings: 2

Heavy Atoms: 15

QED Weighted: 0.69

Np Likeness Score: -0.57

References

1. Colotta V, Catarzi D, Varano F, Calabri FR, Filacchioni G, Costagli C, Galli A..  (2004)  3-hydroxy-quinazoline-2,4-dione as a useful scaffold to obtain selective Gly/NMDA and AMPA receptor antagonists.,  14  (9): [PMID:15081038] [10.1016/j.bmcl.2004.01.109]

2. Falsini M, Squarcialupi L, Catarzi D, Varano F, Betti M, Di Cesare Mannelli L, Tenci B, Ghelardini C, Tanc M, Angeli A, Supuran CT, Colotta V..  (2017)  3-Hydroxy-1H-quinazoline-2,4-dione as a New Scaffold To Develop Potent and Selective Inhibitors of the Tumor-Associated Carbonic Anhydrases IX and XII.,  60  (14): [PMID:28658574] [10.1021/acs.jmedchem.7b00766]

Source

Source(1):

• Scientific Literature