N-(3-(4-tert-butylbenzylamino)propyl)-3,5-bis(trifluoromethyl)benzenesulfonamide

ID: ALA5172198

PubChem CID: 168269652

Max Phase: Preclinical

Molecular Formula: C22H26F6N2O2S

Molecular Weight: 496.52

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(CNCCCNS(=O)(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)cc1

Standard InChI:  InChI=1S/C22H26F6N2O2S/c1-20(2,3)16-7-5-15(6-8-16)14-29-9-4-10-30-33(31,32)19-12-17(21(23,24)25)11-18(13-19)22(26,27)28/h5-8,11-13,29-30H,4,9-10,14H2,1-3H3

Standard InChI Key:  VJGCZXULWOXTIL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
    1.4302    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7157    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4276    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1420    1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8565    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5694   -0.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841    0.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2857    0.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5740    1.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0002    1.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7146    0.8229    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0002    2.0604    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7146    1.6479    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5694   -1.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550   -1.6480    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2839   -1.6480    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5694   -2.0604    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7288    1.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5537    1.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1447    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8591    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5738    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2857    0.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2857    0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5755   -0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8591   -0.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0002   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7146    0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0002   -1.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7146   -0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
 11 10  1  0
 12 11  2  0
  7 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  9 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
  6 21  2  0
  6 22  2  0
  1 23  1  0
 23 24  1  0
 25 24  2  0
 26 25  1  0
 27 26  2  0
 28 27  1  0
 29 28  2  0
 24 29  1  0
 27 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5172198

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 496.52

Molecular Weight (Monoisotopic): 496.1619

AlogP: 5.48

#Rotatable Bonds: 8

Polar Surface Area: 58.20

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.95

CX Basic pKa: 9.25

CX LogP: 5.10

CX LogD: 3.56

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.38

Np Likeness Score: -1.25

References

1. Sun J, Ambrus JI, Baker JR, Russell CC, Cossar PJ, Sakoff JA, Scarlett CJ, McCluskey A..  (2022)  3,5-Bis(trifluoromethyl)phenylsulfonamides, a novel pancreatic cancer active lead. Investigation of the terminal aromatic moiety.,  61  [PMID:35114371] [10.1016/j.bmcl.2022.128591]

Source

Source(1):

• Scientific Literature