4-Cyano-N-(1-ethyl-3-methyl-2-oxo-1,2-dihydroquinolin-6-yl)benzenesulfonamide

ID: ALA4097011

PubChem CID: 118918735

Max Phase: Preclinical

Molecular Formula: C19H17N3O3S

Molecular Weight: 367.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1c(=O)c(C)cc2cc(NS(=O)(=O)c3ccc(C#N)cc3)ccc21

Standard InChI:  InChI=1S/C19H17N3O3S/c1-3-22-18-9-6-16(11-15(18)10-13(2)19(22)23)21-26(24,25)17-7-4-14(12-20)5-8-17/h4-11,21H,3H2,1-2H3

Standard InChI Key:  XPXQVVIBBLAANE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   24.6354  -16.2613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2310  -15.5555    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.8220  -16.2587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6493  -15.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6482  -16.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3562  -16.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3544  -15.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0630  -15.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0619  -16.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7681  -16.7816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4800  -16.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4811  -15.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7704  -15.1403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1865  -16.7851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9415  -15.1471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5261  -15.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5295  -14.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8226  -13.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1140  -14.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1168  -15.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8243  -15.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7658  -17.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4724  -18.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1898  -15.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4065  -13.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6982  -13.5175    0.0000 N   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  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 11 14  2  0
  4 15  1  0
 15  2  1  0
  2 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 10 22  1  0
 22 23  1  0
 12 24  1  0
 25 26  3  0
 19 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097011

   ---

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: 367.43

Molecular Weight (Monoisotopic): 367.0991

AlogP: 3.00

#Rotatable Bonds: 4

Polar Surface Area: 91.96

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.76

CX Basic pKa: ┄

CX LogP: 2.56

CX LogD: 2.42

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.77

Np Likeness Score: -1.76

References

1. Igoe N, Bayle ED, Fedorov O, Tallant C, Savitsky P, Rogers C, Owen DR, Deb G, Somervaille TC, Andrews DM, Jones N, Cheasty A, Ryder H, Brennan PE, Müller S, Knapp S, Fish PV..  (2017)  Design of a Biased Potent Small Molecule Inhibitor of the Bromodomain and PHD Finger-Containing (BRPF) Proteins Suitable for Cellular and in Vivo Studies.,  60  (2): [PMID:28068087] [10.1021/acs.jmedchem.6b01583]

2. Palmer, Wylie S WS and 21 more authors.  2016-02-25  Structure-Guided Design of IACS-9571, a Selective High-Affinity Dual TRIM24-BRPF1 Bromodomain Inhibitor.  [PMID:26061247]

3. Romero, F Anthony FA and 5 more authors.  2016-02-25  Disrupting Acetyl-Lysine Recognition: Progress in the Development of Bromodomain Inhibitors.  [PMID:26572217]

4. Moustakim, Moses; Clark, Peter G K; Hay, Duncan A; Dixon, Darren J and Brennan, Paul E.  2016-12-07  Chemical probes and inhibitors of bromodomains outside the BET family.  [PMID:29170712]

Source

Source(1):

• Scientific Literature