57749-43-6

Usage

Uses

Used in Pharmaceutical Industry:
EQUISETIN is used as an inhibitor for [HIV-1 integrase inhibition]
Equisetin is employed as a potent inhibitor of HIV-1 integrase, which plays a crucial role in the viral replication process. By inhibiting the 3' end-processing and strand transfer activities of the enzyme, equisetin demonstrates its potential as a therapeutic agent in the treatment of HIV.
Used in Antiviral Applications:
EQUISETIN is used as an antiviral agent for [inhibition of HIV-1 replication]
In the field of antiviral research, equisetin is utilized for its ability to inhibit HIV-1 integrase, a key enzyme in the viral replication cycle. This inhibition can potentially lead to the development of new antiviral drugs targeting HIV-1.
Used in Agricultural Industry:
EQUISETIN is used as a phytotoxic agent for [inhibition of seed germination and seedling growth]
Equisetin's phytotoxic properties make it a potential candidate for use in the agricultural industry, where it can be employed to control the growth of certain plants by inhibiting seed germination and the growth of young seedlings.

InChI:InChI=1/C22H31NO4/c1-5-6-15-9-8-14-11-13(2)7-10-16(14)22(15,3)20(26)18-19(25)17(12-24)23(4)21(18)27/h5-6,8-9,13-17,24,27H,7,10-12H2,1-4H3/b6-5+/t13-,14-,15-,16-,17+,22-/m1/s1

Upstream product

• 122902-79-8 (S)-2-({3-[(1S,2R,4aS,6R,8aR)-1,6-Dimethyl-2-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-3-oxo-propionyl}-methyl-amino)-3-hydroxy-propionic acid methyl ester 
• 342375-13-7 (6E,8E)-(R)-10-Methoxymethoxy-4-methyl-deca-6,8-dienal 
• 342374-96-3 (R)-6-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hexanal 
• 122924-30-5 ethyl 3-{(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-[(1E)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl}-3-oxopropanoate 
• 122902-74-3 (1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-[(1E)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-carbaldehyde 
• 122902-71-0 [(1S,2R,4aS,6R,8aR)-1,6-Dimethyl-2-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-methanol 
• 2385-77-5 (R)-Citronellal 
• 342375-12-6 (6E,8E)-(R)-10-Methoxymethoxy-4-methyl-deca-6,8-dien-1-ol 
• 23414-70-2 (R)-5-(1,3-dioxolan-2-yl)-4-methylpentanal 
• 313072-28-5 tert-butyl β-keto-γ-diethylphosphonothiolate 
• 122924-29-2 C₂₂H₃₈O₃Si₂ 
• 122902-57-2 (1S,4aR,7R,8aR)-4,7-Dimethyl-1-((1E,3E)-penta-1,3-dienyl)-hexahydro-isochromene-3,8-dione 
• 122902-65-2 (2R,4aR,5S,6R,8aS)-5-Hydroxymethyl-2,5-dimethyl-6-((E)-propenyl)-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-ol 
• 38339-60-5 2-((1R,4R)-4-Methyl-3-oxo-cyclohexyl)-propionic acid 

Downstream Products

• 1300041-53-5 (+)-fusarisetin A 
• 255377-45-8 5'-epiequisetin 

Relevant academic research and scientific papers

Chemo-enzymatic synthesis of equisetin

We here report that the biosynthesis of equisetin, a fungal tetramate natural product with potent anti-infectious activity, relies on Fsa2, a Diels-Alderase that constructs the trans-decalin system of the molecule in a stereo-selective manner. This finding led to the development of a concise chemo-enzymatic route toward the synthesis of equisetin, which involves facile preparation of a linear polyene precursor via 7-steps and Fsa2 activity for equisetin maturation through an intramolecular Diels-Alder reaction, thus exemplifying the significance of the combination of chemical and biological methods to achieve structurally complex cyclic natural products and their derivatives.

Total synthesis of the Fusarium toxin equisetin: Proof of the stereochemical relationship of the tetramate and terpenoid sectors

A total synthesis of the Fusarium mycotoxin equisetin, in a manner that establishes its stereochemistry, is described. The key steps involve a lactonic variation of the ester enolate Claisen rearrangement and a novel construction of a 1-acyltetramic acid from an L-N-methylserine derivative and a β-keto ester.

Biomimetic synthesis of equisetin and (+)-fusarisetin A

(+)-FusarisetinA belongs to a group of acyl tetramic acid natural products that show potential anticancer activity. Equisetin, a biogenetically related acyl tetramic acid, contains the basic skeleton of (+)-fusarisetinA. We proposed that equisetin and (+)-fusarisetinA share a biosynthetic pathway that starts with naturally occurring (S)-serine and an unsaturated fatty acid. In support of this hypothesis, we have demonstrated that a cyclization sequence involving an intramolecular Diels-Alder reaction followed by a Dieckmann cyclization of polyenoylamino acid yielded equisetin. The aerobic oxidation of equisetin, promoted by either MnIII/O2 or a reactive oxygen species (ROS) produced by visible-light chemistry, gave peroxyfusarisetin, which could be easily reduced to (+)-fusarisetinA. We report herein detailed information on the biogenetic synthesis of equisetin and (+)-fusarisetinA. Make the change to bio! Biomimetic synthesis of equisetin and (+)-fusarisetinA was achieved based on a biosynthetic hypothesis. An intramolecular Diels-Alder reaction followed by a Dieckmann cyclization of polyenoylamino ester furnished equisetin. The aerobic oxidation of equisetin to give (+)-fusarisetinA was mediated by a MnIII/O2 system or reactive oxygen species (ROS) (see scheme). Copyright

Enantioselective total synthesis of (-)-equisetin using a Me3Al-mediated intramolecular Diels-Alder reaction

An efficient and enantioselective total synthesis of (-)-equisetin 1 has been accomplished using a diastereoselective Me3Al-mediated intramolecular Diels-Alder (IMDA) reaction as a key reaction step.