24985-85-1

Usage

Uses

Used in Organic Synthesis:
Ethyl 5-hydroxyindole-2-carboxylate is used as a key intermediate for the synthesis of various organic compounds. Its versatile chemical properties enable it to be a valuable building block in the creation of complex molecules and structures.
Used in Pharmaceuticals:
In the pharmaceutical industry, Ethyl 5-hydroxyindole-2-carboxylate is utilized as a vital raw material for the development of new drugs. Its unique structure allows it to be incorporated into the design of novel therapeutic agents, potentially leading to the discovery of innovative treatments for various medical conditions.
Used in Agrochemicals:
Ethyl 5-hydroxyindole-2-carboxylate is also employed in the agrochemical sector, where it is used as a starting material for the synthesis of various agrochemical products. Its application in this industry contributes to the development of new pesticides, herbicides, and other agricultural chemicals that can help improve crop yields and protect plants from pests and diseases.
Used in Dyestuffs:
In the dyestuffs industry, Ethyl 5-hydroxyindole-2-carboxylate is used as an essential raw material for the production of various dyes and pigments. Its chemical properties make it suitable for the creation of a wide range of colorants, which can be used in various applications, such as textiles, plastics, and printing inks.

InChI:InChI=1/C13H19NO/c15-11-13-7-4-8-14(10-13)9-12-5-2-1-3-6-12/h1-3,5-6,13,15H,4,7-11H2

Upstream product

• 37033-95-7 5-benzyloxy-1H-indole-2-carboxylic acid ethyl ester 
• 21598-06-1 5-hydroxyindole-2-carboxylic acid 
• 4382-54-1 5-methoxy-1H-indole-2-carboxylic acid 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 123-30-8 4-amino-phenol 
• 64-17-5 ethanol 
• 4792-58-9 ethyl 5-methoxy-1H-indole-2-carboxylate 

Downstream Products

• 50630-45-0 5-(toluene-4-sulfonyloxy)-indole-2-carboxylic acid ethyl ester 
• 667422-92-6 5-(3-isopropyl-4-methoxyphenoxy)-2-carboxyindol ethyl ester 
• 31720-89-5 ethyl 5-acetoxyindole-2-carboxylate 
• 1037758-36-3 6-(2,5-difluorobenzyl)-8-(2-oxo-1,2-dihydropyridin-3-yl)-6H-furo[3,2-e]indole-7-carboxylic acid 
• 37033-95-7 5-benzyloxy-1H-indole-2-carboxylic acid ethyl ester 
• 6640-09-1 5-benzyloxy-1H-indole-2-carboxylic acid 
• 1037757-73-5 C₂₄H₁₇F₂N₃O₅S 

Relevant academic research and scientific papers

AROMATIC RING DERIVATIVE AS IMMUNOREGULATION AND PREPARATION METHOD AND APPLICATION OF AROMATIC RING DERIVATIVE

Relating to a compound represented by formula (I) and a pharmaceutically acceptable salt of the compound, and an application of the compound as an S1P1 agonist.

Scaffold Hopping of Natural Product Evodiamine: Discovery of a Novel Antitumor Scaffold with Excellent Potency against Colon Cancer

Inspired by the natural product evodiamine, a novel antitumor indolopyrazinoquinazolinone scaffold was designed by scaffold hopping. Structure-activity relationship studies led to the discovery of compound 15j, which shows low nanomolar inhibitory activity against the HCT116 cell line. Further antitumor mechanism studies indicated that compound 15j acted by the dual inhibition of topoisomerase 1 and tubulin and induced apoptosis with G2 cell-cycle arrest. The quaternary ammonium salt of compound 15j (compound 15js) exhibited excellent in vivo antitumor activity (TGI = 66.6%) in the HCT116 xenograft model with low toxicity. Indolopyrazinoquinazolinone derivatives represent promising multitargeting antitumor leads for the development of novel antitumor agents.

Synthesis method for preparing 2-substituted indole derivative

The invention relates to a synthesis method for preparing a 2-substituted indole derivative. The method includes the following steps: mixing aromatic amine compounds (I), ketone compounds (II) and a drying agent in an organic solvent; adding a palladium catalyst; and reacting in an aerobic weak acid environment to prepare the indole compounds (III). (I), (II) and (III) are as shown in the specification, wherein R1 is selected from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkanoyl, C2-C6 alkenyl, C2-C6 alkynyl, halogen, hydroxyl, substituted or unsubstituted amino, substituted or unsubstituted phenyl, pyridyl and heterocyclic aryl; (I) can be pyridylamine, pyrimidylamine, pyridazinam or pyrazinamide which may further be substituted or unsubstituted; and the substituents are selected fromone or more C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkanoyl, C2-C6 alkenyl, C2-C6 alkynyl, halogen, hydroxyl, amino; and R2 is selected from C1-C6 alkyl, formate groups or C1-C6 alkylamide groups.

Carboxylic Acid-Promoted Single-Step Indole Construction from Simple Anilines and Ketones via Aerobic Cross-Dehydrogenative Coupling

The cross-dehydrogenative coupling (CDC) reaction is an efficient strategy for indole synthesis. However, most CDC methods require special substrates, and the presence of inherent groups limits the versatility for further transformation. A carboxylic acid-promoted aerobic catalytic system is developed herein for a single-step synthesis of indoles from simple anilines and ketones. This versatile system is featured by the broad substrate scope and the use of ambient oxygen as an oxidant and is convenient and economical for both laboratory and industry applications. The existence of the labile hydrogen at C-3 and the highly transformable carbonyl at C-2 makes the indoles versatile building blocks for organic synthesis in different contexts. Computational studies based on the density functional theory (DFT) suggest that the rate-determining step is carboxylic acid-assisted condensation of the substrates, rather than the functionalization of aryl C-H. Accordingly, a pathway via imine intermediates is deemed to be the preferred mechanism. In contrast to the general deduction, the in situ formed imine, instead of its enamine isomer, is believed to be involved in the first ligand exchange and later carbopalladation of the α-Me, which shed new light on this indolization mechanism.

Influence of a Basic Side Chain on the Properties of Hypoxia-Selective Nitro Analogues of the Duocarmycins: Demonstration of Substantial Anticancer Activity in Combination with Irradiation or Chemotherapy

A new series of nitro analogues of the duocarmycins was prepared and evaluated for hypoxia-selective anticancer activity. The compounds incorporate 13 different amine-containing side chains designed to bind in the minor groove of DNA while spanning a wide range of base strength from pKa 9.64 to 5.24. The most favorable in vitro properties were associated with strongly basic side chains, but the greatest in vivo antitumor activity was found for compounds containing a weakly basic morpholine. This applies to single-agent activity and for activity in combination with irradiation or chemotherapy (gemcitabine or docetaxel). In combination with a single dose of γ irradiation 50 at 42 μmol/kg eliminated detectable clonogens in some SiHa cervical carcinoma xenografts, and in combination with gemcitabine using a well-tolerated multidose schedule, the same compound caused regression of all treated A2780 ovarian tumor xenografts. In the latter experiment, three of seven animals receiving the combination treatment were completely tumor free at day 100.

Initial development of a cytotoxic amino-seco-CBI warhead for delivery by prodrug systems

Abstract Cyclopropabenzaindoles (CBIs) are exquisitely potent cytotoxins which bind and alkylate in the minor groove of DNA. They are not selective for cancer cells, so prodrugs are required. CBIs can be formed at physiological pH by Winstein cyclisation of 1-chloromethyl-3-substituted-5-hydroxy-2,3-dihydrobenzo[e]indoles (5-OH-seco-CBIs). Corresponding 5-NH2-seco-CBIs should also undergo Winstein cyclisation similarly. A key triply orthogonally protected intermediate on the route to 5-NH2-seco-CBIs has been synthesised, via selective monotrifluoroacetylation of naphthalene-1,3-diamine, Boc protection, electrophilic iodination, selective allylation at the trifluoroacetamide and 5-exo radical ring-closure with TEMPO. This intermediate has potential for introduction of peptide prodrug masking units (deactivating the Winstein cyclisation and cytotoxicity), addition of diverse indole-amide side-chains (enhancing non-covalent binding prior to alkylation) and use of different leaving groups (replacing the usual chlorine, allowing tuning of the rate of Winstein cyclisation). This key intermediate was elaborated into a simple model 5-NH2-seco-CBI with a dimethylaminoethoxyindole side-chain. Conversion to a bio-reactive entity and the bioactivity of this system were confirmed through DNA-melting studies (ΔTm = 13°C) and cytotoxicity against LNCaP human prostate cancer cells (IC50 = 18 nM).

IRE-1α INHIBITORS

PROBLEM TO BE SOLVED: To provide compounds which directly inhibit inositol requiring enzyme 1 (IRE-1α activity) in vitro, prodrugs, and pharmaceutically acceptable salts thereof. SOLUTION: The present invention provides a compound represented by formula (A) [R3 and R4 are H or the like; Q5-Q8, together with the benzene ring to which they are attached, form a benzofused ring, where at least one of Q5-Q8 is a heteroatom selected from N, O, and S. COPYRIGHT: (C)2016,JPOandINPIT

N-methyl-N-((1-methyl-5-(3-(1-(2-methylbenzyl)piperidin-4-yl)propoxy)-1H-indol-2-yl)methyl)prop-2-yn-1-amine, a new cholinesterase and monoamine oxidase dual inhibitor

On the basis of N-((5-(3-(1-benzylpiperidin-4-yl)propoxy)-1-methyl-1H-indol-2-yl)methyl)-N-methylprop-2-yn-1-amine (II, ASS234) and QSAR predictions, in this work we have designed, synthesized, and evaluated a number of new indole derivatives from which we have identified N-methyl-N-((1-methyl-5-(3-(1-(2-methylbenzyl)piperidin-4-yl)propoxy)-1H-indol-2-yl)methyl)prop-2-yn-1-amine (2, MBA236) as a new cholinesterase and monoamine oxidase dual inhibitor.

Efficient microwave combinatorial synthesis of novel indolic arylpiperazine derivatives as serotoninergic ligands

An easy and convenient microwave-assisted synthesis of a small library of indolic arylpiperazine derivatives is described. Parallel and mixed pool combinatorial methods are reported and compared. The described reactions are nucleophilic substitutions of several aromatic piperazines in presence of K2CO3. Good yields and short reaction times are the main aspect of these procedures. Binding assays shed additional light on the influence of the LCAPs on the 5-HT1A, 5-HT2A and 5-HT2C receptors affinity and allowed to disclose three interesting compounds as 5-HT2C, mixed 5-HT2A/5-HT2C and 5-HT1A/5-HT2C ligands (4i, 4l and 4d, respectively), with potential antiepileptic, anxiolytic or atypical antipsychotic agent therapeutical profiles.

Indole derivatives as MCP-1 receptor antagonists

A compound of Formula I, wherein: R1 is hydrogen, halo, methyl, ethyl or methoxy; R2 is hydrogen, halo, methyl, ethyl or methoxy; R3 is a halo group, lower alkyl, lower alkenyl, lower alkynyl, alkoxy, trifluoromethyl, nitro, cyano, trifluoromethoxy, C(O)R7, or S(O)nR7 where n is 0, 1 or 2 and R7 is an alkyl group; R4 is a halo, trifluoromethyl, methylthio, methoxy, trifluoromethoxy or lower alkyl, lower alkenyl or lower alkynyl or COR8 where R8 is lower alkyl; R6 is hydrogen, halo, lower alkyl, lower alkenyl, lower alkynyl or COR9 where R9 is lower alkyl; provided that when R1 is hydrogen, halo or methoxy, R2 is hydrogen, halo, methyl, ethyl or methoxy, R5 and R6 are both hydrogen, and one of R3 or R4 is not halo or trifluoromethyl; or a pharmaceutically acceptable salt or prodrug thereof. These compounds have useful activity for the treatment of inflammatory disease, specifically in antagonizing an MCP-1 mediated effect in a warm-blooded animal such as a human being.