4-(4-chlorobenzamido)phenyl 4-tert-butylbenzenesulfonate

ID: ALA4515940

PubChem CID: 155540276

Max Phase: Preclinical

Molecular Formula: C23H22ClNO4S

Molecular Weight: 443.95

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(S(=O)(=O)Oc2ccc(NC(=O)c3ccc(Cl)cc3)cc2)cc1

Standard InChI:  InChI=1S/C23H22ClNO4S/c1-23(2,3)17-6-14-21(15-7-17)30(27,28)29-20-12-10-19(11-13-20)25-22(26)16-4-8-18(24)9-5-16/h4-15H,1-3H3,(H,25,26)

Standard InChI Key:  STEZWIXGPSDPIM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   14.7425   -9.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1552  -10.4171    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.5636   -9.7048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5735   -9.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5724  -10.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2804  -10.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9901  -10.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9873   -9.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2786   -9.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6934   -9.1850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4027   -9.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1088   -9.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4058  -10.4081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8644  -10.8275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4489  -10.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7422  -10.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0364  -10.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0372  -11.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7497  -12.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4526  -11.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8164   -9.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5221   -9.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5195   -8.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8053   -7.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1025   -8.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2251   -7.9483    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.3307  -12.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6218  -11.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3331  -12.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6181  -12.4560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  5 14  1  0
 14  2  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 12 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 12  1  0
 23 26  1  0
 18 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4515940

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 443.95

Molecular Weight (Monoisotopic): 443.0958

AlogP: 5.66

#Rotatable Bonds: 5

Polar Surface Area: 72.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.43

CX LogD: 6.43

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.52

Np Likeness Score: -1.36

References

1. Semreen MH, El-Gamal MI, Ullah S, Jalil S, Zaib S, Anbar HS, Lecka J, Sévigny J, Iqbal J..  (2019)  Synthesis, biological evaluation, and molecular docking study of sulfonate derivatives as nucleotide pyrophosphatase/phosphodiesterase (NPP) inhibitors.,  27  (13): [PMID:31088715] [10.1016/j.bmc.2019.04.031]

2. Nadel, Yael Y and 11 more authors.  2014-06-12  Highly potent and selective ectonucleotide pyrophosphatase/phosphodiesterase I inhibitors based on an adenosine 5'-(α or γ)-thio-(α,β- or β,γ)-methylenetriphosphate scaffold.  [PMID:24846781]

3. Lee, Sang-Yong SY and 5 more authors.  2016-07-15  Thiazolo[3,2-a]benzimidazol-3(2H)-one derivatives: Structure-activity relationships of selective nucleotide pyrophosphatase/phosphodiesterase1 (NPP1) inhibitors.  [PMID:27265686]

4. Zelikman, Vadim V and 8 more authors.  2018-05-10  Highly Selective and Potent Ectonucleotide Pyrophosphatase-1 (NPP1) Inhibitors Based on Uridine 5'-Pα,α-Dithiophosphate Analogues.  [PMID:29681152]

5. Nassir, Molhm and 8 more authors.  2019-12-15  Structure-activity relationship study of NPP1 inhibitors based on uracil-N1-(methoxy)ethyl-β-phosphate scaffold.  [PMID:31610377]

6. Ahmad, Haseen and 7 more authors.  2020-12-15  Synthesis of biphenyl oxazole derivatives via Suzuki coupling and biological evaluations as nucleotide pyrophosphatase/phosphodiesterase-1 and -3 inhibitors.  [PMID:32883636]

Source

Source(1):

• Scientific Literature