2-{3'-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid

ID: ALA253083

PubChem CID: 10345293

Max Phase: Preclinical

Molecular Formula: C29H27NO4S

Molecular Weight: 485.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(c1cc(-c2cccc(-c3ccc(C4CC4C(=O)O)cc3)c2)c2ncccc2c1)S(C)(=O)=O

Standard InChI:  InChI=1S/C29H27NO4S/c1-29(2,35(3,33)34)23-15-22-8-5-13-30-27(22)25(16-23)21-7-4-6-20(14-21)18-9-11-19(12-10-18)24-17-26(24)28(31)32/h4-16,24,26H,17H2,1-3H3,(H,31,32)

Standard InChI Key:  LWGNZANWYDVSLC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
    4.3944   -9.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3932  -10.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1081  -10.5402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1062   -8.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8216   -9.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8224  -10.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5377  -10.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2527  -10.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2480   -9.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5321   -8.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9599   -8.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6708   -8.4542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.3776   -9.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5424   -8.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3833   -8.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2534   -7.7426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0879   -9.1660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5385  -11.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8232  -11.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8246  -12.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5404  -13.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2564  -12.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2515  -11.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9694  -12.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9727  -13.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6886  -14.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4017  -13.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3944  -12.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6779  -12.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1182  -14.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5356  -14.9262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9432  -14.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6579  -13.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3752  -14.1960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6521  -12.9634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12 17  2  0
  5  4  1  0
  8  9  1  0
 18 19  2  0
  4  1  2  0
 19 20  1  0
  9 10  2  0
 20 21  2  0
 10  5  1  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  7 18  1  0
  9 11  1  0
  2  3  2  0
 24 25  2  0
 11 12  1  0
 25 26  1  0
  5  6  2  0
 26 27  2  0
 11 13  1  0
 27 28  1  0
  3  6  1  0
 28 29  2  0
 29 24  1  0
 22 24  1  0
 31 30  1  0
 32 31  1  0
 30 32  1  0
 11 14  1  0
  6  7  1  0
 12 15  1  0
 30 27  1  0
  1  2  1  0
 12 16  2  0
  7  8  2  0
 33 34  1  0
 33 35  2  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA253083

   2-{3'-[6-(1-Methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid

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: 485.61

Molecular Weight (Monoisotopic): 485.1661

AlogP: 6.04

#Rotatable Bonds: 6

Polar Surface Area: 84.33

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.76

CX Basic pKa: 3.83

CX LogP: 4.72

CX LogD: 2.38

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.36

Np Likeness Score: -0.33

References

1. Gallant M, Chauret N, Claveau D, Day S, Deschênes D, Dubé D, Huang Z, Lacombe P, Laliberté F, Lévesque JF, Liu S, Macdonald D, Mancini J, Masson P, Mastracchio A, Nicholson D, Nicoll-Griffith DA, Perrier H, Salem M, Styhler A, Young RN, Girard Y..  (2008)  Design, synthesis, and biological evaluation of 8-biarylquinolines: a novel class of PDE4 inhibitors.,  18  (4): [PMID:18207397] [10.1016/j.bmcl.2008.01.004]

2. Gallant M, Chauret N, Claveau D, Day S, Deschênes D, Dubé D, Huang Z, Lacombe P, Laliberté F, Lévesque JF, Liu S, Macdonald D, Mancini J, Masson P, Mastracchio A, Nicholson D, Nicoll-Griffith DA, Perrier H, Salem M, Styhler A, Young RN, Girard Y..  (2008)  Design, synthesis, and biological evaluation of 8-biarylquinolines: a novel class of PDE4 inhibitors.,  18  (4): [PMID:18207397] [10.1016/j.bmcl.2008.01.004]

3. Gallant M, Aspiotis R, Day S, Dias R, Dubé D, Dubé L, Friesen RW, Girard M, Guay D, Hamel P, Huang Z, Lacombe P, Laliberté S, Lévesque JF, Liu S, Macdonald D, Mancini J, Nicholson DW, Styhler A, Townson K, Waters K, Young RN, Girard Y..  (2010)  Discovery of MK-0952, a selective PDE4 inhibitor for the treatment of long-term memory loss and mild cognitive impairment.,  20  (22): [PMID:20933411] [10.1016/j.bmcl.2010.09.087]

4. Gallant M, Aspiotis R, Day S, Dias R, Dubé D, Dubé L, Friesen RW, Girard M, Guay D, Hamel P, Huang Z, Lacombe P, Laliberté S, Lévesque JF, Liu S, Macdonald D, Mancini J, Nicholson DW, Styhler A, Townson K, Waters K, Young RN, Girard Y..  (2010)  Discovery of MK-0952, a selective PDE4 inhibitor for the treatment of long-term memory loss and mild cognitive impairment.,  20  (22): [PMID:20933411] [10.1016/j.bmcl.2010.09.087]

Source

Source(1):

• Scientific Literature