72755-19-2

Basic information

• Product Name: 1-(Ethoxycarbonyl)-β-carboline
• Synonyms: 1-(Ethoxycarbonyl)-β-carboline;1-Ethoxycarbonyl-beta-carboline;ethyl 9H-pyrido[3,4-b]indole-1-carboxylate;9H-Pyrido[3,4-b]indole-1-carboxylic acid ethyl ester
• CAS NO: 72755-19-2
• Molecular Formula: C₁₄H₁₂N₂O₂
• Molecular Weight: 240.25728
• Mol File: 72755-19-2.mol

Chemical Properties

• Melting Point: 145-146 °C
• Boiling Point: 470.9±25.0 °C(Predicted)
• Appearance: /
• Density: 1.308±0.06 g/cm3(Predicted)
• PKA: 14.21±0.40(Predicted)
• CAS DataBase Reference: 1-(Ethoxycarbonyl)-β-carboline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(Ethoxycarbonyl)-β-carboline(72755-19-2)
• EPA Substance Registry System: 1-(Ethoxycarbonyl)-β-carboline(72755-19-2)

Safety Data

• Hazardous Substances Data: 72755-19-2(Hazardous Substances Data)

Usage

Class

β-carboline alkaloids

Biological activities

Diverse

Characteristic feature

Presence of an ethoxycarbonyl group attached to the β-carboline core

Potential properties

Anti-inflammatory and anti-cancer

Relevance

Interest in medicinal chemistry and drug discovery

Chemical structure

Unique

Therapeutic potential

Valuable target for further studies

Upstream product

• 64-17-5 ethanol 
• 26052-96-0 9H-pyrido<3,4-b>indole-1-carboxylic acid 
• 288839-76-9 4,9-dihydro-3H-β-carboline-1-carboxylic acid ethyl ester 
• 102991-38-8 1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid 
• 61-54-1 tryptamine 
• 882853-03-4 C₁₄H₁₆N₂O₂ 
• 76907-13-6 2-acetyl-1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid ethyl ester 
• 343-94-2 tryptamine hydochloride 
• 6649-92-9 ethyl 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylate 
• 77-76-9 2,2-dimethoxy-propane 
• 120-72-9 indole 
• 6498-02-8 ethyl 1,2,4-triazine-3-carboxylate 

Downstream Products

• 38940-60-2 9H-pyrido[3,4-b]indole-1-carboxamide 
• 5023-08-5 4-methoxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one 
• 20127-60-0 pavettine 
• 479-43-6 canthin-6-one 
• 1160060-56-9 ethyl 9-(3-phenylpropyl)-β-carboline-1-carboxylate 

Relevant articles and documents

Total synthesis of cordatanine, structural reassignment of drymaritin, and anti-inflammatory activity of synthetic precursor

Abstract In this study, cordatanine, with a canthin-6-one skeleton, was totally synthesized in four steps via a Pictet-Spengler reaction using tryptamine and methyl glyoxylate with a total yield of 8%. The NMR spectra of synthesized cordatanine compared well with those of drymaritin isolated by Hsieh et al., confirming the need to revise the original structural assignment. In addition, kumujian A, a synthetic intermediate, showed significant anti-inflammatory effects, inhibiting both superoxide anion generation (IC50 4.87 μg/mL) and elastase release (IC50 6.29 μg/mL).

Pd(OAc)2-catalysed regioselective alkoxylation of aryl (β-carbolin-1-yl)methanones via β-carboline directed ortho-C(sp2)-H activation of an aryl ring

Synthesis of (2-alkoxyphenyl)(9H-pyrido[3,4-b]indol-1-yl)methanone via Pd(OAc)2-catalyzed regioselective alkoxylation of aryl (β-carbolin-1-yl) methanones employing β-carboline directed ortho-C(sp2)-H activation of an aryl ring under

Total syntheses of eudistomins Y1-Y7 by an efficient one-pot process of tandem benzylic oxidation and aromatization of 1-benzyl-3,4-dihydro-β-carbolines

The first total synthesis of eudistomin Y7 (7) and total syntheses of eudistomins Y1-Y6 (1-6) are described. An efficient room-temperature conversion of 1-benzyl-3,4-dihydro-β-carbolines (11) into 1-benzoyl-β-carbolines (14) by a one-pot process of tandem benzylic oxidation and aromatization as the key step of these total syntheses was also studied in detail. The first total synthesis of eudistomin Y 7 (7) and total syntheses of eudistomins Y1-Y6 (1-6) are described. An efficient room-temperature conversion of 1-benzyl-3,4-dihydro-β-carbolines (11) into 1-benzoyl-β-carbolines (14) by a one-pot process of tandem benzylic oxidation and aromatization as the key step of these total syntheses was also studied in detail. Copyright

Synthesis and structure of the β-carboline derivatives and their binding intensity with cyclin-dependent kinase 2

Series of 3-substituted of 6-aminosulfonyl-β-carbolines were designed and synthesized. In addition, the binding mode of these β-carboline derivatives with cyclin-dependent kinase 2 (CDK2) was studied by means of fluorescence measurements and molecular doc

Synthesis and cytotoxic evaluation of 1-carboxamide and 1-amino side chain substituted β-carbolines

The condensation of alkylenediamine with ethyl β-carboline-1- carboxylate and 1-bromo-β-carboline gave β-carboline-1-carboxamides and 1-amino-β-carbolines, respectively. Some of these β-carbolines were active against a panel of human tumor cell lines, and 1-amino derivatives were more potent than their 1-carboxamide congeners. In particular, among the 1-amino-β-carbolines, the N9-arylated alkyl substituted β-carbolines exhibited the most interesting cytotoxic activities with IC50 value of lower than 20 μM. The preliminary structure-activity relationships (SARs) analysis suggested that (1) 1-amino substituents were the advisable pharmacophoric group for enhanced cytotoxic activities; (2) the introduction of appropriate arylated alkyl groups into position-9 of β-carboline facilitated their cytotoxic potencies.

CHEMOKINE RECEPTOR MODULATORS

The invention provides compounds of Formula (I) and pharmaceutically acceptable salts, solvates, tautomers, stereoisomers, and/or esters thereof. These compounds, and pharmaceutical composition comprising such compounds are useful treating or preventing H

Development of the Pictet-Spengler reaction catalyzed by AuCl 3/AgOTf

Mild and efficient AuCl3/AgOTf-catalyzed Pictet-Spengler reactions were developed to afford in good yields a variety of tetrahydroisoquinoline and tetrahydro-β-carboline ring systems, which constitute important motifs in biologically active nat

Synthesis and evaluation of β-carbolinium cations as new antimalarial agents based on π-delocalized lipophilic cation (DLC) hypothesis

Several β-carbolines including naturally occurring substances and their corresponding cationic derivatives were synthesized and evaluated for antimalarial (antiplasmodial) activity in vitro and in vivo. A tetracyclic carbolinium salt was elucidated for antileishmanial and antitrypanosomal activities in vitro as well as antiplasmodial activity. Quarternary carbolinium cations showed much higher potencies in vitro than electronically neutral β-carbolines and a good correlation was observed between π-delocalized lipophilic cationic (DLC) structure and antimalarial efficacy. β-Carbolinium compounds exhibit medium suppressive activity in vivo against rodent malaria.

π-Delocalized β-carbolinium cations as potential antimalarials

Several β-carboline compounds including natural products and their corresponding salts were synthesized and evaluated for antimalarial activity and cytotoxicity levels. Quaternary carbolinium cations showed much higher potencies than neutral β-carbolines

Indole as a Dienophile in Inverse Electron Demand Diels-Alder Reactions: Reactions with 1,2,4-Triazines and 1,2-Diazines

Indole reacts with 1,2,4-triazines in the absence of solvent or in the presence of limited amounts of solvent to produce β- or γ-carbolines, benzonaphthyridines, or the noncyclized 3-indoles.The combined yields of cycloadducts with tricarbalkoxytriazines exceeds 90 percent, with the production of γ-carbolines exceeding 80 percent.The regiochemistry of the adduct and the ratio of the products is determined mainly by electronic effects of the triazine substituents.Indole also ungergoes a cyclocondensation reaction with tetramethyl 1,2-diazine-3,4,5,6-tetracarboxylate to give trimethyl 5H-6-oxophenanthridine-2,3,4-tricarboxylate.