3464-66-2

Usage

Uses

Used in Pharmaceutical Industry:
Methyl β-carboline-1-carboxylate is used as an anxiolytic agent for its anti-anxiety effects, providing a potential alternative to benzodiazepines in the treatment of anxiety disorders.
Used in Neuropharmacology Research:
Methyl β-carboline-1-carboxylate is used as a research tool to study the interactions between benzodiazepine receptors and the central nervous system, as well as its role in modulating neurotransmitter production.
Used in Drug Development:
Methyl β-carboline-1-carboxylate is used as a lead compound in the development of new medications targeting anxiety disorders and other neurological conditions, due to its unique binding properties and enzyme inhibition capabilities.

InChI:InChI=1/C13H10N2O2/c1-17-13(16)12-11-9(6-7-14-12)8-4-2-3-5-10(8)15-11/h2-7,15H,1H3

Upstream product

• 67-56-1 methanol 
• 26052-96-0 9H-pyrido<3,4-b>indole-1-carboxylic acid 
• 18110-86-6 4-methoxy-5-hydroxyl-canthin-6-one 
• 18110-87-7 4,5-dimethoxy-canthin-6-one 
• 127661-45-4 methyl 2,3,4,9-tetrahydro-1H-pyrido [3,4-b]indole-1-carboxylate 
• 108061-48-9 methyl 1,2,3,4-tetrahydro-β-carboline-1-carboxylate hydrochloride 
• 343-94-2 tryptamine hydochloride 
• 102991-38-8 1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid 
• 61-54-1 tryptamine 
• 96-35-5 glycolic acid methyl ester 

Downstream Products

• 203717-10-6 9-benzyl-1-methoxycarbonyl-β-carboline 
• 203717-13-9 9-benzyl-9H-pyrido[3,4-b]indole-1-carbaldehyde 
• 203717-17-3 1-(9-Benzyl-9H-β-carbolin-1-yl)-but-3-en-1-ol 
• 203717-20-8 9-Benzyl-1-[1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-9H-β-carboline 
• 203717-24-2 3-(9-Benzyl-9H-β-carbolin-1-yl)-3-(tert-butyl-dimethyl-silanyloxy)-propionaldehyde 
• 203717-22-0 4-(9-Benzyl-9H-β-carbolin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-butane-1,2-diol 
• 203717-27-5 (E)-5-(9-Benzyl-9H-β-carbolin-1-yl)-5-(tert-butyl-dimethyl-silanyloxy)-pent-2-enoic acid methyl ester 
• 17337-22-3 1-(hydroxymethyl)-β-carboline 
• 1174589-29-7 C₁₈H₁₄N₄O₃S 
• 1174589-30-0 C₁₉H₁₆N₄O₃S 
• 1309918-64-6 C₁₈H₁₃FN₄O₃S 
• 38940-60-2 9H-pyrido[3,4-b]indole-1-carboxamide 

Relevant academic research and scientific papers

Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b] indole-1-carboxylate: Concise synthesis of alangiobussinine

The carboline ring system is an important pharmacophore found in a number of biologically important targets. Development of synthetic routes for the preparation of these compounds is important in order to prepare a range of analogues containing the carboline heterocyclic moiety. A manganese dioxide mediated one-pot method starting with an activated alcohol and consisting of alcohol oxidation, Pictet-Spengler cyclisation, and oxidative aromatisation, offers a convenient process that allows access to β-carbolines. This one-pot process for the preparation of methyl 9H-pyrido[3,4-b]indole-1- carboxylate has subsequently been used as the key step in the synthesis of alangiobussinine and a closely related analogue.

In vivo potent antifilarial ss-carbolines

1-Methoxycarbonyl/carboxamido/cyano-9H-pyrido (3, 4-b) indoles have been found to exhibit interesting in vivo filaricidal activity against Litomosoides carinii and Acanthocheilonema viteae in rodents. Copyright

Facile synthesis of C1-substituted β-carbolines as CDK4 inhibitors for the treatment of cancer

Cyclin-dependent kinase 4 (CDK4), which is involved in dynamic regulation of cell cycle, has gained particularly attention for its role in controlling tumor growth. Increasing evidence showed that β-carboline derivatives have the potential to inhibit CDK4. Herein, on the basis of previous work, we designed and synthesized a series of novel β-carbolines and evaluated their antitumor activity. Among them, compounds ZDLD13 and ZDLD20, with the most potent anti-proliferative activity and CDK4 enzymatic inhibition activity, were selected for further pharmacological research in vitro and in vivo. The results in vitro showed that ZDLD13 and ZDLD20 exhibited potent anti-HCT116 activity including inhibition of colony formation, inhibition of invasion and migration, inducing of apoptosis, and arresting of G1 phase in cell cycle. In vivo, ZDLD13 showed significant tumor growth inhibition in HCT116 tumor xenograft model without causing significant weight loss and toxicity consistent with the acute toxicity test. In addition, silico study showed ZDLD13 and ZDLD20 not only have good biological actions, but also acceptable predicted ADME and physicochemical properties. Taken together, compounds ZDLD13 and ZDLD20 could be selected for further modification and preclinical evaluation.

Discovery and preliminary mechanism of 1-carbamoyl β-carbolines as new antifungal candidates

Natural β-carboline alkaloids are ideal models for the discovery of pharmaceutically important entities. Various 1-substituted β-carbolines were synthesized from commercially inexpensive tryptophan and demonstrated significant in vitro antifungal activity against G. graminis. Significantly, compound 4m (EC50 = 0.45 μM) with carboxamide at 1-position displayed the best efficacy and nearly 20 folds enhancement in antifungal potential compared to Silthiopham (EC50 = 8.95 μM). Moreover, compounds 6, 7, and 4i exhibited excellent in vitro antifungal activities and in vivo protective and curative activities against B. cinerea and F. graminearum. Preliminary mechanism studies revealed that compound 4m caused reactive oxygen species accumulation, cell membrane destruction, and deregulation of histone acetylation. These findings indicated that 1-carbamoyl β-carboline can be selected as a promising model for the discovery of novel and broad-spectrum fungicide candidates.

Pityriacitrin alkaloid derivative containing acylthiourea structure as well as preparation method and application of pityriacitrin alkaloid derivative

The invention discloses a pityriacitrin alkaloid derivative containing an acylthiourea structure as well as a preparation method and application of the pityriacitrin alkaloid derivative, and relates to a biocide of the pityriacitrin alkaloid derivative co

pityriacitrin Alkaloid derivative containing acylhydrazone structure, and preparation method and application thereof

The pityriacitrin alkaloid derivative containing the acylhydrazone structure and a preparation method and application thereof relate to a biocide containing β - carboline and 1-position of pityriacitrin alkaloids containing an acylhydrazone structure, pit

First total synthesis of the β-carboline alkaloids trigonostemine A, trigonostemine B and a new synthesis of pityriacitrin and hyrtiosulawesine

The total synthesis of four natural products, trigonostemine A, trigonostemine B, pityriacitrin, and hyrtiosulawesine was accomplished. The key intermediates, variously substituted 1-formyl-β-carbolines, were prepared in five steps via a novel synthetic approach using readily available starting materials. These formyl derivatives were then further transformed, providing a general route for the synthesis of the four title alkaloids. The method reported herein represents the first total synthesis of the two trigonostemines and a new pathway to pityriacitrin and hyrtiosulawesine.

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

Design, synthesis and biological evaluation of β-carboline derivatives as novel inhibitors targeting B-Raf kinase

β-Carboline family of compounds is a large group of alkaloids widely distributed in nature and exhibits broad-spectrum anti-tumor activities. We designed and synthesized two series of novel 1-carboxamide- and 6-sulfonamide-substituted β-carboline derivatives 7a-p and 12a-b, and their wild type B-Raf kinase inhibitory activities were described. Most compounds showed moderate to excellent inhibitory activities. Among them, 1-carboxamide-6-(N-(3-(dimethylamino)propyl)-sulfamoyl)-β-carboline, 7e exhibited potent activity (IC50 = 1.62 μM), showing the potential for further investigation as a lead compound.