4-bromo-N-{2,2-dichloro-1-[N'-(6-chloropyridin-3-yl)-N''-cyanoguanidino]propyl}benzamide

ID: ALA391369

PubChem CID: 10118048

Max Phase: Preclinical

Molecular Formula: C17H14BrCl3N6O

Molecular Weight: 504.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cl)(Cl)C(NC(=O)c1ccc(Br)cc1)N/C(=N/C#N)Nc1ccc(Cl)nc1

Standard InChI:  InChI=1S/C17H14BrCl3N6O/c1-17(20,21)15(26-14(28)10-2-4-11(18)5-3-10)27-16(24-9-22)25-12-6-7-13(19)23-8-12/h2-8,15H,1H3,(H,26,28)(H2,24,25,27)

Standard InChI Key:  NNTNBYRPLFTPRX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   -4.5014    1.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5026    0.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7878   -0.1694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0713    0.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0742    1.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7896    1.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3613    1.4897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6453    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9323    1.4951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6421    0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3551   -0.1603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0750   -0.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2163    1.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4966    1.5005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2132    0.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208   -0.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6118    0.2580    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0382    0.2603    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2126    1.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9255    1.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2157    0.2657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6387    1.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3511    1.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3484    2.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6274    2.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9179    2.3270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2174   -0.1684    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0608    2.7504    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  5  7  1  0
 13 15  1  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
 15 17  1  0
 15 18  1  0
  8  9  1  0
 14 19  1  0
  4  5  1  0
 19 20  1  0
  8 10  2  0
 19 21  2  0
  2  3  1  0
 20 22  2  0
 10 11  1  0
 22 23  1  0
  5  6  2  0
 23 24  2  0
 11 12  3  0
 24 25  1  0
  6  1  1  0
 25 26  2  0
 26 20  1  0
  9 13  1  0
  2 27  1  0
  1  2  2  0
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA391369

   4-bromo-N-[2,2-dichloro-1-[(Z)-[[(6-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: 504.60

Molecular Weight (Monoisotopic): 501.9478

AlogP: 4.29

#Rotatable Bonds: 5

Polar Surface Area: 102.20

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.59

CX LogD: 4.59

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.14

Np Likeness Score: -1.54

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]

Source

Source(1):

• Scientific Literature