827304-63-2

Basic information

• Product Name: 1H-Pyrido[3,4-b]indole-3-carboxylicacid,2,3,4,9-tetrahydro-1-methyl-,(3R)-(9CI)
• Synonyms: 1H-Pyrido[3,4-b]indole-3-carboxylicacid,2,3,4,9-tetrahydro-1-methyl-,(3R)-(9CI)
• CAS NO: 827304-63-2
• Molecular Formula: C13H14N2O2
• Molecular Weight: 0
• Product Categories: METHYL
• Mol File: 827304-63-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Pyrido[3,4-b]indole-3-carboxylicacid,2,3,4,9-tetrahydro-1-methyl-,(3R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrido[3,4-b]indole-3-carboxylicacid,2,3,4,9-tetrahydro-1-methyl-,(3R)-(9CI)(827304-63-2)
• EPA Substance Registry System: 1H-Pyrido[3,4-b]indole-3-carboxylicacid,2,3,4,9-tetrahydro-1-methyl-,(3R)-(9CI)(827304-63-2)

Safety Data

• Hazardous Substances Data: 827304-63-2(Hazardous Substances Data)

Upstream product

• 75-07-0 acetaldehyde 
• 54-12-6 Trp 
• 18070-61-6 1-methyl-1,2,3,4-tetrahydro-β-carboline-1,3-dicarboxylic acid 
• 73-22-3 L-Tryptophan 
• 153-94-6 D-tryptophan 
• 27732-43-0 tryptophan 
• 34368-37-1 (1S,3R)-methyl 1-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate 
• 132685-02-0 1,1'-ethylidenebis 
• 75-05-8 acetonitrile 
• 78-98-8 2-oxopropanal 

Downstream Products

• 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 
• 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 method of chloroindole hydrazide

The invention relates to a synthesis method of chloroindole hydrazide, and belongs to the technical field of pesticides. The specific preparation method comprises the following steps: (1) uniformly mixing a compound shown as a formula (I), a solvent I, acetonitrile and a catalyst I, and then adding a hydrogen source for reaction; after the reaction is finished, treating to obtain a compound shown as a formula (II); (2) mixing the compound shown in the formula (II), (4-chlorphenyl) methylene hydrazine, a solvent II and a catalyst II for reaction, and after the reaction is completed, performing post-treatment to obtain chloroindole hydrazide; a novel synthetic route is provided, catalytic hydrogenation cyclization is performed on tryptophan or ester thereof and acetonitrile, and then reacts with (4-chlorphenyl) methylene hydrazine to obtain the chloroindole hydrazide through two steps. Compared with the prior art, the preparation method has the advantages of short synthesis steps, high reaction yield, no use of high-toxicity, strong-corrosivity and strong-irritation reagents, and convenience in realization of industrial production.

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 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.

Design and synthesis of β-carboline derivatives with nitrogen mustard moieties against breast cancer

To discover the promising antitumor agents, a series of β-carboline derivatives with nitrogen mustard moieties were designed and synthesized. Most target derivatives showed antiproliferative activity against MCF-7 and MDA-MB-231 cells. Among them, (1-meth

A class β . Preparation method and anti-tumor application

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Discovery of pyridoindole derivatives as potential inhibitors for phosphodiesterase 5A: in silico and in?vivo studies

The aim of this work was to synthesise derivatives from identified plant based pyridoindole lead scaffold, and to assess phosphodiesterase 5A inhibitory potential by in silico and in?vivo. Pyridoindole derivatives were synthesised by using six-stage reactor. In silico screening was carried out by grip-based docking methodology. In step-I, tryptophan as a starting material was reacted with different aldehydes and ketones to obtain 11 molecules. In step-II, obtained molecules were reacted with ethanol and benzyl alcohols to obtain D1 to D22 derivatives. In silico investigation resulted in best three molecules D12, D4 and D8 with promising BE score. Oral acute toxicity study of selected molecules resulted in LD50 value 500 mg/kg in rats. The result of in?vivo antihypertensive study shown that molecule D12 was found to be the best antihypertensive lead molecule. This study could be a best platform to tailor novel biomolecules for inhibiting phosphodiesterase 5A enzyme in hypertension management.

3-di-amine β- carboline base compound, preparation method and pharmaceutical composition and application thereof

The invention discloses a 3-position diamine connected beta-carboline alkali compound, and a preparation method, a medicinal composition and a use thereof. The above di-beta-carboline alkali compound and its medicinal salt are represented by general formu

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.

Compound and preparation method and application thereof

The invention relates to the field of anticancer and analgesic drugs. The present invention provides compounds useful for the preparation of cancer treatment and analgesic agents. The invention also provides a preparation method of the compound. The synthesis method provided by the invention is simple to operate, has universality and is suitable for batch production. The invention provides an application of the compound in preparation of drugs for treating cancers and pains. The medicine prepared from the compound can effectively resist cancer and reduce dependence on opioid medicines in cancer pain treatment, and a good pain management mechanism is established.

Design, synthesis, characterization, and biological activities of novel spirooxindole analogues containing hydantoin, thiohydantoin, urea, and thiourea moieties

On the basis of the scaffolds widely used in drug design, a series of novel spirooxindole derivatives containing hydantoin, thiohydantoin, urea, and thiourea moieties have been designed, synthesized, characterized, and first evaluated for their biological activities. The diastereoselectivity mechanism is proposed, and the systematic conformational analysis is performed. The bioassay results show that the target compounds possess moderate to good antiviral activities against tobacco mosaic virus (TMV), among which compound 22 shows the highest antiviral activity in vitro as well as inactivation, curative, and protection activities in vivo (45 ± 1, 47 ± 3, 50 ± 1, and 51 ± 1%, 500 mg/L, respectively), higher than ribavirin (38 ± 1, 36 ± 1, 38 ± 1, and 36 ± 1%, 500 mg/L, respectively). Thus, compound 22 is a promising candidate for anti-TMV development. Most of these compounds show broad-spectrum fungicidal activities against 14 kinds of phytopathogenic fungi and selective fungicidal activities against Physalospora piricola, Sclerotinia sclerotiorum, and Rhizoctonia cerealis. Additionally, some of these compounds exhibit insecticidal activity against Culex pipiens pallens, Mythimna separata, Helicoverpa armigera, and Pyrausta nubilalis. Compound 17 exhibits the highest larvicidal activity (LC50 was 0.32 mg/L) against C. pipiens pallens.