62495-85-6

Upstream product

• 59-88-1 phenylhydrazine hydrochloride 
• 15853-98-2 (+)-usnic acid 
• 100-63-0 phenylhydrazine 
• 15853-98-2 usnic acid 
• 17669-01-1 (+)-usnic acid 
• 125-46-2 usnic acid 

Downstream Products

• 1392215-84-7 (4aR)-8-((S)-1-hydroxyethyl)-5,7-dihydroxy-3,4a,6-trimethyl-1-phenyl-1H-benzofuro[3,2-f]indazol-4-one 
• 1392215-85-8 (4aR)-8-((R)-1-hydroxyethyl)-5,7-dihydroxy-3,4a,6-trimethyl-1-phenyl-1H-benzofuro[3,2-f]indazol-4-one 
• 1392216-06-6 C₂₄H₂₂N₂O₅ 
• 1354957-12-2 (4R,4aS)-8-acetyl-4,7-dihydroxy-5-methoxy-3,4a,6-trimethyl-1-phenyl-4,4a-dihydro-1H-benzofuro[3,2 f]indazole 
• 1392446-32-0 (E)-1-[(4R,4aS)-4,7-dihydroxy-5-methoxy-3,4a,6-trimethyl-1-phenyl-4,4a-dihydro-1H-benzofuro[3,2-f]indazol-8-yl]-3-phenylprop-2-en-1-one 
• 1392446-33-1 (E)-1-[(4R,4aS)-4,7-dihydroxy-5-methoxy-3,4a,6-trimethyl-1-phenyl-4,4a-dihydro-1H-benzofuro[3,2-f]indazol-8-yl]-3-(4-fluorophenyl)prop-2-en-1-one 
• 1392446-35-3 (E)-1-[(4R,4aS)-4,7-dihydroxy-5-methoxy-3,4a,6-trimethyl-1-phenyl-4,4a-dihydro-1H-benzofuro[3,2-f]indazol-8-yl]-3-(4-methoxyphenyl)prop-2-en-1-one 
• 1392446-36-4 (E)-1-[(4R,4aS)-4,7-dihydroxy-5-methoxy-3,4a,6-trimethyl-1-phenyl-4,4a-dihydro-1H-benzofuro[3,2-f]indazol-8-yl]-3-(2-fluorophenyl)prop-2-en-1-one 
• 1392446-37-5 (E)-1-[(4R,4aS)-4,7-dihydroxy-5-methoxy-3,4a,6-trimethyl-1-phenyl-4,4a-dihydro-1H-benzofuro[3,2-f]indazol-8-yl]-3-(2-methoxyphenyl)prop-2-en-1-one 
• 1392446-38-6 (E)-1-[(4R,4aS)-4,7-dihydroxy-5-methoxy-3,4a,6-trimethyl-1-phenyl-4,4a-dihydro-1H-benzofuro[3,2-f]indazol-8-yl]-3-(3-nitrophenyl)prop-2-en-1-one 
• 1392446-39-7 (E)-1-[(4R,4aS)-4,7-dihydroxy-5-methoxy-3,4a,6-trimethyl-1-phenyl-4,4a-dihydro-1H-benzofuro[3,2-f]indazol-8-yl]-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 
• 1392446-40-0 (E)-1-[(4R,4aS)-4,7-dihydroxy-5-methoxy-3,4a,6-trimethyl-1-phenyl-4,4a-dihydro-1H-benzofuro[3,2-f]indazol-8-yl]-3-(3,4-dimethoxyphenyl)prop-2-en-1-one 

Relevant academic research and scientific papers

Synthesis and antiproliferative activity of novel (+)- usnic acid analogues

Twenty one novel (+)- usnic acid-based analogues belonging to three classes such as enamines, imines, and pyrazoles were synthesized. All the synthesized compounds were characterized by their spectral data (1H NMR, 13C NMR, IR, and H

Synthesis of Usnic Acid Derivatives and Evaluation of Their Antiproliferative Activity against Cancer Cells

Usnic acid is a secondary metabolite abundantly found in lichens, for which promising cytotoxic and antitumor potential has been shown. However, knowledge concerning activities of its derivatives is limited. Herein, a series of usnic acid derivatives were synthesized and their antiproliferative potency against cancer cells of different origin was assessed. Some of the synthesized compounds were more active than usnic acid. Compounds 2a and 2b inhibited survival of all tested cancer cell lines in a dose- and time-dependent manner. Their IC50 values after 48 h of treatment were ca. 3 μM for MCF-7 and PC-3 cells and 1 μM for HeLa cells, while 3a and 3b revealed antiproliferative activity only against HeLa cells. All active usnic acid derivatives induced G0/G1 arrest and a drop in the fraction of HeLa cells in the S and G2/M phases. Compounds 2a and 2b decreased the clonogenic potential of the cancer cells evaluated and induced cell cycle arrest at the G0/G1 phase and apoptosis in MCF-7 cells. Moreover, they induced massive cytoplasmic vacuolization, which was associated with elevated dynein-dependent endocytosis, a process that has not been reported for usnic acid and indicates a novel mechanism of action of its synthetic derivatives. This work also shows that naturally occurring usnic acids are promising lead compounds for the synthesis of derivatives with more favorable properties against cancer cells.

Synthesis and Biological Evaluation of (+)-Usnic Acid Derivatives as Potential Anti- Toxoplasma gondii Agents

Six series of (+)-usnic acid derivatives were synthesized. The IC50 values of these compounds were determined in T. gondii infected HeLa cells (μM) and in HeLa cells (μM), and their selectivity indexes (SI) were calculated. In vitro, most of th

Novel derivatives of usnic acid effectively inhibiting reproduction of influenza A virus

Influenza virus is serious human pathogen leading to high morbidity and mortality all over the world. Due to high rate of mutation, it is able to fast development of drug resistance that makes necessary to search novel antivirals with broad range and alternative targets. In the present study we describe synthesis and anti-viral activity of novel derivatives of usnic acid (2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bH)-dibenzo-furandione). It is shown that anti-viral activity of usnic acid can be increased by side moieties introduction. The modification with chalcones appeared to be the most effective. Our study revealed that (-)-usnic acid exhibited higher antiviral activity than its (+)-enantiomer, but in the pairs of enantiomer derivatives such as enamines, pyrazoles and chalcones, the (+)-enantiomers were more potent inhibitors of the virus. For other groups of compounds the inhibiting activities of the enantiomers were comparable. Further optimization of the structure could therefore result in development of novel anti-influenza compound with alternative target and mechanism of virus-inhibiting action.

Synthesis of new (+)-usnic acid derivatives with the flavone structure

Reactions of a chalcone derivative (synthesized earlier from usnic acid) with various oxidants (hydrogen peroxide, tert-butyl hydroperoxide, and dichlorodicyanobenzoquinone) gave new flavonols, dihydroflavonols, and flavones. Treatment of the starting chalcone with a nucleophilic reagent (NH 2NH2·H2O) afforded a dihydropyrazole-containing derivative.

Anti-viral activity of (-)- and (+)-usnic acids and their derivatives against influenza virus A(H1N1)2009

Influenza is a widespread respiratory infection. Every year it causes epidemics, quickly spreading from country to country, or even pandemics, involving a significant part of the human population of the earth. Being a highly variable infection, influenza