41373-37-9

Usage

InChI:InChI=1/C13H10N2O/c14-10-6-7-12-11(8-10)15-13(16-12)9-4-2-1-3-5-9/h1-8H,14H2

Upstream product

• 1523-15-5 2,4-dinitrophenyl benzoate 
• 891-43-0 5-nitro-2-phenylbenzo[d]oxazole 
• 137-09-7 2,4-diaminophenol dihydrochloride 
• 65-85-0 benzoic acid 
• 3230-49-7 2-hydroxy-5-nitro-N-benzylideneaniline 
• 100-52-7 benzaldehyde 
• 99-57-0 2-hydroxy-5-nitroaniline 
• 51-28-5 2,4-Dinitrophenol 
• 98-88-4 benzoyl chloride 
• 95-86-3 2,4-diaminophenol 

Downstream Products

• 33832-28-9 N-(2-phenyl-1,3-benzoxazol-5-yl)benzamide 
• 132212-86-3 bis(o-nitrobenzyl) 2,5-bis<(2-phenyl-5-benzoxazolyl)carbamoyl>terephthalate 
• 118383-48-5 methyl 3-(2-phenylbenzoxazol-5-yl)-2-chloropropionate 
• 301646-89-9 4-methyl-N-(2-phenylbenzo[d]oxazol-5-yl)benzamide 

Relevant academic research and scientific papers

Synthesis, quantum mechanical calculations, antimicrobial activities and molecular docking studies of five novel 2,5-disubstituted benzoxazole derivatives

In this study, five new 2-(p-(Substituted)phenyl)-5-(3-(4-ethylpiperazine-1-yl) propionamido)benzoxazole derivatives (B7-B11) were designed, synthesized, and their antimicrobial activities were determined by the microdilution method. The novel benzoxazole compounds were characterized using FTIR, 1H NMR, and 13C NMR spectroscopy, mass spectroscopy, and elemental analysis. B7 and B11 showed promising activity against P. aeruginosa isolate at 16 μg/mL compared to the reference drugs. Quantum mechanical calculations were performed on five compounds in the ground state using density functional theory (DFT) with the B3LYP/6–311G(d,p) level. Molecular docking studies of the compounds were also performed a complex structure of the DNA gyrase enzyme with ciprofloxacin (PDB: 2XCT), and it was observed that the binding poses were similar to ciprofloxacin. Theoretical ADME profiles of the compounds conform to Lipinski and other limiting rules.

Discovery of 6-Arylurea-2-arylbenzoxazole and 6-Arylurea-2-arylbenzimidazole Derivatives as Angiogenesis Inhibitors: Design, Synthesis and in vitro Biological Evaluation

We embarked on a structural optimization campaign aimed at the discovery of novel anti-angiogenesis agents with previously reported imidazole kinase inhibitors as a lead compound. A library of 29 compounds was synthesized. Several title compounds exhibite

Design, synthesis and in vitro evaluation of 6-amide-2-aryl benzoxazole/benzimidazole derivatives against tumor cells by inhibiting VEGFR-2 kinase

Herein, we have carried out a structural optimization campaign to discover the novel anti-tumor agents with our previously screened YQY-26 as the hit compound. A library of thirty-seven 6-amide-2-aryl benzoxazole/benzimidazole derivatives has been designe

Enantioselective 2-alkylation of 3-substituted indoles with dual chiral lewis acid/hydrogen-bond-mediated catalyst

A chiral-at-metal bis-cyclometalated iridium complex combines electrophile activation via metal coordination with nucleophile activation through hydrogen bond formation. This new bifunctional chiral Lewis acid/hydrogenbond-mediated catalyst permits the challenging enantioselective 2-alkylation of 3-substituted indoles with α, β-unsaturated 2-acyl imidazoles in up to 99% yield and with up to 98% enantiomeric excess at a catalyst loading of 2 mol %. As an application, the straightforward synthesis of a chiral pyrrolo- [1, 2-a]indole is demonstrated.

Urea Derivatives of 2-Aryl-benzothiazol-5-amines: A New Class of Potential Drugs for Human African Trypanosomiasis

A previous publication from this lab (Patrick, et al. Bioorg. Med. Chem. 2016, 24, 2451-2465) explored the antitrypanosomal activities of novel derivatives of 2-(2-benzamido)ethyl-4-phenylthiazole (1), which had been identified as a hit against Trypanosoma brucei, the causative agent of human African trypanosomiasis. While a number of these compounds, particularly the urea analogues, were quite potent, these molecules as a whole exhibited poor metabolic stability. The present work describes the synthesis of 65 new analogues arising from medicinal chemistry optimization at different sites on the molecule. The most promising compounds were the urea derivatives of 2-aryl-benzothiazol-5-amines. One such analogue, (S)-2-(3,4-difluorophenyl)-5-(3-fluoro-N-pyrrolidylamido)benzothiazole (57) was chosen for in vivo efficacy studies based upon in vitro activity, metabolic stability, and brain penetration. This compound attained 5/5 cures in murine models of both early and late stage human African trypanosomiasis, representing a new lead for the development of drugs to combat this neglected disease.

COMPOUNDS FOR TREATMENT OF TRYPANOSOMES AND NEUROLOGICAL PATHOGENS AND USES THEREOF

The present invention relates to novel compounds that cross the blood-brain barrier and are effective inhibitors of neurological pathogens such as trypanosomes. The invention further relates to the use of these compounds for treating disorders related to trypanosomes and neurological pathogens.

Synthesis, molecular docking and antimicrobial evaluation of novel benzoxazole derivatives

In this research, previously and newly synthesized 5-amino-2-(4-substitutedphenyl/benzyl)benzoxazoles (3a-3l) and 2-substituted-5-(4-nitro/aminophenylsulfonamido)benzoxazoles (5a-5l, 6a-6l) were evaluated for their antimicrobial activities against Pseudom

Synthesis of some piperazinobenzoxazole derivatives and their antimicrobial properties

A series of 2-(p-substitutedphenyl/benzyl)-5-[3-[4-[(p-chlorophenyl)/phenyl]piperazin-1-yl]propionamido]-benzoxazoles (3-22) have been synthesized towards discovering new antimicrobial compounds in order to fight against pathogens, which have become resistant to antibiotics and are the cause of increased mortality and morbidity throughout the world. Structures of new derivatives have been elucidated by spectral techniques. New and previously synthesized benzoxazoles have been evaluated for their antibacterial and antifungal activity against standard strains, and their drug-resistant isolates in comparison with reference drugs. This study is aimed to investigate the efficacy of the antimicrobial effect of different amido bridges on the same homologue structures of benzoxazole compounds. Compounds 3-22 exhibit broad antibacterial activity with MIC (Minimum Inhibitory Concentration) values of 128-256 μg/mL against Staphylococcus aureus and its isolate except for derivative 7 that has a MIC value of 32 μg/mL against S. aureus isolate and compounds 3 and 22 which have MIC value of 512 μg/mL against S. aureus. Also, the tested compounds 3-22 possess low antifungal activity with MIC values of 128 μg/mL against Candida albicans in comparison with antifungal reference drugs, fluconazole and amphotericin B.

Synthesis and biological evaluation of 2-substituted-5-(4- nitrophenylsulfonamido)benzoxazoles as human GST P1-1 inhibitors, and description of the binding site features

Glutathione-S-transferases (GSTs) are enzymes involved in cellular detoxification by catalyzing the nucleophilic attack of glutathione (GSH) on the electrophilic center of numerous of toxic compounds and xenobiotics, including chemotherapeutic drugs. Huma

Optimization of benzoxazole-based inhibitors of Cryptosporidium parvum inosine 5′-monophosphate dehydrogenase

Cryptosporidium parvum is an enteric protozoan parasite that has emerged as a major cause of diarrhea, malnutrition, and gastroenteritis and poses a potential bioterrorism threat. C. parvum synthesizes guanine nucleotides from host adenosine in a streamlined pathway that relies on inosine 5′-monophosphate dehydrogenase (IMPDH). We have previously identified several parasite-selective C. parvum IMPDH (CpIMPDH) inhibitors by high-throughput screening. In this paper, we report the structure-activity relationship (SAR) for a series of benzoxazole derivatives with many compounds demonstrating CpIMPDH IC50 values in the nanomolar range and >500-fold selectivity over human IMPDH (hIMPDH). Unlike previously reported CpIMPDH inhibitors, these compounds are competitive inhibitors versus NAD +. The SAR study reveals that pyridine and other small heteroaromatic substituents are required at the 2-position of the benzoxazole for potent inhibitory activity. In addition, several other SAR conclusions are highlighted with regard to the benzoxazole and the amide portion of the inhibitor, including preferred stereochemistry. An X-ray crystal structure of a representative E·IMP·inhibitor complex is also presented. Overall, the secondary amine derivative 15a demonstrated excellent CpIMPDH inhibitory activity (IC 50 = 0.5 ± 0.1 nM) and moderate stability (t1/2 = 44 min) in mouse liver microsomes. Compound 73, the racemic version of 15a, also displayed superb antiparasitic activity in a Toxoplasma gondii strain that relies on CpIMPDH (EC50 = 20 ± 20 nM), and selectivity versus a wild-type T. gondii strain (200-fold). No toxicity was observed (LD 50 > 50 μM) against a panel of four mammalian cells lines.