174726-87-5

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 7-chloro-1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylate, 7-chloro-1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid ethyl ester is used as an intermediate in the synthesis of antimicrobial and antiviral drugs. Its unique structure and functional groups enable the development of bioactive compounds with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, ethyl 7-chloro-1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylate, 7-chloro-1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid ethyl ester serves as a key intermediate in the production of pesticides and herbicides. Its properties contribute to the creation of effective biocides for agricultural applications, enhancing crop protection and yield.
Used in Chemical Industry:
Ethyl 7-chloro-1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylate, 7-chloro-1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid ethyl ester is utilized as a building block in the chemical industry for the synthesis of various bioactive compounds. Its unique structure and functional groups make it an important component in the development of novel chemical entities with potential applications in different fields.

Upstream product

• 58584-83-1 2,6-dichloronicotinoyl chloride 
• 96-50-4 2-thiazolylamine 
• 157373-27-8 ethyl 2-[(2,6-dichloropyridin-3-yl)carbonyl]-3-ethoxyacrylate 
• 38496-18-3 2,6-dichloropyridine-3-carboxylic acid 
• 174727-36-7 ethyl 3-(2,6-dichloropyridin-3-yl)-3-oxopropanoate 
• 6148-64-7 ethyl potassium malonate 
• 122-51-0 orthoformic acid triethyl ester 
• 174726-89-7 ethyl 2-(2,6-dichloro-3-nicotinoyl)-3-(2-thiazolylamino)acrylate 

Downstream Products

• 685880-20-0 ethyl 1,4-dihydro-4-oxo-1-(2-thiazolyl)-7-(2-trimethylsilylethynyl)-1,8-naphthyridine-3-carboxylate 
• 175414-77-4 1,4-dihydro-7-(3-methoxy-4-methylamino-1-pyrrolidinyl)-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid 
• 175414-77-4 1,4-dihydro-7-[(R,R)-3-methoxy-4-methylamino-1-pyrrolidinyl]-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid 
• 175414-77-4 vosaroxin 

Relevant academic research and scientific papers

NOVEL PYRIDONE CARBOXYLIC ACID DERIVATIVE OR SALT THEREOF

It is intended to provide a novel compound having high antitumor activity and low toxicity to normal cells. The present invention provides a pyridone carboxylic acid derivative represented by the following formula (1) or a salt thereof wherein R1 represents a hydrogen atom, a halogen atom or the like; R2 represents a hydrogen atom, a halogen atom or the like; R3 to R6 each represent a hydrogen atom or the like; R7 represents a hydrogen atom or the like; R8 represents a hydrogen atom, a halogen atom, the following formula (a) (wherein Ra1 and Ra2 each represent a hydrogen atom, a hydroxy group, an optionally substituted lower alkyl group or the like) or the like, or R7 and R8 together represent —N—OR10 (wherein R10 represents a hydrogen atom, an optionally substituted lower alkyl group, or an aralkyl group), or R7 and R8 form an optionally substituted 4- to 6-membered saturated hetero ring together with the adjacent carbon atom, or the like; R9 represents a hydrogen atom or the like; X represents a nitrogen atom or the like; and Y represents a nitrogen atom or the like.

Synthesis and in vitro antitumor activity of novel naphthyridinone derivatives

A series of naphthyridinone derivatives based on 1a (a precursor of Voreloxin) were designed and synthesized. Seven compounds having >70% inhibition against HL60 at 30 μmol/L were further evaluated for their in vitro antitumor activity by SRB assay. Results reveal that thiazol-2-yl and 3-aminomethyl-4-benzyloxyimino-3-methylpyrrolidin-1-yl groups are optimal at the N-1 and C-7 positions of naphthyridinone core, respectively. 10j exhibits broad-spectrum activity (IC50: 100-fold more potent than the two references against eight of these cell lines.

STABLE SNS-595 COMPOSITIONS AND METHODS OF PREPARATION

Methods of preparing substantially pure SNS-595 substance are disclosed. Also provided are compositions comprising SNS-595 substance that are substantially pure and essentially free of visible particles.

METHOD OF PREPARING (+)-1,4-DIHYDRO-7-[(3S,4S)-3METHOXY-4-(METHYLAMINO)-1-PYRROLIDINYL]-4-OXO-1-(2-THIAZOLYL)-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID

Methods of preparing (+)-1, 4-dihydro-7-[(3S,45)-3-methoxy-4-(methylamino)-1 - pyrrolidinyl]-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid are disclosed. Also provided are pharmaceutical compositions comprising (+)-1,4-dihydro-7-[(3S,4S)-3-methoxy-4-(methylamino)-1-pyrrolidinyl]-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid, and methods of treatment using such compositions.

Synthesis and Structure-Activity Relationships of Novel 7-Substituted 1,4-Dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic Acids as Antitumor Agents. Part 2

We have previously reported that a series of 7-substituted 6-fluoro-1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acids possess moderate cytotoxic activity. In a further attempt to find clinically useful antitumor agents, we investigated the structure-activity relationships (SARs) of a new series of compounds obtained by changing the C-6 position of the fluorine atom in addition to the C-5 and C-7 positions and evaluating their cytotoxic activity against several murine and human tumor cell lines. Our results showed that the 6-unsubstituted 1,8-naphthyridine structure had the most potent cytotoxic activity against murine P388 leukemia twice that of the 6-fluoro analogue. In addition, introduction of an amino group at the C-5 position did not have any substantial effect on the cytotoxic activity, while both the 5-chloro and 5-trifluoromethyl groups decreased the cytotoxic activity by 5- to 10-fold. Moreover, aminopyrrolidine derivatives at the C-7 position showed more potent cytotoxic activity than other amines or carbon derivatives. Among the 7-(3-aminopyrrolidinyl) derivatives, the trans-3-methoxy-4-methylaminopyrrolidinyl derivative (271) was determined to have potent cytotoxic activity in both in vitro and in vivo assays and high water solubility. Finally, the (S,S)-isomer (AG-7352, 3) of 271, with a cytotoxic activity against human tumor cell lines more potent than that of etoposide, was selected for further development.

Compounds, processes for the preparation thereof and anti-tumor agents

This invention relates to pyridone-carboxylic acid derivatives of the following formula or salts thereof: STR1 wherein R1 is a hydrogen atom, a halogen atom, etc., R2 is a carboxyl group etc., R3 is a hydrogen atom etc., A