(S)-3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-(4-ethyl-3-methylpiperazin-1-yl)-2H-chromen-2-one

ID: ALA4100874

Cas Number: 1446311-56-3

PubChem CID: 89657166

Max Phase: Preclinical

Molecular Formula: C24H27N5O2

Molecular Weight: 417.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1CCN(c2ccc3cc(-c4cn5cc(C)nc(C)c5n4)c(=O)oc3c2)C[C@@H]1C

Standard InChI:  InChI=1S/C24H27N5O2/c1-5-27-8-9-28(13-16(27)3)19-7-6-18-10-20(24(30)31-22(18)11-19)21-14-29-12-15(2)25-17(4)23(29)26-21/h6-7,10-12,14,16H,5,8-9,13H2,1-4H3/t16-/m0/s1

Standard InChI Key:  PETSCYDXCUXNIW-INIZCTEOSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
    9.4334  -12.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4323  -13.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1403  -13.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1385  -12.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8472  -12.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8460  -13.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5522  -13.6655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2641  -13.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2652  -12.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5545  -12.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9706  -13.6690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9739  -12.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7176  -12.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0593  -11.2175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8590  -11.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2618  -11.7557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0704  -11.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4823  -11.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0795  -10.3533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2648  -10.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8589   -9.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2995  -11.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7278  -13.6647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0206  -13.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3146  -13.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3098  -14.4755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0170  -14.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7291  -14.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6088  -13.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6002  -14.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8944  -14.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  8 11  2  0
  9 12  1  0
 12 13  2  0
 13 16  1  0
 15 14  2  0
 14 12  1  0
 15 16  1  0
 15 20  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 18 22  1  0
 23 24  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
  2 23  1  0
 25 29  1  1
 26 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100874

   (S)-3-(6,8-Dimethylimidazo[1,2-a]pyrazin-2-yl)-7-(4-ethyl-3-methylpiperazin-1-yl)-2H-chromen-2-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: 417.51

Molecular Weight (Monoisotopic): 417.2165

AlogP: 3.65

#Rotatable Bonds: 3

Polar Surface Area: 66.88

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.28

CX LogP: 2.40

CX LogD: 1.46

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.47

Np Likeness Score: -1.00

References

1. Pinard E, Green L, Reutlinger M, Weetall M, Naryshkin NA, Baird J, Chen KS, Paushkin SV, Metzger F, Ratni H..  (2017)  Discovery of a Novel Class of Survival Motor Neuron 2 Splicing Modifiers for the Treatment of Spinal Muscular Atrophy.,  60  (10): [PMID:28441483] [10.1021/acs.jmedchem.7b00406]

2. Ratni H, Karp GM, Weetall M, Naryshkin NA, Paushkin SV, Chen KS, McCarthy KD, Qi H, Turpoff A, Woll MG, Zhang X, Zhang N, Yang T, Dakka A, Vazirani P, Zhao X, Pinard E, Green L, David-Pierson P, Tuerck D, Poirier A, Muster W, Kirchner S, Mueller L, Gerlach I, Metzger F..  (2016)  Specific Correction of Alternative Survival Motor Neuron 2 Splicing by Small Molecules: Discovery of a Potential Novel Medicine To Treat Spinal Muscular Atrophy.,  59  (13): [PMID:27299419] [10.1021/acs.jmedchem.6b00459]

3. Woll MG, Qi H, Turpoff A, Zhang N, Zhang X, Chen G, Li C, Huang S, Yang T, Moon YC, Lee CS, Choi S, Almstead NG, Naryshkin NA, Dakka A, Narasimhan J, Gabbeta V, Welch E, Zhao X, Risher N, Sheedy J, Weetall M, Karp GM..  (2016)  Discovery and Optimization of Small Molecule Splicing Modifiers of Survival Motor Neuron 2 as a Treatment for Spinal Muscular Atrophy.,  59  (13): [PMID:27299569] [10.1021/acs.jmedchem.6b00460]

Source

Source(1):

• Scientific Literature