9-chloro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

ID: ALA429599

PubChem CID: 16759933

Max Phase: Preclinical

Molecular Formula: C15H9ClN2O2S

Molecular Weight: 316.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S1(=O)Nc2c(ccc3cccnc23)-c2cc(Cl)ccc21

Standard InChI:  InChI=1S/C15H9ClN2O2S/c16-10-4-6-13-12(8-10)11-5-3-9-2-1-7-17-14(9)15(11)18-21(13,19)20/h1-8,18H

Standard InChI Key:  JVPPTVNJBXFSPQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
   -5.4869   -4.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4869   -5.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7753   -5.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7753   -3.8345    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0592   -4.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0627   -5.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3529   -5.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6350   -5.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3458   -3.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6341   -4.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6205   -2.6074    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3422   -3.0133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9087   -3.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9218   -3.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2174   -4.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4953   -3.8753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4822   -3.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1911   -2.6234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2185   -1.8944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0402   -1.8944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2090   -4.2984    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  5  6  1  0
  9 12  1  0
 10 14  1  0
 13 11  1  0
 11 12  1  0
 13 14  1  0
  1  2  1  0
  1  4  2  0
  2  3  2  0
  5  9  2  0
  6  7  2  0
  7  8  1  0
 13 18  2  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  8 10  2  0
 11 19  2  0
  9 10  1  0
 11 20  2  0
  3  6  1  0
 16 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA429599

   9-chloro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

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: 316.77

Molecular Weight (Monoisotopic): 316.0073

AlogP: 3.67

#Rotatable Bonds: ┄

Polar Surface Area: 59.06

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.53

CX Basic pKa: 3.49

CX LogP: 2.90

CX LogD: 2.24

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: -1.05

References

1. Xie Y, Deng S, Thomas CJ, Liu Y, Zhang YQ, Rinderspacher A, Huang W, Gong G, Wyler M, Cayanis E, Aulner N, Többen U, Chung C, Pampou S, Southall N, Vidović D, Schürer S, Branden L, Davis RE, Staudt LM, Inglese J, Austin CP, Landry DW, Smith DH, Auld DS..  (2008)  Identification of N-(quinolin-8-yl)benzenesulfonamides as agents capable of down-regulating NFkappaB activity within two separate high-throughput screens of NFkappaB activation.,  18  (1): [PMID:18024113] [10.1016/j.bmcl.2007.10.100]

2. Tsai KC, Teng LW, Shao YM, Chen YC, Lee YC, Li M, Hsiao NW..  (2009)  The first pharmacophore model for potent NF-kappaB inhibitors.,  19  (19): [PMID:19726185] [10.1016/j.bmcl.2009.08.021]

3.  (2014)  Novel sulfonaminoquinoline Hepcidin antagonists, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data