59908-53-1

Basic information

• Product Name: 1H-Indole-2-carboxylic acid, 5-chloro-1-Methyl-, ethyl ester
• Synonyms: 1H-Indole-2-carboxylic acid, 5-chloro-1-Methyl-, ethyl ester;Ethyl 5-chloro-1-Methyl-1H-indole-2-carboxylate
• CAS NO: 59908-53-1
• Molecular Formula: C₁₂H₁₂ClNO₂
• Molecular Weight: 237.68218
• Mol File: 59908-53-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1H-Indole-2-carboxylic acid, 5-chloro-1-Methyl-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-2-carboxylic acid, 5-chloro-1-Methyl-, ethyl ester(59908-53-1)
• EPA Substance Registry System: 1H-Indole-2-carboxylic acid, 5-chloro-1-Methyl-, ethyl ester(59908-53-1)

Safety Data

• Hazardous Substances Data: 59908-53-1(Hazardous Substances Data)

Usage

Molecular Weight

229.67 g/mol

Structure

A bicyclic indole ring system with a carboxylic acid group at position 2, a chlorine atom at position 5, a methyl group at position 1, and an ethyl ester group attached to the carboxylic acid.

Physical Properties

The physical properties of 1H-Indole-2-carboxylic acid, 5-chloro-1-Methyl-, ethyl ester are not specified in the material provided.

Applications

Potential applications in the pharmaceutical industry for therapeutic purposes, but specific uses and effects are still being investigated.

Importance

Valuable compound for further research and exploration in the field of medicinal chemistry due to its chemical structure and properties.

Upstream product

• 4792-67-0 5-chloro-indole-2-carboxylic acid ethyl ester 
• 74-88-4 methyl iodide 
• 80-48-8 methyl p-toluene sulfonate 
• 106-47-8 4-chloro-aniline 
• 5296-86-6 2-[(4-chlorophenyl)-hydrazono]-propionic acid ethyl ester 
• 74-83-9 methyl bromide 

Downstream Products

• 883529-71-3 5-chloro-1-methyl-1H-indole-2-carbaldehyde 
• 1620065-09-9 C₂₈H₃₅ClNO₄P 
• 1620064-73-4 C₂₄H₂₁ClNO₃P 

Relevant articles and documents

Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics

Cyclopropenylmethyl sulfonamides with tethered heteroaromatics have been demonstrated to undergo divergent gold-catalysed cyclisation reactions. A formal dearomative (4+3) cycloaddition takes place with furan-tethered substrates, yielding densely functionalised 5,7-fused heterocycles related to the bioactive curcusone natural products. Indole-tethered substrates display divergent reactivity giving biologically important tetrahydro-β-carbolines via a Friedel-Crafts mechanism.

Structure-activity relationship study of β-oxidation resistant indole-based 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) receptor antagonists

5-Oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is formed from 5S-hydroxy-6,8,11,14-eicosatetraenoic acid (5-HETE) by the 5-lipoxygenase (5-LO) pathway under conditions associated with oxidative stress. 5-Oxo-ETE is an important pro-inflammatory mediator, which stimulates the migration of eosinophils via a selective G-protein coupled receptor, known as the OXE receptor (OXE-R). Previously, we designed and synthesized structural mimics of 5-oxo-ETE such as 1 using an indole scaffold. In the present work, we added various substituents at C-3 of this moiety to block potential β-oxidation of the 5-oxo-valerate side chain, and investigated the structure-activity relationships of the resulting novel β-oxidation-resistant antagonists. Cyclopropyl and cyclobutyl substituents were well tolerated in this position, but were less potent as the highly active 3S-methyl compound. It seems likely that 3-alkyl substituents can affect the conformation of the 5-oxovalerate side chain containing the critical keto and carboxyl groups, thereby affecting interaction with the OXE-receptor.

Cycloaddition of in Situ Formed Azaoxyallyl Cations with 2-Alkenylindoles: An Approach to Tetrahydro-β-carbolinones

A novel [3 + 3] cycloaddition between in situ formed azaoxyallyl cations and 2-alkenylindoles has been developed. This concise method allows the efficient construction of a series of tetrahydro-β-carbolinones in good yields under mild conditions. Gram-sca

Acyl indoles, compositions containing such compounds and methods of use

The present invention relates to substituted indoles, compositions containing such compounds and methods of treatment The compounds are glucagon receptor antagonists and thus are useful for treating, preventing or delaying the onset of type 2 diabetes mellitus and related conditions.

1H-pyrido[3,4-b]indole-4-carboxamide derivatives, preparation and application thereof in therapeutics

PCT No. PCT/FR97/01750 Sec. 371 Date Apr. 7, 1999 Sec. 102(e) Date Apr. 7, 1999 PCT Filed Oct. 8, 1997 PCT Pub. No. WO98/15552 PCT Pub. Date Apr. 16, 1998Compounds of general formula (I) in which the variables are as defined in the specification, their pr

Benzo-fused heterocyclic compounds having a 5-membered ring processes for their preparation their use as medicaments their use as diagnostic agents and medicaments containing them

Benzo-fused heterocyclic compounds having a 5-membered ring, processes for their preperation, their use as medicaments, their use as diagnostic agents and medicaments containing them. Benzo-fused heterocyclic compounds having a 5-membered ring, of the formula I STR1 where X is N or CR(6); Y is oxygen, S or NR(7); A and B together are a bond or are both hydrogen, if, at the same time, X is CR(6) and Y is NR(7), one of the substituents R(1) to R(6) is a --CO--N=C(NH2)2 group; the other respective substituents R(1) to R(6) are H, Hal or alkyl; up to two of the other substituents R(1) to R(6) are CN, NO2, N3, (C1 -C4)-alkoxy, CF3 ; up to one of the other substituents is R(8)--Cn H2n --Z-- or phenyl; R(7) is H, alk(en)yl or R(8)--Cn H2n --, and pharmaceutically tolerated salts there of, are described. A process f or the preparation of the compounds I which comprises reacting a compound of the formula II STR2 in which one of the substituents R(1)' to R(5)' is a --CO--L group and L is a leaving group which can easily be replaced nucleophilically, with guanidine, and, if appropriate, converting the product into the pharmacologically tolerated salt, furthermore is also described.

Synthesis, biological evaluation, and structure-activity relationships of 3-acylindole-2-carboxylic acids as inhibitors of the cytosolic phospholipase A2

3-Acylindole-2-carboxylic acid derivatives were prepared and evaluated for their ability to inhibit the cytosolic phospholipase A2 of intact bovine platelets. To define the structural requirements for enzyme inhibition, the carboxylic acid group, the acyl residue, and the moiety in position 1 were systematically modified. Furthermore, different substituents were introduced into the phenyl part of the indole. Replacement of the carboxylic acid group in position 2 of the indole with an acetic or propionic acid substituent led to a decrease of inhibitory potency. Enzyme inhibition was optimal when the acyl residue in position 3 had a length of 12 or more carbons. Conformational restriction of the acyl residue did not influence activity. Introduction of alkyl chains at position 1 of the indole with 8 or more carbons resulted in a loss of activity. However, replacing the Ω-methyl group of such compounds with a carboxylic acid moiety was found to increase inhibitory potency significantly. Among the tested indole derivatives, 1-[2-(4- carboxyphenoxy)ethyl]-3-dodecanoylindole-2-carboxylic acid (29b) had the highest potency. With an IC50 of 0.5 μM it was about 20-fold more active than the standard cPLA2 inhibitor arachidonyl trifiuoromethyl ketane (IC50: 11μM).

ANTIDEPRESSANT 2-(4,5-DIHYDRO-1H-IMIDAZOLYL)-DIHYDRO-1H-INDOLES, -1,2,3,4-TETRAHYDROQUINOLINES AND -1H-INDOLES, AND METHODS OF USE THEREAS

2-(4,5-Dihydro-1H-imidazol-2-yl)-2,3-dihydro-1H-indoles, 2-(4, 5-dihydro-1H-imidazol-2-yl)-1,2,3,4-tetrahydroquinolines and 2-(4,5-dihydro-1H-imidazol-2-yl)-1H-indoles, useful as antidepressant agents, are prepared by reacting a respective lower-alkyl 2,3-dihydro-1H-indole-2-carboxylate 1,2,3,4-tetrahydroquinoline-2-carboxylate or 1H-indole-2-carboxylate derivative with ethylenediamine or an N-lower-alkylethylenediamine in the presence of a Lewis-type acid.

Indoline Analogues of Idazoxan: Potent α2-Antagonists and α1-Agonists

The synthesis and α-adrenergic activity of a series of substituted 2-imidazolinylindolines are described.Substitution in the indoline ring generated compounds with a spectrum of adrenoceptor antagonist/agonist profiles that proved sensitive to both the nature and position of the substituent.Many of the derivatives possess greater presynaptic antagonist potency that the corresponding benzodioxan 1, dihydrobenzofuran 2, and indan 3 analogues; however, this α2-antagonism is often accompanied by α1-agonist activity.It was not possible to separate α2-antagonist from α1-agonist properties in this series.Compounds of most interest proved to be the N-ethyl 6, 5-chloro-N-methyl 18 and 5-chloro-N-ethyl 23 derivatives, all being potent α2-antagonists and α1-agonists.Substitution at the 4- and 7-position of the indoline ring generally gave compounds with nonselective agonist properties.

2,5-Dihydro-1,2-thiazino(5,6-b)indole-3-carboxamide-1,1-dioxides and salts thereof

Compounds of the formula STR1 WHEREIN R1 is hydrogen, methyl or ethyl; R2 is methyl or ethyl; Y is hydrogen, fluorine, chlorine, bromine, methoxy, methyl, ethyl or trifluoromethyl; and Ar is 2-thiazolyl which may have one or two meth