55179-53-8

Upstream product

• 75542-36-8 2-(1,1-dimethyl-2-propenyl)-1-methoxymethylindole-3-aldehyde 
• 55454-18-7 9-(3-methylbut-2-enyl)-9-borabicyclo[3.3.1.]nonane 
• 7697-03-2 glycyl-L-serine methyl ester hydrochloride 
• 16863-96-0 3-chloro-1H-indole 
• 108849-83-8 N-(N-benzyloxycarbonyl-glycyl)-L-serine methyl ester 
• 598-25-4 Dimethylallene 
• 22102-59-6 2-(2-methylbut-3-en-2-yl)-1H-indole 
• 64395-12-6 3-methylene-piperazine-2,5-dione 
• 51551-30-5 2-(1,1-dimethyl-2-propen-1-yl)-1H-indole-3-carboxaldehyde 
• 120-72-9 indole 

Relevant academic research and scientific papers

Synthesis and Antiviral Activities of Neoechinulin B and Its Derivatives

We have previously reported that neoechinulin B (1a), a prenylated indole diketopiperazine alkaloid, shows antiviral activities against hepatitis C virus (HCV) via the inactivation of the liver X receptors (LXRs) and the resultant disruption of double-membrane vesicles. In this study, a two-step synthesis of the diketopiperazine scaffold of 1a was achieved by the base-induced coupling of 1,4-diacetyl-3-{[(tert-butyldimethylsilyl)oxy]methyl}piperazine-2,5-dione with aldehydes, followed by the treatment of the resultant coupling products with tetra-n-butylammonium fluoride. Compound 1a and its 16 derivatives 1b–q were prepared using this method. Furthermore, variecolorin H, a related alkaloid, was obtained by the acid treatment of 1a in MeOH. The antiviral evaluation of 1a and its derivatives revealed that 1a, 1c, 1d, 1h, 1j, 1l, and 1o exhibited both anti-HCV and anti-severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) activities. The results of this study indicate that the exomethylene moiety on the diketopiperazine ring is important for the antiviral activities. The antiviral compounds can inhibit the production of HCV and SARS-CoV-2 by inactivating LXRs.

Concise total syntheses of variecolortides A and B through an unusual hetero-Diels-Alder reaction

A fusion of certain anthraquinones and diketopiperazines is an apt description of the variecolortides, a family of unusual fungal alkaloids. In a new, concise total synthesis of the variecolortides A and B, the natural racemates are obtained highly convergently and almost without protecting-group manipulations. The spirocyclic core is generated in a hetero-Diels-Alder reaction of a 1,4-anthraquinone with a didehydrodiketopiperazine.