4-(3-methoxybenzylamino)-N-(thiazol-2-yl)benzene sulfonamide

ID: ALA3113377

PubChem CID: 70701447

Max Phase: Preclinical

Molecular Formula: C17H17N3O3S2

Molecular Weight: 375.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(CNc2ccc(S(=O)(=O)Nc3nccs3)cc2)c1

Standard InChI:  InChI=1S/C17H17N3O3S2/c1-23-15-4-2-3-13(11-15)12-19-14-5-7-16(8-6-14)25(21,22)20-17-18-9-10-24-17/h2-11,19H,12H2,1H3,(H,18,20)

Standard InChI Key:  XELKSCBGLRFYJZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.7019   -9.7727    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2772  -10.4708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0941  -10.4896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769  -10.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797  -10.5490    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2845   -9.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5432   -9.3887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9861   -9.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0014   -9.3463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4165   -9.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1128   -9.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8268   -9.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8434   -8.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1400   -8.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4288   -8.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5585   -8.1975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2586   -8.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9737   -8.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6714   -8.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3861   -8.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4016   -7.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6965   -7.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9848   -7.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7087   -6.1955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4224   -5.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  4  2  0
  6  9  1  0
  9  1  1  0
  1 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 22 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3113377

   4-[(3-methoxyphenyl)methylamino]-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: 375.48

Molecular Weight (Monoisotopic): 375.0711

AlogP: 3.56

#Rotatable Bonds: 7

Polar Surface Area: 80.32

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.92

CX Basic pKa: 2.03

CX LogP: 2.84

CX LogD: 2.37

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.66

Np Likeness Score: -1.95

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