4-(2-hydroxy-3-methoxybenzylamino)-N-(4-(piperazin-1-yl)phenyl)benzenesulfonamide

ID: ALA3113184

PubChem CID: 70701364

Max Phase: Preclinical

Molecular Formula: C24H28N4O4S

Molecular Weight: 468.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(CNc2ccc(S(=O)(=O)Nc3ccc(N4CCNCC4)cc3)cc2)c1O

Standard InChI:  InChI=1S/C24H28N4O4S/c1-32-23-4-2-3-18(24(23)29)17-26-19-7-11-22(12-8-19)33(30,31)27-20-5-9-21(10-6-20)28-15-13-25-14-16-28/h2-12,25-27,29H,13-17H2,1H3

Standard InChI Key:  YFJVIPWBEBHHAX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    6.0445   -9.1284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2263   -9.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8197   -9.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2266  -10.5423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0448  -10.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4560   -9.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4482   -8.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4426   -7.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0359   -7.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2573   -7.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1870   -6.7016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4299   -2.0412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4821   -6.2907    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.7237   -4.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8965   -5.5815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7184   -5.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3769   -2.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1373   -3.4510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3823   -1.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6081   -2.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1319   -4.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9591   -3.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4773   -7.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4883   -4.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1987   -2.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8477   -1.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6028   -3.4603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2040   -1.3277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9645   -2.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9019   -4.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6649   -6.2918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6704   -7.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2672   -8.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
 10  8  2  0
  9  7  2  0
 32 10  1  0
  8  9  1  0
  7 33  1  0
 15 13  1  0
 15 24  2  0
 17 25  1  0
 23 13  2  0
 28 19  2  0
 25 20  2  0
 16 21  2  0
 20 12  1  0
 22 17  1  0
 14 18  1  0
 14 30  2  0
 18 22  1  0
 21 14  1  0
 15 16  1  0
 13 11  2  0
 12 26  1  0
 19 29  1  0
 30 24  1  0
 20 28  1  0
 25 27  1  0
 17 29  2  0
 13 31  1  0
 31 10  1  0
 32 33  2  0
  7  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3113184

   4-[(2-hydroxy-3-methoxyphenyl)methylamino]-N-(4-piperazin-1-ylphenyl)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: 468.58

Molecular Weight (Monoisotopic): 468.1831

AlogP: 3.22

#Rotatable Bonds: 8

Polar Surface Area: 102.93

Molecular Species: BASE

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.15

CX Basic pKa: 8.61

CX LogP: 2.21

CX LogD: 1.28

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.40

Np Likeness Score: -1.20

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