83-73-8

Usage

Uses

Used in Antiamoebic Applications:
5,7-Diiodo-8-quinolinol is used as an amebicide for the treatment of amoebiasis, a disease caused by the protozoan parasite E. histolytica. It is particularly effective against moderate intestinal amebiasis and is considered the drug of choice for this condition.
Used in Balantidiasis Treatment:
In addition to amoebiasis, 5,7-Diiodo-8-quinolinol is also used in the treatment of balantidiasis, an infection caused by the protozoan Balantidium coli. It acts as an amoebicidal agent, helping to eliminate the parasite and alleviate symptoms.
Used in Pharmaceutical Industry:
5,7-Diiodo-8-quinolinol is used in the pharmaceutical industry under various brand names, such as Quinadome (Bayer) and Yodoxin (Glenwood). These formulations make the drug more accessible and convenient for patients and healthcare providers in the treatment of the aforementioned conditions.

Originator

Diiodohydroxyquinoline,Adco Co.

Indications

Iodoquinol (diiodohydroxyquin, Yodoxin, Moebiquin) is a halogenated 8-hydroxyquinoline derivative whose precise mechanism of action is not known but is thought to involve an inactivation of essential parasite enzymes. Iodoquinol kills the trophozoite forms of E. histolytica, B. coli, B. hominis, and Dientamoeba fragilis. Iodoquinol is absorbed from the gastrointestinal tract and is excreted in the urine as glucuronide and sulfate conjugates. Most of an orally administered dose is excreted in the feces. Iodoquinol has a plasma half-life of about 12 hours. Iodoquinol is the drug of choice in the treatment of asymptomatic amebiasis and D. fragilis infections. It is also used in combination with other drugs in the treatment of other forms of amebiasis and as an alternative to tetracycline in the treatment of balantidiasis. Adverse reactions are related to the iodine content of the drug; the toxicity is often expressed as skin reactions, thyroid enlargement, and interference with thyroid function studies. Headache and diarrhea also occur. Chronic use of clioquinol, a closely related agent, has been linked to a myelitislike illness and to optic atrophy with permanent loss of vision.

Manufacturing Process

5,7-Diiodo-8-quinolinol widely used as an intestinal antiseptic, especially as an antiamebic agent. It is also used topically in other infections and may cause CNS and eye damage. It is known by very many similar trade names worldwide.0.01 mol 8-oxychinoline and 0.01 mol salicylic acid were dissolved in 500 ml of water and then 0.05 mol potassium iodide was added. The mixture was heated to temperature 90°-100°C. After that 0.01 mol of KIO3 by little tiles was added. The next tile was added after a disappearence of discharging iodine. Then 10 ml 2 N HCl was added. The solid product was fallen, filtered off, washed with hot water and in 0.25 N NaOH dissolved. The solution was filtered and the clear filtrate precipitated with a very little excess of HCl. The product 5,7-diiodo-8-quinolinol was filtered, washed with hot water and dried. MP: 200°-250°C (with decomposition).

Therapeutic Function

Antibacterial

Flammability and Explosibility

Nonflammable

Clinical Use

5,7-Diiodo-8-quinolinol, 5,7-diiodo-8-hydroxyquinoline,or diiodohydroxyquin (Yodoxin, Diodoquin, Diquinol) is ayellowish to tan microcrystalline, light-sensitive substancethat is insoluble in water. It is recommended for acute andchronic intestinal amebiasis but is not effective in extraintestinaldisease. Because a relatively high incidence of topicneuropathy has occurred with its use, iodoquinol should notbe used routinely for traveler’s diarrhea.

Safety Profile

Poison by ingestion and intravenous routes. Human systemic effects by ingestion: eye effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of Iand Nox

Synthesis

Iodoquinol, 5,7-diiodo-8-quinolinol (37.2.2), is made by iodination of 8-oxyquinoline (37.2.1) using a mixture of potassium iodide/potassium iodate. The initial 8-hydroxyquinolin (37.2.1) is made from 2-aminophenol and glycerol in the presence of sulfuric acid and nitrobenzene (Skraup synthesis).

Purification Methods

It crystallises from xylene and is dried at 70o in a vacuum. [Beilstein 21 II 58.]

InChI:InChI=1/C9H5I2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H

Upstream product

• 148-24-3 8-quinolinol 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 7790-99-0 Iodine monochloride 
• 123-91-1 1,4-dioxane 
• 130-26-7 5-chloro-7-iodoquinolin-8-ol 
• 220819-28-3 1-(5,7-diiodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>phthalate 
• 220819-23-8 1-(5,7-diiodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>butandioate 

Downstream Products

• 773-76-2 chloroxine 
• 112465-95-9 8-hydroxyquinoline-d5,7 
• 220819-28-3 1-(5,7-diiodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>phthalate 
• 784210-31-7 4-chloro-benzenesulfonic acid 5,7-diiodo-quinolin-8-yl ester 
• 134143-82-1 5,7-Diiodo-8-(5-phenyl-[1,3,4]oxadiazol-2-yloxy)-quinoline 
• 134143-96-7 5,7-Diiodo-8-[5-((E)-styryl)-[1,3,4]oxadiazol-2-yloxy]-quinoline 
• 134143-93-4 4-[5-(5,7-Diiodo-quinolin-8-yloxy)-[1,3,4]oxadiazol-2-yl]-phenylamine 
• 134143-85-4 8-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yloxy]-5,7-diiodo-quinoline 
• 134143-88-7 4-[5-(5,7-Diiodo-quinolin-8-yloxy)-[1,3,4]oxadiazol-2-yl]-phenol 
• 134143-92-3 3-[5-(5,7-Diiodo-quinolin-8-yloxy)-[1,3,4]oxadiazol-2-yl]-phenylamine 
• 134143-84-3 8-[5-(3-Chloro-phenyl)-[1,3,4]oxadiazol-2-yloxy]-5,7-diiodo-quinoline 
• 134143-87-6 3-[5-(5,7-Diiodo-quinolin-8-yloxy)-[1,3,4]oxadiazol-2-yl]-phenol 
• 134143-83-2 8-[5-(2-Chloro-phenyl)-[1,3,4]oxadiazol-2-yloxy]-5,7-diiodo-quinoline 
• 134143-86-5 2-[5-(5,7-Diiodo-quinolin-8-yloxy)-[1,3,4]oxadiazol-2-yl]-phenol 

Relevant academic research and scientific papers

One-pot method for preparing chloroquine chloroquine and diiodoquinoline

The method effectively solves the problems of (1) solving the problem of high isomer ratio in reaction products due to the fact that hydroxyl groups are ortho-alignment positioning groups when no guide groups are first C5 halogenated and C7 iodo, and purification difficulty is also increased. (2) The problems of poor atom economy, harsh reaction conditions, tedious aftertreatment steps and the like in first 66% steps C5 C7 C7 are effectively overcome by the method provided by the invention, and the C5-position halogenated product is 60% effectively overcome by overcoming the defects of poor atom economy, harsh reaction conditions, complicated post-treatment steps and the like in the two methods. The method has the advantages of economy of atoms, simplicity in operation, easiness in amplification and the like.

Study on Relationship Between Fluorescence Properties and Structure of Substituted 8-Hydroxyquinoline Zinc Complexes

Organic light-emitting diodes (OLEDs) produced from 8-hydroxyquinoline metal complexes play a vital role in modern electroluminescent devices. In this manuscript, a series of 8-hydroxyquinoline derivatives were synthesized by different methods and their corresponding zinc metal complexes were prepared. The UV and fluorescence properties of the complexes were measured aiming to understand the effect of substituents at the quinoline ring on the fluorescence properties of the complexes. When the C-5 of 8-hydroxyquinoline was replaced by halogen group, the fluorescence emission wavelengths had been red-shifted, at the same time, blue-shifted of fluorescence emission wavelength was observed when the C-5 position of 8-hydroxyquinoline was substituted by electron-withdrawing group. When the C-4 position of 8-hydroxyquinolie was substituted by methyl or the C-5 position was substituted by sulfonic acid group, the corresponding zinc complexes had higher fluorescence intensity than 8-hydroxyquinolie zinc.

NOVEL RECYCLABLE IODINATING AGENT AND ITS APPLICATIONS

The present invention provides a novel recyclable catalysts of formula A, [Formula A should be inserted here] wherein X is selected from the group consisting of [Formula should be inserted here] The present invention also provides a novel recyclable iodinating agent of formula I, II or III and a process for the synthesis thereof. [ Formula I, II & III should be inserted here] Further, the present invention provides a process of halogenation of amines and heterocyclic compounds by employing recyclable catalyst of formula (I).

Iodination of industrially important aromatic compounds with aqueous potassium triiodide

A new reagent system consisting of aqueous KI3in AcOH and NaIO4as oxidant has been found to be effective in iodinating a variety of commercially important aromatic substrates under ambient conditions. The presence of Na2SO3enhances the yield and the product purity. The procedure ensures high yields (72–98%) at room temperature in a short reaction time. A remarkable feature of this system is that even acidsensitive functionalities like anilines can be iodinated quantitatively.

A simple method for iodination of heterocyclic compounds using HIO 4/NaCl/silica gel/H2SO4 in water

A fast and simple method for iodination of some heterocycles is reported. The reactions were carried out in water, using HIO4/H 2SO4/NaCl/silica gel at moderate temperatures of 25-50 °C. Springer-Verlag 2011.

Mild and efficient iodination of aromatic and heterocyclic compounds with the NaClO2/NaI/HCl system

NaClO2/NaI in the presence of HCl is a mild, cheap, and non-toxic reagent for the iodination of phenols, including estradiol and naphthol, aromatic amines, and heterocyclic substrates, e.g., indoles, 8-hydroxyquinoline, imidazole, in fair to excellent yields by a very simple isolation protocol. The scope of the procedure is exemplified by the first iodination of 5-nitroindole to 3-iodo-5-nitroindole in 75% yield.

QUINOLINE DERIVATIVES

The invention relates to new quinoline derivatives which are active CLK-1 inhibitors. More specifically, the CLK-1 inhibitors of the invention are compounds of formula (A). The invention also relates to pharmaceutical compositions comprising such compounds and to methods for the prophylaxis and/or treatment of disorders or their associated symptoms for which the inhibition of CLK-1 is beneficial.

Eco-friendly oxidative iodination of various arenes with sodium percarbonate as the oxidant http://www.mdpi.org

Six easy laboratory procedures are presented for the oxidative iodination of various aromatics, mostly arenes, with either molecular iodine or potassium iodide (used as the sources of iodinating species, I+ or I 3+), in the presence of sodium percarbonate (SPC), a stable, cheap, easy to handle, and eco-friendly commercial oxidant.

Aromatic iodination in aqueous solution. A new lease of life for aqueous potassium dichloroiodate

A re-investigation of the use of aqueous potassium dichloroiodate (KICl2) as an iodinating agent for aromatic compounds has found the reagent to be more generally applicable than previously known. The reagent has been found to give excellent yields of iodinated heterocyclic compounds, such as isatin, imidazole and pyrazole.

Metronidazole twin ester prodrugs II: Non identical twin esters of metronidazole and some antiprotozoal halogenated hydroxyquinoline derivatives

New non identical twin ester prodrugs 3a-d were synthesized by linking metronidazole and some antiprotozoal halogented 8-hydroxyquinoline derivatives via dicarboxylic acid spacers with the aim of improving the therapeutic efficacy of both drugs. The synthesis necessitates the preparation of the precursor metronidazole hemisuccinate or hemiphthalate followed by estrification with the respective hydroxyquinoline derivative. To assess their suitability as prodrugs, the lipophilic properties, chemical stability as well as in vitro and in vivo enzymatic hydrolysis were investigated. The lipophilic properties, expressed as Rm values were determined using RP-TLC and showing enhanced lipophilicity as compared with the parent drugs. Hydrolysis kinetics of the prepared twin esters at 37°C using HPLC, indicated a quantitative release of the parent drugs in two step reaction (K1 and K2) via formation of metronidazole hemiesters followed by spontaneous hydrolysis of the later to metronidazole. The twin esters were adequately stable in aqueous buffer solutions than in biological media and the second rate (K2) of hydrolysis is more accelerated than the first (K1). Bioavailability study of 1-(5-chloro-7-iodoquinolin-8-yl)-4-[2-(2-methyl-5- nitro-1-H-imidazolyl)ethyl]butandioate, 3a, as well as equivalent amount of the corresponding physical mixture of metronidazole and 5-chloro 7-iodo-8- hydroxyquinoline in rabbits has shown that, the plasma level of the released metronidazole from the prodrug is higher than that resulting from the physical combination. A considerable amount of 5-chloro-7-iodo- hydroxyquinoline was detected in plasma, however, no measurable concentration of the quinoline derivative was observed in rabbit plasma from the physical mixture.