2-(2-aminothiazol-5-ylthio)-6,7-dimethoxy-3-phenylquinazolin-4(3H)-one

ID: ALA2376069

PubChem CID: 72196522

Max Phase: Preclinical

Molecular Formula: C19H16N4O3S2

Molecular Weight: 412.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2nc(Sc3cnc(N)s3)n(-c3ccccc3)c(=O)c2cc1OC

Standard InChI:  InChI=1S/C19H16N4O3S2/c1-25-14-8-12-13(9-15(14)26-2)22-19(28-16-10-21-18(20)27-16)23(17(12)24)11-6-4-3-5-7-11/h3-10H,1-2H3,(H2,20,21)

Standard InChI Key:  YSMFZZMOCGSFSZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    2.1527  -10.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1515  -11.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8663  -11.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8645  -10.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799  -10.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5833  -11.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3025  -11.7954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0229  -11.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0195  -10.5451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2957  -10.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2911   -9.3043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7316  -10.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4476  -10.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1603  -10.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1582   -9.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4374   -8.8928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7277   -9.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7385  -11.7887    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7407  -12.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0743  -13.1016    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3314  -13.8856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1565  -13.8833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4091  -13.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8483  -14.5543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4381  -10.1423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4379   -9.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4367  -11.7940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7226  -11.3809    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
 25 26  1  0
  2 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2376069

   2-[(2-Amino-1,3-thiazol-5-yl)sulfanyl]-6,7-dimethoxy-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: 412.50

Molecular Weight (Monoisotopic): 412.0664

AlogP: 3.59

#Rotatable Bonds: 5

Polar Surface Area: 92.26

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.96

CX LogP: 3.77

CX LogD: 3.77

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.50

Np Likeness Score: -1.12

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