19749-93-0

Basic information

• Product Name: ETHYL 2-(2-CHLOROACETAMIDO)-4-THIAZOLEACETATE
• Synonyms: TIMTEC-BB SBB003081;OTAVA-BB BB7020310250;ETHYL 2-(2-[(2-CHLOROACETYL)AMINO]-1,3-THIAZOL-4-YL)ACETATE;ETHYL 2-(2-CHLOROACETAMIDO)-4-THIAZOLEACETATE;ETHYL (2-((CHLOROACETYL)AMINO)-1,3-THIAZOL-4-YL)ACETATE;2-[2-[(2-chloro-1-oxoethyl)amino]-4-thiazolyl]acetic acid ethyl ester;2-[2-[(2-chloroacetyl)amino]thiazol-4-yl]acetic acid ethyl ester;4-Carbethoxymethyl-2-[(.alpha.-haloacyl)amino]thiazole
• CAS NO: 19749-93-0
• Molecular Formula: C₉H₁₁ClN₂O₃S
• Molecular Weight: 262.71
• Product Categories: Heterocyclic Compounds;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Thiazoles;ThiazolesHeterocyclic Building Blocks;Building Blocks;C8 to C9;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 19749-93-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: 146-148 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.413g/cm³
• Refractive Index: 1.586
• CAS DataBase Reference: ETHYL 2-(2-CHLOROACETAMIDO)-4-THIAZOLEACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-(2-CHLOROACETAMIDO)-4-THIAZOLEACETATE(19749-93-0)
• EPA Substance Registry System: ETHYL 2-(2-CHLOROACETAMIDO)-4-THIAZOLEACETATE(19749-93-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 19749-93-0(Hazardous Substances Data)

Usage

General Description

ETHYL 2-(2-CHLOROACETAMIDO)-4-THIAZOLEACETATE is a chemical compound with the molecular formula C9H10ClNO3S. It is a thiazole derivative with a chloroacetamide functional group. ETHYL 2-(2-CHLOROACETAMIDO)-4-THIAZOLEACETATE has potential applications in the pharmaceutical industry, particularly as a building block in the synthesis of various pharmaceuticals. It is often used as an intermediate in the production of drugs and agrochemicals. Additionally, it may also have potential uses in the field of medicinal chemistry and drug discovery.ETHYL 2-(2-CHLOROACETAMIDO)-4-THIAZOLEACETATE is available for purchase from various chemical suppliers and may be used for research and development purposes.

InChI:InChI=1/C9H11ClN2O3S/c1-2-15-8(14)3-6-5-16-9(11-6)12-7(13)4-10/h5H,2-4H2,1H3,(H,11,12,13)

Upstream product

• 53266-94-7 ethyl 2-amino-1,3-thiazol-4-acetate 
• 79-04-9 chloroacetyl chloride 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 541-88-8 Chloroacetic anhydride 
• 122352-22-1 [4-(2-Amino-thiazol-4-yl)-phenyl]-acetic acid ethyl ester 
• 141-97-9 ethyl acetoacetate 
• 13176-46-0 4-bromoethyl acetoacetate 
• 84911-18-2 ethyl 2-bromoacetoacetate 
• 2104-04-3 4-(4-methoxyphenyl)-1,3-thiazol-2-amine 

Downstream Products

• 94417-82-0 2-Chloroacetamido-4-diphenylmethoxycarbonylmethylthiazole N-Oxide 
• 79540-64-0 2-Chloroacetamido-4-diphenylmethoxycarbonylmethylthiazole 
• 84164-44-3 sodium cis-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone-1-sulfonate 
• 84164-44-3 sodium trans-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone-1-sulfonate 
• 84164-45-4 sodium cis-3-<2-(2-aminothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone-1-sulfonate 
• 84164-45-4 sodium trans-3-<2-(2-aminothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone-1-sulfonate 
• 84208-37-7 2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetyl chloride hydrochloride 
• 84208-38-8 trans-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone 
• 84208-38-8 cis-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone 
• 84208-36-6 2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyloxyimino]acetic acid 
• 65243-18-7 2-(2-chloroacetamidothiazol-4-yl)acetic acid 

Relevant articles and documents

Design, synthesis, and biological evaluation of novel 1,3,4-thiadiazole derivatives as potential antitumor agents against chronic myelogenous leukemia: Striking effect of nitrothiazole moiety

In an attempt to develop potent antitumor agents, new 1,3,4-thiadiazole derivatives were synthesized and evaluated for their cytotoxic effects on multiple human cancer cell lines, including the K562 chronic myelogenous leukemia cell line that expresses the Bcr-Abl tyrosine kinase. N-(5-Nitrothiazol-2-yl)-2-((5-((4-(trifluoromethyl)phenyl)amino)-1,3,4-thiadiazol-2-yl)thio)acetamide (2) inhibited the Abl protein kinase with an IC50 value of 7.4 μM and showed selective activity against the Bcr-Abl positive K562 cell line. Furthermore, a Bcr-Abl-compound 2 molecular modelling simulation highlighted the anchoring role of the nitrothiazole moiety in bonding and hydrophobic interaction with the key amino acid residues. These results provide promising starting points for further development of novel kinase inhibitors.

Preparation method and application of 2-(4-oxo-thiazoline-2-imino)thiazole-4-acetic acid derivative

The invention discloses a 2-(4-oxo-thiazoline-2-imino)thiazole-4-acetic acid derivative as shown in the structural formulas I and II, a pharmaceutically acceptable salt thereof, a preparation method thereof, a pharmaceutical composition comprising the derivative and the pharmaceutically acceptable salt of the derivative, as well as application of the derivative to preparation of an influenza virus neuraminidase inhibitor.

Chromophore-linked substrate (CLS405): Probing metallo-β-lactamase activity and inhibition

Serine- and metallo-β-lactamases present a threat to the clinical use of nearly all β-lactam antibiotics, including penicillins, cephalosporins, and carbapenems. Efforts to develop metallo-β-lactamase (MBL) inhibitors require suitable screening platforms to allow the rapid determination of β-lactamase activity and efficient inhibition. Unfortunately, the platforms currently available are not ideal for this purpose. Further progress in MBL inhibitor identification requires inexpensive and widely applicable assays. Herein the identification of an inexpensive and stable chromogenic substrate suitable for use in assays of clinically relevant MBLs is described. (6R,7R)-3-((4-Nitrophenoxy)methyl)-8-oxo-7-(2-phenylacetamido) -5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 5,5-dioxide (CLS405) was synthesised in a three-step protocol. CLS405 was then characterised spectroscopically, and its stability and kinetic properties evaluated. With a Δλmax value of 100 nm between the parent and hydrolysis product, a higher analytical accuracy is possible with CLS405 than with commonly used chromogenic substrates. The use of CLS405 in assays was validated by MBL activity measurements and inhibitor screening that resulted in the identification of N-hydroxythiazoles as new inhibitor scaffolds for MBLs. Further evaluation of the identified N-hydroxythiazoles against a panel of clinically relevant MBLs showed that they possess inhibitory activities in the mid- to low-micromolar range. The findings of this study provide both a useful tool compound for further inhibitor identification, and novel scaffolds for the design of improved MBL inhibitors with potential as antibiotics against resistant strains of bacteria. Monitoring MBLs! Resistance to β-lactam antibiotics, mediated by metallo-β-lactamases (MBLs), is an increasing clinical problem. While compounds that target MBLs could be useful antibacterial agents, their identification is hampered by the lack of suitable assay platforms. To this end, CLS405, a chromophore-linked MBL substrate, was developed and its applicability demonstrated by the identification of N-hydroxythiazoles as potential inhibitors against a panel of clinically relevant MBLs. Copyright