518-80-9

Usage

Uses

Used in Antifungal Applications:
HELMINTHOSPORIN is used as an antifungal agent for its potent activity against various fungi, making it a potential candidate for the development of antifungal therapeutics.
Used in Cancer Therapeutics:
HELMINTHOSPORIN is used as a cytotoxic agent for its ability to target and eliminate cancer cells, showing promise as a potential candidate for the development of cancer treatments.
Used in Inflammatory Disease Treatment:
HELMINTHOSPORIN is used as an anti-inflammatory molecule for its potential to treat inflammatory diseases by reducing inflammation and alleviating symptoms.
Used in Agriculture:
HELMINTHOSPORIN is used as a biopesticide for its antifungal properties, offering a potential solution for controlling fungal infections in crops and protecting agricultural yields.

InChI:InChI=1/C15H10O5/c1-6-4-7-11(10(18)5-6)15(20)13-9(17)3-2-8(16)12(13)14(7)19/h2-5,16-18H,1H3

Upstream product

• 14918-68-4 2-chloro-5,8-dihydroxy-[1,4]naphthoquinone 
• 76927-59-8 (E)-((1-methoxy-3-methylbuta-1,3-dien-1-yl)oxy)trimethylsilane 
• 58070-21-6 (E)-1,1,4-trimethoxy-buta-1,3-diene 
• 62993-89-9 2-chloro-8-hydroxy-6-methylnaphthalene-1,4-dione 
• 76695-98-2 1,5,8-Trihydroxy-3-methyl-1,4,4a,9a-tetrahydro-anthraquinone 
• 73311-51-0 1-methoxy-3-methyl-1-trimethylsilyloxy-1,3-butadiene 
• 475-38-7 5,8-Dihydroxy-1,4-naphthoquinone 
• 155787-91-0 3-methyl-1-triethylsilyloxy-1-trimethylsilyloxy-1,3-butadiene 
• 84399-90-6 (4α,4aβ,9aβ)-9a-chloro-8-hydroxy-1,1,4-trimethoxy-6-methyl-1,4,4a,9a-tetrahydroanthraquinone 
• 123-31-9 hydroquinone 
• 34911-96-1 1-Ethoxy-5,8-dihydroxy-3-methyl-anthraquinone 
• 76695-97-1 5,8-Dihydroxy-3-methyl-1-trimethylsilanyloxy-1,4,4a,9a-tetrahydro-anthraquinone 
• 372-42-9 3-methylpent-2-enedioic acid 
• 67116-21-6 6-methoxy-4-methyl-2H-pyran-2-one 

Downstream Products

• 602-14-2 3-hydroxy-5-methyl-2,4,6-trinitro-benzoic acid 
• 144-62-7 oxalic acid 

Relevant academic research and scientific papers

Synthesis of 4,5,8-trimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid, an analogue of rhein with improved systemic exposure in the guinea pig

N,N-Diethyl-(2-methoxy-4-methyl)benzamide 4 has been lithiated and treated with 2,5-dimethoxybenzaldehyde to give 3-(2',5'-dimethoxyphenyl)-7-methoxy-5-methylisobenzofuran-1(3H)-one 5.Reduction and cyclisation gives 4,5,8-trimethoxy-2-methylanthracen-10-o

An expedient and efficient synthesis of naturally occurring hydroxy substituted anthraquinones

A general method for the synthesis of naturally occurring anthraquinones in high yield via Diels-Alder reaction is reported.

New Reagents for the Regiospecific Synthesis of Naturally Occurring Quinizarins

A modified Nef reaction applied to 4-nitrobutanoates gives the corresponding acetals which after hydrolysis and enol silylation yield the new 1,3-dienes 1-methoxy-1,4-bis(trimethylsiloxy)butadiene and its 3-methyl derivative.The latter reacts smoothly with chloronaphthoquinones and provides simple and efficient syntheses of 2-methylquinizarin, islandicin, digitopurpone, and erythroglaucin.

REACTIONS OF KETENE ACETALS-14; THE USE OF SIMPLE MIXED VINYLKETENE ACETALS IN THE ANNULATION OF QUINONES

α,β- and β,γ-unsaturated esters can be converted by strong base and chlorotrimethylsilane to the corresponding mixed vinylketene acetals which are shown to be particularly useful and generally applicable reagents for the regiospecific annulation of halogenoquinones.The reaction proceeds readily with a variety of substrates including benzoquinones.

Regiospecific Synthesis of Quinizarin and Naphthazarin Derivatives by Cycloaddition

The diene (E)-1,1,4-trimethoxybuta-1,3-diene underwent regiospecific cycloaddition to derivatives of 2(3)-chloro-1,4-naphthoquinone.The resulting adducts were aromatized to give 1,4-dioxygenated anthraquinones.The latter were obtained as derivatives of quinizarin dimethyl ether or of quinizarin monomethyl ether depending on the conditions of aromatization.Cycloaddition of the diene to non-halogenated naphthoquinones proceeded similarly, orientation being controlled by substituents in the benzenoid ring.Analogous reaction of the diene with benzoquinones gave 5,8-dioxygenated naphthoquinones (naphthazarins), generally in limited yield.The procedure has been applied to synthesis of the mould metabolites helminthosporin and cynodontin

REGIOSPECIFIC SYNTHESIS OF QUINIZARIN DERIVATIVES BY CYCLOADDITION

Cycloaddition of (E)-1,1,4-trimethoxy-1,3-butadiene (1) to naphthoquinones affords regiospecific syntheses of derivatives of 1,4-dihydroxyanthraquinone including the mould metabolites helminthosporin (21) and cynodontin (22).

SYNTHETISCHE ANTHRACYCLINONE XVI SYNTHESE HYDROXYLIERTER ANTHRACHINONE DURCH REGIOSELEKTIVE DIELS-ALDER-REAKTION

Naturally occuring quinones such as 7-methyljuglone, chrysophanol, emodin, helminthosporin, phomarin and physcion were prepared via Diels-Alder reaction and PCC-oxidation of the allylic alcohols obtained from the adducts.