104-10-9Relevant articles and documents
p-Tyrosol: a new synthetic method and new types of pharmacological activity
Sysolyatin,Kryukov, Yu. A.,Malykhin,Muradov,Chernysheva,Aliev,Smol’yakova,Anishchenko,Sidekhmenova,Shamanaev, A. Yu.,Plotnikov
, p. 2210 - 2214 (2015)
A new method for the synthesis of p-tyrosol, i.e., 2-(4-hydroxyphenyl)ethanol, has been developed, which considerably simplified the process of preparation of this pharmaceutical substance. The method includes nitration of 2-phenylethanol, catalytic hydrogenation of 2-(4nitrophenyl)ethyl nitrate, and nitrosation of 2-(4-aminophenyl)ethanol, followed by acid hydrolysis of the intermediate diazo compound. The method is easily feasible, furnishes the pharmaceutical substance of high quality, and is quite acceptable for commercialization. Antihypertensive and hemorheologic activities of p-tyrosol in spontaneously hypertensive rats were investigated per se and in combination with captopril. p-Tyrosol in the course administration with captopril was found to enhance the antihypertensive effect of the latter and eliminate its negative effect on red blood cell aggregation.
Thermal dehydration of 2-(4-aminophenyl)ethanol
Schul'Tsev
, p. 2300 - 2303 (2011)
The influence of inorganic nucleophilic agents on the liquid-phase process of thermal dehydration of 2-(4-aminophenyl)ethanol at 200-260°C was investigated. It was found that K2CO3, BaCO3, BaO, CaH2, and NaOH did not catalyze the dehydration, but the process takes place easily with the formation of 4-aminostyrene in high yield, using KOH in the range of 100-180 mol % with respect to 2-(4-aminophenyl)ethanol.
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Woodburn,Stuntz
, p. 1361,1363 (1950)
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Direct and practical synthesis of primary anilines through iron-catalyzed C-H bond amination
Legnani, Luca,Cerai, Gabriele Prina,Morandi, Bill
, p. 8162 - 8165 (2016)
The direct C-H amination of arenes is an important strategy to streamline the discovery and preparation of functional molecules. Herein, we report an operationally simple arene C-H amination reaction that, in contrast to most literature precedent, affords directly the synthetically versatile primary aniline products without relying on protecting group manipulations. Inexpensive Fe(II)-sulfate serves as a convenient catalyst for the transformation. The reaction tolerates a wide scope of arenes, including structurally complex drugs. Importantly, the arene substrates are used as limiting reagents in the transformation. This operationally simple transformation should considerably accelerate the discovery of medicines and functional molecules.
A mild deprotection of trichloroethyl carbamates using indium metal
Mineno, Tomoko,Choi, Seoung-Ryoung,Avery, Mitchell A.
, p. 883 - 886 (2002)
The trichloroethoxycarbonyl moiety was efficiently removed from carbamates to furnish the corresponding amines using indium metal in good to excellent yields.
Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications
Zhao, Lixing,Hu, Chenyang,Cong, Xuefeng,Deng, Gongda,Liu, Liu Leo,Luo, Meiming,Zeng, Xiaoming
supporting information, p. 1618 - 1629 (2021/01/25)
Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.
Iodinated Choline Transport-Targeted Tracers
?vec, Pavel,Novy, Zbyněk,Ku?ka, Jan,Pet?ík, Milo?,Sedlá?ek, Ond?ej,Kucha?, Martin,Li?ková, Barbora,Medvedíková, Martina,Kolouchová, Kristyna,Groborz, Ond?ej,Loukotová, Lenka,Konefa?, Rafa? ?.,Hajdúch, Marián,Hruby, Martin
supporting information, p. 15960 - 15978 (2020/12/23)
We present a novel series of radioiodinated tracers and potential theranostics for diseases accompanied by pathological function of proteins involved in choline transport. Unlike choline analogues labeled with 11C or 18F that are currently used in the clinic, the iodinated compounds described herein are applicable in positron emission tomography, single-photon emission computed tomography, and potentially in therapy, depending on the iodine isotope selection. Moreover, favorable half-lives of iodine isotopes result in much less challenging synthesis by isotope exchange reaction. Six of the described compounds were nanomolar ligands, and the best compound possessed an affinity 100-fold greater than that of choline. Biodistribution data of 125I-labeled ligands in human prostate carcinoma bearing (PC-3) mice revealed two compounds with a biodistribution profile superior to that of [18F]fluorocholine.
