4790-81-2

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 30, p. 62, 1987 DOI: 10.1021/jm00384a011

InChI:InChI=1/C8H6O2/c9-7-3-1-2-6-4-5-10-8(6)7/h1-5,9H

Upstream product

• 4790-80-1 7-hydroxybenzo(b)furan-2-carboxylic acid 
• 4790-79-8 7-methoxybenzofuran-2-carboxylic acid 
• 24410-55-7 7-chloro benzo[b]furan 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 7168-85-6 7-methoxybenzofuran 

Downstream Products

• 94242-00-9 7-benzofuranyl N-(4-methoxyphenyl)carbamate 
• 110677-54-8 benzofuran-6-amine 
• 1309209-02-6 1-benzhydryl-3-(benzofuran-7-yloxy)azetidine 
• 879093-09-1 2,3-dihydro-7-hydroxybenzofuran 

Relevant academic research and scientific papers

One-Pot Generation of Benzynes from Phenols: Formation of Primary Anilines by the Deoxyamination of Phenols

Benzynes were selectively generated in situ from phenols and trapped regioselectively with potassium hexamethyldisilazide to form primary anilines following acidic workup. The direct conversion of a phenolic hydroxyl group into a free amino group is a useful method for the preparation of primary aryl amines that are hard to synthesize by using coupling reactions involving phenol derivatives with ammonia. Whereas reactions of ortho- and meta-substituted phenols produced meta-substituted anilines exclusively, those of para-substituted phenols provided ortho-silylanilines.

INHIBITORS OF BRUTON'S TYROSINE KINASE AND METHODS OF THEIR USE

Compounds of formula (I') and methods of their use and preparation, as well as compositions comprising compounds of formula (I').

INHIBITORS OF BRUTON'S TYROSINE KINASE AND METHODS OF THEIR USE

The present disclosure is directed to compounds of formula I and methods of their use and preparation, as well as compositions comprising compounds of formula I.

Substituted aromatic four ring anti-fungal compound and its preparation method and application

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COMPOUNDS AND METHODS FOR TREATING HIV INFECTIONS

The present invention is directed to novel nanomolar and picomolar inhibitors of HIV reverse transcriptase, pharmaceutical compositions therefrom and methods for inhibiting reverse transcriptase and treating HIV infections, especially included drug resistant strains of HIV-1 and HIV-2 and/or secondary disease states and/or conditions which occur as a consequence of HIV infection.

Scaffold hopping of sampangine: Discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans

Discovery of novel antifungal agents against Aspergillus fumigatus and Cryptococcus neoformans remains a significant challenge in current antifungal therapy. Herein the antifungal natural product sampangine was used as the lead compound for novel antifungal drug discovery. A series of D-ring scaffold hopping derivatives were designed and synthesized to improve antifungal activity and water solubility. Among them, the thiophene derivative S2 showed broad-spectrum antifungal activity, particularly for Aspergillus fumigatus and Cryptococcus neoformans. Moreover, compound S2 also revealed better water solubility than sampangine, which represents a promising antifungal lead compound for further structural optimization.

Palladium-catalyzed hydroxylation of aryl and heteroaryl halides enabled by the use of a palladacycle precatalyst

A method for the hydroxylation of aryl and heteroaryl halides, promoted by a catalyst based on a biarylphosphine ligand tBuBrettPhos (L5) and its corresponding palladium precatalyst (1), is described. The reactions allow the cross-coupling of both potassium and cesium hydroxides with (hetero)aryl halides to afford a variety of phenols and hydroxylated heteroarenes in high to excellent yield.

Picomolar inhibitors of HIV reverse transcriptase featuring bicyclic replacement of a cyanovinylphenyl group

Members of the catechol diether class are highly potent non-nucleoside inhibitors of HIV-1 reverse transcriptase (NNRTIs). The most active compounds yield EC50 values below 0.5 nM in assays using human T-cells infected by wild-type HIV-1. However, these compounds such as rilpivirine, the most recently FDA-approved NNRTI, bear a cyanovinylphenyl (CVP) group. This is an uncommon substructure in drugs that gives reactivity concerns. In the present work, computer simulations were used to design bicyclic replacements for the CVP group. The predicted viability of a 2-cyanoindolizinyl alternative was confirmed experimentally and provided compounds with 0.4 nM activity against the wild-type virus. The compounds also performed well with EC50 values of 10 nM against the challenging HIV-1 variant that contains the Lys103Asn/Tyr181Cys double mutation in the RT enzyme. Indolyl and benzofuranyl analogues were also investigated; the most potent compounds in these cases have EC50 values toward wild-type HIV-1 near 10 nM and high-nanomolar activities toward the double-variant. The structural expectations from the modeling were much enhanced by obtaining an X-ray crystal structure at 2.88 A resolution for the complex of the parent 2-cyanoindolizine 10b and HIV-1 RT. The aqueous solubilities of the most potent indolizine analogues were also measured to be ～40 μg/mL, which is similar to that for the approved drug efavirenz and ～1000-fold greater than for rilpivirine.

9-AZABICYCLO [3 . 3 . 1] NONANE DERIVATIVES AS MONOAMINE REUPTAKE INHIBITORS

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9-Azabicyclo[3.3.1]nonane derivatives

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