526-55-6 Usage
Description
Tryptophol, also known as indolyl ethanol, is an indole derivative and a metabolite formed in the liver after disulfiram treatment. It is characterized by its off-white to brown crystalline mass and is known to induce sleep in humans. Tryptophol is also a secondary product of alcoholic fermentation and has a wide range of applications in various industries due to its unique chemical properties.
Uses
Used in Pharmaceutical Industry:
Tryptophol is used as a reactant for the preparation of various pharmaceutical compounds, including:
1. Inhibitors of the C-terminal domain of RNA polymerase II and their antitumor activities: Tryptophol is utilized in the development of inhibitors that target the C-terminal domain of RNA polymerase II, which play a crucial role in the regulation of gene expression and have potential antitumor activities.
2. Anti-HIV-1 agents: Tryptophol serves as a reactant in the synthesis of compounds with anti-HIV-1 properties, contributing to the development of treatments for HIV-1 infection.
3. Inhibitors of Protein-Protein Interactions: Tryptophol is used in the creation of inhibitors that disrupt protein-protein interactions, which are essential for various cellular processes and can be targeted for therapeutic purposes.
4. Partial agonists of the serotonin 5-HT1A receptor: Tryptophol is employed in the development of partial agonists that bind to the serotonin 5-HT1A receptor, which is involved in the regulation of mood, anxiety, and other neurological functions.
5. Growth hormone secretagogues: Tryptophol is used as a reactant in the synthesis of compounds that stimulate the secretion of growth hormone, which can be beneficial for various medical conditions.
6. Vascular endothelial growth factor (VEGF) inhibitors: Tryptophol is utilized in the development of VEGF inhibitors, which can be used to treat conditions characterized by abnormal blood vessel growth, such as certain types of cancer.
7. A2B adenosine receptor ligands: Tryptophol is used in the synthesis of ligands that target the A2B adenosine receptor, which is involved in various physiological processes, including inflammation and immune response.
8. Potential detoxification inhibitors of the crucifer phytoalexin brassinin: Tryptophol is used in the development of compounds that inhibit the detoxification of brassinin, a phytoalexin found in cruciferous plants with potential applications in agriculture and medicine.
9. Inhibitors of interleukin 6: Tryptophol is employed in the synthesis of inhibitors that target interleukin 6, a cytokine involved in immune response and inflammation, which can be used to treat various inflammatory diseases.
10. Dual binding site acetylcholinesterase inhibitors: Tryptophol is used as a reactant in the development of dual binding site acetylcholinesterase inhibitors, which can be used to treat conditions such as Alzheimer's disease and other neurodegenerative disorders.
Synthesis Reference(s)
Canadian Journal of Chemistry, 42, p. 485, 1964 DOI: 10.1139/v64-070
Purification Methods
Crystallise it from diethyl ether/pet ether, *C6H6, *C6H6/pet ether. The picrate has m 100-101o (from *C6H6). [Beilstein 21 I 218, 21 II 49, 21 III/IV 788, 21/3 V 61.]
Check Digit Verification of cas no
The CAS Registry Mumber 526-55-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 6 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 526-55:
(5*5)+(4*2)+(3*6)+(2*5)+(1*5)=66
66 % 10 = 6
So 526-55-6 is a valid CAS Registry Number.
InChI:InChI=1/C10H11NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,7,11-12H,5-6H2
526-55-6Relevant articles and documents
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Snyder,Pilgrim
, p. 3770 (1948)
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S -indole benzamide derivative as well as preparation method and application thereof
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, (2021/09/15)
S - Indole benzamide derivatives as well as a preparation method and application thereof relate to the technical field of pharmacy. The derivative has a structural formula. The specific preparation method comprises the following steps: taking indole as a starting raw material and performing acylation reaction. Reaction, oxidation reaction, (R)- (+) -tert-butylsulfenamide asymmetric synthesis reaction, hydrolysis reaction and acylation reaction to give the target product. By means of the method, a novel antiviral drug with a development prospect can be obtained, and the yield is high.
Synthesis of chiral [2,3]-fused indolines through enantioselective dearomatization inverse-electron-demand Diels-Alder reaction/oxidation of indoles with 2-(2-nitrovinyl)-1,4-benzoquinone
Cheng, Shaobing,Liu, Hui,Liu, Min,Yuan, Weicheng,Zhang, Jiayan,Zhang, Xiaomei,Zhao, Sihan
supporting information, p. 4200 - 4203 (2020/04/22)
Enantioselective dearomatization inverse-electron-demand Diels-Alder reaction/oxidation of indoles with 2-(2-nitrovinyl)-1,4-benzoquinone was realised using a chiral bisoxazoline/zinc complex as a catalyst. This transformation allowed for the synthesis of enantioenriched six-membered [2,3]-fused indolines (up to 99% yield and 88% ee).
Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes
Kawauchi, Daichi,Noda, Kenta,Komatsu, Yoshiyuki,Yoshida, Kei,Ueda, Hirofumi,Tokuyama, Hidetoshi
supporting information, p. 15793 - 15798 (2020/10/12)
An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.