ID: ALA21053

Max Phase: Preclinical

Molecular Formula: C14H14N4O2

Molecular Weight: 270.29

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cn1c(=O)c2c(nc(-c3ccccc3)n2C)n(C)c1=O

Standard InChI:  InChI=1S/C14H14N4O2/c1-16-10-12(17(2)14(20)18(3)13(10)19)15-11(16)9-7-5-4-6-8-9/h4-8H,1-3H3

Standard InChI Key:  MBYIBRUTNFFDFL-UHFFFAOYSA-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: 270.29

Molecular Weight (Monoisotopic): 270.1117

AlogP: 0.64

#Rotatable Bonds: 1

Polar Surface Area: 61.82

Molecular Species: NEUTRAL

HBA: 6

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 1.48

CX LogD: 1.48

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.65

Np Likeness Score: -1.25

References

1. Shamim MT, Ukena D, Padgett WL, Daly JW..  (1989)  Effects of 8-phenyl and 8-cycloalkyl substituents on the activity of mono-, di-, and trisubstituted alkylxanthines with substitution at the 1-, 3-, and 7-positions.,  32  (6): [PMID:2724296] [10.1021/jm00126a014]

2. Grahner B, Winiwarter S, Lanzner W, Müller CE..  (1994)  Synthesis and structure-activity relationships of deazaxanthines: analogs of potent A1- and A2-adenosine receptor antagonists.,  37  (10): [PMID:8182711] [10.1021/jm00036a019]

3. Jacobson KA, Shi D, Gallo-Rodriguez C, Manning M, Müller C, Daly JW, Neumeyer JL, Kiriasis L, Pfleiderer W..  (1993)  Effect of trifluoromethyl and other substituents on activity of xanthines at adenosine receptors.,  36  (18): [PMID:8410976] [10.1021/jm00070a007]

4. Müller CE, Thorand M, Qurishi R, Diekmann M, Jacobson KA, Padgett WL, Daly JW..  (2002)  Imidazo[2,1-i]purin-5-ones and related tricyclic water-soluble purine derivatives: potent A(2A)- and A(3)-adenosine receptor antagonists.,  45  (16): [PMID:12139454] [10.1021/jm011093d]

5. Müller CE, Geis U, Hipp J, Schobert U, Frobenius W, Pawłowski M, Suzuki F, Sandoval-Ramírez J..  (1997)  Synthesis and structure-activity relationships of 3,7-dimethyl-1-propargylxanthine derivatives, A2A-selective adenosine receptor antagonists.,  40  (26): [PMID:9435909] [10.1021/jm970515+]

6. Daly JW, Padgett W, Shamim MT, Butts-Lamb P, Waters J..  (1985)  1,3-Dialkyl-8-(p-sulfophenyl)xanthines: potent water-soluble antagonists for A1- and A2-adenosine receptors.,  28  (4): [PMID:2984420] [10.1021/jm00382a018]

7. Pretorius J, Malan SF, Castagnoli N, Bergh JJ, Petzer JP..  (2008)  Dual inhibition of monoamine oxidase B and antagonism of the adenosine A(2A) receptor by (E,E)-8-(4-phenylbutadien-1-yl)caffeine analogues.,  16  (18): [PMID:18723354] [10.1016/j.bmc.2008.07.088]

8. Van der Walt MM, Terre'Blanche G..  (2015)  1,3,7-Triethyl-substituted xanthines--possess nanomolar affinity for the adenosine A1 receptor.,  23  (20): [PMID:26392370] [10.1016/j.bmc.2015.09.012]

9. Harmse R, van der Walt MM, Petzer JP, Terre'Blanche G..  (2016)  Discovery of 1,3-diethyl-7-methyl-8-(phenoxymethyl)-xanthine derivatives as novel adenosine A1 and A2A receptor antagonists.,  26  (24): [PMID:27836398] [10.1016/j.bmcl.2016.10.086]

Source

Source(1):

• Scientific Literature