1953-54-4 Usage
Description
5-Hydroxyindole, a hydroxylated indole, is a metabolite of Tryptophan (T894800) and serves as a building block in the preparation of various pharmaceutical compounds, particularly indole-based neurochemicals. It exhibits a beige to brown crystalline appearance, either in needle or powder form.
Uses
Used in Pharmaceutical Industry:
5-Hydroxyindole is used as a reactant for the preparation of (oxoimidazolidinyl/oxopyrimidinyl)benzenesulfonates, which are antitumor agents and tubulin inhibitors. This application is crucial for developing treatments targeting cancer cells and their mechanisms of growth and division.
Used in Chemical Synthesis:
5-Hydroxyindole is used as a reactant for the preparation of anthranilic acids, which are important in the synthesis of various pharmaceuticals and agrochemicals. These compounds contribute to the development of new drugs and chemical products.
Used in Neurochemistry:
5-Hydroxyindole is used as a reactant for the preparation of indole compounds that act as dopamine D2 receptor antagonists. These antagonists are significant in the study and treatment of neurological disorders associated with dopamine imbalances.
Used in Human β-Adrenoceptor Ligand Preparation:
5-Hydroxyindole is used as a reactant for the preparation of naphthalimideor carbazole-containing human β-adrenoceptor ligands. These ligands are vital for research into adrenergic signaling and the development of drugs targeting these receptors.
Used in Radioprotector Development:
5-Hydroxyindole is used as a reactant for the preparation of melanins, which serve as nature-inspired radioprotectors. Melanins have potential applications in protecting against radiation damage, particularly in medical and industrial settings.
Used in PKCθ Inhibitor Preparation:
5-Hydroxyindole is used as a reactant for the preparation of 5-vinyl-3-pyridinecarbonitriles, which are PKCθ inhibitors. These inhibitors are important in the study of protein kinase C theta (PKCθ) and its role in various cellular processes, including those related to diabetes and immune function.
Additionally, 5-Hydroxyindole has displayed weak inhibitory activity on human melanoma tyrosinase and has shown inhibition of serotonin transport by blood platelets, indicating potential uses in dermatology and neuroscience research.
Synthesis Reference(s)
Journal of the American Chemical Society, 76, p. 5579, 1954 DOI: 10.1021/ja01651a001The Journal of Organic Chemistry, 49, p. 4833, 1984 DOI: 10.1021/jo00199a017
Check Digit Verification of cas no
The CAS Registry Mumber 1953-54-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,9,5 and 3 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1953-54:
(6*1)+(5*9)+(4*5)+(3*3)+(2*5)+(1*4)=94
94 % 10 = 4
So 1953-54-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H7NO/c10-7-1-2-8-6(5-7)3-4-9-8/h1-5,9-10H
1953-54-4Relevant articles and documents
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Bergel,Morrison
, p. 49 (1943)
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Visible-light-promoted aerobic oxidative hydroxylation of arylboronic acids in water by hydrophilic organic semiconductor
Yu, Kunyi,Zhang, Hanjie,Sheng, Yuqiang,Zhu, Yongfa
supporting information, (2020/06/23)
A green and sustainable catalytic system was developed based on perylenediimide (PDI) organic semiconductor for the aerobic oxidative hydroxylation of arylboronic acids in aqueous solution with visible light. By using PDI-SN, a hydrophilic organic semiconductor, which can activate oxygen to produce superoxide radicals in aqueous solution, this reaction proceeds under ambient conditions: water as the solvent and air as the oxidant, giving various phenols as products with high yields. In contrast to methods using organic solvents, this novel process has the potential of green industrial application.
Diaryliodonium Salt-Mediated Intramolecular C-N Bond Formation Using Boron-Masking N-Hydroxyamides
Matsumoto, Makoto,Wada, Kohei,Urakawa, Kazuki,Ishikawa, Hayato
supporting information, p. 781 - 785 (2020/02/04)
Intramolecular aromatic C-N bond formation reactions using electron-rich aromatic tethered boron-masking N-hydroxyamide as substrate were realized. These new C-N bond formation reactions involve the in situ generation of a diaryliodonium salt by treatment with hypervalent iodine, deborylation by base treatment, spontaneous N → O acyl migration, cyclization, reductive elimination, elimination of benzoic acid, and tautomerization to indole formation. Hereby, we obtained highly functionalized electron-rich indoles and quinoline in practical yields.