20862-91-3

Usage

Molecular Weight

285.30 g/mol The molecular weight is the mass of one mole of the compound, calculated by adding the atomic weights of all the atoms in the molecular formula.

Structure

1H-Indole-3-carboxylic acid, 5-(acetyloxy)-2-methyl-, ethyl ester The structure of the compound is a combination of an indole ring with a carboxylic acid group attached to the 3rd carbon position, an acetyloxy group attached to the 5th carbon position, and a methyl group attached to the 2nd carbon position, with an ethyl ester group attached to the carboxylic acid.

Solubility

Insoluble in water, soluble in organic solvents The compound's polarity and the presence of the ethyl ester group make it insoluble in water but soluble in organic solvents such as ethanol, methanol, and dichloromethane.

Reactivity

Reactive The presence of the carboxylic acid and acetyloxy groups makes the compound reactive and able to undergo various chemical reactions, such as esterification, amidation, and condensation reactions.

Uses

Building block for pharmaceuticals and agrochemicals, organic synthesis, and medicinal chemistry research The compound is commonly used as a building block for the development of pharmaceuticals and agrochemicals, as well as a valuable reagent in chemical research and drug discovery due to its unique structure and functional groups.

Upstream product

• 7598-91-6 ethyl 5-hydroxy-2-methylindole-3-carboxylate 
• 108-24-7 acetic anhydride 
• 100-02-7 4-nitro-phenol 
• 13871-68-6 p-aminophenyl acetate 
• 830-03-5 4-nitrophenol acetate 

Downstream Products

• 40945-79-7 1,2-dimethyl-5-acetoxy-1H-indole-3-carboxylic acid ethyl ester 
• 1615239-28-5 ethyl 5-hydroxy-2-((2-methoxyphenylthio)methyl)-1-methyl-1H-indole-3-carboxylate 
• 1615239-29-6 ethyl 5-hydroxy-2-((4-methoxyphenylthio)methyl)-1-methyl-1H-indole-3-carboxylate 
• 1615239-30-9 ethyl 5-hydroxy-1-methyl-2-((4-(trifluoromethoxy)phenylthio)methyl)-1H-indole-3-carboxylate 
• 1615239-31-0 ethyl 5-hydroxy-1-methyl-2-((2-(trifluoromethyl)phenylthio)methyl)-1H-indole-3-carboxylate 
• 1615239-32-1 ethyl 5-hydroxy-1-methyl-2-((4-(trifluoromethyl)phenylthio)methyl)-1H-indole-3-carboxylate 
• 1615239-33-2 ethyl 2-((4-fluorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate 
• 1615239-34-3 ethyl 2-((3-chlorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate 
• 1615239-35-4 ethyl 2-((2,4-difluorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate 
• 1615239-36-5 ethyl 2-((2,6-dichlorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate 
• 1615239-37-6 ethyl 2-((2,6-dimethylphenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate 
• 1615239-38-7 ethyl 2-((3,5-dimethylphenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate 
• 1615239-39-8 ethyl 5-hydroxy-2-(mesitylthiomethyl)-1-methyl-1H-indole-3-carboxylate 
• 26065-16-7 ethyl 5-hydroxy-1-methyl-2-(phenylthiomethyl)-1H-indole-3-carboxylate 

Relevant academic research and scientific papers

Design of inhibitors of influenza virus membrane fusion: Synthesis, structure-activity relationship and in vitro antiviral activity of a novel indole series

The fusion of virus and endosome membranes is an essential early stage in influenza virus infection. The low pH-induced conformational change which promotes the fusogenic activity of the haemagglutinin (HA) is thus an attractive target as an antiviral strategy. The anti-influenza drug Arbidol is representative of a class of antivirals which inhibits HA-mediated membrane fusion by increasing the acid stability of the HA. In this study two series of indole derivatives structurally related to Arbidol were designed and synthesized to further probe the foundation of its antiviral activity and develop the basis for a structure-activity relationship (SAR). Ethyl 5-(hydroxymethyl)-1-methyl-2-(phenysulphanylmethyl)-1. H-indole-3-carboxylate (15) was identified as one of the most potent inhibitors and more potent than Arbidol against certain subtypes of influenza A viruses. In particular, 15 exhibited a much greater affinity and preference for binding group 2 than group 1 HAs, and exerted a greater stabilising effect, in contrast to Arbidol. The results provide the basis for more detailed SAR studies of Arbidol binding to HA; however, the greater affinity for binding HA was not reflected in a comparable increase in antiviral activity of 15, apparently reflecting the complex nature of the antiviral activity of Arbidol and its derivatives.

ARBIDOL ANALOGS WITH IMPROVED INFLUENZA HEMAGGLUTININ POTENCY

The invention provides a series of analogs of arbidol having enhanced binding activity with respect to influenza hemagglutinin. Accordingly, the invention can provide a method of inhibiting the bioactivity of viral hemagglutinin activity, which is an essential step in the entry of infectious viral particles into host cells. The invention also can provide a method of treatment of influence, comprising administering an effective amount of a compound of formula (A), wherein X is S or O, to a patient afflicted therewith.

Structure-based optimization and synthesis of antiviral drug Arbidol analogues with significantly improved affinity to influenza hemagglutinin

Influenza is a highly contagious respiratory viral infection responsible for up to 50,000 deaths per annum in the US alone. The need for new therapeutics with novel modes of action is of paramount importance. We determined the X-ray structure of Arbidol with influenza hemagglutinin and found it was located in a distinct binding pocket. Herein, we report a structure-activity relationship study based on the co-complex combined with bio-layer interferometry to assess the binding of our compounds. Addition of a meta-hydroxy group to the thiophenol moiety of Arbidol to replace a structured water molecule in the binding pocket resulted in a dramatic increase in affinity against both H3 (1150-fold) and H1 (98-fold) hemagglutinin subtypes. Our analogues represent novel leads to yield more potent compounds against hemagglutinin that block viral entry.

Preparation method of arbidol hydrochloride

The invention discloses a preparation method of arbidol hydrochloride. P-nitrophenol which is cheap and easy to obtain is innovatively adopted as the raw material, and through acetylation, nitroreduction, an indole ring reaction, a methylation reaction, bromination, a reaction with thiophenol and deprotection, a Mannich reaction and salification, arbidol hydrochloride is obtained. Reaction conditions of the whole synthesis process are mild, the raw material can be conveniently obtained, the character of the product is good, the yield is high, few by-products are generated, reaction selectivity and purity are high, environmental friendliness is achieved, production cost is low, and the method is suitable for industrial production; the defects that in the prior art, selectivity is low, many by-products are generated, the yield is low, precious catalysts are used, and serious environmental pollution is caused are overcome.

Further studies on ethyl 5-hydroxy-indole-3-carboxylate scaffold: Design, synthesis and evaluation of 2-phenylthiomethyl-indole derivatives as efficient inhibitors of human 5-lipoxygenase

5-Lipoxygenase (5-LO), an enzyme that catalyzes the initial steps in the biosynthesis of pro-inflammatory leukotrienes, is an attractive drug target for the pharmacotherapy of inflammatory and allergic diseases. Here, we present the design, synthesis and

An Application of the Nenitszescu Reaction to the Synthesis of 1,2-Annulated Indoles and Benzindoles

The Nenitszescu reaction has been investigated as a means of preparing several indoles, benzindoles and 1,2-annulated indoles (5), (9), (13), (17) and (18) and a number of their derivatives.Reactions between benzoquinone and enaminones to form Michael