64987-16-2

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 2-AMINO-4-THIAZOLEACETATE is used as a reactant for the preparation of N-[4-(substituted)-1,3-thiazol-2-yl]-2-(substituted)acetamides, which are antibacterial agents. These agents are effective against a range of bacterial strains, including S. aureus, E. coli, P. aeruginosa, and K. pneumonia, making them valuable in the development of new antibiotics to combat drug-resistant infections.

InChI:InChI=1/C6H8N2O2S/c1-10-5(9)2-4-3-11-6(7)8-4/h3H,2H2,1H3,(H2,7,8)

Synthetic route

methanol (67-56-1) + 2-amino-4-thiazoleacetic acid (29676-71-9) → (2-amino-thiazol-4-yl)-acetic acid methyl ester (64987-16-2)

Conditions	Yield
Stage #1: methanol; 2-amino-4-thiazoleacetic acid With sulfuric acid In methanol at 0℃; Reflux; Stage #2: With sodium hydrogencarbonate pH=8 - 9;	93%
Stage #1: methanol; 2-amino-4-thiazoleacetic acid With sulfuric acid at 0 - 5℃; for 5h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In water pH=8 - 9;	93%
With thionyl chloride for 12h;	91%

Methyl 4-chloroacetoacetate (32807-28-6) + thiourea (17356-08-0) → (2-amino-thiazol-4-yl)-acetic acid methyl ester (64987-16-2)

Conditions	Yield
In ethanol Reflux;	89.5%
With ethanol Reflux;	89.5%
In ethanol for 4h; Heating;

2-amino-4-thiazoleacetic acid (29676-71-9) + diazomethyl-trimethyl-silane (18107-18-1) → (2-amino-thiazol-4-yl)-acetic acid methyl ester (64987-16-2)

Conditions	Yield
In methanol; benzene at 20℃;

trityl chloride (76-83-5) + (2-amino-thiazol-4-yl)-acetic acid methyl ester (64987-16-2) → methyl 2-tritylamino-4-thiazolylacetate (78287-71-5)

Conditions	Yield
With triethylamine In dichloromethane for 15h;	96%

(2-amino-thiazol-4-yl)-acetic acid methyl ester (64987-16-2) + methyl iodide (74-88-4) → methyl (2-imino-3-methyl-2,3-dihydrothiazol-4-yl)acetate hydroiodide (1586872-68-5)

Conditions	Yield
In tetrahydrofuran at 20℃; for 72h;	93%

di-tert-butyl dicarbonate (24424-99-5) + (2-amino-thiazol-4-yl)-acetic acid methyl ester (64987-16-2) → methyl 2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetate (103053-96-9)

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 90℃;	79%
In toluene at 85℃; for 24h;
In toluene at 85℃; for 24h;
at 85℃; for 24h;

4,5-dibromopyrrol-2-yl trichloromethyl ketone (50371-52-3) + (2-amino-thiazol-4-yl)-acetic acid methyl ester (64987-16-2) → methyl 2-(2-(4,5-dibromo-1H-pyrrole-2-carboxamido)thiazol-4-yl)acetate

Conditions	Yield
Stage #1: (2-amino-thiazol-4-yl)-acetic acid methyl ester With sodium carbonate In N,N-dimethyl-formamide Stage #2: 4,5-dibromopyrrol-2-yl trichloromethyl ketone In N,N-dimethyl-formamide at 80℃;	77%
Stage #1: (2-amino-thiazol-4-yl)-acetic acid methyl ester With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 4,5-dibromopyrrol-2-yl trichloromethyl ketone In N,N-dimethyl-formamide at 80℃;	77%

Upstream product

• 67-56-1 methanol 
• 29676-71-9 2-amino-4-thiazoleacetic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 32807-28-6 Methyl 4-chloroacetoacetate 
• 17356-08-0 thiourea 

Downstream Products

• 263169-24-0 2-(2-bromothiazol-4-yl)ethanol 
• 62557-05-5 2-(2-methanesulfonamidothiazol-4-yl)-acetic acid 
• 89336-46-9 2-{2[(tert-butoxycarbonyl)amino]-1,3-thiazol-4-yl}acetic acid 
• 1610728-72-7 N,N'-(5,5'-((1S,3S)-cyclohexane-1,3-diyl)bis(1,3,4-thiadiazole-5,2-diyl))bis(2-(2-methoxythiazol-4-yl)acetamide) 
• 1324935-54-7 methyl 2-(2-(2-(3-methoxyphenyl)acetamido)thiazol-4-yl)acetate 
• 1390409-52-5 methyl 2-(2-(2-m-tolylacetamido)thiazol-4-yl)acetate 
• 1154358-30-1 methyl 2-(2-(2-p-tolylacetamido)thiazol-4-yl)acetate 
• 56826-61-0 (2-methylpyridin-3-yl)methanol 
• 1421928-97-3 methyl 2-(2-(((2-methylpyridin-3-yl)methyl)amino)thiazol-4-yl)acetate 
• 1416810-89-3 C₂₃H₂₅Cl₂N₃O₄S 
• 1416811-05-6 C₂₃H₁₈Cl₂FN₃O₄S 
• 64220-26-4 [2-[(triphenyl-methyl)-amino]-thiazol-4-yl] acetic acid 
• 1351823-25-0 C₄₆H₄₆N₄O₄S₂ 
• 78287-71-5 methyl 2-tritylamino-4-thiazolylacetate 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of 4,5-dibromo-N-(thiazol-2-yl)-1H-pyrrole-2-carboxamide derivatives as novel DNA gyrase inhibitors

Development of novel DNA gyrase B inhibitors is an important field of antibacterial drug discovery whose aim is to introduce a more effective representative of this mechanistic class into the clinic. In the present study, two new series of Escherichia coli DNA gyrase inhibitors bearing the 4,5-dibromopyrrolamide moiety have been designed and synthesized. 4,5,6,7-Tetrahydrobenzo[1,2-d]thiazole-2,6-diamine derivatives inhibited E. coli DNA gyrase in the submicromolar to low micromolar range (IC50values between 0.891 and 10.4 μM). Their “ring-opened” analogues, based on the 2-(2-aminothiazol-4-yl)acetic acid scaffold, displayed weaker DNA gyrase inhibition with IC50values between 15.9 and 169 μM. Molecular docking experiments were conducted to study the binding modes of inhibitors.

NLRP MODULATORS

In one aspect, compounds of Formula AA, or a pharmaceutically acceptable salt thereof, are featured: or a pharmaceutically acceptable salt thereof, wherein the variables shown in Formula A can be as defined anywhere herein.

NLRP MODULATORS

In one aspect, compounds of Formula AA, or a pharmaceutically acceptable salt thereof, are featured: or a pharmaceutically acceptable salt thereof, wherein the variables shown in Formula A can be as defined anywhere herein, useful to treat connected to the modulation of NRLP3.

COMPOUNDS AND THEIR METHODS OF USE

Compounds and compositions comprising compounds that inhibit glutaminase are described herein. Also described herein are methods of using the compounds that inhibit glutaminase in the treatment of cancer.

COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USES AS GLUTAMINASE INHIBITORS FOR TREATING CANCERS THEREOF

Provided are compounds of formula (I), wherein X, Y, Z, W, m, n, o, p, R1, R2 and R6 are defined as in the description. Pharmaceutical compositions and uses as glutaminase inhibitors for treating cancers thereof are also provided.

COMPOUNDS AND THEIR METHODS OF USE

Provided are compounds of formula (I), which can inhibit glutaminase. Pharmaceutical compositions comprising these compounds and uses as glutaminase inhibitors for treating cancers thereof are also provided.

Synthesis, characterization and antimicrobial studies of a few novel thiazole derivatives

A series of novel N-[4-(substituted)-1,3-thiazol-2-yl]-2-(substituted) acetamide (9a-m) and methyl 2-(2-(2-(substituted)acetamido)thiazol-4-yl)acetate (9n-o) derivatives have been synthesized and compounds were characterised by spectral and analytical studies. All compounds were screened for their in vitro antibacterial activity against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and Klebsiella pneumonia by disc diffusion method and for antifungal activity against Penicillium marneffei, Trichophyton mentagrophytes, Aspergillus flavus and Aspergillus fumigatus by serial plate dilution method. Compounds 9b, 9e, 9m and 9o exhibited growth inhibition against all the tested bacterial strains, with MIC values varying from 12.5 to 6.25 μg/ml. Among the compounds tested for antifungal activity, 9a, 9b, 9d, 9j, 9k, 9p and 9n showed wide range of activity against all the tested strains. Most of the newly synthesized compounds were effective against fungal strains rather than bacterial strains. However, some of the compounds like 9a, 9e, 9j, 9k and 9i showed selective sensitivity against some of the bacterial strains whereas they were unable to sustain the growth of other strains.

Thiazole- and imidazole-containing peptidomimetic inhibitors of protein farnesyltransferase

Mimetics of the C-terminal CAAX tetrapeptide of Ras protein were designed replacing internal dipeptide AA with 4-amino-2-phenylbenzoic acid and cysteine (C) with 2-amino-4-thiazolyl-, 2-mercapto-4-thiazolyl-, 2-mercapto-4-imidazolyl- and 2-methylmercapto-4-thiazolyl-acetic or propionic acid. The compound in which C is replaced by 2-amino-4-thiazolylacetic acid inhibited FTase activity in the low nanomolar range and showed antiproliferative effect on rat aortic smooth muscle cells interfering with Ras farnesylation. On the basis of these results, 2-aminothiazole can be considered as an alternative to heterocycles, such as pyridine and imidazole, normally used in FTase inhibitors designed as non-thiol CAAX mimetics.

Novel Heterocyclic Compounds

The present invention relates to novel compounds of the general formula (I), their derivatives, their analogs, their stereoisomers, their pharmaceutically acceptable salts and compositions. The present invention more particularly provides novel heterocyclic compounds of the general formula (I).

NOVEL HETEROCYCLIC COMPOUNDS

The present invention relates to novel compounds of the general formula (I), their derivatives, their analogs, their stereoisomers, their pharmaceutically acceptable salts and compositions. The present invention more particularly provides novel heterocyclic compounds of the general formula (I).(I).