4-amino-6-methyl-2-(3-(4-p-tolylpiperazin-1-yl)propyl)-5-vinylpyridazin-3(2H)-one

ID: ALA584606

PubChem CID: 44596863

Max Phase: Preclinical

Molecular Formula: C21H29N5O

Molecular Weight: 367.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=Cc1c(C)nn(CCCN2CCN(c3ccc(C)cc3)CC2)c(=O)c1N

Standard InChI:  InChI=1S/C21H29N5O/c1-4-19-17(3)23-26(21(27)20(19)22)11-5-10-24-12-14-25(15-13-24)18-8-6-16(2)7-9-18/h4,6-9H,1,5,10-15,22H2,2-3H3

Standard InChI Key:  SSHKNPUBWWFZGC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -4.0583   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0583   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3463   -3.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6343   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6343   -2.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3463   -1.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7740   -1.8313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9204   -3.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3463   -4.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7722   -3.4802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318   -4.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3463   -1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318   -0.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318    0.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9174    0.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2027    0.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4903    0.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4861    1.4703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2004    1.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9190    1.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2296    1.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9428    1.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583    1.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6619    2.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440    3.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2314    2.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3774    3.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  1  7  2  0
 14 15  1  0
 15 16  1  0
  1  2  1  0
  4  8  1  0
  1  6  1  0
  3  9  1  0
  2  3  2  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  2 10  1  0
  3  4  1  0
 21 22  2  0
  9 11  2  0
 22 23  1  0
  4  5  2  0
 23 24  2  0
  6 12  1  0
 24 25  1  0
  5  6  1  0
 25 26  2  0
 26 21  1  0
 18 21  1  0
 12 13  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA584606

   4-amino-6-methyl-2-(3-(4-p-tolylpiperazin-1-yl)propyl)-5-vinylpyridazin-3(2H)-one

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: 367.50

Molecular Weight (Monoisotopic): 367.2372

AlogP: 2.30

#Rotatable Bonds: 6

Polar Surface Area: 67.39

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.88

CX LogP: 1.91

CX LogD: 1.31

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.85

Np Likeness Score: -1.50

References

1. Biancalani C, Giovannoni MP, Pieretti S, Cesari N, Graziano A, Vergelli C, Cilibrizzi A, Di Gianuario A, Colucci M, Mangano G, Garrone B, Polenzani L, Dal Piaz V..  (2009)  Further studies on arylpiperazinyl alkyl pyridazinones: discovery of an exceptionally potent, orally active, antinociceptive agent in thermally induced pain.,  52  (23): [PMID:19788200] [10.1021/jm900458r]

2. Vergelli C, Ciciani G, Cilibrizzi A, Crocetti L, Di Cesare Mannelli L, Ghelardini C, Guerrini G, Iacovone A, Giovannoni MP..  (2015)  Synthesis of five and six-membered heterocycles bearing an arylpiperazinylalkyl side chain as orally active antinociceptive agents.,  23  (19): [PMID:26361735] [10.1016/j.bmc.2015.08.043]

Source

Source(1):

• Scientific Literature