65474-79-5

Basic information

• Product Name: 3-HYDROXYMETHYL-BETA-CARBOLINE
• Synonyms: 3-HMC;3-HYDROXYMETHYL-BETA-CARBOLINE;(9H-B-CARBOLIN-3-YL)-METHANOL;3-HYDROXYMETHYL-B-CARBOLINE (3-HMC);(9H-pyrido[3,4-b]indol-3-yl)methanol;3-Hydroxymethyl-b-carboline
• CAS NO: 65474-79-5
• Molecular Formula: C₁₂H₁₀N₂O
• Molecular Weight: 198.22
• Mol File: 65474-79-5.mol

Chemical Properties

• Melting Point: 225-228°
• Boiling Point: 466 °C at 760 mmHg
• Flash Point: 235.6 °C
• Appearance: Yellow solid
• Density: 1.385 g/cm³
• Vapor Pressure: 1.74E-09mmHg at 25°C
• Refractive Index: 1.795
• PKA: 13?+-.0.10(Predicted)
• CAS DataBase Reference: 3-HYDROXYMETHYL-BETA-CARBOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXYMETHYL-BETA-CARBOLINE(65474-79-5)
• EPA Substance Registry System: 3-HYDROXYMETHYL-BETA-CARBOLINE(65474-79-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 65474-79-5(Hazardous Substances Data)

Usage

Uses

As tools for studying benzodiazepine receptors.

InChI:InChI=1/C12H10N2O/c15-7-8-5-10-9-3-1-2-4-11(9)14-12(10)6-13-8/h1-6,14-15H,7H2

Upstream product

• 69954-48-9 methyl 9H-β-carboline-3-carboxylate 
• 74214-62-3 ethyl 9H-pyrido[3,4-b]indole-3-carboxylate 
• 73-22-3 L-Tryptophan 
• 84518-77-4 ethyl 1,2,3,4-tetrahydro-β-carboline-3-carboxylate 
• 80994-42-9 ethyl (S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 42021-12-5 dl-methyl-1,2,3,4-tetrahydro-9H-pyrido-<3,4-b>indole-3-carboxylate hydrochloride 
• 79815-18-2 methyl (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate 
• 42438-90-4 3-carboxy-1,2,3,4-tetrahydro-2-carboline 
• 6052-68-2 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 
• 42021-11-4 methyl 1,2,3,4-tetrahydro-β-carboline-3-carboxylate 

Downstream Products

• 88932-14-3 3-acetoxymethyl-β-carboline 
• 274919-20-9 [9-(2,5-dichlorobenzyl)-9H-β-carbolin-3-yl]methyl acetate 
• 1001672-35-0 3-(4-((9H-pyrido[3,4-b]indol-3-yl)methyl)piperazin-1-yl)phenol 

Relevant articles and documents

Structure-Based Design and Synthesis of N-Substituted 3-Amino-β-Carboline Derivatives as Potent αβ-Tubulin Degradation Agents

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Carboline derivative/analogue as well as preparation method and application thereof

The invention belongs to the field of chemical medicines, and provides a compound shown as a formula I or pharmaceutically acceptable salt thereof. The invention also provides analogues of the compound as shown in the formula I in the specification. Biological experiments show that the compound disclosed by the invention has anti-tumor activity and serves as a good tubulin inhibitor; the compound91b has excellent antitumor activity, can effectively promote degradation of tubulin; drug resistance caused by overexpression of beta-tubulin III and P-gp can be eliminated, and a new choice is provided for clinical medication.

Design, synthesis, and biological evaluation of novel N-acylhydrazone bond linked heterobivalent β-carbolines as potential anticancer agents

Utilizing a pharmacophore hybridization approach, we have designed and synthesized a novel series of 28 new heterobivalent β-carbolines. The in vitro cytotoxic potential of each compound was evaluated against the five cancer cell lines (LLC, BGC-823, CT-26, Bel-7402, and MCF-7) of different origin—murine and human, with the aim of determining the potency and selectivity of the compounds. Compound 8z showed antitumor activities with half-maximal inhibitory concentration (IC50) values of 9.9 ± 0.9, 8.6 ± 1.4, 6.2 ± 2.5, 9.9 ± 0.5, and 5.7 ± 1.2 μM against the tested five cancer cell lines. Moreover, the effect of compound 8z on the angiogenesis process was investigated using a chicken chorioallantoic membrane (CAM) in vivo model. At a concentration of 5 μM, compound 8z showed a positive effect on angiogenesis. The results of this study contribute to the further elucidation of the biological regulatory role of heterobivalent β-carbolines and provide helpful information on the development of vascular targeting antitumor drugs.

Synthesis and biological evaluation of novel 3,9-substituted β-carboline derivatives as anticancer agents

Abstract In our previous studies on 1-benzyl-3-(5-hydroxymethyl-2-furyl)indazole (YC-1) analogs, we synthesised numerous substituted carbazole and α-carboline derivatives, which exhibited anticancer activity. In this study, we designed and synthesised a series of 3,9-substituted β-carbolines, by replacing the tricyclic rings of carbazole and α-carboline derivatives with isosteric β-carboline, and evaluated anticancer activity. We observed that 9-(2-methoxybenzyl)-β-carboline-3-carboxylic acid (11a) inhibited the growth of HL-60 cells by inducing apoptosis, with a half maximal inhibitory concentration of 4.0 μM. Our findings indicate that β-carboline derivatives can be used as lead compounds for developing novel antitumor agents.

A facile synthesis of 3-substituted 9H-pyrido[3,4-b]indol- 1(2H)-one derivatives from 3-substituted β-carbolines

A mild and efficient two-step synthesis of 3-substituted β-carbolinone derivatives from 3-substituted β-carboline in good yields is described. A possible reaction mechanism for the formation of the skeleton of β-carbolin-1-one is proposed. The structures of these compounds were established by IR, 1H-NMR, 13C-NMR, mass spectrometry and elemental analysis, as well as X-ray crystallographic analysis of 4-2 and 6-2.

HETEROCYCLIC COMPOUNDS AS SEROTONERGIC AND DOPAMINERGIC AGENTS AND USES THEREOF

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This invention relates to compounds of general formula (I), wherein R1, R2, R3, R4 and R5 are as defined specification; intermediates used in their preparation, preparation processes and use thereof. The present invention produce harmine derivatives with enhanced antihumour activity and lower nervous system toxicity by structurally modification parent structure of β-carboline of harmines at position 1, 2, 3, 7 and 9, The compounds of the present invention can be pre easily with high yield. They can be used in manufacture of a variety of antitumour medicines and medicines used in treatm tumour diseases in combination of light or radiation therapy.