(+/-)-Ethyl 2-Methyl-4-(thiophen-3-yl)-1,4-dihydrobenzo[4,5]-imidazo[1,2-a]pyrimidine-3-carboxylate

ID: ALA3785618

Chembl Id: CHEMBL3785618

PubChem CID: 127033325

Max Phase: Preclinical

Molecular Formula: C18H17N3O2S

Molecular Weight: 339.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)Nc2nc3ccccc3n2C1c1ccsc1

Standard InChI:  InChI=1S/C18H17N3O2S/c1-3-23-17(22)15-11(2)19-18-20-13-6-4-5-7-14(13)21(18)16(15)12-8-9-24-10-12/h4-10,16H,3H2,1-2H3,(H,19,20)

Standard InChI Key:  FRCVFFDEURQUBC-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3785618

   ---

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: 339.42

Molecular Weight (Monoisotopic): 339.1041

AlogP: 3.95

#Rotatable Bonds: 3

Polar Surface Area: 56.15

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.87

CX Basic pKa: 6.15

CX LogP: 3.58

CX LogD: 3.55

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.73

Np Likeness Score: -1.91

References

1. El Maatougui A, Azuaje J, González-Gómez M, Miguez G, Crespo A, Carbajales C, Escalante L, García-Mera X, Gutiérrez-de-Terán H, Sotelo E..  (2016)  Discovery of Potent and Highly Selective A2B Adenosine Receptor Antagonist Chemotypes.,  59  (5): [PMID:26824742] [10.1021/acs.jmedchem.5b01586]

2. Mallo-Abreu A, Majellaro M, Jespers W, Azuaje J, Caamaño O, García-Mera X, Brea JM, Loza MI, Gutiérrez-de-Terán H, Sotelo E..  (2019)  Trifluorinated Pyrimidine-Based A2B Antagonists: Optimization and Evidence of Stereospecific Recognition.,  62  (20): [PMID:31557025] [10.1021/acs.jmedchem.9b01340]

3. Mallo-Abreu A, Prieto-Díaz R, Jespers W, Azuaje J, Majellaro M, Velando C, García-Mera X, Caamaño O, Brea J, Loza MI, Gutiérrez-de-Terán H, Sotelo E..  (2020)  Nitrogen-Walk Approach to Explore Bioisosteric Replacements in a Series of Potent A_2B Adenosine Receptor Antagonists.,  63  (14): [PMID:32573250] [10.1021/acs.jmedchem.0c00564]

Source

Source(1):

• Scientific Literature