22112-03-4

Basic information

• Product Name: 5-chloro-7-iodo-quinolin-8-ol
• CAS NO: 22112-03-4
• Molecular Formula: C9H5ClINO
• Molecular Weight: 305.49957
• Mol File: 22112-03-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-chloro-7-iodo-quinolin-8-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-chloro-7-iodo-quinolin-8-ol(22112-03-4)
• EPA Substance Registry System: 5-chloro-7-iodo-quinolin-8-ol(22112-03-4)

Safety Data

• Hazardous Substances Data: 22112-03-4(Hazardous Substances Data)

Upstream product

• 148-24-3 8-quinolinol 
• 27037-46-3 5-chloro-7-iodoquinolin-8-yl ethanoate 
• 7385-89-9 8-hydroxy-7-iodoquinoline 
• 2598-29-0 8-acetyloxyquinoline 
• 10173-02-1 5-chloroquinoline-8-yl acetate 
• 1371439-48-3 5-chloro-7-iodo-8-quinolinyl-β-D-glucopyranoside 
• 130-16-5 5-Chloro-8-hydroxyquinoline 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 220819-25-0 1-(5-chloro-7-iodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>phthalate 
• 220819-20-5 1-(5-chloro-7-iodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>butandioate 

Downstream Products

• 91240-91-4 chloro-5 iodo-7 methoxy-8 quinoline 
• 220819-25-0 1-(5-chloro-7-iodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>phthalate 
• 17012-44-1 chloro-5 methoxy-8 quinoleine 
• 1165802-39-0 8-(benzyloxy)-5-chloro-7-iodoquinoline 

Relevant articles and documents

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.

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.

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).

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.

Aza-and polyaza-naphthalenly ketones useful as hiv integrase inhibitors

Certain aza- and polyaza-naphthalenyl ketones including certain quinolinyl and naphthyridinyl ketones are described as inhibitors of HIV integrase and inhibitors of HIV replication. These compounds are useful in the prevention or treatment of infection by HIV and the treatment or the delay in the onset of AIDS, as compounds or pharmaceutically acceptable salts, or as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating or delaying the onset of AIDS and methods of preventing or treating infection by HIV are also described.

Nonreductive deiodination of ortho-iodo-hydroxylated arenes using tertiary amines

A convenient and nonreductive deiodination is reported for the ortho-iodo-hydroxylated arenes inch ding derivatives of quinolinol, phenol, and naphthol. Tertiary amines pyridine, triethylamine, and N-methylmorpholine in the presence of water initiated deiodination of ortho-iodo-hydroxylated arenes without affecting para-iodine and other reduction-susceptible groups. This reported method also works efficiently for polyiodinated systems. Simplicity, short reaction times, and absence of reducing catalyst are features of this method.

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.

3-Imino-1,2,4-benzotriazine-1-oxides

New 3-Imino-1,2,4-benzotriazine-1-oxides of formula I SPC1 wherein R represents an alkyl, alkenyl or haloalkyl radical, a phenyl or aralkyl radical optionally substituted by alkyl, alkoxy, haloalkyl, halogen or hydroxy, X and Y each independently represent hydrogen, halogen, an alkyl or alkoxy radical, or one of the two symbols represents a phenoxy or phenylsulphonyl radical optionally substituted by halogen, alkyl, haloalkyl and/or alkoxy which are active against harmful microorganisms are disclosed.