N-Benzyl-6-(4-(2-(trifluoromethyl)benzoyl)piperazin-1-yl)-pyridazine-3-carboxamide

ID: ALA2315104

PubChem CID: 71521050

Max Phase: Preclinical

Molecular Formula: C24H22F3N5O2

Molecular Weight: 469.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccccc1)c1ccc(N2CCN(C(=O)c3ccccc3C(F)(F)F)CC2)nn1

Standard InChI:  InChI=1S/C24H22F3N5O2/c25-24(26,27)19-9-5-4-8-18(19)23(34)32-14-12-31(13-15-32)21-11-10-20(29-30-21)22(33)28-16-17-6-2-1-3-7-17/h1-11H,12-16H2,(H,28,33)

Standard InChI Key:  CKIBNNYWZAXTRH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   17.3614  -27.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1786  -27.8179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5878  -27.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4050  -27.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1797  -26.4025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8105  -27.8178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6269  -27.8188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0369  -27.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6245  -26.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8094  -26.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8544  -27.1119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2622  -27.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0758  -27.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4878  -27.1166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0801  -26.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2603  -26.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3050  -27.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7113  -27.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7159  -26.4129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2974  -28.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7030  -29.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5211  -29.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9318  -28.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5238  -27.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9312  -27.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7484  -27.1160    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.5213  -26.4105    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.3317  -26.4060    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.9602  -28.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1472  -28.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7461  -29.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1576  -29.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9744  -29.9247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3718  -29.2183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  4  1  0
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  8 11  1  0
 14 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 18  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 29  1  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2315104

   N-benzyl-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide

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: 469.47

Molecular Weight (Monoisotopic): 469.1726

AlogP: 3.39

#Rotatable Bonds: 5

Polar Surface Area: 78.43

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.40

CX Basic pKa: 1.61

CX LogP: 3.47

CX LogD: 3.47

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.62

Np Likeness Score: -1.96

References

1. Zhang Z, Sun S, Kodumuru V, Hou D, Liu S, Chakka N, Sviridov S, Chowdhury S, McLaren DG, Ratkay LG, Khakh K, Cheng X, Gschwend HW, Kamboj R, Fu J, Winther MD..  (2013)  Discovery of piperazin-1-ylpyridazine-based potent and selective stearoyl-CoA desaturase-1 inhibitors for the treatment of obesity and metabolic syndrome.,  56  (2): [PMID:23245208] [10.1021/jm301661h]

2. Llona-Minguez S, Höglund A, Ghassemian A, Desroses M, Calderón-Montaño JM, Burgos Morón E, Valerie NCK, Wiita E, Almlöf I, Koolmeister T, Mateus A, Cazares-Körner C, Sanjiv K, Homan E, Loseva O, Baranczewski P, Darabi M, Mehdizadeh A, Fayezi S, Jemth AS, Warpman Berglund U, Sigmundsson K, Lundbäck T, Jenmalm Jensen A, Artursson P, Scobie M, Helleday T..  (2017)  Piperazin-1-ylpyridazine Derivatives Are a Novel Class of Human dCTP Pyrophosphatase 1 Inhibitors.,  60  (10): [PMID:28508636] [10.1021/acs.jmedchem.7b00182]

3. Llona-Minguez S, Fayezi S, Alihemmati A, Juárez-Jiménez J, Piedrafita FJ, Helleday T..  (2017)  Tetrahydrobenzothiophene carboxamides: Beyond the kinase domain and into the fatty acid realm.,  27  (18): [PMID:28807439] [10.1016/j.bmcl.2017.08.006]

Source

Source(1):

• Scientific Literature