79815-18-2

Basic information

• Product Name: (S)-2,3,4,9-Tetrahydro-1H-pyridol[3,4-b]-3-indolecarboxylic acid methyl ester
• Synonyms: (S)-2,3,4,9-Tetrahydro-1H-pyridol[3,4-b]-3-indolecarboxylic acid methyl ester;methyl 1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate hydrochloride
• CAS NO: 79815-18-2
• Molecular Formula: C₁₃H₁₄N₂O₂
• Molecular Weight: 266.7234
• Mol File: 79815-18-2.mol
• Article Data: 46

Chemical Properties

• Melting Point: 143-145 °C
• Boiling Point: 401.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.262±0.06 g/cm3(Predicted)
• PKA: 17.21±0.40(Predicted)
• CAS DataBase Reference: (S)-2,3,4,9-Tetrahydro-1H-pyridol[3,4-b]-3-indolecarboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2,3,4,9-Tetrahydro-1H-pyridol[3,4-b]-3-indolecarboxylic acid methyl ester(79815-18-2)
• EPA Substance Registry System: (S)-2,3,4,9-Tetrahydro-1H-pyridol[3,4-b]-3-indolecarboxylic acid methyl ester(79815-18-2)

Safety Data

• Hazardous Substances Data: 79815-18-2(Hazardous Substances Data)

Usage

Description

(S)-2,3,4,9-Tetrahydro-1H-pyridol[3,4-b]-3-indolecarboxylic acid methyl ester, also known as Methyl (3S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate, is a synthetic organic compound with a unique chemical structure. It features a tetrahydro-1H-pyrido[3,4-b]indole core, which is a fused ring system consisting of a pyridine and an indole. The presence of a carboxylic acid group and a methyl ester group further characterizes its chemical properties, making it a versatile molecule for various applications.

Uses

Used in Pharmaceutical Industry:
(S)-2,3,4,9-Tetrahydro-1H-pyridol[3,4-b]-3-indolecarboxylic acid methyl ester is used as a key intermediate in the synthesis of β-carboline-phenylsulfonylfuroxan hybrids. These hybrids are of significant interest in the pharmaceutical industry due to their potential as anti-cancer agents. The unique chemical structure of (S)-2,3,4,9-tetrahydro-1H-pyridol[3,4-b]-3-indolecarboxylic acid methyl ester allows for the development of novel compounds that can target specific cancer cells, offering new therapeutic options for patients.
In the synthesis of β-carboline-phenylsulfonylfuroxan hybrids, (S)-2,3,4,9-tetrahydro-1H-pyridol[3,4-b]-3-indolecarboxylic acid methyl ester serves as a building block, providing the necessary structural elements for the formation of the final product. The resulting hybrids are then evaluated for their anti-cancer properties, with the potential to be developed into new drugs for the treatment of various types of cancer.
Overall, (S)-2,3,4,9-tetrahydro-1H-pyridol[3,4-b]-3-indolecarboxylic acid methyl ester plays a crucial role in the development of innovative anti-cancer agents, contributing to the advancement of cancer research and the discovery of new therapeutic options.

Upstream product

• 67-56-1 methanol 
• 6052-68-2 L-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 
• 73-22-3 L-tryptophan 
• 320589-55-7 (1R,3S)-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid 
• 50-00-0 formaldehyd 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 14558-49-7 tetrahydro-1,3-oxazine 
• 4299-70-1 L-tryptophan methyl ester 
• 462-95-3 formaldehyde diethyl acetal 
• 42438-90-4 3-carboxy-1,2,3,4-tetrahydro-2-carboline 
• 73-22-3 L-Tryptophan 
• 6159-33-7 L-tryptophan hydrochloride 
• 83159-19-7 methyl (S)-(-)-2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indole-3-carboxylate hydrochloride 

Downstream Products

• 69954-48-9 methyl 9H-β-carboline-3-carboxylate 
• 160024-55-5 (S)-1,3,4,9-Tetrahydro-β-carboline-2,3-dicarboxylic acid 2-benzyl ester 3-methyl ester 
• 365216-82-6 2-(2-acetyl-benzoyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 354764-98-0 S-(-)-methyl 2-α-[N-t-butoxycarbonyl]amino-β-phenylpropionyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate 
• 365216-79-1 methyl 2-(4-chlorobenzoyl)-1,2,3,4-tetrahydro-9H-pyrido-[3,4-b]indole-3-carboxylate 
• 365216-84-8 2-(4-fluoromethyl-benzoyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 365216-85-9 (S)-2-[(2E,4E)-5-(2-Methoxy-phenyl)-penta-2,4-dienoyl]-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 365216-83-7 2-(3-fluoro-benzoyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 944072-85-9 (3S)-2-(Boc-L-tyrosinyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester 
• 944072-96-2 (3S)-2-[Boc-L-aspartyl(OBzl)]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester 
• 944072-98-4 (3S)-2-(Boc-L-histidinyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester 
• 944073-03-4 (3S)-2-[Boc-L-lysinyl(Z)]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester 
• 944073-28-3 (3S,12aS)-3-(benzyloxycarbonylmethyl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione 
• 945651-07-0 (3S,12aS)-3-(4'-benzyloxycarbonylaminobutyl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione 

Relevant articles and documents

Structure-based discovery of (S)-2-amino-6-(4-fluorobenzyl)-5,6,11,11a-tetrahydro-1H-imidazo[1′,5′:1,6]pyrido[3,4-b]indole-1,3(2H)-dione as low nanomolar, orally bioavailable autotaxin inhibitor

Inhibition of extracellular secreted enzyme autotaxin (ATX) represents an attractive strategy for the development of new therapeutics to treat various diseases and a few inhibitors entered in clinical trials. We herein describe structure-based design, syn

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.

Nanoparticles of a new small-molecule P-selectin inhibitor attenuate thrombosis, inflammation, and tumor growth in two animal models

Purpose: To assess whether the newly designed small-molecule oral P-selectin inhibitor 3S-1,2,3,4-tetrahydro-β-carboline-3-methyl aspartyl ester (THCMA) as a nanomedicine enhances antithrombosis, anti-inflammation, and antitumor activity more than the clinical trial drug PSI-697. Methods: THCMA was designed as an amphiphile containing pharmacophores of PSI-697. Its nanofeatures were explored with TEM, SEM, Tyndall effect, ζ-potential, FT-ICR-MS, and NOESY 2D1H NMR. The P-selectin inhibitory effect of THCMA was demonstrated with molecular docking, ultraviolet (UV) spectra, and competitive ELISA. In vivo and in vitro assays — anti-arterial thrombosis, anti–venous thrombosis, anti-inflammation, antitumor growth, anti–platelet aggregation, rat-tail bleeding time, anticoagulation index, soluble P-selectin (sP-selectin) expression, and serum TNFα expression — were performed to explore bioactivity and potential mechanisms. Water solubility of THCMA was measured using UV-absorption spectra. Results: THCMA self-assembled into nanorings of approximately 100 nm in diameter. Its water solubility was about 1,030-fold that of PSI-697. THCMA exhibited more potent P-selectin inhibitory effect than PSI-697. The oral efficacy of THCMA was 100-fold that of PSI-697 in inhibiting arterial and venous thrombosis and tenfold in inhibiting inflamma-tion. THCMA inhibited thrombosis at a dose that produces no coagulation disorders and no bleeding risk. THCMA exhibited enhanced antitumor activity over PSI-697 without systemic chemotherapy toxicity. THCMA significantly inhibited platelet aggregation in vitro and downregulated the expression levels of serum sP-selectin and TNFα in vivo. Conclusion: A new small-molecule P-selectin inhibitor, THCMA, has been successfully designed as a nanomedicine with largely enhanced oral efficacy compared to the clinical trial drug PSI-697, and thus might be developed for the oral treatment of arterial thrombosis, venous thrombosis, inflammation, and cancer-associated thrombosis.