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4-Bromotryptophol is a chemical compound belonging to the tryptophol family, derived from tryptophan with a bromine atom at the 4th position of the indole ring. 4-BROMOTRYPTOPHOL is known for its unique chemical and physical properties, which are attributed to the presence of the bromine atom. It is widely recognized for its valuable biological activities, such as antimicrobial, antifungal, and algicidal properties, and has demonstrated significant effects as a serotonin receptor antagonist, making it a promising candidate for treating various health conditions. However, it is important to note that details regarding its toxicity and safety are limited, and there are potential risks associated with improper handling.

202753-56-8

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202753-56-8 Usage

Uses

Used in Scientific Research:
4-Bromotryptophol is used as a research compound for its antimicrobial, antifungal, and algicidal properties, making it valuable in the study of biological activities and potential applications in various fields.
Used in Pharmaceutical Development:
4-Bromotryptophol is used as a pharmaceutical agent for its role as a serotonin receptor antagonist, which can be beneficial in treating a variety of health conditions. Its potential applications in this industry are currently being explored, with a focus on understanding its safety and efficacy.
Used in Chemical Synthesis:
4-Bromotryptophol is used as a chemical intermediate in the synthesis of other compounds, particularly those with potential applications in the pharmaceutical and biotechnology industries. Its unique properties make it a useful building block for the development of new drugs and therapeutic agents.
Used in Environmental Applications:
4-Bromotryptophol is used as an algicide to control the growth of algae in aquatic environments, which can be harmful to ecosystems and water quality. Its effectiveness in this application is currently being studied, with a focus on understanding its impact on the environment and potential for use in various settings.

Check Digit Verification of cas no

The CAS Registry Mumber 202753-56-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,0,2,7,5 and 3 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 202753-56:
(8*2)+(7*0)+(6*2)+(5*7)+(4*5)+(3*3)+(2*5)+(1*6)=108
108 % 10 = 8
So 202753-56-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H10BrNO/c11-8-2-1-3-9-10(8)7(4-5-13)6-12-9/h1-3,6,12-13H,4-5H2

202753-56-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(4-bromo-1H-indol-3-yl)ethanol

1.2 Other means of identification

Product number -
Other names 4-BROMO-1H-INDOLE-3-ETHANOL

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:202753-56-8 SDS

202753-56-8Relevant articles and documents

Evolution of a Unified, Stereodivergent Approach to the Synthesis of Communesin F and Perophoramidine

Han, Seo-Jung,Vogt, Florian,May, Jeremy A.,Krishnan, Shyam,Gatti, Michele,Virgil, Scott C.,Stoltz, Brian M.

, p. 528 - 547 (2015)

Expedient synthetic approaches to the highly functionalized polycyclic alkaloids communesin F and perophoramidine are described using a unified approach featuring a key decarboxylative allylic alkylation to access a crucial and highly congested 3,3-disubs

Au(I)-Catalyzed Domino Cyclization of 1,6-Diynes Incorporated with Indole

Chen, Guzhou,Liu, Peng-Yu,Zou, Huanhuan,Hu, Jiadong,Fang, Xiaowu,Xu, Dongyang,He, Yu-Peng,Wei, Hongbo,Xie, Weiqing

supporting information, p. 2279 - 2284 (2021/04/05)

We disclose herein a Au(I)-catalyzed domino cyclization of 1,6-diynes incorporated with indole. This protocol enabled the diastereoselective buildup of indole-fused azabicyclo[3.3.1]nonanes from linear precursors. Density functional theory calculations showed that the reaction proceeded via an unprecedented cascade dearomatization/rearomatization/dearomatization process. Independent gradient model analysis revealed that a noncovalent attractive interaction between the distal alkyne and the Au/proximal complex was responsible for the chemoselectivity of the first spirocyclization step.

Asymmetric Synthesis of Lysergic Acid via an Intramolecular (3+2) Dipolar Cycloaddition/Ring-Expansion Sequence

Rathnayake, Upendra,Garner, Philip

supporting information, p. 6756 - 6759 (2021/09/02)

An effective, potentially scalable asymmetric synthesis of lysergic acid, a core component of the ergot alkaloid family, is reported. The synthesis features the strategic combination of an intramolecular azomethine ylide cycloaddition and Cossy-Charette r

Rapid One-Pot Access to Unique 3,4-Dihydrothiopyrano[3,4-b]indol-1(9H)-imines via Bi(OTf)3-Catalysed Tandem Friedel–Crafts Alkylation/Thia-Michael Addition

Dethe, Dattatraya H.,Boda, Vijay Kumar,Mandal, Anupam

supporting information, p. 5417 - 5421 (2018/10/20)

A highly efficient and atom economical one-pot annulation strategy for novel tetrahydrothiopyrano[3,4-b]indoles is presented. This protocol involves a Bi(OTf)3 catalyzed tandem Friedel–Crafts alkylation and intramolecular thia-Michael addition reactions to furnish target molecules in an efficient manner. The method works effectively on substrates with unprotected indoles and also it is successfully employed to make tetrahydrothiepino[3,4-b]indoles. The scaffolds synthesized are diverse and first of the kind. The reaction is practically simple with broad substrate scope and vast functional group compatibility.

Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds

Fu, Liangbing,Davies, Huw M. L.

supporting information, p. 1504 - 1507 (2017/04/13)

An efficient synthesis of tetrahydrocarboline-type products and polycyclic spiroindolines has been achieved. The transformation proceeds via rhodium(II)-catalyzed intramolecular annulations of indolyl- and pyrrolyl-tethered N-sulfonyl-1,2,3-triazoles. The reaction could be tuned toward either the formal [3 + 2] cycloaddition or the C-H functionalization reaction depending on the electronic and structural features of the substrates, leading to the production of a variety of structurally related heterocyclic compounds.

A diastereodivergent synthetic strategy for the syntheses of communesin F and perophoramidine

Han, Seo-Jung,Vogt, Florian,Krishnan, Shyam,May, Jeremy A.,Gatti, Michele,Virgil, Scott C.,Stoltz, Brian M.

, p. 3316 - 3319 (2014/07/08)

An efficient, unified, and stereodivergent approach toward communesin F and perophoramidine was examined. The C(3) all-carbon quaternary center of an oxindole was smoothly constructed by base-promoted indolone-malonate alkylation chemistry. The complement

Nickel-mediated inter- and intramolecular C-S coupling of thiols and thioacetates with aryl iodides at room temperature

Xu, Xiao-Bo,Liu, Jian,Zhang, Jian-Jian,Wang, Ya-Wen,Peng, Yu

supporting information, p. 550 - 553 (2013/04/11)

A Ni(0)-catalyzed intermolecular cross-coupling of various functionalized thiols and aryl iodides has been developed and successfully extended to less explored intramolecular versions, where thioacetates could also be utilized as the strategic surrogate. Air-stable precatalysts, very mild conditions, and an easy protocol allow rapid access to medicinally useful aryl thioethers, as demonstrated in the facile synthesis of (±)-chuangxinmycin as a key step.

A2 ADENOSINE RECEPTOR AGONISTS

-

Page/Page column 26, (2009/03/07)

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.

Total synthesis of (±)-communesin F

Yang, Jun,Wu, Haoxing,Shen, Liqun,Qin, Yong

, p. 13794 - 13795 (2008/09/18)

Total synthesis of the complex polycyclic indole alkaloid (±)-communesin F has been accomplished in 23 reaction steps in about 3% overall yield. The key steps relied on a highly efficient methodology for assembling the pentacyclic substructure 2 with the

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

Adachi, Hayamitsu,Palaniappan, Krishnan K.,Ivanov, Andrei A.,Bergman, Nathaniel,Gao, Zhan-Guo,Jacobson, Kenneth A.

, p. 1810 - 1827 (2008/02/06)

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.

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