33821-71-5

Basic information

• Product Name: 9H-Pyrido[3,4-b]indole-3-carboxylic acid, 1-methyl-, ethyl ester
• Synonyms: ethyl 1-methylpyrido<3,4-b>indole-3-carboxylate;ethyl harman-3-carboxylate
• CAS NO: 33821-71-5
• Molecular Formula: C15H14N2O2
• Molecular Weight: 254.28400
• Mol File: 33821-71-5.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: 9H-Pyrido[3,4-b]indole-3-carboxylic acid, 1-methyl-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 9H-Pyrido[3,4-b]indole-3-carboxylic acid, 1-methyl-, ethyl ester(33821-71-5)
• EPA Substance Registry System: 9H-Pyrido[3,4-b]indole-3-carboxylic acid, 1-methyl-, ethyl ester(33821-71-5)

Safety Data

• Hazardous Substances Data: 33821-71-5(Hazardous Substances Data)

Upstream product

• 95202-46-3 2-isopropyl-1-methoxymethylindole-3-carbaldehyde 
• 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 
• 6519-66-0 DL-tryptophan ethyl ester 
• 54-12-6 Trp 
• 5470-37-1 1-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid 
• 39824-90-3 ethyl 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate 
• 95202-49-6 ethyl 2-azido-3-(2-isopropyl-1-methoxymethylindol-3-yl)propenoate 
• 84543-23-7 ethyl 2-azido-3-(2-ethyl-1-methoxymethylindol-3-yl)propenoate 
• 95202-44-1 2-isopropyl-1H-indole-3-carbaldehyde 
• 95202-42-9 2-ethyl-1H-indole-3-carboxaldehyde 
• 17790-93-1 2-isopropyl-1H-indole 
• 3484-18-2 2-ethylindole 
• 84543-19-1 2-ethyl-1-methoxymethylindole-3-carbaldehyde 

Downstream Products

• 22329-38-0 harman-3-carboxylic acid 
• 33821-72-6 (1-methyl-9H-pyrido[3,4-b]indol-3-yl)methanol 
• 777062-70-1 1-methyl-9H-pyrido[3,4-b]indole-3-carbaldehyde 

Relevant articles and documents

Synthesis of beta-carbolines and azepino[4,5-b]indoles from azidoacrylates

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Molecular hybrid design, synthesis, in vitro and in vivo anticancer evaluation, and mechanism of action of N-acylhydrazone linked, heterobivalent β-carbolines

A series of N-acylhydrazone-linked, heterobivalent β-carboline derivatives was designed and synthesized from L-tryptophan in a nine-step reaction sequence. The effort resulted in the heterobivalent β-carbolines 10a–t in good yields. The target compounds were characterized by 1H NMR, 13C NMR and high-resolution mass spectrometry (HRMS). The in vitro cytotoxic activity of the synthesized compounds was evaluated against normal EA.HY926 cells and five cancer cell lines: LLC (Lewis lung carcinoma), BGC-823 (gastric carcinoma), CT-26 (murine colon carcinoma), Bel-7402 (liver carcinoma), and MCF-7 (breast carcinoma). Compound 10e, with an IC50 value of 2.41 μM against EA.HY926 cells, was the most potent inhibitor. It showed cytotoxicity against all five cancer cell lines of different origin – murine and human, with IC50 values ranging from 4.2 ± 0.7 to 18.5 ± 3.1 μM. A study of structure-activity relationships indicated that the influence on cytotoxic activities of the substituent in the R9′-position followed the tendency, 2,3,4,5,6-perfluorophenylmethyl > 4-fluorobenzyl > 3-phenylpropyl group. The antitumor efficacies of the selected compounds were also evaluated in mice. Compound 10e exhibited potent antitumor activity, with tumor inhibition of more than 40% for Sarcoma 180 and 36.7% for Lewis lung cancer. Furthermore, the pharmacological mechanisms showed that compound 10e has a certain impairment in the motility of LLC cells, which suggests the anti-metastatic potential. And compound 10e inhibited angiogenesis in chicken chorioallantoic membrane assay, and the anti-angiogenetic potency was more potent than the reference drug combretastatin A4-phosphate (CA4P) at a concentration 50 μM.

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.