4-((1H-indol-7-yl)methylamino)-N-(thiazol-2-yl)benzenesulfonamide

ID: ALA3113384

PubChem CID: 70701424

Max Phase: Preclinical

Molecular Formula: C18H16N4O2S2

Molecular Weight: 384.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(Nc1nccs1)c1ccc(NCc2cccc3cc[nH]c23)cc1

Standard InChI:  InChI=1S/C18H16N4O2S2/c23-26(24,22-18-20-10-11-25-18)16-6-4-15(5-7-16)21-12-14-3-1-2-13-8-9-19-17(13)14/h1-11,19,21H,12H2,(H,20,22)

Standard InChI Key:  QQQHALYEHUNHEX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   21.1521   -5.7741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8235   -5.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6285   -7.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4052   -6.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3919   -7.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2242   -6.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9891   -7.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2124   -7.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4821   -5.7842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5297   -7.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4712   -7.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0637   -5.8579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7130   -5.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3005   -6.5618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8155   -5.1609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2414   -5.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0167   -5.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7130   -7.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7557   -6.9472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4801   -6.5598    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.9472   -6.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9421   -6.5618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5297   -5.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7037   -6.4856    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.7629   -6.5618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1715   -7.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  4  1  0
  3  8  2  0
  6  4  2  0
  9  6  1  0
  5  7  2  0
  2  9  2  0
  8  5  1  0
  6  3  1  0
  1  4  1  0
  1  2  1  0
 14 20  1  0
 14 18  2  0
 14 13  1  0
 22 10  2  0
 15 17  1  0
 20 11  2  0
 24 21  1  0
 22 25  1  0
 16 15  2  0
 17 21  2  0
 19 20  2  0
 20 12  1  0
 12 16  1  0
 13 23  2  0
 10 18  1  0
 24 16  1  0
 23 22  1  0
 25 26  1  0
 26  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3113384

   4-(1H-indol-7-ylmethylamino)-N-(1,3-thiazol-2-yl)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: 384.49

Molecular Weight (Monoisotopic): 384.0715

AlogP: 4.04

#Rotatable Bonds: 6

Polar Surface Area: 86.88

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.92

CX Basic pKa: 1.97

CX LogP: 3.10

CX LogD: 2.63

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.47

Np Likeness Score: -1.65

References

1. Luci DK, Jameson JB, Yasgar A, Diaz G, Joshi N, Kantz A, Markham K, Perry S, Kuhn N, Yeung J, Kerns EH, Schultz L, Holinstat M, Nadler JL, Taylor-Fishwick DA, Jadhav A, Simeonov A, Holman TR, Maloney DJ..  (2014)  Synthesis and structure-activity relationship studies of 4-((2-hydroxy-3-methoxybenzyl)amino)benzenesulfonamide derivatives as potent and selective inhibitors of 12-lipoxygenase.,  57  (2): [PMID:24393039] [10.1021/jm4016476]

Source

Source(1):

• Scientific Literature