773-76-2

Usage

Uses

Chloroxine, is an impurity of Cioquinol, which is an antifungal and antiprotozoal drug.

Indications

Chloroxine (Capitrol) shampoo contains a synthetic antibacterial compound similar to the hydroxyquinoline compounds used in dermatology for many years.

Definition

ChEBI: Quinolin-8-ol in which the hydrogens at positions 5 and 7 have been substituted by chlorine. An synthetic antibacterial prepared by chlorination of quinolin-8-ol, it is used for the treatment of dandruff and seborrhoeic dermatitis of the scalp.

Brand name

Capitrol (Westwood- Squibb).

Purification Methods

Crystallise the dichloro-oxine from acetone/EtOH. [Beilstein 21 H 95.]

InChI:InChI=1/C9H5Cl2NO/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 
• 521-74-4 broxyquinoline 
• 687638-05-7 5,7,7-trichloro-7H-quinoline-8-one 
• 609-89-2 2,4-dichloro-6-nitrophenol 
• 56-81-5 glycerol 
• 83-73-8 5,7-diiodo-8-hydroxyquinoline 
• 123-91-1 1,4-dioxane 
• 130-26-7 5-chloro-7-iodoquinolin-8-ol 
• 7732-18-5 water 
• 88005-20-3 tetrakis(5,7-dichloro-8-quinolinolato)thorium(IV) * 5,7-dichloro-8-quinolinol 
• 1419402-06-4 5,7-dichloro-8-quinolinyl-β-D-glucopyranoside 
• 130-16-5 5-Chloro-8-hydroxyquinoline 

Downstream Products

• 49638-84-8 undec-10-enoic acid-(5,7-dichloro-[8]quinolyl ester) 
• 18193-10-7 benzoic acid-(5,7-dichloro-[8]quinolyl ester) 
• 120015-12-5 7-chloro-5-(4'-diethylamino-2'-methylphenylimino)quinoline-8-one 
• 120015-13-6 7-chloro-5-(4'-dimethylaminophenylimino)quinoline-8-one 
• 84165-45-7 8-Benzyloxy-5,7-dichloro-quinoline 
• 84165-43-5 2-(5,7-Dichloro-quinolin-8-yloxy)-1-phenyl-ethanone 
• 84165-44-6 5,7-Dichloro-8-(2,4-dinitro-phenoxy)-quinoline 
• 21168-33-2 5,7-dichloro-8-hydroxyquinoline 1-oxide 
• 59460-86-5 [Cu(5,7-Cl-8-HQ)₂] 
• 92951-86-5 Rh(5,7-dichloro-8-hydroxyquinolate)(CO)(2-bromo-3,4,5,6-tetrafluorophenyldiphenylphosphine) 
• 1221161-38-1 5,7-dichloro-8-quinolyl-N-(3,5-dichlorophenyl)carbamate 
• 1221161-40-5 5,7-dichloroquinolin-8-yl 4-fluorophenylcarbamate 

Relevant academic research and scientific papers

Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)

N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent.

A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines

An operationally simple and metal-free protocol for geometrically inaccessible C5-H halogenation of a range of 8-substituted quinoline derivatives has been established. The reaction proceeds under air, with inexpensive and atom economical trihaloisocyanuric acid as a halogen source (only 0.36 equiv.), at room temperature. Exceptionally high generality with respect to quinoline is observed, and in most instances, the reaction proceeded with complete regioselectivity. Quinoline with a variety of substituents at the 8-position gave, exclusively, the C5-halogenated product in good to excellent yields. Phosphoramidates, tertiary amides, N-alkyl/N,N-dialkyl, and urea derivatives of quinolin-8-amine as well as alkoxy quinolines were halogenated at the C5-position via remote functionalization for the first time. This methodology provides a highly economical route to halogenated quinolines with excellent functional group tolerance, thus providing a good complement to existing remote functionalization methods of quinolin-8-amide derivatives and broadening the field of remote functionalization. The utility of the method is further showcased through the synthesis of several compounds of biological and pharmaceutical interest.

Recyclable ionic liquid iodinating reagent for solvent free, regioselective iodination of activated aromatic and heteroaromatic amines

This article describes a simple, efficient method for iodination of activated aromatic and heteroaromatic amines using recyclable 1-butyl-3-methylpyridinium dichloroiodate (BMPDCI) as an ionic liquid iodinating reagent, in the absence of any solvent. The main advantages are a simple efficient procedure, good yields and no need for any base/toxic heavy metals, or oxidizing agents. The ionic liquid was recovered and recycled in five subsequent reactions, without much loss of activity. This method was applied for the synthesis of the antiprotozoal drug iodoquinol and the antifungal drug clioquinol.

Glycosylated copper(ii) ionophores as prodrugs for β-glucosidase activation in targeted cancer therapy

8-Hydroxyquinoline derivatives are metal-binding compounds that have recently attracted interest as therapeutic agents for cancer therapy. In this scenario, we designed and synthesized three new glucoconjugates, 5,7-dichloro-8-quinolinyl-β-d-glucopyranoside, 5-chloro-8-quinolinyl- β-d-glucopyranoside and 2-methyl-8-quinolinyl-β-d-glucopyranoside and investigated their biological properties in comparison to the parent 8-hydroxyquinoline derivatives in the presence of Cu2+. In vitro data show that 2 out of 3 glycosylated compounds possess a pharmacologically- relevant antiproliferative activity against tumor cells, similar to that of their parent compounds; this activity is associated with a relevant triggering of apoptosis. The pharmacological profile of the glucoconjugates depends on the cellular enzymatic β-glucosidase activity, as demonstrated by the inhibition of antiproliferative activity in the presence of the 2,5-dideoxy-2,5-imino-d-mannitol. The Royal Society of Chemistry 2013.

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.

Pyridine hydrochloride: A new reagent for the synthesis of o-chloro hydroxy derivatives in pyridine and quinoline series

Pyridine hydrochloride has been widely used in the cleavage of ethers. It is shown herein that his reagent is also efficient for the synthesis of chloro compounds starting from the corresponding bromo derivatives in π-deficient series such as pyridine and quinoline. Thus, for example, 7-bromo-8-hydroxyquinoline was almost quantitatively converted into 7-chloro-8-hydroxyquinoline. The scope of the reaction has been studied.

Cosmetic composition

Compositions containing an ester of nicotinic acid and a cosmetically acceptable surfactant are provided. These compositions, when applied topically to the human body produce a response such as a sensory or therapeutic response, for example a tingling or warming sensation or an increase in blood flow, which persists after the composition is rinsed from the body. The compositions are particularly suitable for application to the hair and/or scalp where they may encourage hair growth. Compositions for application to the hair and/or scalp preferably additionally comprise hair benefit agents such as hair growth promoters.

Hydroformylation of olefins using azoxy-dentated ligands

At a temperature in the range 100° C to 225° C the destructive dissociation of cobalt carbonyl compounds to cobalt metal and residue is inhibited by the action of one or more azoxy-dentated chelation ligands.