15591-70-5

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 4-(indol-3-yl)butyrate is used as a reactant for the synthetic preparation of 4-[4-(1H-indol-3-yl)butyl]piperazine, a common precursor in the development of pharmaceutical compounds. This application is due to its ability to serve as a building block for the synthesis of various drugs, potentially contributing to the creation of new medications with diverse therapeutic effects.

InChI:InChI=1/C13H15NO2/c1-16-13(15)8-4-5-10-9-14-12-7-3-2-6-11(10)12/h2-3,6-7,9,14H,4-5,8H2,1H3

Upstream product

• 186581-53-3 diazomethane 
• 133-32-4 4-indol-3-yl-butyric acid 
• 818-57-5 Methyl 4-pentenoate 
• 201230-82-2 carbon monoxide 
• 100-63-0 phenylhydrazine 
• 2047-91-8 2,3-dihydro-1H-cyclopentindole 
• 1022576-81-3 ethyl 4-[4-(1H-indol-3-yl)butanoyl]piperazine-1-carboxylate 
• 67-56-1 methanol 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 180910-58-1 methyl 1-hydroxyindole-3-butylate 
• 74-88-4 methyl iodide 
• 100116-53-8 5-(2-amino-phenyl)-6-chloro-hex-5-enoic acid 
• 550-71-0 6-chloromethylene-3,4,5,6-tetrahydro-1H-benz[b]azocin-2-one 

Downstream Products

• 6245-91-6 3-indolebutyramide 
• 21903-93-5 4-(1H-indol-3-yl)butyl 4-methylbenzenesulfonate 
• 1169708-30-8 methyl 4-(1-(3-methoxyphenyl)-1H-indol-3-yl)-butanoate 
• 1169708-29-5 methyl 4-(1-phenyl-1H-indol-3-yl)-butanoate 
• 1166184-86-6 methyl 4-(1-benzyl-1H-indol-3-yl)butanoate 
• 6245-89-2 Homotryptamine 
• 4281-79-2 3-{4-[4-(2-methoxy-phenyl)-piperazin-1-yl]-butyl}-indole 
• 147817-50-3 siramesine 
• 163630-97-5 4-<1-(4-fluorophenyl)-1H-indol-3-yl>-1-butanol methanesulfonate ester 

Relevant academic research and scientific papers

Synthesis, spectral analysis and in vitro cytotoxicity of diorganotin (IV) complexes derived from indole-3-butyric hydrazide

A series (1–20) of diorganotin (IV) complexes with general formula R2SnL were formed by the reaction of R2SnCl2 (where R = Me, Et, Bu and Ph) with Schiff base ligands (H2L1–4) derived from the reaction of indole-3-butyric hydrazide with the salicylaldehyde and its derivatives. The structure elucidation of compounds were done by using UV–Vis, FT-IR, NMR (1H, 13C, 119Sn), Mass spectrometry and thermal gravimetric analysis. Spectroscopic evidences suggested tridentate nature (ONO) of Schiff base ligands and coordinated to the dialkyl/diaryltin (IV) moieties through nitrogen and oxygen donor sites giving pentacoordinated geometry to complexes. The compounds were tested for the antimicrobial activity against bacterial and fungal strains which showed promising biological activity with compound 20 (Ph2SnL4) as most active against microbes. The in silico study of the compounds was carried and observed that the compounds are used as orally active drugs and promote the formation of different hydrazide based drugs. The synthesized compounds were tested against human carcinoma cell lines namely A549, MCF7 and one normal cell line IMR 90 using MTT assay. The diethyl and dibutyltin complexes of Schiff bases displayed good cytotoxic activities. Compound 3 (H2L3) and 10 (Et2SnL2) were most potent against cancer cell lines with lowest IC50 values and 7–8 times less toxic against the normal cell line.

Radical C?H-Amination of Heteroarenes using Dual Initiation by Visible Light and Iodine

A novel light-induced C?H amination of heteroarenes can be accomplished with preformed iodine(III) reagents as the combined oxidant and nitrogen source. The reaction requires the use of a small amount of molecular iodine, which under photochemical activation generates in situ an iodine(I) reagent as the initiator of the radical amination reaction. A total of 32 examples exemplify the broad scope of the transformation. (Figure presented.).

Synthesis of Various Bridged Ring Systems via Rhodium-Catalyzed Bridged (3+2) Cycloadditions

Here, we describe the rhodium-catalyzed bridged (3+2) cycloaddition cascade reactions of N-sulfonyl-1,2,3-triazoles, which allowed the efficient diastereoselective construction of various functionalized and synthetically challenging bridged ring systems. This simple, direct transformation had a broad substrate scope and excellent functional group tolerance. The highly strained polycyclic bicyclo[2.2.2]octa[b]indole core of fruticosine was synthesized efficiently using this methodology.

Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite

In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.

Method for synthesizing 3-hydroxyl oxoindole derivative

The invention discloses a method for synthesizing a 3-hydroxyl oxoindole derivative. The synthetic route is as shown in the specification, wherein R1 is methyl, ethyl, propyl, butyl, isopropyl, cyclohexyl, allyl, benzyloxyethyl or n-butyric acid methyl ester; a substituent R2 is methyl, methoxy, benzyloxy, fluorine, chlorine or bromine; and a substituent R3 is methyl, bromine or phenyl. The synthetic process comprises the following steps: dissolving a compound I and iodobenzene diacetate in acetic acid and reacting completely at 40-100 DEG C, and postprocessing and purifying to obtain a product II. The raw materials used in the method are easy to prepare, and iodobenzene diacetate can be sold in the market; there is no need to use a catalyst such as a metal catalyst or an organic catalyst, and cost is reduced and the method is environment-friendly.

A double-indole hydrazone compound and use thereof

The invention provides a bisindole acylhydrazone compound shown as the formula I or salt, hydrate or crystals, accepted in the pharmacy, of the bisindole acylhydrazone compound. According to the bisindole acylhydrazone compound, R does not exist or is selected from alkylene of C1-5. The bisindole acylhydrazone compound has a certain antibacterial activity, and can serve as potential antibiotics or a daily chemical product. What is beyond the expectation is that compounds 4e-4h and compounds 4a-4c are quite similar in structure, the antibacterial activity of the compounds 4e-4h and the antibacterial activity of the compounds 4a-4c are obviously better than that of other compounds, particularly, the activity of the compound 4h is best and is remarkably better than that of compounds 4e-4g. The formula I is shown in the specification.

Indole hydrazone compounds

The invention provides a compound of the formula I as shown in the description. In the formula, R is connected with the carbon atom at the 2nd or 3rd site of indolyl and is selected from none or C1-3 alkylene. Molecular tweezers of bisindole acylhydrazone have a good recognition cooperation function on inspected malic acid, tartaric acid, ascorbic acid and tryptophan, and have no recognition cooperation function on other inspected organic acids such as lactic acid, oxalic acid, tyrosine, histidine and serine. Therefore, due to the selective recognition property of a molecular tweezers receptor has the potential to be applied to fields such as analysis and separation of relevant organic acids in biological medicines, and transportation of organic acid medicines.

Microwave-assisted synthesis and molecular recognition properties of novel indole acylhydrazone receptors

Indole acylhydrazones were synthesised in high yields under microwave irradiation By using indole carboxylic acid and 1,4-benzenedialdehyde as starting materials. Their structures were characterised by 1H NMR, IR, MS spectra and elemental analysis. Selective recognition properties of these receptors have been investigated by UV-Vis spectra titration indicating that these receptors can form 1:1 supramolecular complexes with malic acid, tartaric acid, ascorbic acid and tryptophan.

Synthesis of 1-substituted 4-[4-(1H-indol-3-yl)butyl]piperazines

A convenient synthetic route for preparation of various 4-[4-(1H-indol-3-yl)butyl]piperazines bearing heterocyclic and aliphatic substituents in position 1 has been developed. During this work some synthetic possibilities of common precursor, 4-[4-(1H-indol-3-yl)butyl]piperazine, were studied and evaluated. ARKAT-USA, Inc.

CARBOXYLIC DERIVATIVES FOR USE IN THE TREATMENT OF CANCER

The invention provides novel compounds of formula (I), wherein: R1 is a radical derived from one of the known ring systems; R2 is a phenyl radical optionally substituted; Xn represents a birradical selected from the group consisting of: -(CH2)1-4-, (C2-C4)-alkenyl, (C2-C4)alkynyl, -S-(CH2)1-3-#, and -(CH2)1-3-O-#; wherein the symbol # indicates the position at which Xn is attached to R1; Yn is a birradical selected from the group consisting of: -(CH2)2-4-, -S-(CH2)1-3#, and -O-(CH2)1-3-#,; where in the symbol # indicates the position at which Yn is attached to R2; and R3 is a radical selected from the group consisting of: -OR4. The compounds of formula (I) are useful in the treatment of cancer