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

ID: ALA1236677

Chembl Id: CHEMBL1236677

Cas Number: 1246770-52-4

PubChem CID: 49867823

Max Phase: Preclinical

Molecular Formula: C26H19Cl2N5O2

Molecular Weight: 504.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](Cn1ccnc1)c1ccc(Cl)cc1Cl)c1ccc(-c2nnc(-c3ccccc3)o2)cc1

Standard InChI:  InChI=1S/C26H19Cl2N5O2/c27-20-10-11-21(22(28)14-20)23(15-33-13-12-29-16-33)30-24(34)17-6-8-19(9-7-17)26-32-31-25(35-26)18-4-2-1-3-5-18/h1-14,16,23H,15H2,(H,30,34)/t23-/m0/s1

Standard InChI Key:  CJPLMXOWZZCYHJ-QHCPKHFHSA-N

Alternative Forms

1. Parent:

   

   ALA1236677

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

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: 504.38

Molecular Weight (Monoisotopic): 503.0916

AlogP: 6.08

#Rotatable Bonds: 7

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: ┄

CX Basic pKa: 6.78

CX LogP: 4.98

CX LogD: 4.91

Aromatic Rings: 5

Heavy Atoms: 35

QED Weighted: 0.29

Np Likeness Score: -1.37

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, Wawrzak Z, Blobaum AL, Rachakonda G, Lindsley CW, Villalta F, Nes WD, Botta M, Guengerich FP, Lepesheva GI..  (2018)  Sterol 14α-Demethylase Structure-Based Design of VNI (( R)- N-(1-(2,4-Dichlorophenyl)-2-(1 H-imidazol-1-yl)ethyl)-4-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamide)) Derivatives To Target Fungal Infections: Synthesis, Biological Evaluation, and Crystallographic Analysis.,  61  (13): [PMID:29894182] [10.1021/acs.jmedchem.8b00641]

3. 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]

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