4-chloro-N-{2,2-dichloro-1-[N'-(2-fluoropyridin-3-yl)-N''-cyanoguanidino]propyl}benzamide

ID: ALA540965

PubChem CID: 10115466

Max Phase: Preclinical

Molecular Formula: C17H14Cl4N6O

Molecular Weight: 460.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cl)(Cl)C(NC(=O)c1ccc(Cl)cc1)N/C(=N/C#N)Nc1cccnc1Cl

Standard InChI:  InChI=1S/C17H14Cl4N6O/c1-17(20,21)15(26-14(28)10-4-6-11(18)7-5-10)27-16(24-9-22)25-12-3-2-8-23-13(12)19/h2-8,15H,1H3,(H,26,28)(H2,24,25,27)

Standard InChI Key:  CYJNNAUMOWSXGY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   14.2202  -23.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9341  -24.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6479  -23.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6479  -23.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9282  -22.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2174  -23.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6458  -24.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6417  -25.1208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9251  -25.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2083  -25.9375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9335  -23.8797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3624  -23.8869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9376  -23.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0748  -24.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7913  -23.8942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0706  -25.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0625  -25.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8956  -25.1342    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.2456  -25.1249    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.5037  -24.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4995  -25.1353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6560  -22.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6606  -21.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9476  -21.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2287  -21.8203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2277  -22.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3616  -22.6636    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.5126  -23.0546    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
 14 15  1  0
  7  8  2  0
 14 16  1  0
 16 17  1  0
  8  9  1  0
 16 18  1  0
  4  5  1  0
 16 19  1  0
  9 10  3  0
 15 20  1  0
 20  1  1  0
  2  3  1  0
 20 21  2  0
  7 11  1  0
 13 22  2  0
  5  6  2  0
 22 23  1  0
  7 12  1  0
 23 24  2  0
  6  1  1  0
 24 25  1  0
 11 13  1  0
 25 26  2  0
 26 13  1  0
  1  2  2  0
  4 27  1  0
 12 14  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA540965

   4-chloro-N-[2,2-dichloro-1-[(Z)-[[(2-chloropyridin-3-yl)amino]-(cyanoamino)methylidene]amino]propyl]benzamide

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: 460.15

Molecular Weight (Monoisotopic): 457.9983

AlogP: 4.18

#Rotatable Bonds: 5

Polar Surface Area: 102.20

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.42

CX LogD: 4.42

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.16

Np Likeness Score: -1.52

References

1. Perez-Medrano A, Brune ME, Buckner SA, Coghlan MJ, Fey TA, Gopalakrishnan M, Gregg RJ, Kort ME, Scott VE, Sullivan JP, Whiteaker KL, Carroll WA..  (2007)  Structure-activity studies of novel cyanoguanidine ATP-sensitive potassium channel openers for the treatment of overactive bladder.,  50  (24): [PMID:17973362] [10.1021/jm7010194]

2. Perez-Medrano A, Donnelly-Roberts DL, Honore P, Hsieh GC, Namovic MT, Peddi S, Shuai Q, Wang Y, Faltynek CR, Jarvis MF, Carroll WA..  (2009)  Discovery and biological evaluation of novel cyanoguanidine P2X(7) antagonists with analgesic activity in a rat model of neuropathic pain.,  52  (10): [PMID:19397270] [10.1021/jm8015848]

Source

Source(1):

• Scientific Literature