ID: ALA373700

Max Phase: Preclinical

Molecular Formula: C23H25FN8O2

Molecular Weight: 464.51

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1nc(N2CCN3C[C@@H](COc4cccc(F)c4)CC[C@H]3C2)nc2nc(-c3ccco3)nn12

Standard InChI:  InChI=1S/C23H25FN8O2/c24-16-3-1-4-18(11-16)34-14-15-6-7-17-13-31(9-8-30(17)12-15)22-27-21(25)32-23(28-22)26-20(29-32)19-5-2-10-33-19/h1-5,10-11,15,17H,6-9,12-14H2,(H2,25,26,27,28,29)/t15-,17-/m0/s1

Standard InChI Key:  FARQWWRBQXFTDH-RDJZCZTQSA-N

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

Properties

Molecular Weight: 464.51

Molecular Weight (Monoisotopic): 464.2085

AlogP: 2.48

#Rotatable Bonds: 5

Polar Surface Area: 110.84

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 7.59

CX LogP: 3.99

CX LogD: 3.58

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.48

Np Likeness Score: -1.96

References

1. Peng H, Kumaravel G, Yao G, Sha L, Wang J, Van Vlijmen H, Bohnert T, Huang C, Vu CB, Ensinger CL, Chang H, Engber TM, Whalley ET, Petter RC..  (2004)  Novel bicyclic piperazine derivatives of triazolotriazine and triazolopyrimidines as highly potent and selective adenosine A2A receptor antagonists.,  47  (25): [PMID:15566292] [10.1021/jm0494321]

2. Mantri M, de Graaf O, van Veldhoven J, Göblyös A, von Frijtag Drabbe Künzel JK, Mulder-Krieger T, Link R, de Vries H, Beukers MW, Brussee J, Ijzerman AP..  (2008)  2-Amino-6-furan-2-yl-4-substituted nicotinonitriles as A2A adenosine receptor antagonists.,  51  (15): [PMID:18637670] [10.1021/jm701594y]

3. Federico S, Paoletta S, Cheong SL, Pastorin G, Cacciari B, Stragliotto S, Klotz KN, Siegel J, Gao ZG, Jacobson KA, Moro S, Spalluto G..  (2011)  Synthesis and biological evaluation of a new series of 1,2,4-triazolo[1,5-a]-1,3,5-triazines as human A(2A) adenosine receptor antagonists with improved water solubility.,  54  (3): [PMID:21214204] [10.1021/jm101349u]

Source

Source(1):

• Scientific Literature