(R)-N-(1-(3,4'-difluorobiphenyl-4-yl)-2-(1H-imidazol-1-yl)ethyl)-4-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamide

ID: ALA3629567

Chembl Id: CHEMBL3629567

PubChem CID: 119081677

Max Phase: Preclinical

Molecular Formula: C32H23F2N5O2

Molecular Weight: 547.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](Cn1ccnc1)c1ccc(-c2ccc(F)cc2)cc1F)c1ccc(-c2nnc(-c3ccccc3)o2)cc1

Standard InChI:  InChI=1S/C32H23F2N5O2/c33-26-13-10-21(11-14-26)25-12-15-27(28(34)18-25)29(19-39-17-16-35-20-39)36-30(40)22-6-8-24(9-7-22)32-38-37-31(41-32)23-4-2-1-3-5-23/h1-18,20,29H,19H2,(H,36,40)/t29-/m0/s1

Standard InChI Key:  YTJXXDVLDUKYHV-LJAQVGFWSA-N

Alternative Forms

1. Parent:

   

   ALA3629567

   ---

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: 547.57

Molecular Weight (Monoisotopic): 547.1820

AlogP: 6.72

#Rotatable Bonds: 8

Polar Surface Area: 85.84

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.30

CX Basic pKa: 6.78

CX LogP: 5.70

CX LogD: 5.64

Aromatic Rings: 6

Heavy Atoms: 41

QED Weighted: 0.23

Np Likeness Score: -1.28

References

1. de Oliveira Filho GB, de Oliveira Cardoso MV, Espíndola JW, Ferreira LF, de Simone CA, Ferreira RS, Coelho PL, Meira CS, Magalhaes Moreira DR, Soares MB, Lima Leite AC..  (2015)  Structural design, synthesis and pharmacological evaluation of 4-thiazolidinones against Trypanosoma cruzi.,  23  (23): [PMID:26549870] [10.1016/j.bmc.2015.10.048]

2. Friggeri L, Hargrove TY, Rachakonda G, Blobaum AL, Fisher P, de Oliveira GM, da Silva CF, Soeiro MNC, Nes WD, Lindsley CW, Villalta F, Guengerich FP, Lepesheva GI..  (2018)  Sterol 14α-Demethylase Structure-Based Optimization of Drug Candidates for Human Infections with the Protozoan Trypanosomatidae.,  61  (23): [PMID:30451500] [10.1021/acs.jmedchem.8b01671]

3. Friggeri L, Hargrove TY, Wawrzak Z, Guengerich FP, Lepesheva GI..  (2019)  Validation of Human Sterol 14α-Demethylase (CYP51) Druggability: Structure-Guided Design, Synthesis, and Evaluation of Stoichiometric, Functionally Irreversible Inhibitors.,  62  (22): [PMID:31663733] [10.1021/acs.jmedchem.9b01485]

4. Hargrove TY, Wawrzak Z, Rachakonda G, Nes WD, Villalta F, Guengerich FP, Lepesheva GI..  (2021)  Relaxed Substrate Requirements of Sterol 14α-Demethylase from Naegleria fowleri Are Accompanied by Resistance to Inhibition.,  64  (23.0): [PMID:34842434] [10.1021/acs.jmedchem.1c01710]

5. Beltran-Hortelano I, Alcolea V, Font M, Pérez-Silanes S..  (2020)  The role of imidazole and benzimidazole heterocycles in Chagas disease: A review.,  206  [PMID:32818869] [10.1016/j.ejmech.2020.112692]

Source

Source(1):

• Scientific Literature