22329-38-0

Basic information

• Product Name: 1-methyl-beta-carboline-3-carboxylic acid
• Synonyms: 1-methyl-beta-carboline-3-carboxylic acid;1-Methyl-9H-pyrido[3,4-b]indole-3-carboxylic acid
• CAS NO: 22329-38-0
• Molecular Formula: C₁₃H₁₀N₂O₂
• Molecular Weight: 226.24
• Mol File: 22329-38-0.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 520.3°Cat760mmHg
• Flash Point: 268.5°C
• Appearance: /
• Density: 1.431g/cm³
• Vapor Pressure: 1.19E-11mmHg at 25°C
• Refractive Index: 1.778
• CAS DataBase Reference: 1-methyl-beta-carboline-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-beta-carboline-3-carboxylic acid(22329-38-0)
• EPA Substance Registry System: 1-methyl-beta-carboline-3-carboxylic acid(22329-38-0)

Safety Data

• Hazardous Substances Data: 22329-38-0(Hazardous Substances Data)

Usage

Uses

Harman-3-carboxylic acid is part of a group of canthinone alkaloids used as novel protein tyrosine phosphatase 1B inhibitors as potential therapy for diabetes.

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

Upstream product

• 16641-82-0 1-methyl-β-carboline-3-carboxylic acid methyl ester 
• 40678-46-4 (1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 
• 55857-67-5 ethyl (1S,3S)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 
• 33821-71-5 ethyl 1-methyl-9H-pyrido[3,4-b]indole-3-carboxylateyl-2,3,4,9-tetrahydro-1Hpyrido[3,4-b]indole-3-carboxylate 
• 10022-82-9 D,L-1-Methyl-3,4-dihydro-β-carboline-3-carboxylic acid 
• 16108-10-4 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester 
• 5470-37-1 1-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid 
• 54-12-6 Trp 
• 84543-27-1 ethyl 9-methoxymethyl-1-methylpyrido<3,4-b>indole-3-carboxylate 
• 191279-38-6 (3S)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester 
• 93598-06-2 (1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester 
• 4299-70-1 L-tryptophan methyl ester 
• 73-22-3 L-Tryptophan 
• 191279-37-5 (3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 

Downstream Products

• 777062-70-1 1-methyl-9H-pyrido[3,4-b]indole-3-carbaldehyde 

Relevant articles and documents

Photosensitized conversion of tryptophan to beta-carboline derivatives.

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Discovery of β-Carboline Derivatives as a Highly Potent Cardioprotectant against Myocardial Ischemia-Reperfusion Injury

Timely myocardial reperfusion salvages ischemic myocardium from infarction, whereas reperfusion itself induces cardiomyocyte death, which is called myocardial ischemia/reperfusion (MI/R) injury. Herein, β-carboline derivative 17c was designed and synthesized with obvious myocardial protective activity for the first time. Pretreatment of 17c effectively protected the cardiomyocyte H9c2 cells from H2O2-induced lactate dehydrogenase leakage and restored the endogenous antioxidants, superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px). Besides, 17c effectively protected the mitochondria through decreasing the reactive oxygen species overproduction and enhancing the mitochondrial membrane potential. As a result, 17c significantly reduced the necrosis of cardiomyocytes in H2O2-induced oxidative stress, which was more potent than polydatin. In MI/R injury rats, 17c pretreatment obviously increased the levels of SOD and GSH-Px and inhibited the apoptosis of cardiomyocytes. Through this way, the size of myocardial infarction was significantly reduced after MI/R injury in vivo, better than that of polydatin, suggesting that 17c is a promising cardioprotectant for the prevention of MI/R injury.

Design and Synthesis of Biotinylated Bivalent Carboline Derivatives as Potent Antitumor Agents

Compound 6, a novel β-carboline comprising two 1-methyl-9H-β-carboline-3-carboxylic acids and a biotin moiety conjugated together using tris(2-Aminoethyl)amine, was synthesized and tested for its cytotoxicity toward MCF-7 and HepG2 cell lines and antitumor potency in an S180 tumor-bearing mouse model. Compound 6 was delivered via biotin receptor-mediated endocytosis and exerted its therapeutic effects by intercalation binding with DNA. In vivo antitumor evaluations of 6 revealed that it is efficacious and exhibits low systemic toxicity.