(S)-N-(1-(3-(5-(ethylamino)-8-methyl-8H-imidazo[4,5-d]thiazolo[5,4-b]pyridin-2-yl)phenyl)ethyl)acetamide

ID: ALA1642546

Cas Number: 1266240-89-4

PubChem CID: 50941935

Max Phase: Preclinical

Molecular Formula: C20H22N6OS

Molecular Weight: 394.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNc1nc2sc(-c3cccc([C@H](C)NC(C)=O)c3)nc2c2c1ncn2C

Standard InChI:  InChI=1S/C20H22N6OS/c1-5-21-18-15-17(26(4)10-22-15)16-20(25-18)28-19(24-16)14-8-6-7-13(9-14)11(2)23-12(3)27/h6-11H,5H2,1-4H3,(H,21,25)(H,23,27)/t11-/m0/s1

Standard InChI Key:  UOVILLRJCVEGLB-NSHDSACASA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    8.6331  -11.2444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3495  -10.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6313   -9.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3438  -10.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9561   -9.4533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6219   -8.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8031   -8.7863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2516   -8.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0653  -11.2412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7784  -10.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9182  -10.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9195  -10.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1359   -9.7512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6503  -10.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1339  -11.0850    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8253  -10.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4178   -9.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5936   -9.7004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792  -10.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5951  -11.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4180  -11.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1841  -11.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3591  -11.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5981  -12.5612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1870  -13.2765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6010  -13.9901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3620  -13.2782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4943  -11.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  1  0
  6  7  1  0
 14 16  1  0
  7  3  1  0
 16 17  2  0
  3  4  2  0
 17 18  1  0
  7  8  1  0
 18 19  2  0
 11  1  1  0
 19 20  1  0
  2  9  1  0
 20 21  2  0
 21 16  1  0
 20 22  1  0
  9 10  1  0
 22 23  1  1
 11 12  2  0
 22 24  1  0
  1  2  2  0
 24 25  1  0
  2  4  1  0
 25 26  1  0
  3 12  1  0
 25 27  2  0
  4  5  1  0
 10 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1642546

   (S)-N-(1-(3-(5-(ethylamino)-8-methyl-8H-imidazo[4,5-d]thiazolo[5,4-b]pyridin-2-yl)phenyl)ethyl)acetamide

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: 394.50

Molecular Weight (Monoisotopic): 394.1576

AlogP: 3.87

#Rotatable Bonds: 5

Polar Surface Area: 84.73

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.60

CX LogP: 2.58

CX LogD: 2.58

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: -1.18

References

1. Dyckman AJ, Langevine CM, Quesnelle C, Kempson J, Guo J, Gill P, Spergel SH, Watterson SH, Li T, Nirschl DS, Gillooly KM, Pattoli MA, McIntyre KW, Chen L, McKinnon M, Dodd JH, Barrish JC, Burke JR, Pitts WJ..  (2011)  Imidazo[4,5-d]thiazolo[5,4-b]pyridine based inhibitors of IKK2: synthesis, SAR, PK/PD and activity in a preclinical model of rheumatoid arthritis.,  21  (1): [PMID:21087862] [10.1016/j.bmcl.2010.10.133]

2. Watterson SH, Langevine CM, Van Kirk K, Kempson J, Guo J, Spergel SH, Das J, Moquin RV, Dyckman AJ, Nirschl D, Gregor K, Pattoli MA, Yang X, McIntyre KW, Yang G, Galella MA, Booth-Lute H, Chen L, Yang Z, Wang-Iverson D, McKinnon M, Dodd JH, Barrish JC, Burke JR, Pitts WJ..  (2011)  Novel tricyclic inhibitors of IKK2: discovery and SAR leading to the identification of 2-methoxy-N-((6-(1-methyl-4-(methylamino)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl)pyridin-2-yl)methyl)acetamide (BMS-066).,  21  (23): [PMID:22018461] [10.1016/j.bmcl.2011.09.111]

Source

Source(1):

• Scientific Literature