2-(2-aminothiazol-5-ylthio)-6-methyl-3-phenylquinazolin-4(3H)-one

ID: ALA2376066

PubChem CID: 72196353

Max Phase: Preclinical

Molecular Formula: C18H14N4OS2

Molecular Weight: 366.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2nc(Sc3cnc(N)s3)n(-c3ccccc3)c(=O)c2c1

Standard InChI:  InChI=1S/C18H14N4OS2/c1-11-7-8-14-13(9-11)16(23)22(12-5-3-2-4-6-12)18(21-14)25-15-10-20-17(19)24-15/h2-10H,1H3,(H2,19,20)

Standard InChI Key:  ODAGZVIAGIOEFH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    2.0110   -3.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0098   -4.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7246   -4.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7228   -2.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382   -3.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4416   -4.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1608   -4.4954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8812   -4.0782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8778   -3.2451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1540   -2.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1495   -2.0043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5899   -2.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3060   -3.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0187   -2.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0165   -2.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2958   -1.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5860   -2.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5968   -4.4888    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5990   -5.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9327   -5.8017    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1897   -6.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0148   -6.5833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2675   -5.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7066   -7.2543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -2.8423    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
  5 10  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  9 12  1  0
  8 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  2  0
 21 24  1  0
  1 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2376066

   2-[(2-Amino-1,3-thiazol-5-yl)sulfanyl]-6-methyl-3-phenylquinazolin-4-one

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: 366.47

Molecular Weight (Monoisotopic): 366.0609

AlogP: 3.88

#Rotatable Bonds: 3

Polar Surface Area: 73.80

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.96

CX LogP: 4.60

CX LogD: 4.60

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.56

Np Likeness Score: -1.51

References

1. Al-Omary FA, Hassan GS, El-Messery SM, Nagi MN, Habib el-SE, El-Subbagh HI..  (2013)  Nonclassical antifolates, part 3: synthesis, biological evaluation and molecular modeling study of some new 2-heteroarylthio-quinazolin-4-ones.,  63  [PMID:23454532] [10.1016/j.ejmech.2012.12.061]

2. Al-Rashood ST, Hassan GS, El-Messery SM, Nagi MN, Habib el-SE, Al-Omary FA, El-Subbagh HI..  (2014)  Synthesis, biological evaluation and molecular modeling study of 2-(1,3,4-thiadiazolyl-thio and 4-methyl-thiazolyl-thio)-quinazolin-4-ones as a new class of DHFR inhibitors.,  24  (18): [PMID:25139568] [10.1016/j.bmcl.2014.07.070]

Source

Source(1):

• Scientific Literature