2-((4-(Benzo[d]thiazol-5-ylamino)-6-(tert-butylsulfonyl)quinazolin-7-yl)oxy)ethanol

ID: ALA4514780

Cas Number: 1423186-80-4

PubChem CID: 71258526

Product Number: R613200, Order Now?

Max Phase: Preclinical

Molecular Formula: C21H22N4O4S2

Molecular Weight: 458.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)S(=O)(=O)c1cc2c(Nc3ccc4scnc4c3)ncnc2cc1OCCO

Standard InChI:  InChI=1S/C21H22N4O4S2/c1-21(2,3)31(27,28)19-9-14-15(10-17(19)29-7-6-26)22-11-23-20(14)25-13-4-5-18-16(8-13)24-12-30-18/h4-5,8-12,26H,6-7H2,1-3H3,(H,22,23,25)

Standard InChI Key:  UHDOJINBFLDQJM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    4.0364   -3.1119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4492   -3.8218    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8576   -3.1094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1576   -4.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1565   -5.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8645   -5.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8627   -3.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5714   -4.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5721   -5.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2806   -5.4529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9889   -5.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9842   -4.2199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2751   -3.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2707   -2.9994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9763   -2.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7422   -4.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0344   -3.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4484   -5.4579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4478   -6.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7424   -5.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0294   -4.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7398   -6.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7391   -7.5004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6816   -2.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6679   -1.3609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9657   -1.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3827   -1.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3865   -2.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1643   -2.8309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6413   -2.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1582   -1.5097    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 13 14  1  0
 14 15  1  0
  4  2  1  0
  2 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  1  0
 16 20  1  0
 16 21  1  0
 19 22  1  0
 22 23  1  0
 15 24  2  0
 24 28  1  0
 27 25  1  0
 25 26  2  0
 26 15  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4514780

   GSK2983559 active metabolite

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 458.57

Molecular Weight (Monoisotopic): 458.1082

AlogP: 3.93

#Rotatable Bonds: 6

Polar Surface Area: 114.30

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.00

CX LogP: 3.10

CX LogD: 3.10

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.45

Np Likeness Score: -1.17

References

1. Haile PA, Casillas LN, Votta BJ, Wang GZ, Charnley AK, Dong X, Bury MJ, Romano JJ, Mehlmann JF, King BW, Erhard KF, Hanning CR, Lipshutz DB, Desai BM, Capriotti CA, Schaeffer MC, Berger SB, Mahajan MK, Reilly MA, Nagilla R, Rivera EJ, Sun HH, Kenna JK, Beal AM, Ouellette MT, Kelly M, Stemp G, Convery MA, Vossenkämper A, MacDonald TT, Gough PJ, Bertin J, Marquis RW..  (2019)  Discovery of a First-in-Class Receptor Interacting Protein 2 (RIP2) Kinase Specific Clinical Candidate, 2-((4-(Benzo[d]thiazol-5-ylamino)-6-(tert-butylsulfonyl)quinazolin-7-yl)oxy)ethyl Dihydrogen Phosphate, for the Treatment of Inflammatory Diseases.,  62  (14): [PMID:31265286] [10.1021/acs.jmedchem.9b00575]

2. Asquith CRM, Naegeli KM, East MP, Laitinen T, Havener TM, Wells CI, Johnson GL, Drewry DH, Zuercher WJ, Morris DC..  (2019)  Design of a Cyclin G Associated Kinase (GAK)/Epidermal Growth Factor Receptor (EGFR) Inhibitor Set to Interrogate the Relationship of EGFR and GAK in Chordoma.,  62  (9): [PMID:30973735] [10.1021/acs.jmedchem.9b00350]

3. Asquith CRM, Berger BT, Wan J, Bennett JM, Capuzzi SJ, Crona DJ, Drewry DH, East MP, Elkins JM, Fedorov O, Godoi PH, Hunter DM, Knapp S, Müller S, Torrice CD, Wells CI, Earp HS, Willson TM, Zuercher WJ..  (2019)  SGC-GAK-1: A Chemical Probe for Cyclin G Associated Kinase (GAK).,  62  (5): [PMID:30768268] [10.1021/acs.jmedchem.8b01213]

Source

Source(1):

• Scientific Literature