55747-66-5

Usage

Chemical structure

complex structure containing functional groups like indole, methoxy, and isoindole

Functional groups

indole, methoxy, isoindole

Substitution

methoxy substitution at the 5th position of the indole group

Potential pharmacological activity

due to indole and isoindole moieties

Further research needed

to determine specific properties and potential uses of the compound

Upstream product

• 85-44-9 phthalic anhydride 
• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 

Downstream Products

• 53157-46-3 N,N-phthalimido-2-(5-hydroxy-1H-indole-3-yl)ethylamine 
• 1592897-34-1 2-(2-(1-benzyl-5-methoxy-1H-indol-3-yl)ethyl)isoindoline-1,3-dione 
• 340809-41-8 2-[2-(3,5-dimethyl-phenyl)-5-methoxy-1H-indol-3-yl]-ethylamine 
• 192182-36-8 2-{2-[2-(3,5-Dimethyl-phenyl)-5-methoxy-1H-indol-3-yl]-ethyl}-isoindole-1,3-dione 

Relevant academic research and scientific papers

Structural understanding of 5-(4-hydroxy-phenyl)-N-(2-(5-methoxy-1H-indol-3-yl)-ethyl)-3-oxopentanamide as a neuroprotectant for Alzheimer's disease

In our continuing efforts to develop novel neuroprotectants for Alzheimer's disease (AD), a series of analogs based on a lead compound that was recently shown to target the mitochondrial complex I were designed, synthesized and biologically characterized to understand the structure features that are important for neuroprotective activities. The results from a cellular AD model highlighted the important roles of the 4-OH on the phenyl ring and the 5-OCH3 on the indole ring of the lead compound. The results also demonstrated that the β-keto moiety can be modified to retain or improve the neuroprotective activity. Docking studies of selected analogs to the FMN site of mitochondrial complex I also supported the observed neuroprotective activities. Collectively, the results provide further information to guide optimization and development of analogs based on this chemical scaffold as neuroprotectants with a novel mechanism of action for AD.

Quinazoline and phthalazine derivatives as novel melatonin receptor ligands analogues of agomelatine

For further development of successors of Agomelatine through modulation of its pharmacokinetic properties, we report herein the design, synthesis and pharmacological results of a new family of melatonin receptor ligands. Issued from the introduction of quinazoline and phthalazine scaffolds carrying an ethyl amide lateral chain and a methoxy group as bioisosteric ligands analogues of previously developed Agomelatine. The biological activity of the prepared analogues was compared with that of Agomelatine. Quinazoline and phthalazine rings proved to be a versatile scaffold for easy feasible MT1 and MT2 ligands. Potent agonists with sub-micromolar binding affinity were obtained. However, the presence of two nitrogen atoms resulted in compounds with lower affinity for both MT1 and MT2, in comparison with the parent compound, balanced by the exhibition of good pharmacokinetic properties.

Enantioselective Total Synthesis and Absolute Configuration Assignment of (+)-Tronocarpine Enabled by an Asymmetric Michael/Aldol Reaction

We present the first asymmetric total synthesis and absolute configuration determination of (+)-tronocarpine. The [6.5.7.6.6] pentacyclic core was constructed at an early stage by using a sequential cyclization strategy through a newly developed catalytic asymmetric Michael/aldol cascade to build the aza[3.3.1]-bridged cycle and a tandem reduction/hemiamidation procedure to assemble the seven-membered lactam. The side-chain functionalities were incorporated at a late stage by several appropriately orchestrated manipulations under mild conditions. The synthesis of enantiomerically pure (+)-tronocarpine was achieved through a 20-step longest linear sequence from tryptamine.

Structure-Activity Relationships of Novel Tryptamine-Based Inhibitors of Bacterial Transglycosylase

Penicillin-binding proteins represent well-established, validated, and still very promising targets for the design and development of new antibacterial agents. The transglycosylase domain of penicillin-binding proteins is especially important, as it catalyzes polymerization of glycan chains, using the peptidoglycan precursor lipid II as a substrate. On the basis of the previous discovery of a noncovalent small-molecule inhibitor of transglycosylase activity, we systematically explored the structure-activity relationships of these tryptamine-based inhibitors. The main aim was to reduce the nonspecific cytotoxic properties of the initial hit compound and concurrently to retain the mode of its inhibition. A focused library of tryptamine-based compounds was synthesized, characterized, and evaluated biochemically. The results presented here show the successful reduction of the nonspecific cytotoxicity, and the retention of the inhibition of transglycosylase enzymatic activity, as well as the ability of these compounds to bind to lipid II and to have antibacterial actions.

Scaffold Diversity Inspired by the Natural Product Evodiamine: Discovery of Highly Potent and Multitargeting Antitumor Agents

A critical question in natural product-based drug discovery is how to translate the product into drug-like molecules with optimal pharmacological properties. The generation of natural product-inspired scaffold diversity is an effective but challenging strategy to investigate the broader chemical space and identify promising drug leads. Extending our efforts to the natural product evodiamine, a diverse library containing 11 evodiamine-inspired novel scaffolds and their derivatives were designed and synthesized. Most of them showed good to excellent antitumor activity against various human cancer cell lines. In particular, 3-chloro-10-hydroxyl thio-evodiamine (66c) showed excellent in vitro and in vivo antitumor efficacy with good tolerability and low toxicity. Antitumor mechanism and target profiling studies indicate that compound 66c is the first-in-class triple topoisomerase I/topoisomerase II/tubulin inhibitor. Overall, this study provided an effective strategy for natural product-based drug discovery. (Figure Presented).

Asymmetric synthesis of tetrahydro-β-carbolines via chiral phosphoric acid catalyzed transfer hydrogenation reaction

Chiral phosphoric acid catalyzed enantioselective transfer hydrogenation of hydroxylactams has been realized to provide enantioenriched tetrahydro-β-carbolines in dioxane at room temperature (up to 94% yield, 90% ee).

NOVEL PYRONE-INDOLE DERIVATIVES AND PROCESS FOR THEIR PREPARATION

The present invention relates to novel pyrone-indole derivatives, pharmaceutical formulations containing them, and use of the compounds in the manufacture of Medicaments for treating or preventing various diseases.

Indole Derivatives. 130. Synthesis of Disubstituted Tryptamines by Nitration of 5-Methoxy-N-Phthalyltryptamine

It was shown that nitration of 5-methoxy-N-phthalyltryptamine in acetic acid gives principally the 4-nitro derivative.The 4-nitro, 4-amino, and 4-acetylamino-derivatives of 5-methoxy-N-phthalyltryptamine were also prepared.