53157-48-5

Usage

Uses

Used in Pharmaceutical Industry:
3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole is used as a key intermediate in the synthesis of protein kinase inhibitors and receptor agonists for the pharmaceutical industry. The application reason is that 3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole serves as a building block for the development of new drugs targeting various diseases, including neurological disorders and cancer.
Used in Research and Development:
In the research and development sector, 3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole is used as a valuable tool for studying the structure-activity relationships of serotonin and its analogs. The application reason is to gain insights into the molecular mechanisms underlying the biological activities of these compounds, which can ultimately lead to the design of more effective therapeutic agents.
Used in Chemical Synthesis:
3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole is also used as a protected amino acid in various chemical synthesis processes. The application reason is that the Boc group provides a stable and easily removable protecting group for the amino functionality, allowing for the selective protection of amino groups during multi-step synthesis.

Upstream product

• 61-47-2 serotonin creatinine sulfate monohydrate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 584-08-7 potassium carbonate 
• 21591-86-6 5-hydroxytryptamine hydrochloride 
• 34619-03-9 tert-butyldicarbonate 
• 153-98-0 serotonin hydrochloride 
• 119768-45-5 (S)-2-((tert-butoxycarbonyl)amino)-3-(5-hydroxy-1H-indol-3-yl)propanoic acid 
• 50-67-9 3-(2-aminoethyl)-1H-indol-5-ol 
• 971-74-4 serotonin creatinine sulfate 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 

Downstream Products

• 947766-67-8 C₂₃H₂₆N₂O₄ 
• 1373764-85-2 C₂₇H₂₆N₂O₂ 
• 1373764-86-3 6-hydroxy-1-methyl-N-phenylacetyl-1,3,4,9-tetrahydro-β-carboline 
• 20776-45-8 5-benzyloxytryptamine 
• 17952-78-2 6-(benzyloxy)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 
• 53157-47-4 [2-(5-benzyloxy-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester 
• 189288-97-9 2-(3-{2-[N-(tert-butoxycarbonyl)amino]ethyl}-1H-indol-5-yloxy)-N-(4-aminomethylphenyl)acetamide 
• 174021-76-2 (2-{5-[2-(4-o-tolyl-piperazin-1-yl)-ethoxy]-1H-indol-3-yl}-ethyl)-carbamic acid tert-butyl ester 
• 774160-04-2 2-{5-[2-(4-o-tolyl-piperazin-1-yl)-ethoxy]-1H-indol-3-yl}-ethylamine 
• 725682-24-6 methyl-(2-{5-[2-(4-o-tolyl-piperazin-1-yl)-ethoxy]-1H-indol-3-yl}-ethyl)-amine 
• 162646-79-9 2-(3-{2-[N-(tert-butoxycarbonyl)amino]ethyl}-1H-indol-5-yloxy)-N-(4-cyanophenyl)acetamide 
• 162646-78-8 2-(3-{2-[N-(tert-butoxycarbonyl)amino]ethyl}-1H-indol-5-yloxy)-N-(4-nitrophenyl)acetamide 

Relevant academic research and scientific papers

Structure-activity relationship of serotonin derived tocopherol lipids

Tocopherol-based lipids are widely used for nucleic acid delivery. Using tocopherol molecules, we designed and synthesized 5-HT functionalized lipids by tethering 5-hydroxytryptamine (5-HT), a small molecule ligand as the head group to a natural amphiphilic molecule namely α-tocopherol (Vitamin E). This is with the aim of delivering nucleic acids specifically into cells expressing the serotonin receptors (5-hydroxytryptamine[5-HT]) which are abundant in the central nervous system. In order to achieve target recognition, we adopted an approach wherein two structurally different lipid molecules having serotonin as the head group was conjugated to tocopherol via different linkers thus generating lipids with either free –NH2 or –OH moiety. The corresponding lipids designated as Lipid A (Tocopheryl carbonate serotonin-NH2) and Lipid B (Tocopheryl 2-hydroxy propyl ammonium serotonin-OH), were formulated with co-lipids 1,2-dioleoyl-sn-glycero-3-phosphatidyl-ethanolamine (DOPE) and 1,2-dioleoyl-sn-glycero-sn-3-phosphatidylcholine (DOPC) and evaluated for their ability to deliver plasmid DNA through reporter gene expression assays in vitro. Furthermore, the physicochemical characteristics and cellular interactions of the formulations were examined using serotonin-receptor enriched cells in order to distinguish the structural and functional attributes of both lipids. Cell-based gene expression studies reveal that in comparison to Lipid A, a formulation of Lipid B prepared with DOPE as the co-lipid, contributes to efficient uptake leading to significant enhancement in transfection. Specific interactions explored by molecular docking studies suggests the role of the hydroxyl moiety and the enantiospecific significance of serotonin- conjugated tocopherol lipids in recognizing these receptors thus signifying a promising lipid-based approach to target the serotonin receptors in the central nervous system.

Synthesis and enantioseparation of atropisomers of serotonin dimer

Abstract A preparative scale synthesis of a dimer of serotonin (5-HT) is described. DHBT or 5,5′-dihydroxy-4,4′-bitryptamine was prepared in good yields using methanol in the presence of copper(II) chloride and air at room temperature. Exclusion of air resulted in no DHBT. Neither 5-HT hydrochloride nor N-BOC-protected 5-HT yielded DHBT under identical reaction conditions, evidence that the primary amino group of 5-HT plays a critical role in the dimerization reaction. The atropisomers of DHBT can be resolved by chiral capillary electrophoresis.

Method for preparing 5-hydroxytryptamine hydrochloride by utilizing enzymatic fermentation liquor containing 5-hydroxytryptamine

The invention discloses a method for preparing 5-hydroxytryptamine hydrochloride from 5-hydroxytryptamine-containing enzymatic fermentation liquor, and relates to the technical field of 5-hydroxytryptamine extraction. The method comprises the following steps: concentrating 5-hydroxytryptamine-containing enzymatic fermentation liquor under reduced pressure, mixing the concentrated 5-hydroxytryptamine-containing enzymatic fermentation liquor with an organic solvent, sequentially dropwise adding triethylamine and BOC anhydride at low temperature, heating to 20-25 DEG C after dropwise adding is finished, reacting to obtain an N-BOC-5-hydroxytryptamine reaction solution, adding ethyl acetate, and extracting to obtain an ethyl acetate organic phase; adding ethyl acetate containing hydrochloric acid into the ethyl acetate organic phase for reaction, and performing suction filtration after the reaction is finished to obtain a 5-hydroxytryptamine hydrochloride crude product; and further purifying the obtained 5-hydroxytryptamine hydrochloride crude product to obtain 5-hydroxytryptamine hydrochloride. According t o the invention, high-purity 5-hydroxytryptamine hydrochloride is prepared by optimizing the method for purifying 5-hydroxytryptamine in an enzymatic fermentation liquor, so that the current situation that 5-hydroxytryptamine hydrochloride is difficult to prepare by simply extracting serotonin in the enzymatic fermentation liquor is changed.

Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea

We report highly β-selective bis-thioureas-catalyzed 1,2-cis-O-pyranosylations employing easily accessible acetonide-protected donors. A wide variety of alcohol nucleophiles, including complex natural products, glycosides, and amino acids were β-mannosylated and β-rhamnosylated successfully using an operationally simple protocol under mild and neutral conditions. Less nucleophilic acceptors such as phenols were also glycosylated efficiently in excellent yields and with high β-selectivities.

Nanosensor for Sensitive Detection of the New Psychedelic Drug 25I-NBOMe

This work reports the synthesis, characterization, and sensing behavior of a hybrid nanodevice for the detection of the potent abuse drug 25I-NBOMe. The system is based on mesoporous silica nanoparticles, loaded with a fluorescent dye, functionalized with

Serotonin Analogues as Inhibitors of Breast Cancer Cell Growth

Serotonin (5-hydroxytryptamine, 5-HT) is a critical local regulator of epithelial homeostasis in the breast and exerts its actions through a number of receptors. Dysregulation of serotonin signaling is reported to contribute to breast cancer pathophysiology by enhancing cell proliferation and promoting resistance to apoptosis. Preliminary analyses indicated that the potent 5-HT1B/1D serotonin receptor agonist 5-nonyloxytryptamine (5-NT), a triptan-like molecule, induced cell death in breast cancer cell lines. Thus, we synthesized a series of novel alkyloxytryptamine analogues, several of which decreased the viability of various human cancer cell lines. Proteomic and metabolomic analyses showed that compounds 6 and 10 induced apoptosis and interfered with signaling pathways that regulate protein translation and survival, such as the Akt/mTOR pathway, in triple-negative breast cancer cells.

5-Alkyloxytryptamines are membrane-targeting, broad-spectrum antibiotics

Antibiotic adjuvant therapy represents an exciting opportunity to enhance the activity of clinical antibiotics by co-dosing with a secondary small molecule. Successful adjuvants decrease the concentration of antibiotics used to defeat bacteria, increase activity (in some cases introducing activity against organisms that are drug resistant), and reduce the frequency at which drug-resistant bacteria emerge. We report that 5-alkyloxytryptamines are a new class of broad-spectrum antibacterial agents with exciting activity as antibiotic adjuvants. We synthesized 5-alkyloxytryptamine analogs and found that an alkyl chain length of 6–12 carbons and a primary ammonium group are necessary for the antibacterial activity of the compounds, and an alkyl chain length of 6–10 carbons increased the membrane permeability of Gram-positive and Gram-negative bacteria. Although several of the most potent analogs also have activity against the membranes of human embryonic kidney cells, we demonstrate that below the minimum inhibitory concentration (MIC)—where mammalian cell toxicity is low—these compounds may be successfully used as adjuvants for chloramphenicol, tetracycline, ciprofloxacin, and rifampicin against clinical strains of Salmonella typhimurium, Acinetobacter baumannii and Staphylococcus aureus, reducing MIC values by as much as several logs.

Synthesis and biological evaluation of novel tetrahydro-β-carboline derivatives as antitumor growth and metastasis agents through inhibiting the transforming growth factor-β signaling pathway

The transforming growth factor beta (TGFβ) signaling cascade is considered as one of the pivotal oncogenic pathways in most advanced cancers. Inhibition of the TGFβ signaling pathway by specific antagonists, neutralizing antibodies, or small molecules is considered as an effective strategy for the treatment of tumor growth and metastasis. Here we demonstrated the identification of a series of tetrahydro-β-carboline derivatives from virtual screening which potentially inhibit the TGFβ signaling pathway. Optimization of the initial hit compound 2-benzoyl-1,3,4,9-tetrahydro-β- carboline (8a) through substitution at different positions to define the structure-activity relationship resulted in the discovery of potent inhibitors of the TGFβ signaling pathway. Among them, compound 8d, one of the tested compounds, not only showed potent inhibition of lung cancer cell proliferation and migration in vitro but also strongly suppressed growth of lung cancer and breast cancer in vivo.

PATHWAY SPECIFIC ASSAYS FOR PREDICTING IRRITABLE BOWEL SYNDROME DIAGNOSIS

The present invention provides antibodies and methods for preparing antibodies to metabolites in the serotonin, tryptophan, kynurenine pathways. The prepared antibodies have low cross-reactivity to related metabolites, and are useful reagents for specific and sensitive immunoassays The present invention also provides stable derivatives of various metabolites and short chain fatty acids. The derivative can be conjugated to a biomolecule such as a carrier protein and combined with an adjuvant to stimulate an immune response. The derivatives can also be conjugated to other biomolecules.

NOVEL COMPOSITIONS AND METHODS FOR TREATING CANCER

Provided herein are methods and compositions inter alia for treating diseases, including hyperproliferative diseases, migraine headaches, and depression.