18504-81-9

Usage

Chemical family

Thiazine

Type of compound

Heterocyclic organic compound

Known for

Potential antifungal and antibacterial properties

Structure

Bicyclic, with a thiazine ring fused to a pyridine ring

Used in

Pharmaceutical research and drug development

Potential applications

Treatment of neurological disorders, anti-cancer agent

InChI:InChI=1/C7H6N2OS/c10-6-4-11-7-5(9-6)2-1-3-8-7/h1-3H,4H2,(H,9,10)

Upstream product

• 6298-19-7 2-chloro-3-aminopyridine 
• 758-08-7 Thioglycolamide 
• 2365-48-2 Methyl thioglycolate 
• 18504-80-8 2-[(3-nitropyridin-2-yl)sulfanyl]acetic acid 
• 24100-65-0 ethyl 2-[(3-nitropyridin-2-yl)sulfanyl]acetate 
• 5470-18-8 2-Chloro-3-nitropyridine 

Downstream Products

• 639825-91-5 2-methylsulfanyl-3H-pyrido[2,3-b][1,4]thiazine 

Relevant academic research and scientific papers

Anticholinesterasic, nematostatic and anthelmintic activities of pyridinic and pyrazinic compounds

In the search for acetylcholinesterase inhibitors as a potential target for the discovery of anthelmintic drugs, a series of 27 pyridinic and pyrazinic compounds have been designed on the basis of molecular hybridization of two known AChE inhibitors, namely, tacrine and (-)-3-O-acetylspectaline, and on the concept of isosterism. The synthesized compounds generally presented moderate anticholinesterasic activities when compared with the positive control physostigmine, but one compound (ethyl 2-[(6-chloropyrazin-2-yl)sulfanyl] acetate, 11) exhibited an in vitro ability to immobilize the root-knot nematode Meloidogyne incognita that was highly comparable to that of the positive control Temik. Moreover, in anthelmintic assays against the gastrointestinal parasitic nematode Nippostrongylus brasiliensis (L4), some of the compounds, such as (6-chloropyrazin-2-yl)sulfanyl ethanol (32, EC50 = 33 nM), presented activities that were considerably stronger than that of the positive control albendazole (EC50 = 340 nM). In the light of the positive results obtained in the anthelmintic evaluations, the acute oral toxicity of the representative compound diethyl 2,2'-[(3-nitropyridine-2,6-diyl) bissulfanediyl] diacetate (7) was determined in rats, and the drug was shown to be non-toxic at a dose of 2000 mg/kg. These results, allied with the relatively simple structures of the active compounds and their facile synthesis, highlight their potential use as anthelmintic or nematicidic agents.

Synthesis and antitumor activity of some new substituted quinolin-4- one and 1,7-naphthyridin-4-one analogs

The synthesis of some new analogs of quinolin-4-one and 1,7- naphthyridin-4-one is described. The prepared compounds were tested for their in vitro antitumor and cdc2 kinase or cdc25 phosphatase inhibitory activity. Compound ethyl 7-oxo-2,3-dihydro-7H-pyrido [1,2,3-de][2,3- b]pyrido-1,4-thiazine-6-carboxylate (6b) showed antitumor activity against CNS SNB-75, breast T-47D, and lung NCI-H522 cancer cell lines with GI50 values of 8.3, 17.6, and 22.7 μM, respectively. Meanwhile, the compounds ethyl 4-oxo-8-phenylthio-1H,4H-quinoline-3-carboxylate (11a) and 4-oxo-8- phenylthio-1H,4H-1,7-naphthyridine-3-carboxylic acid (12b) have proved to be cdc25 phosphatase inhibitors at IC50 values of 11 and 5 μM, respectively.

The Synthesis of Pyridothiazinones

Both 2 and 4 halogenated 3-aminopyridines react thermally with α-mercapto esters and amides to afford pyrido and pyridothiazinones.N-alkylation and oxidation of the products were investigated.

Heterocyclic aldose reductase inhibitors and methods of using them

The invention relates to new compounds of the formula: STR1 Aldose reductase inhibitors. Treatment of certain complications of diabetes.