40678-46-4

Usage

Uses

Used in Pharmaceutical Research and Development:
(1S,3S)-2,3,4,9-TETRAHYDRO-1-METHYL-1H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLIC ACID is utilized as a research compound for studying its potential impact on neurotransmitter pathways, which may contribute to the development of treatments for neurological disorders or psychological conditions.
Used in Neuropharmacology:
In the field of neuropharmacology, (1S,3S)-2,3,4,9-TETRAHYDRO-1-METHYL-1H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLIC ACID is used as a compound of interest for its possible effects on neurotransmitter pathways, with ongoing research exploring its therapeutic potential for various neurological and psychological conditions.

InChI:InChI=1/C13H14N2O2/c1-7-12-9(6-11(14-7)13(16)17)8-4-2-3-5-10(8)15-12/h2-5,7,11,14-15H,6H2,1H3,(H,16,17)/t7-,11-/m0/s1

Upstream product

• 75-07-0 acetaldehyde 
• 54-12-6 Trp 
• 73-22-3 L-Tryptophan 
• 78-98-8 2-oxopropanal 
• 132685-02-0 1,1'-ethylidenebis 
• 18070-61-6 1-methyl-1,2,3,4-tetrahydro-β-carboline-1,3-dicarboxylic acid 
• 75-05-8 acetonitrile 

Downstream Products

• 16108-10-4 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester 
• 10022-82-9 D,L-1-Methyl-3,4-dihydro-β-carboline-3-carboxylic acid 
• 74914-76-4 3-methoxycarbonyl-1-styryl-β-carbolin 
• 22329-38-0 harman-3-carboxylic acid 
• 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 
• 486-84-0 harmane 
• 16641-82-0 1-methyl-β-carboline-3-carboxylic acid methyl ester 
• 129201-72-5 (5S,11aS)-5-methyl-2-phenyl-5,6,11,11a-tetrahydro-1H-imidazo-[1′,5′:1,6]pyrido[3,4-b]indole-1,3(2H)-dione 

Relevant academic research and scientific papers

Synthesis and Antiviral/Fungicidal/Insecticidal Activities Study of Novel Chiral Indole Diketopiperazine Derivatives Containing Acylhydrazone Moiety

On the basis of the mechanism of acylhydrazone compounds inhibiting the assembly of TMV CP and the unique structural characteristics of diketopiperazine ring, a series of optically pure indole diketopiperazine acylhydrazone were designed and synthesized. In order to systematically study the effect of the spatial configuration of the compounds on the antiviral activity, four compounds with different spatial configurations at C6 and C12a were also prepared. The bioassay results indicated that most of these new compounds displayed moderate to good antiviral activity, among which compounds 23, 25, 27, 28, 31, and 5d showed a significantly higher activity than that of commercial ribavirin. An in-depth structure-activity relationship investigation showed that the spatial conformation was one of the most important factors in adjusting antiviral activity; the research results provided information about the possible optimum configuration for interaction of this molecular with its target protein. At the same time, these new compounds also exhibited broad-spectrum fungicidal activities against 14 kinds of phytopathogenic fungi. What's more, some of these compounds exhibited good insecticidal activity to Plutella xylostella and Culex pipiens pallens.

Structural Basis for β-Carboline Alkaloid Production by the Microbial Homodimeric Enzyme McbB

Summary The β-carboline (βC) alkaloids occur throughout nature and exhibit diverse biological activities. In contrast to βC alkaloid synthesis in plants, the biosynthesis in microorganisms remains poorly understood. The recently reported McbB from Marinactinospora thermotolerans is a novel enzyme proposed to catalyze the Pictet-Spengler (PS) reaction of L-tryptophan and oxaloacetaldehyde to produce the βC scaffold of marinacarbolines. In this study, we solved the crystal structure of McbB complexed with L-tryptophan at 2.48 ? resolution, which revealed the novel protein folding of McbB and the totally different structure from those of other PS condensation catalyzing enzymes, such as strictosidine synthase and norcoclaurine synthase from plants. Structural analysis and site-directed mutagenesis confirmed that the previously proposed catalytic Glu97 at the active-site center functions as an acid and base catalyst. Remarkably, the structure-based mutants R72A and H87A, with expanded active-site cavities, newly accepted bulky phenylglyoxal as the aldehyde substrate, to produce 1-benzoyl-3-carboxy-β-carboline.

Docking based design of diastereoisomeric MTCA as GPIIb/IIIa receptor inhibitor

In GPIIb/IIIa mediated arterial thrombosis platelet activation plays a central role. To discover platelet activation inhibitor the pharmacophores of GPIIb/IIIa receptor inhibitors and anti-thrombotic agents were analyzed. This led to the design of (1R,3S)- and (1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acids as GPIIb/IIIa inhibitors. Comparing to (1S,3S)-isomer (1R,3S)-isomer had lower cdocker interaction energy. AFM image showed that the minimal effective concentration of (1S,3S)-isomer and (1R,3S)-isomer inhibiting platelet activation were 10?5 M and 10?6 M, respectively. In vivo 1 μmol/kg of oral (1S,3S)-isomer effectively inhibited the rats to form arterial thrombus and down regulated GPIIb/IIIa expression, but the activities were significantly lower than those of 1 μmol/kg of oral (1R,3S)-isomer. Both (1S,3S)-isomer and (1R,3S)-isomer can be safely used for structural modifications, but (1R,3S)-isomer should be superior to (1S,3S)-isomer.

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 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.

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.

Preparation method and application of [beta]-carboline compound intermediate

The invention provides a preparation method and application of a [beta]-carboline compound intermediate, and belongs to the technical field of chemical engineering, the preparation method comprises the following steps: mixing an aqueous solution of L-tryptophan, acetaldehyde and methanol, lewis acid, Bronsted acid and chiral amine, carrying out a synthetic reaction on the obtained mixture, and obtaining a [beta]-carboline compound intermediate (1S, 3S)-1-methyl-2, 3, 4, 9-tetrahydropyrido[3, 4-b]indole-3-formic acid. The (1S, 3S)-1-methyl-2, 3, 4, 9-tetrahydropyrido[3, 4-b]indole-3-formic acidprepared by adopting the method is high in product yield and high in ee value.

Carboline derivative, production method of carboline derivative and application of carboline derivative on aspects of plant virus control, fungus killing and insect killing

The invention relates to a tetrahydro-beta-carboline derivative containing a diketopiperazine acylhydrazone structure, a production method of the tetrahydro-beta-carboline derivative containing the diketopiperazine acylhydrazone structure and application

Novel β-carboline-based indole-4,7-quinone derivatives as NAD(P)H: Quinone-oxidoreductase-1 inhibitor with potent antitumor activities by inducing reactive oxygen species, apoptosis, and DNA damage

Eighteen new β-carboline-based indole-4,7-quinone derivatives (12a–i and 13a–i) were designed and synthesized, and their in vitro and in vivo antiproliferative activities were studied. Most of target compounds showed strong inhibition on three human tumor cells' proliferation. In particular, the most active compound 13g not only displayed more prominent antiproliferative activities than β-lapachone, a clinical antitumor candidate, but also exerted significant NAD(P)H: quinone-oxidoreductase-1 (NQO1) inhibitory activity and NQO1-dependent cytotoxicity in HT29 cells. Furthermore, 13g dose-dependently induced high ROS levels in HT29 cells, and selectively inhibited cancer cell but not non-tumor colon cell proliferation in vitro. Importantly, 13g promoted HT29 cell apoptosis and DNA damage by regulating relative apoptotic proteins and H2AX expression. Finally, 13g displayed significant growth inhibition of HT29 human colorectal adenocarcinoma xenograft in mice without overt toxicity.

Synthesis and biological evaluation of novel N9-heterobivalent β-carbolines as angiogenesis inhibitors

A series of novel N9-heterobivalent β-carbolines has been synthesized. All the novel compounds were tested for their anticancer activity against six tumour cell lines in vitro. Among these molecules, compounds 5b, and 5w exhibited strong cytotoxic activities with IC50 value of lower than 20 μM. Acute toxicities and antitumor efficacies of the selected compounds in mice were also evaluated, compounds 5b and 5w exhibited that tumour inhibition rate of over 40% in the Sarcoma 180 and Lewis lung cancer animal models. Preliminary structure–activity relationships (SARs) analysis indicated that: (1) C1-methylation and C7-methoxylation were favorable for increased activities; (2) 3-Pyridyl or 2-thienyl group substituent into position-1 of the β-carboline core, and the aryl substituent into another β-carboline ring might be detrimental to cytotoxic effects of this class compounds. Investigation of the preliminary mechanism of action demonstrated that compound 5b had obvious angiogenesis inhibitory effects in the chicken chorioallantoic membrane (CAM) assay.