8-(2-Amino-4-chloro-phenyl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

ID: ALA273671

Chembl Id: CHEMBL273671

Cas Number: 85872-51-1

PubChem CID: 92411

Max Phase: Preclinical

Molecular Formula: C17H20ClN5O2

Molecular Weight: 361.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCn1c(=O)c2nc(-c3ccc(Cl)cc3N)[nH]c2n(CCC)c1=O

Standard InChI:  InChI=1S/C17H20ClN5O2/c1-3-7-22-15-13(16(24)23(8-4-2)17(22)25)20-14(21-15)11-6-5-10(18)9-12(11)19/h5-6,9H,3-4,7-8,19H2,1-2H3,(H,20,21)

Standard InChI Key:  SENJBFBVCXOUFE-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA273671

   1,3-Dipropyl-8-(2-amino-4-chlorophenyl)xanthine

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: 361.83

Molecular Weight (Monoisotopic): 361.1306

AlogP: 2.61

#Rotatable Bonds: 5

Polar Surface Area: 98.70

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.63

CX Basic pKa: 2.56

CX LogP: 2.75

CX LogD: 2.58

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: -1.00

References

1. Hamilton HW, Ortwine DF, Worth DF, Badger EW, Bristol JA, Bruns RF, Haleen SJ, Steffen RP..  (1985)  Synthesis of xanthines as adenosine antagonists, a practical quantitative structure-activity relationship application.,  28  (8): [PMID:2991519] [10.1021/jm00146a016]

2. Daly JW, Padgett WL, Shamim MT..  (1986)  Analogues of 1,3-dipropyl-8-phenylxanthine: enhancement of selectivity at A1-adenosine receptors by aryl substituents.,  29  (8): [PMID:3016270] [10.1021/jm00158a034]

3. Snyder SH..  (1983)  Neurotransmitter receptor binding and drug discovery.,  26  (12): [PMID:6315938] [10.1021/jm00366a001]

4. van Galen PJ, van Vlijmen HW, IJzerman AP, Soudijn W..  (1990)  A model for the antagonist binding site on the adenosine A1 receptor, based on steric, electrostatic, and hydrophobic properties.,  33  (6): [PMID:2342066] [10.1021/jm00168a027]

5. Jacobson KA, van Galen PJ, Williams M..  (1992)  Adenosine receptors: pharmacology, structure-activity relationships, and therapeutic potential.,  35  (3): [PMID:1738138] [10.1021/jm00081a001]

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. Faudone G, Arifi S, Merk D..  (2021)  The Medicinal Chemistry of Caffeine.,  64  (11.0): [PMID:34019396] [10.1021/acs.jmedchem.1c00261]

Source

Source(1):

• Scientific Literature