5152-84-1

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-cinnoline is used as a key intermediate in the synthesis of pharmaceuticals for its ability to be tailored for specific applications. Its unique structure allows for the development of new chemical entities that can address various medical needs.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Chloro-cinnoline is utilized as a starting material for the preparation of compounds with pesticidal properties, contributing to the development of effective crop protection agents.
Used in Heterocyclic Compound Production:
4-Chloro-cinnoline is employed as a reagent in the production of heterocyclic compounds, which are important in various chemical and pharmaceutical applications due to their diverse chemical and biological properties.
Used in Chemical Research:
As a member of the cinnoline family, 4-Chloro-cinnoline is also used in chemical research for studying the properties and reactions of heterocyclic systems, furthering the understanding of organic chemistry and its applications.

InChI:InChI=1/C8H5ClN2/c9-7-5-10-11-8-4-2-1-3-6(7)8/h1-5H

Upstream product

• 1066-54-2 trimethylsilylacetylene 
• 613-89-8 2-Aminoacetophenone 
• 551-93-9 2-aminoacetophenone 
• 1197991-11-9 1-(4-bromo-2-iodophenyl)-3-ethyl-3-phenyltriaz-1-ene 
• 103529-16-4 2-[(trimethylsilyl)ethynyl]aniline 
• 615-43-0 2-iodophenylamine 
• 18514-84-6 4(1H)-cinnolon 
• 10026-13-8 phosphorus pentachloride 
• 10025-87-3 trichlorophosphate 
• 875-66-1 cinnolin-4-ol 
• 1416562-59-8 1-[4-bromo-2-(hex-1-yn-1-yl)phenyl]-3-ethyl-3-phenyltriaz-1-ene 

Downstream Products

• 173415-11-7 (4-chloro-3-cinnolinyl)phenylmethanol 
• 173415-12-8 (4-chloro-3-cinnolinyl)-2-methoxyphenylmethanol 
• 173415-33-3 4-chloro-3-methylcinnoline 
• 82452-99-1 4-chloro-3-iodocinnoline 
• 253-66-7 Cinnoline 
• 21905-79-3 4,4'-bicinnoline 
• 90141-86-9 4-(4'-methoxyphenyl)cinnoline 
• 297133-99-4 4-(3'-nitrophenyl)cinnoline 
• 297133-98-3 4-(4'-trifluoromethylphenyl)cinnoline 
• 1726-85-8 4-Methylmercapto-cinnolin 
• 766548-11-2 4-phenylsulfanylcinnoline 
• 74227-75-1 4-azidocinnoline 1-oxide 
• 62196-38-7 4-(p-tolylsulfonyl)cinnoline 
• 18592-06-8 4-(phenylethynyl)cinnoline 

Relevant academic research and scientific papers

TOLL-LIKE RECEPTOR 8 (TLR8)-SPECIFIC ANTAGONISTS AND METHODS OF MAKING AND USES THEREOF

Toll-like receptor 8 (TLR8)-specific inhibitors and methods of using the same in individuals having an autoimmune disease or an inflammatory disorder.

4-Aminoquinolone piperidine amides: Noncovalent inhibitors of DprE1 with long residence time and potent antimycobacterial activity

4-Aminoquinolone piperidine amides (AQs) were identified as a novel scaffold starting from a whole cell screen, with potent cidality on Mycobacterium tuberculosis (Mtb). Evaluation of the minimum inhibitory concentrations, followed by whole genome sequencing of mutants raised against AQs, identified decaprenylphosphoryl-β-d-ribose 2′-epimerase (DprE1) as the primary target responsible for the antitubercular activity. Mass spectrometry and enzyme kinetic studies indicated that AQs are noncovalent, reversible inhibitors of DprE1 with slow on rates and long residence times of ～100 min on the enzyme. In general, AQs have excellent leadlike properties and good in vitro secondary pharmacology profile. Although the scaffold started off as a single active compound with moderate potency from the whole cell screen, structure-activity relationship optimization of the scaffold led to compounds with potent DprE1 inhibition (IC50 10 nM) along with potent cellular activity (MIC = 60 nM) against Mtb.

Study of cyclyzation of o-(1-Alkynyl)- and o-(1,3-Butadiynyl)aryltriazenes under the action of acids

The investigation of Richter cyclization of o-(1-alkynyl)- and o-(1,3-butadiynyl)arenediazonium salts generated by acid cleavage of triazenes was carried out by the methods of NMR and ESI MS (Electrospray Ionization Mass Spectrometry). The effect was show

On the tautomerism of cinnolin-4-ol, cinnoline-4-thiol, and cinnolin-4-amine

Detailed NMR spectroscopic investigations (1H, 13C, 15N) with cinnolin-4-ol (1) reveal this compound to exist exclusively in the cinnolin-4(1H)-one form in deuteriodimethyl sulfoxide solution. This finding is confirmed by comparison of the NMR spectroscopic data of 1 with those of the corresponding 'fixed' O-methyl and N-methyl derivatives, i.e. 4-methoxycinnoline (3) and 1-methylcinnolin-4(1H)-one (5). Similarly, cinnoline-4-thiol (4) is present in the thione form in deuteriodimethyl sulfoxide, whereas cinnolin-4-amine (7) exists in the amino form. In addition, in-depth analyses of the NMR spectra of some simple 4-substituted cinnolines are provided.

11H-Isoquino[4,3-c]cinnolin-12-ones: Novel anticancer agents with potent topoisomerase I-targeting activity and cytotoxicity

Recent studies have identified 2,3-dimethoxy-8,9-methylenedioxy-11-[(2- dimethylamino)ethyl]-11H-isoquino[4,3-c]cinnolin-12-one (1a) as a novel topoisomerase I-targeting agent with potent cytotoxic activity. The effect of varied substituents at the 11-pos

NITRO AND AMINO SUBSTITUTED TOPOISOMERASE AGENTS

The invention provides compounds of formula 1 : wherein R1-R9, W, and X have any of the meanings defined in the specification and their pharmaceutically acceptable salts. The invention also provides pharmaceutical compositions comprising a compound of formula 1, processes for preparing compounds of formula 1, intermediates useful for preparing compounds of formula 1, and therapeutic methods for treating cancer using compounds of formula 1.

Synthesis of 4,8-diarylcinnolines and quinazolines with potential applications in nonlinear optics. Diazines. Part 28

New 4,8-diarylbenzodiazines have been synthesized using cross-coupling reactions and regioselective metalation at the peri-position C8 of the benzene moiety of various cinnolines and quinazolines. Some of these compounds have been tested to assess their nonlinear optical properties. (C) 2000 Elsevier Science Ltd.

Solid-phase synthesis of substituted cinnolines by a Richter type cleavage protocol

Starting from triazene bound ortho-halo arenes on a solid support, palladium-catalyzed alkynylations and subsequent cleavage reactions under acidic conditions give rise to ortho-alkynylaryldiazonium salts, which in turn undergo cyclization to afford substituted 4-halo- and 4- hydroxycinnolines in moderate to good yields. The method is applicable to automated synthesis.

Metallation of diazines XIV. First O-directed metallation of cinnolines. Metallation of 3-, 4-chloro and 3-, 4-methoxycinnolines

The lithiation of 3-, 4-chloro and 3-, 4-methoxycinnolines was studied and good yields were obtained. When iodine was used as electrophile, 4,8-diiodo or 4,8-iodochloro compounds were prepared. A xanthone and diazepine were synthetized.