2027-70-5

Upstream product

• 130781-66-7 5-chloro-2-benzyl-1,3,4-oxadiazole 
• 62-53-3 aniline 
• 18233-63-1 N⁴-phenyl-phenylacetic acid thio-semicarbazide 
• 103-82-2 phenylacetic acid 
• 5351-69-9 4-Phenyl-3-thiosemicarbazide 
• 1711-94-0 2-hydroxy-5-benzyl-1,3,4-oxadiazole 
• 103-72-0 phenyl isothiocyanate 
• 622-44-6 phenylcarbonimidic dichloride 
• 937-39-3 2-phenylacetylhydrazine 

Relevant academic research and scientific papers

Efficient and mild synthesis of substituted 2-amino-1,3,4-oxadiazoles mediated by (tosylimino)phenyl-γ3-iodane

A simple and convenient one-pot protocol for the synthesis of substituted 2-amino-1,3,4-oxadiazoles mediated by (tosylimino)phenyl-γ3- iodane has been described. Acylthiosemicarbazides prepared from the corresponding acylhydrazides undergo effi

O -iodoxybenzoic acid mediated oxidative desulfurization initiated domino reactions for synthesis of azoles

A systematic exploration of thiophilic ability of o-iodoxybenzoic acid (IBX) for oxidative desulfurization to trigger domino reactions leading to new methodologies for synthesis of different azoles is described. A variety of highly substituted oxadiazoles, thiadiazoles, triazoles, and tetrazoles have been successfully synthesized in good to excellent yields, starting from readily accessible thiosemicarbazides, bis-diarylthiourea, 1,3-disubtituted thiourea, and thioamides.

Hypervalent iodine(V) mediated mild and convenient synthesis of substituted 2-amino-1,3,4-oxadiazoles

A simple protocol for the synthesis of 2-amino-1,3,4-oxadiazoles starting from the corresponding acylhydrazides by cyclodesulfurization of intermediate acylthiosemicarbazides mediated by o-iodoxybenzoic acid in good yields has been described. The protocol

NOVEL AZOLES AND RELATED DERIVATIVES AS NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS (NNRTIS) IN ANTIVIRAL THERAPY (HIV)

The present invention relates to novel heterocyclic compounds, including oxadiazole compounds, pharmaceutical compositions and their use in the inhibition of reverse transcriptase and the treatment of HIV (1 and 2) infections, AIDS and ARC and other viral

Efficient one-pot synthesis of substituted 2-amino-1,3,4-oxadiazoles

A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles has been developed. The method is a significant improvement over previously reported syntheses. Reaction of carboxylic acids with thiosemicarbazides afforded the corresponding oxadiazoles in moderate to good yields. In general, the products precipitated from the reaction mixture, and were collected by filtration. In most of the cases, no chromatographic separations were required. To explore the scope and limitations of this reaction, various aliphatic, aromatic, and heteroaromatic carboxylic acids were reacted with different substituted thiosemicarbazides. The influence of R1 and R2 substituents on the reaction yield and additional results demonstrating the versatility of this method are presented.

Optimization of azoles as anti-human immunodeficiency virus agents guided by free-energy calculations

Efficient optimization of an inactive 2-anilinyl-5-benzyloxadiazole core has been guided by free energy perturbation (FEP) calculations to provide potent non-nucleoside inhibitors of human immunodeficiency virus (HIV) reverse transcriptase (NNRTIs). An FEP "chlorine scan" was performed to identify the most promising sites for substitution of aryl hydrogens. This yielded NNRTIs 8 and 10 with activities (EC50) of 820 and 310 nM for protection of human T-cells from infection by wild-type HIV-1. FEP calculations for additional substituent modifications and change of the core heterocycle readily led to oxazoles 28 and 29, which were confirmed as highly potent anti-HIV agents with activities in the 10-20 nM range. The designed compounds were also monitored for possession of desirable pharmacological properties by use of additional computational tools. Overall, the trends predicted by the FEP calculations were well borne out by the assay results. FEP-guided lead optimization is confirmed as a valuable tool for molecular design including drug discovery; chlorine scans are particularly attractive since they are both straightforward to perform and highly informative.

From docking false-positive to active anti-HIV agent

Virtual screening of the Maybridge library of ca. 70 000 compounds was performed using a similarity filter, docking, and molecular mechanics- generalized Born/surface area postprocessing to seek potential non-nucleoside inhibitors of human immunodeficienc

Superior reactivity of thiosemicarbazides in the synthesis of 2-amino-1,3,4-oxadiazoles

(Chemical Equation Presented) A facile and general protocol for the preparation of 2-amino-1,3,4-oxadiazoles is reported. This method relies on a tosyl chloride/pyridine-mediated cyclization of a thiosemicarbazide, which is readily prepared by acylation o