[11C]-N-sec-butyl-1-(2-chlorophenyl)-N-methylisoquinoline-3-carboxamide

ID: ALA1817977

Cas Number: 124236-60-8

PubChem CID: 450825

Max Phase: Preclinical

Molecular Formula: C21H21ClN2O

Molecular Weight: 352.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C)N([11CH3])C(=O)c1cc2ccccc2c(-c2ccccc2Cl)n1

Standard InChI:  InChI=1S/C21H21ClN2O/c1-4-14(2)24(3)21(25)19-13-15-9-5-6-10-16(15)20(23-19)17-11-7-8-12-18(17)22/h5-14H,4H2,1-3H3/i3-1

Standard InChI Key:  RAVIZVQZGXBOQO-KTXUZGJCSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -3.3139   -6.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3151   -7.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003   -7.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6021   -5.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8867   -6.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859   -7.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1706   -7.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4556   -7.1360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4604   -6.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1763   -5.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2516   -5.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9685   -6.2974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2466   -5.0642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1689   -8.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8851   -8.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8838   -9.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1679  -10.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4519   -9.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568   -8.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2551   -8.3637    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9736   -7.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6805   -5.8805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3975   -6.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6755   -5.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1094   -5.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  5  6  1  0
 11 13  2  0
  3  6  2  0
  7 14  1  0
  6  7  1  0
 14 15  2  0
  1  2  2  0
 15 16  1  0
  7  8  2  0
 16 17  2  0
  5  4  2  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
 19 14  1  0
  4  1  1  0
 19 20  1  0
  9 10  2  0
 12 21  1  0
 10  5  1  0
 12 22  1  0
 22 23  1  0
  9 11  1  0
 22 24  1  0
  2  3  1  0
 23 25  1  0
M  ISO  1  21  11
M  END

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: 352.87

Molecular Weight (Monoisotopic): 352.1342

AlogP: 5.43

#Rotatable Bonds: 4

Polar Surface Area: 33.20

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 0.88

CX LogP: 5.36

CX LogD: 5.36

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.63

Np Likeness Score: -1.09

References

1. Damont A, Boisgard R, Kuhnast B, Lemée F, Raggiri G, Scarf AM, Da Pozzo E, Selleri S, Martini C, Tavitian B, Kassiou M, Dollé F..  (2011)  Synthesis of 6-[¹⁸F]fluoro-PBR28, a novel radiotracer for imaging the TSPO 18 kDa with PET.,  21  (16): [PMID:21741237] [10.1016/j.bmcl.2011.06.048]

2. Wadsworth H, Jones PA, Chau WF, Durrant C, Fouladi N, Passmore J, O'Shea D, Wynn D, Morisson-Iveson V, Ewan A, Thaning M, Mantzilas D, Gausemel I, Khan I, Black A, Avory M, Trigg W..  (2012)  [¹⁸F]GE-180: a novel fluorine-18 labelled PET tracer for imaging Translocator protein 18 kDa (TSPO).,  22  (3): [PMID:22244939] [10.1016/j.bmcl.2011.12.084]

3. Wadsworth H, Jones PA, Chau WF, Durrant C, Morisson-Iveson V, Passmore J, O'Shea D, Wynn D, Khan I, Black A, Avory M, Trigg W..  (2012)  Exploration of the structure-activity relationship of the diaryl anilide class of ligands for translocator protein--potential novel positron emitting tomography imaging agents.,  22  (18): [PMID:22902658] [10.1016/j.bmcl.2012.07.093]

4. O'Shea D, Ahmad R, Årstad E, Avory M, Chau WF, Durrant C, Hirani E, Jones PA, Khan I, Luthra SK, Mantzilas D, Morisson-Iveson V, Passmore J, Robins EG, Shan B, Wadsworth H, Walton S, Zhao Y, Trigg W..  (2013)  Exploration of the structure-activity relationship of a novel tetracyclic class of TSPO ligands-potential novel positron emitting tomography imaging agents.,  23  (8): [PMID:23489633] [10.1016/j.bmcl.2013.02.057]

5. Médran-Navarrete V, Damont A, Peyronneau MA, Kuhnast B, Bernards N, Pottier G, Marguet F, Puech F, Boisgard R, Dollé F..  (2014)  Preparation and evaluation of novel pyrazolo[1,5-a]pyrimidine acetamides, closely related to DPA-714, as potent ligands for imaging the TSPO 18kDa with PET.,  24  (6): [PMID:24560538] [10.1016/j.bmcl.2014.01.080]

Source

Source(1):

• Scientific Literature