22329-38-0

Usage

Uses

Used in Pharmaceutical Industry:
1-methyl-beta-carboline-3-carboxylic acid is used as a novel protein tyrosine phosphatase 1B inhibitor for potential therapy in diabetes management. Its ability to inhibit this enzyme may help regulate glucose metabolism and improve insulin sensitivity, offering a promising approach to treating diabetes and its complications.

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

• 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 
• 55857-67-5 ethyl (1S,3S)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 
• 40678-46-4 (1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 
• 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 
• 186816-24-0 9-Methoxymethyl-1-methyl-9H-β-carboline-3-carboxylic acid 

Downstream Products

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

Relevant academic research and scientific papers

Discovery of β-carboline-(phenylsulfonyl)furoxan hybrids as potential anti-breast cancer agents

The cytotoxicity properties of the β-carboline alkaloids have been broadly investigated. However, the potential application of β-carbolines was hindered due to the moderate activity in cancer. In the present study, thirty β-carboline-(phenylsulfonyl)furoxan hybrids (11a–j, 12a–j and 13a–j) were designed and synthesized through esterification and amidation reaction strategy, and their inhibitory activities against the human breast cancer cell lines MCF-7 and MDA-MB-231 were evaluated by CCK-8 assay. Biological evaluation presented that the most promising amide derivative 13h, substituted with p-methoxyphenyl group at position 1, generated high concentration of NO and evidently depressed the MCF-7 (IC50 = 0.89 μM) and MDA-MB-231 (IC50 = 0.62 μM) cells proliferation. Particularly, the wound healing and transwell assays demonstrated that 13h significantly inhibited the migration and invasion of MDA-MB-231cells. Furthermore, the preliminary mechanisms studies indicated that 13h induced G2/M phase arrest and apoptosis possibly causing by ROS accumulation and ROS-mediated DNA damage. Based on these considerations, 13h may be a promising antimetastatic agent for breast cancer, which is noteworthy for further exploration.

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.

1-substituted beta-carboline derivative and application thereof

The invention discloses 1-substituted beta-carboline derivatives and an application of the 1-substituted beta-carboline derivatives. According to the invention, beta-carboline is used as a parent nucleus; the 1-substituted beta-carboline derivatives are mainly synthesized by introducing alkyl and electron withdrawing groups at the No.1 position, agriculturally important plant pathogenic fungi andbacteria are selected, the inhibitory activity of the compound on fungi and bacteria is tested, and bacteriostatic activity test results show that the 1-substituted beta-carboline derivatives have inhibitory activity on various plant pathogenic bacteria.

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.

O-(2-oxazolinyl)aniline heterocyclic amide compound and application as agricultural fungicide

The invention relates to a novel o-(2-oxazolinyl) aniline heterocyclic amide compound and application of the compound as agricultural fungicide. The chemical structural formula of the compound is represented by a following formula (I), the meaning of each group is shown in the specification, and the stereo configuration of carboxylic acid and amine structural fragments of the compound has a significant effect on the bacteriostatic activity; (please see the specification for the formula) and the stereo configuration of a carbon atom attached to the substituent R in the general formula (I) is Ror S.

Synthesis and structure-activity relationships of asymmetric dimeric β-carboline derivatives as potential antitumor agents

A series of newly asymmetric dimeric β-carbolines with a spacer of 4–6 methylene units between the indole nitrogen and the harmine oxygen were synthesized. Structures of all the novel synthesized compounds were confirmed by their spectral and analytical studies. All of the synthesized compounds were screened for their in vitro cytotoxic activity against nine cancer cell lines. The results revealed that compounds 7c, 7o and 7s exhibited the highest cytotoxic activities with IC50 values of less than 20 μM against the tumor cell lines tested. Acute toxicities and antitumor efficacies of the selected compounds in mice were also evaluated, and compound 7o exhibited potent antitumor activities with the tumor inhibition rate of over 40%. The wound healing assay displayed a specific impairment in the motility of the HT-29 cells, which suggested the anti-metastatic potential of compound 7o. Moreover, compound 7o had obvious angiogenesis inhibitory effects in the chicken chorioallantoic membrane (CAM) assay. Preliminary structure-activity relationship (SAR) analysis indicated that: (1) 3-phenylpropyl substituent at the N9-position of the indole ring was the most suitable group giving rise to potent cytotoxic agents; (2) the spacer length affected the antitumor potencies, and four methylene units were more favorable.

Design and Discovery of Novel Chiral Antifungal Amides with 2-(2-Oxazolinyl)aniline as a Promising Pharmacophore

Inspired by established succinate dehydrogenase inhibitors (SDHIs), our continuing efforts toward the discovery of chiral antifungal amides turned to the optimization of their polar regions with 2-(2-oxazolinyl)aniline as a known pharmacophore. Scaffold hopping and bioactivity-guided convergent synthesis enabled the identification of promising antifungal categories. Fine tuning of the substituents and chirality furnished seven amides (1s, 1t, 2d, 2h, 2j, 3k, and 2l) as antifungal candidates, with EC50 values lower than 5 mg/L. The first investigation of chiral amides of acyclic acids as SDHIs was conducted, and compound 2d was selected as a promising candidate against Botrytis cinerea, with a preventative efficacy of up to 93.9% at 50 mg/L, which is better than that of boscalid. The different binding models between compounds with different configurations were simulated for compound 2d and its diastereoisomers. The benefits of synthetic accessibility and cost-effectiveness highlight the practical potential for compound 2d as a good alternative to known SDHI fungicides.

Development of novel β-carboline-based hydroxamate derivatives as HDAC inhibitors with DNA damage and apoptosis inducing abilities

A series of novel β-carboline-based hydroxamate derivatives (8a-n) as HDAC inhibitors have been designed and synthesized. Most of these compounds displayed potent histone deacetylase inhibitory effects and good antiproliferative activity with IC50/s

?-CARBOLINE, DIHYDRO-?-CARBOLINE AND TETRAHYDRO-?-CARBOLINE ALKALOID DERIVATIVES AND PREPARATION METHODS SAME AND USE IN ASPECTS OF PREVENTING AND TREATING PLANT VIRUSES, FUNGICIDES AND INSECTICIDES

The present invention relates to β-carboline, dihydro-β-carboline and tetrahydro-β-carboline alkaloid derivatives (I) and a method for preparing same and the use in the aspects of preventing and treating plant viruses, fungicides and insecticides. For the meaning of each group in formula (I) see the description. The β-carboline, dihydro-β-carboline and tetrahydro-β-carboline alkaloid derivatives of the present invention show a particularly ourstanding anti-plant virus activity, and also have fungicidal and insecticidal activities.

He krien-β- [...] multifunctional particle with two cholinesterase inhibitors

The invention relates to the field of medicinal chemistry, and particularly relates to tacrine-beta-carboline conjoined compounds (I, II and III). The pharmacodynamic test proves that the compound disclosed by the invention can be used as a multifunction cholinesterase inhibitor, and can be clinically applied to treatment of an alzheimer disease.