ID: ALA212625

Max Phase: Preclinical

Molecular Formula: C25H28N6O4S

Molecular Weight: 508.60

Molecule Type: Small molecule

Representations

Synonyms (1): PSB-601
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCCn1c(=O)[nH]c2nc(-c3ccc(S(=O)(=O)N4CCN(Cc5ccccc5)CC4)cc3)[nH]c2c1=O

Standard InChI:  InChI=1S/C25H28N6O4S/c1-2-12-31-24(32)21-23(28-25(31)33)27-22(26-21)19-8-10-20(11-9-19)36(34,35)30-15-13-29(14-16-30)17-18-6-4-3-5-7-18/h3-11H,2,12-17H2,1H3,(H,26,27)(H,28,33)

Standard InChI Key:  HHNGYTVWOXXKET-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: 508.60

Molecular Weight (Monoisotopic): 508.1893

AlogP: 2.00

#Rotatable Bonds: 7

Polar Surface Area: 124.16

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.15

CX Basic pKa: 6.05

CX LogP: 3.32

CX LogD: 3.18

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.39

Np Likeness Score: -1.53

References

1. Yan L, Bertarelli DC, Hayallah AM, Meyer H, Klotz KN, Müller CE..  (2006)  A new synthesis of sulfonamides by aminolysis of p-nitrophenylsulfonates yielding potent and selective adenosine A2B receptor antagonists.,  49  (14): [PMID:16821798] [10.1021/jm060277v]

2. Borrmann T, Hinz S, Bertarelli DC, Li W, Florin NC, Scheiff AB, Müller CE..  (2009)  1-alkyl-8-(piperazine-1-sulfonyl)phenylxanthines: development and characterization of adenosine A2B receptor antagonists and a new radioligand with subnanomolar affinity and subtype specificity.,  52  (13): [PMID:19569717] [10.1021/jm900413e]

3. Cheng F, Cheng F, Xu Z, Liu G, Tang Y..  (2010)  Insights into binding modes of adenosine A(2B) antagonists with ligand-based and receptor-based methods.,  45  (8): [PMID:20537438] [10.1016/j.ejmech.2010.04.039]

4. El-Tayeb A, Michael S, Abdelrahman A, Behrenswerth A, Gollos S, Nieber K, Müller CE..  (2011)  Development of Polar Adenosine A2A Receptor Agonists for Inflammatory Bowel Disease: Synergism with A2B Antagonists.,  2  (12): [PMID:24900277] [10.1021/ml200189u]

Source

Source(1):

• Scientific Literature