61220-51-7

Basic information

• Product Name: 5-CHLOROTRYPTOPHOL
• Synonyms: 2-(5-CHLORO-1H-INDOL-3-YL)ETHANOL;5-CHLOROTRYPTOPHOL;5-CHLOROTRYPTOPHOL, 98+%;5-Chloro-1H-indole-3-ethanol;1H-Indole-3-ethanol,5-chloro-
• CAS NO: 61220-51-7
• Molecular Formula: C₁₀H₁₀ClNO
• Molecular Weight: 195.65
• Mol File: 61220-51-7.mol

Chemical Properties

• Boiling Point: 390.7 °C at 760 mmHg
• Flash Point: 190.1 °C
• Appearance: /
• Density: 1.357 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-CHLOROTRYPTOPHOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLOROTRYPTOPHOL(61220-51-7)
• EPA Substance Registry System: 5-CHLOROTRYPTOPHOL(61220-51-7)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 61220-51-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
5-CHLOROTRYPTOPHOL is used as a key compound in the development of new pharmaceuticals for [application reason] its sedative and hypnotic effects, which are beneficial in the treatment of insomnia and anxiety-related disorders.
Used in Sleep Aid Formulations:
In the Sleep Aid Industry, 5-CHLOROTRYPTOPHOL is used as an active ingredient for [application reason] its ability to induce sleep and improve sleep quality, making it a potential alternative or adjunct to existing sleep medications.
Used in Anxiety Management Therapies:
5-CHLOROTRYPTOPHOL is utilized as a therapeutic agent in the Mental Health Industry for [application reason] its calming effects, which can help alleviate symptoms of anxiety and stress.
Used in Research and Development:
In the Scientific Research Industry, 5-CHLOROTRYPTOPHOL is used as a subject of study for [application reason] its potential role in understanding the mechanisms of sleep and anxiety, as well as for discovering new therapeutic targets and compounds.

Upstream product

• 13436-46-9 2-ethoxytetrahydrofuran 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 163160-58-5 (5-chloro-1H-indol-3-yl)-oxo-acetic acid ethyl ester 
• 163160-55-2 (5-chloro-1H-indol-3-yl)oxoacetic acid methylester 
• 17422-32-1 5-chloro-1H-indole 
• 883-55-6 2-(5-chloro-1H-indol-3-yl)-2-oxoacetyl chloride 
• 1191-99-7 2,3-dihydro-2H-furan 
• 526-55-6 2-(3-indole)-ethanol 

Downstream Products

• 325773-39-5 3-(2-bromo-ethyl)-5-chloro-1H-indole 
• 1025906-94-8 5-chloro-3-(p-toluenesulfonyloxyethyl)-1-(p-toluenesulfonyl)indole 
• 936252-63-0 5-chloro-3-(2-iodoethyl)-1-(p-toluenesulfonyl)indole 
• 936252-81-2 6-chloro-2-(3''-(5''-chloro-1''-(p-toluenesulfonyl)indolyl)ethyloxy)-3',4',5'-triacetyladenosine 
• 936252-95-8 2-(3-(5-chloro-1-(p-toluenesulfonyl)indolyl)ethyloxy)adenosine 
• 872674-45-8 methyl 4-[2-(5-chloro-1H-indol-3-yl)ethoxy]benzoate 
• 1026938-90-8 C₁₈H₁₅BrClNO₃ 
• 934284-90-9 methyl 4-{2-[2-bromo-5-chloro-1-(diphenylmethyl)-1H-indol-3-yl]ethoxy}benzoate 
• 934284-92-1 4-{2-[2-bromo-5-chloro-1-(diphenylmethyl)-1H-indol-3-yl]ethoxy}benzoic acid 
• 872674-46-9 methyl 4-[2-[5-chloro-1-(diphenylmethyl)-1H-indol-3-yl]ethoxy]benzoate 
• 850406-55-2 2-(5-chloro-1-methyl-1H-indol-3-yl)-ethanol 
• 1487273-59-5 5-chloro-3-(2-(4-((2,3-dihydro-2-phenylbenzo[b][1,4]dioxin-3-yl)methyl)piperazin-1-yl)ethyl)-1H-indole 
• 898746-66-2 tert-butyl 5-chloro-3-(2-hydroxyethyl)-1H-indole-1-carboxylate 

Relevant articles and documents

Enantioselective Construction of Spirooxindole-Fused Cyclopentanes

The present study reports an asymmetric organocatalytic cascade reaction of oxindole derivates with α,β-unsaturated aldehydes efficiently catalyzed by simple chiral secondary amine. Spirooxindole-fused cyclopentanes were produced in excellent isolated yields (up to 98%) with excellent enantiopurities (up to 99% ee) and moderate to high diastereoselectivities. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spiro compounds. In addition, a study showing the promising biological activity of selected enantioenriched products was accomplished.

Palladium-Catalyzed Asymmetric Allylic Alkylation of 3-Substituted 1 H-Indoles and Tryptophan Derivatives with Vinylcyclopropanes

Vinylcyclopropanes (VCPs) are known to generate 1,3-dipoles with a palladium catalyst that initially serve as nucleophiles to undergo [3 + 2] cycloadditions with electron-deficient olefins. In this report, we reverse this reactivity and drive the 1,3-dipoles to serve as electrophiles by employing 3-alkylated indoles as nucleophiles. This represents the first use of VCPs for the completely atom-economic functionalization of 3-substituted 1H-indoles and tryptophan derivatives via a Pd-catalyzed asymmetric allylic alkylation (Pd-AAA). Excellent yields and high chemo-, regio-, and enantioselectivities have been realized, providing various indolenine and indoline products. The method is amenable to gram scale and works efficiently with tryptophan derivatives that contain a diketopiperazine or diketomorpholine ring, allowing us to synthesize mollenine A in a rapid and ligand-controlled fashion. The obtained indolenine products bear an imine, an internal olefin, and a malonate motif, giving multiple sites with diverse reactivities for product diversification. Complicated polycyclic skeletons can be conveniently constructed by leveraging this unique juxtaposition of functional groups.

Directed evolution of RebH for catalyst-controlled halogenation of indole C-H bonds

RebH variants capable of chlorinating substituted indoles ortho-, meta-, and para-to the indole nitrogen were evolved by directly screening for altered selectivity on deuterium-substituted probe substrates using mass spectrometry. This systematic approach allowed for rapid accumulation of beneficial mutations using simple adaptive walks and should prove generally useful for altering and optimizing the selectivity of C-H functionalization catalysts. Analysis of the beneficial mutations showed that structure-guided selection of active site residues for targeted mutagenesis can be complicated either by activity/selectivity tradeoffs that reduce the possibility of detecting such mutations or by epistatic effects that actually eliminate the benefits of a mutation in certain contexts. As a corollary to this finding, the precise manner in which the beneficial mutations identified led to the observed changes in RebH selectivity is not clear. Docking simulations suggest that tryptamine binds to these variants as tryptophan does to native halogenases, but structural studies will be required to confirm these models and shed light on how particular mutations impact tryptamine binding. Similar directed evolution efforts on other enzymes or artificial metalloenzymes could enable a wide range of C-H functionalization reactions.

Synthesis and evaluation of novel 2,3-dihydrobenzo[b][1,4]dioxin- and indolealkylamine derivatives as potential antidepressants

A series of 2,3-dihydrobenzo[b][1,4]dioxin- and indolealkylamine derivatives were synthesized and the target compounds were evaluated for their binding affinities at the 5-HT1A receptor and serotonin transporter. Antidepressant-like activities of the compounds were screened using the tail suspension and forced swim tests in mice. Preliminary results indicated that the target compounds exhibited high binding affinities at the 5-HT1A receptor and serotonin transporter, and produced marked antidepressant-like effects. The best example from this study, compound 5, exhibited high binding affinities for the 5-HT1A receptor (Ki = 96 nM) and serotonin transporter (Ki = 9.8 nM). The intrinsic activity of compound 5 showed agonistic property to the 5-HT1A receptor and inhibition of the 5-HT transporter. Furthermore, compound 5 exhibited greater antidepressant efficacy than fluoxetine and showed acceptable pharmacokinetic properties. A series of 3-(2-(4-((2,3-dihydrobenzo[b][1,4]dioxin-3-yl)methyl) piperazin-1-yl)ethyl-1H-indole derivatives were synthesized and the target compounds were evaluated for their antidepressant activities in vitro and in vivo. The compounds described were also evaluated for dual 5-HTT and 5-HT 1A receptor activities.

A2 ADENOSINE RECEPTOR AGONISTS

Disclosed are AZB adenosine receptor (AR) agonists of formula (I), in which R1, R2, R3, R4, Z, and n are defined herein. The invention also provides compositions comprising at least one compound of formula I and methods of use thereof, for example, in the treatment of septic shock, cystic fibrosis, restenosis, erectile dysfunction, inflammation, myocardial ischemia, and reperfusion injury.

Discovery of ecopladib, an indole inhibitor of cytosolic phospholipase A2α

The synthesis and structure-activity relationship of a series of indole inhibitors of cytosolic phospholipase A2α (cPLA 2α, type IVA phospholipase) are described. Inhibitors of cPLA2α are predicted to be efficacious in treating asthma as well as the signs and symptoms of osteoarthritis, rheumatoid arthritis, and pain. The introduction of a benzyl sulfonamide substituent at C2 was found to impart improved potency of these inhibitors, and the SAR of these sulfonamide analogues is disclosed. Compound 123 (Ecopladib) is a submicromolar inhibitor of cPLA2α in the GLU micelle and rat whole blood assays. Compound 123 displayed oral efficacy in the rat carrageenan air pouch and rat carrageenan-induced paw edema models.

Structure-activity relationships of 2,N6,5′-substituted adenosine derivatives with potent activity at the A2B adenosine receptor

2, N6, and 5′-substituted adenosine derivatives were synthesized via alkylation of 2-oxypurine nucleosides leading to 2-arylalkylether derivatives. 2-(3-(Indolyl)ethyloxy)adenosine 17 was examined in both binding and cAMP assays and found to be a potent agonist of the human A2BAR. Simplification, altered connectivity, and mimicking of the indole ring of 17 failed to maintain A2BAR potency. Introduction of N6-ethyl or N6-guanidino substitution, shown to favor A2BAR potency, failed to enhance potency in the 2-(3-(indolyl)- ethyloxy)adenosine series. Indole 5″- or 6″-halo substitution was favored at the A2BAR, but a 5′-N-ethylcarboxyamide did not further enhance potency. 2-(3″-(6″-Bromoindolyl)ethyloxy)adenosine 28 displayed an A2BAR EC50 value of 128 nM, that is, more potent than the parent 17 (299 nM) and similar to 5′-N- ethylcarboxamidoadenosine (140 nM). Compound 28 was a full agonist at A 2B and A2AARs and a low efficacy partial agonist at A 1 and A3ARs. Thus, we have identified and optimized 2-(2-arylethyl)oxo moieties in AR agonists that enhance A2BAR potency and selectivity.

3-Thio-1,2,4-triazoles, novel somatostatin sst2/sst5 agonists

Novel 3-thio-1,2,4-triazoles have been obtained via a solution-phase parallel synthesis strategy, affording potent non-peptidic human somatostatin receptor subtypes 2 and 5 agonists.

A novel substitution reaction of tetrahydropyrano[3,4-b]indole derivative - Chain extension and structural correlation study

An unusual cyanation with rearrangement of a 1-chloromethyl-tetrahydropyrano[3,4-b]indole-1-acetic acid ester derivative is reported. The resulting C-1 chain extension product is identified by correlation studies and spectral method.

Indolylalkylpiperidines

1-(Indolyl-3-alkyl)-3 or 4-(ureido or guanidino)-piperidines, e.g. those of the formula STR1 R= H; alkyl; free, etherified or esterified OH or SH; CF3, NO2 or NH2 m= 1-4; n= 2 or 3; X= O, S or NH acyl derivatives and salts thereof are antihypertensive agents.