4-Methyl-N-[4-(4-styryl-indol-1-yl)butyl]benzenesulfonamide

ID: ALA3344400

PubChem CID: 118717759

Max Phase: Preclinical

Molecular Formula: C27H28N2O2S

Molecular Weight: 444.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)NCCCCn2ccc3c(/C=C/c4ccccc4)cccc32)cc1

Standard InChI:  InChI=1S/C27H28N2O2S/c1-22-12-16-25(17-13-22)32(30,31)28-19-5-6-20-29-21-18-26-24(10-7-11-27(26)29)15-14-23-8-3-2-4-9-23/h2-4,7-18,21,28H,5-6,19-20H2,1H3/b15-14+

Standard InChI Key:  FKLWZMUIZNTDNM-CCEZHUSRSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   18.9068  -10.6276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1215  -11.4200    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.7004  -10.8380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7753  -14.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7741  -15.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4822  -15.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4804  -14.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1890  -14.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1893  -15.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9679  -15.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4489  -14.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9675  -14.2628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4844  -16.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7777  -16.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7799  -17.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0718  -18.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0737  -19.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7830  -19.4261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4919  -19.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4866  -18.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2197  -13.4855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0190  -13.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2713  -12.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0706  -12.3679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3228  -11.5906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6691  -12.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4153  -12.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9616  -13.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7618  -13.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0129  -12.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4649  -11.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3096  -13.8478    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  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  1  0
  6 13  1  0
 13 14  2  0
 14 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  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25  2  1  0
  2 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3344400

   ---

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: 444.60

Molecular Weight (Monoisotopic): 444.1871

AlogP: 5.88

#Rotatable Bonds: 9

Polar Surface Area: 51.10

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.40

CX Basic pKa: ┄

CX LogP: 6.36

CX LogD: 6.36

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.26

Np Likeness Score: -1.27

References

1. Ferla S, Gomaa MS, Brancale A, Zhu J, Ochalek JT, DeLuca HF, Simons C..  (2014)  Novel styryl-indoles as small molecule inhibitors of 25-hydroxyvitamin D-24-hydroxylase (CYP24A1): Synthesis and biological evaluation.,  87  [PMID:25240094] [10.1016/j.ejmech.2014.09.035]

2. Bruno, Robert D RD and Njar, Vincent C O VC.  2007-08-01  Targeting cytochrome P450 enzymes: a new approach in anti-cancer drug development.  [PMID:17544277]

3. Taban, Ismail M IM, Zhu, Jinge J, DeLuca, Hector F HF and Simons, Claire C.  2017-08-01  Synthesis, molecular modelling and CYP24A1 inhibitory activity of novel of (E)-N-(2-(1H-imidazol-1-yl)-2-(phenylethyl)-3/4-styrylbenzamides.  [PMID:28601511]

Source

Source(1):

• Scientific Literature