6519-66-0

Usage

InChI:InChI=1/C13H16N2O2/c1-2-17-13(16)11(14)7-9-8-15-12-6-4-3-5-10(9)12/h3-6,8,11,15H,2,7,14H2,1H3/t11-/m0/s1

Upstream product

• 54-12-6 Trp 
• 120-72-9 indole 
• 64-17-5 ethanol 
• 15142-91-3 rac-3-(1H-indol-3-yl)-2-methylpropanoic acid 
• 101427-38-7 2,2'-dinitro-2,2'-(2-aza-propanediyl)-di-malonic acid tetraethyl ester 
• 63971-99-3 ethyl 3-(1H-indol-3-yl)-2-nitropropanoate 
• 125109-04-8 ethyl α-(hydroxyimino)-β-(N-methylindol-3-yl)propanoate 

Downstream Products

• 7479-05-2 L-tryptophan ethyl ester 
• 84518-77-4 ethyl 1,2,3,4-tetrahydro-β-carboline-3-carboxylate 
• 119377-08-1 (+/-) cis-ethyl 1-(3-pyridinyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate 
• 119377-08-1 (+/-) trans-ethyl 1-(3-pyridinyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate 
• 113735-70-9 Br(OC)3Re(NH₂CH(CH₂C₆H₅)CONHCH(CH₂C₈H₅NH)CO₂C₂H₅)2 
• 42717-06-6 acetyltryptophan ethylester 
• 1375081-73-4 ethyl 1-benzoyl-9H-pyrido[3,4-b]indole-3-carboxylate 
• 475101-82-7 N^α-(3-phenylpropionyl)tryptophan 
• 374710-96-0 1-phenyl-9H-pyrido [3,4-b]indole-3-carboxylic acid 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of 1-(thiophen-2-yl)-9H-pyrido[3,4-b]indole derivatives as anti-HIV-1 agents

A novel series of 1-(thiophen-2-yl)-9H-pyrido [3,4-b]indole derivatives were synthesized using DL-tryptophan as starting material. All the compounds were characterized by spectral analysis such as 1H NMR, Mass, IR, elemental analysis and evalua

Harmine-based dual inhibitors targeting histone deacetylase (HDAC) and DNA as a promising strategy for cancer therapy

Overexpression of histone deacetylases (HDACs) are observed in different types of cancers, but histone deacetylase inhibitors (HDACIs) have not shown significant efficacy as monotherapy against solid tumors. Recently, studies demonstrated that it is promi

Design, synthesis and evaluation of novel β-carboline ester analogues as potential anti-leishmanial agents

Leishmaniasis is one of today's most neglected diseases. The emergence of new anti-leishmanial therapies emphasizes several study groups funded by the World Health Organization. The present investigation will focus on the research to determine a few new potential derivatives of β-carboline ester derivatives against leishmaniasis. The in-silico predicted ADMET properties of most of the titled compounds are in an acceptable range and having drug like properties. Among all the tested analogs, compound ES-3 (EC50 3.36 μM; SI > 29.80) showed comparable and equipotent anti-leishmanial activity as that of standard drug miltefosine (EC50 4.80 μM; SI > 20.80) against amastigote forms of the tested L. infantum strain. Two compounds ES-6 and ES-10 exhibited significant activity with EC50 10.16, 13.56 μM; SI > 4.90, 7.37, respectively. In-silico based molecular docking and dynamics study of the significantly active analog also performed to study the putative binding mode, interaction pattern at the active site of the target leishmanial trypanothione reductase enzyme as well as stability of the target-ligand complex. The changes in the conformation of molecules during MD (frame wise trajectory analysis) provided new insights for the development of novel potent molecules. These findings will further give insight that will help modify the compound ES-3 for better potency and the design of novel inhibitors for leishmaniasis. Communicated by Ramaswamy H. Sarma.

A class of DL-tryptophan compounds, preparation method and applications thereof

The invention provides a DL-tryptophan compound represented by a general formula I or a pharmaceutically acceptable salt thereof, a preparation method and applications thereof, especially applicationsin preparation of RANKL inhibitors. According to the DL-tryptophan compound or the pharmaceutically acceptable salt thereof, an OPG-RANKL-RANK signal system can be intervened by inhibiting the interaction of RANKL-RANK, and the activity of RANKL in osteoclast precursor cells is regulated and controlled, so that formation of osteoclasts is inhibited, and bone resorption is reduced; and the DL-tryptophan compound or the pharmaceutically acceptable salt thereof is expected to play a role in preventing and treating bone metabolic diseases, and brings good news to bone metabolic disease patients.

Development of Small-Molecules Targeting Receptor Activator of Nuclear Factor-κB Ligand (RANKL) - Receptor Activator of Nuclear Factor-κB (RANK) Protein-Protein Interaction by Structure-Based Virtual Screening and Hit Optimization

Targeting RANKL/RANK offers the possibility of developing novel therapeutic approaches to treat bone metabolic diseases. Multiple efforts have been made to inhibit RANKL. For example, marketed monoclonal antibody drug Denosumab could inhibit the maturation of osteoclasts by binding to RANKL. This study is an original approach aimed at discovering small-molecule inhibitors impeding RANKL/RANK protein interaction. We identified compound 34 as a potent and selective RANKL/RANK inhibitor by performing structure-based virtual screening and hit optimization. Disruption of the RANKL/RANK interaction by 34 effectively inhibits RANKL-induced osteoclastogenesis and bone resorption. The expression of osteoclast marker genes was also suppressed by treatment of 34. Furthermore, 34 markedly blocked the NFATc1/c-fos pathway. Thus, our current work demonstrates that the chemical tractability of the difficult PPI (RANKL/RANK) target by a small-molecule compound 34 offers a potential lead compound to facilitate the development of new medications for bone-related diseases.

Biological evaluation and structure activity relationship of 9-methyl-1-phenyl-9H-pyrido[3,4-b]indole derivatives as anti-leishmanial agents

A series of piperazinyl-β-carboline-3-carboxamide derivatives were designed through a molecular hybridization approach. Designed analogues were synthesized, characterized and evaluated for anti-leishmanial activity against Leishmania infantum and Leishmania donovani. In L. infantum inhibition assay, compounds 7d, 7g and 7c displayed potent inhibition of promastigotes (EC50 1.59, 1.47 and 3.73 μM respectively) and amastigotes (EC50 1.4, 1.9 and 2.6 μM respectively). SAR studies revealed that, para substitution of methoxy, chloro groups and methyl group on ortho position favored anti-leishmanial activity against L. infantum. Among these analogues 7d, 7h, 7n and 7g exhibited potent inhibition against L. donovani promastigotes (EC50 0.91, 4.0, 4.57 and 5.02 μM respectively), axenic amastigotes (EC50 0.9, 3.5, 2.2 and 3.8 μM respectively) and intracellular amastigotes (EC50 1.3, 7.8, 5.6 and 6.3 μM respectively). SAR studies suggested that, para substitution of methoxy group, para and meta substitution of chloro groups and benzyl replacement recommended for significant anti-leishmanial against L. donovani.

Design, synthesis and biological evaluation of piperazinyl-β-carbolinederivatives as anti-leishmanial agents

Molecular hybridization is a ligand based drug design approach is well known recent medicinal chemistry to design anti-parasitic agents. In the present study, we have designed a series of (1-phenyl-9H-pyrido [3,4-b]indol-3-yl) (4-phenylpiperazin-1-yl)methanone derivatives using molecular hybridization approach. Designed analogues were evaluated for cytotoxicity and inhibition activity against Leishmania infantum and Leishmania donovani. Among these reported analogues 7b, 7d, 7e, 7f and 7m displayed potent inhibition of both L. infantum and L. donovani. Compounds 7i and 7k exhibited selective potent inhibition of L. donovani. Especially, compounds 7e and 7k showed most potent anti-leishmanial activity against L. infantum and L. donovani respectively. Anti-leishmanial activity of these compounds is comparable with standard drugs miltefosine and pentamidine. SAR studies revealed that, electron donating group substitution on phenyl ring recommended for potent anti-leishmanial activity.

ALKOXY BIS-HETEROARYL DERIVATIVES AS MODULATORS OF PROTEIN AGGREGATION

The present invention relates to certain bis-heteroaryl compounds, pharmaceutical compositions containing them, and methods of using them, including methods for preventing, reversing, slowing, or inhibiting protein aggregation, and methods of treating diseases that are associated with protein aggregation, including neurodegenerative diseases such as Parkinson's disease, Alzheimer's disease, Lewy body disease, Parkinson's disease with dementia, fronto-temporal dementia, Huntington's Disease, amyotrophic lateral sclerosis, and multiple system atrophy, and cancer including melanoma.

Pd/C-Catalyzed Dehydrogenative [3+2] Cycloaddition for the Synthesis of Functionalized Tropanes

A Pd/C-catalyzed cascade approach for the synthesis of attractive benzo-fused tropanes was developed. The reaction proceeds through a sequential Pd/C-catalyzed dehydrogenative formation of azomethine ylides from amines and 1,3-dipolar cycloaddition. It allows the generation of structurally complex benzo-fused tropanes in good yields with excellent diastereoselectivities under mild reaction conditions. Preliminary results of asymmetric version of the reaction reveal that the copper catalyst and chiral monophosphoramidite ligand can furnish optically active products with moderate ee.

Β-Carboline derivative or pharmaceutically acceptable salt, a process for their preparation and application of the anti-tumor

The invention discloses a beta-carboline derivative or medicinal salt of a general formula (I) structure with anti-tumour activity, wherein R, R1 and R2 are defined in the specification.