(3,4-dichlorophenyl)((3S,4R)-4-(isobutylamino)-1,1-dioxidotetrahydrothiophen-3-yl)methanone

ID: ALA5289812

Max Phase: Preclinical

Molecular Formula: C15H19Cl2NO3S

Molecular Weight: 364.29

Names and Identifiers

Canonical SMILES:  CC(C)CN[C@H]1CS(=O)(=O)C[C@@H]1C(=O)c1ccc(Cl)c(Cl)c1

Standard InChI:  InChI=1S/C15H19Cl2NO3S/c1-9(2)6-18-14-8-22(20,21)7-11(14)15(19)10-3-4-12(16)13(17)5-10/h3-5,9,11,14,18H,6-8H2,1-2H3/t11-,14-/m0/s1

Standard InChI Key:  WLJURCALYAMAAL-FZMZJTMJSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -1.0300    0.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2050    0.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0451   -0.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6084   -0.9938    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759   -0.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4423    0.9952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2672    0.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6796    0.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5044    0.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2672   -0.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074    0.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0321    0.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4448    1.7094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2671    1.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6796    0.9941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2706    0.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4463    0.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5044    0.9941    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6831   -0.4316    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0215   -1.7094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1967   -1.7094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2050    1.7094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  1  5  1  0
  5  4  1  0
  1  6  1  6
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  2 11  1  1
 11 12  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 12 17  1  0
 15 18  1  0
 16 19  1  0
  4 20  2  0
  4 21  2  0
 11 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5289812

   ---

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: 364.29

Molecular Weight (Monoisotopic): 363.0463

AlogP: 2.83

#Rotatable Bonds: 5

Polar Surface Area: 63.24

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.31

CX LogP: 2.40

CX LogD: 1.44

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.82

Np Likeness Score: -0.98

References

1. Jo J, Kim J, Ibrahim L, Kumar M, Iaconelli J, Tran CS, Moon HR, Jung Y, Wiseman RL, Lairson LL, Chatterjee AK, Bollong MJ, Yun H..  (2023)  Optimization of 3-aminotetrahydrothiophene 1,1-dioxides with improved potency and efficacy as non-electrophilic antioxidant response element (ARE) activators.,  89  [PMID:37116763] [10.1016/j.bmcl.2023.129306]

Source

Source(1):

• Scientific Literature