87223-77-6

Basic information

• Product Name: 3-AMINO-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: 3-AMINO-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER;ETHYL 3-AMINO-1H-INDOLE-2-CARBOXYLATE;1H-Indole-2-carboxylicacid,3-amino-,ethylester(9CI);Ethyl 3-amino-2-indolecarboxylate
• CAS NO: 87223-77-6
• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 204.23
• Product Categories: AMINOACID;pharmacetical
• Mol File: 87223-77-6.mol

Chemical Properties

• Melting Point: 153-154°C
• Boiling Point: 400.1°C at 760 mmHg
• Flash Point: 195.8°C
• Appearance: /
• Density: 1.288
• Vapor Pressure: 1.3E-06mmHg at 25°C
• Refractive Index: 1.669
• Storage Temp.: 2-8°C
• PKA: 15.70±0.30(Predicted)
• CAS DataBase Reference: 3-AMINO-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER(87223-77-6)
• EPA Substance Registry System: 3-AMINO-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER(87223-77-6)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 87223-77-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
3-Amino-1H-indole-2-carboxylic acid ethyl ester is used as a research compound for its potential applications in the development of new pharmaceuticals. Its reactivity and the presence of indole make it a promising candidate for the synthesis of more complex molecules with potential therapeutic effects.
Used in Chemical Research:
3-Amino-1H-indole-2-carboxylic acid ethyl ester is used as a building block in the synthesis of more complex chemical compounds. Its ethyl ester attachment and indole component provide opportunities for further chemical reactions and the creation of new molecules with various properties.
Note: The exact physical or chemical properties, toxicity, or specific uses of 3-Amino-1H-indole-2-carboxylic acid ethyl ester are not readily available without further specification or context.

InChI:InChI=1/C11H12N2O2/c1-2-15-11(14)10-9(12)7-5-3-4-6-8(7)13-10/h3-6,13H,2,12H2,1H3

Upstream product

• 87223-76-5 (2-cyanophenylamino)acetic acid ethyl ester 
• 1885-29-6 anthranilic acid nitrile 

Downstream Products

• 143603-83-2 3-{[1-(4-Trifluoromethyl-phenyl)-meth-(E)-ylidene]-amino}-1H-indole-2-carboxylic acid ethyl ester 
• 143603-71-8 3-{[1-(4-Benzyloxy-phenyl)-meth-(E)-ylidene]-amino}-1H-indole-2-carboxylic acid ethyl ester 
• 132474-79-4 3-(4-Phenyl-piperazin-1-ylazo)-1H-indole-2-carboxylic acid ethyl ester 
• 143603-78-5 3-{[1-(4-Phenoxy-phenyl)-meth-(E)-ylidene]-amino}-1H-indole-2-carboxylic acid ethyl ester 
• 110963-29-6 3-Aminoindole-2-carbohydrazide 
• 61553-71-7 5H-pyrimido<5,4-b>indole-4-one 
• 143603-81-0 3-{[1-p-Tolyl-meth-(E)-ylidene]-amino}-1H-indole-2-carboxylic acid ethyl ester 
• 143603-77-4 3-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-1H-indole-2-carboxylic acid ethyl ester 
• 143603-72-9 3-{[1-(4-Nitro-phenyl)-meth-(E)-ylidene]-amino}-1H-indole-2-carboxylic acid ethyl ester 
• 143603-79-6 3-{[1-(4-Acetylamino-phenyl)-meth-(E)-ylidene]-amino}-1H-indole-2-carboxylic acid ethyl ester 
• 143603-75-2 3-{[1-(3,4,5-Trimethoxy-phenyl)-meth-(E)-ylidene]-amino}-1H-indole-2-carboxylic acid ethyl ester 
• 143603-76-3 3-{[1-Phenyl-meth-(E)-ylidene]-amino}-1H-indole-2-carboxylic acid ethyl ester 
• 143603-80-9 3-{[1-(4-Hydroxy-phenyl)-meth-(E)-ylidene]-amino}-1H-indole-2-carboxylic acid ethyl ester 
• 143603-82-1 3-{[1-(2-Hydroxy-phenyl)-meth-(E)-ylidene]-amino}-1H-indole-2-carboxylic acid ethyl ester 

Relevant articles and documents

Design, synthesis and biological evaluation of 2-alkoxycarbonyl-3-anilinoindoles as a new class of potent inhibitors of tubulin polymerization

A new class of inhibitors of tubulin polymerization based on the 2-alkoxycarbonyl-3-(3′,4′,5′-trimethoxyanilino)indole molecular skeleton was synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization and cell cycle eff

Identification of substituted pyrimido[5,4-b]indoles as selective toll-like receptor 4 ligands

A cell-based high-throughput screen to identify small molecular weight stimulators of the innate immune system revealed substituted pyrimido[5,4-b]indoles as potent NFκB activators. The most potent hit compound selectively stimulated Toll-like receptor 4 (TLR4) in human and mouse cells. Synthetic modifications of the pyrimido[5,4-b]indole scaffold at the carboxamide, N-3, and N-5 positions revealed differential TLR4 dependent production of NFκB and type I interferon associated cytokines, IL-6 and interferon γ-induced protein 10 (IP-10) respectively. Specifically, a subset of compounds bearing phenyl and substituted phenyl carboxamides induced lower IL-6 release while maintaining higher IP-10 production, skewing toward the type I interferon pathway. Substitution at N-5 with short alkyl substituents reduced the cytotoxicity of the leading hit compound. Computational studies supported that active compounds appeared to bind primarily to MD-2 in the TLR4/MD-2 complex. These small molecules, which stimulate innate immune cells with minimal toxicity, could potentially be used as adjuvants or immune modulators.

PYRROLOPYRIMIDINE DERIVATIVES AS MODULATORS OF MULTI-DRUG RESISTANCE (MDR)

A compound which is a pyrrolopyrimidine of formula (I) wherein R1 is selected from H, Cl-C6 alkyl which is unsubstituted or substituted, (CH2)nAr1, (CH2)pNR4R5, halogen and (CH2)pX; R2 is CH2)pArl; R3 is selected from H, Cl -C6 alkyl which is unsubstituted or substituted, (CH2)pZ and (CH2)pArl; P is an unsaturated 5, 6, or 7 membered carbocyclic or heterocyclic ring which is unsubstituted or substituted; R4 and R5 which are the same or different are selected from H, Cl -C6 alkyl which is unsubstituted or substituted, (CH2)nC3-C10 cycloalkyl, (CH2)nAr1 , and (CH2)nOR6, or R4 and R5 together with the nitrogen atom to which they are attached, form a saturated five or six membered nitrogen containing heterocyclic ring which may contain one extra heteroatom selected from 0, N and S and which is unsubstituted or substituted; R6 is selected from H, Cl -C6 alkyl which is unsubstituted or substituted, C3-C10 cycloalkyl, (CH2)nOC1-C6alkyl which is unsubstituted or substituted, (CH2)nO(CH2)nAr1 , (CH2)nCO2C1-C6,alkyl which is unsubstituted or substituted and (CH2)nAr1; X is selected from CN, azide, (CH2)nNHSO2R6 and (CH2)nNHCOR6; Z is selected from CN, CO2R6 and CONR4R5; Ar1 is the same or different when more than one is present within a given substituent group and is an unsaturated C6-C10 membered carbocylic group or an unsaturated 5-11 membered heterocycle, either of which is unsubstituted or substituted; p is an integer of 1 to 6; n is the same or different when more than one is present within a given substituent group and is 0 or an integer of 1 to 6; with the proviso that the pyrrolepyrimidine compound of formula (I) is other than 1-(4-benzyl-piperazin-1-yl)-9H-2,4,9-triaza-fluorene; and the pharmaceutically acceptable salts thereof, have activity as inhibitors of MRP (multidrug resistant protein) and may thus be used to modulate multidrug resistance, for instance in potentiating the cytotoxicity of a chemotherapeutic agent.

Interleukin-4 gene expression inhibitors

This invention discloses and claims a class of indole and benzo(b)thiophene derivatives for use in treating allergy, asthma, rhinitis, dermatitis, B-cell lymphomas, tumors and diseases associated with bacterial, rhinovirus or respiratory syncytial virus (RSV) infections. The compounds of this invention are defined by the Formula (I): wherein X, Y, Z, R1, R2 and R3 are as defined in the specification; or a pharmaceutically acceptable salt thereof. In preferred embodiments of this invention it is also disclosed and claimed that the compounds of this invention are capable of modulating T helper (Th) cells, Th1/Th2, and thereby capable of inhibiting the transcription of interleukin-4 (IL-4) message, IL-4 release or IL-4 production.

CERTAIN ARYL FUSED PYRROLOPYRIMIDINES; A NEW CLASS OF GABA BRAIN RECEPTOR LIGANDS

The present invention encompasses structures of the formula: STR1 and the pharmaceutically acceptable non-toxic salts thereof wherein: STR2 and X represents hydrogen, halogen, or hydroxy; W represents an aryl group unsubstituted or substituted with

Pyridopyrimidoindoles. A New Heterocyclic Ring System

The preparation of the novel pyridopyrimidoindole ring system is described via fusion at 180 deg C of ethyl 3-amino-1H-indole-2-carboxylate 8a and several 6-chloronicotinic acid derivatives.Similar fusion of 8a and thiourea yielded a 2-m