40678-46-4

Basic information

• Product Name: (1S,3S)-2,3,4,9-TETRAHYDRO-1-METHYL-1H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLIC ACID
• Synonyms: (1S,3S)-2,3,4,9-TETRAHYDRO-1-METHYL-1H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLIC ACID;1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid;(1S-cis)-2,3,4,9-Tetrahydro-1-methyl-1H-pyrido(3,4-B)indole-3-carboxylic acid;1H-Pyrido(3,4-B)indole-3-carboxylic acid, 2,3,4,9-tetrahydro-1-methyl-, (1S-cis)-
• CAS NO: 40678-46-4
• Molecular Formula: C₁₃H₁₄N₂O₂
• Molecular Weight: 230.26
• Mol File: 40678-46-4.mol
• Article Data: 41

Chemical Properties

• Boiling Point: 488°Cat760mmHg
• Flash Point: 248.9°C
• Appearance: /
• Density: 1.301g/cm³
• Vapor Pressure: 2.44E-10mmHg at 25°C
• Refractive Index: 1.654
• CAS DataBase Reference: (1S,3S)-2,3,4,9-TETRAHYDRO-1-METHYL-1H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3S)-2,3,4,9-TETRAHYDRO-1-METHYL-1H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLIC ACID(40678-46-4)
• EPA Substance Registry System: (1S,3S)-2,3,4,9-TETRAHYDRO-1-METHYL-1H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLIC ACID(40678-46-4)

Safety Data

• Hazardous Substances Data: 40678-46-4(Hazardous Substances Data)

Usage

General Description

The chemical (1S,3S)-2,3,4,9-Tetrahydro-1-methyl-1H-pyrido[3,4-b]indole-3-carboxylic acid is a compound with a complex molecular structure. It contains a pyrido[3,4-b]indole core with a carboxylic acid functional group and a methyl substituent. This chemical is a specific stereoisomer with a (1S,3S) configuration. It is commonly used in pharmaceutical research and development, particularly in the study of neuropharmacology due to its potential impact on neurotransmitter pathways. (1S,3S)-2,3,4,9-TETRAHYDRO-1-METHYL-1H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLIC ACID may have applications in the treatment of neurological disorders or psychological conditions, and further research is being conducted to explore its potential therapeutic uses.

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 
• 22329-38-0 harman-3-carboxylic acid 
• 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 
• 1256282-52-6 9-(3-phenylpropyl)-1-methyl-β-carboline-3-carboxaldehyde 
• 1256282-49-1 9-benzyl-1-methyl-β-carboline-3-carboxaldehyde 
• 799821-75-3 ethyl 9-phenylpropyl-1-methyl-β-carboline-3-carboxylate 
• 142272-78-4 ethyl 9-benzyl-1-methyl-9H-pyrido[3,4-b]indole-3-carboxylate 

Relevant articles and documents

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.

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.

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.

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.