4-(5,6-dihydrothieno[2,3-h]quinazolin-2-ylamino)-N-(2-hydroxyethyl)benzenesulfonamide

ID: ALA1085310

PubChem CID: 46890390

Max Phase: Preclinical

Molecular Formula: C18H18N4O3S2

Molecular Weight: 402.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(NCCO)c1ccc(Nc2ncc3c(n2)-c2ccsc2CC3)cc1

Standard InChI:  InChI=1S/C18H18N4O3S2/c23-9-8-20-27(24,25)14-4-2-13(3-5-14)21-18-19-11-12-1-6-16-15(7-10-26-16)17(12)22-18/h2-5,7,10-11,20,23H,1,6,8-9H2,(H,19,21,22)

Standard InChI Key:  OLRRJHAWXDSFED-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   14.8926  -14.4884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3093  -15.2051    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.7217  -14.4859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0296  -16.8663    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7460  -16.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7432  -15.6223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0278  -15.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4613  -16.8643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1751  -16.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8869  -16.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6003  -16.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5994  -15.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8793  -15.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1688  -15.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0285  -15.6195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3024  -17.1371    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.7115  -17.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5181  -17.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3194  -16.4582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3239  -15.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6137  -15.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8944  -15.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8899  -16.4504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6047  -16.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7425  -15.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4575  -15.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1716  -15.2049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0
 13 14  2  0
 14  9  1  0
 12  2  1  0
  7 20  1  0
  2 15  1  0
 19  4  1  0
  5  8  1  0
  2  1  2  0
 23 16  1  0
 16 17  1  0
 17 18  2  0
 18 24  1  0
 19 20  2  0
  8  9  1  0
  4  5  2  0
  9 10  2  0
  3  2  2  0
 10 11  1  0
  5  6  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 11 12  2  0
 15 25  1  0
 25 26  1  0
 12 13  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1085310

   4-(5,6-dihydrothieno[2,3-h]quinazolin-2-ylamino)-N-(2-hydroxyethyl)benzenesulfonamide

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: 402.50

Molecular Weight (Monoisotopic): 402.0820

AlogP: 2.32

#Rotatable Bonds: 6

Polar Surface Area: 104.21

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.63

CX Basic pKa: 1.37

CX LogP: 2.82

CX LogD: 2.82

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.58

Np Likeness Score: -1.62

References

1. Crombie AL, Sum FW, Powell DW, Hopper DW, Torres N, Berger DM, Zhang Y, Gavriil M, Sadler TM, Arndt K..  (2010)  Synthesis and biological evaluation of tricyclic anilinopyrimidines as IKKbeta inhibitors.,  20  (12): [PMID:20471256] [10.1016/j.bmcl.2010.04.022]

Source

Source(1):

• Scientific Literature