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ETHYL 2-(2-CHLOROACETAMIDO)-4-THIAZOLEACETATE is a chemical compound with the molecular formula C9H10ClNO3S. It is a thiazole derivative featuring a chloroacetamide functional group, which contributes to its potential applications in the pharmaceutical industry.

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  • 19749-93-0 Structure
  • Basic information

    1. Product Name: ETHYL 2-(2-CHLOROACETAMIDO)-4-THIAZOLEACETATE
    2. 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
    3. CAS NO:19749-93-0
    4. Molecular Formula: C9H11ClN2O3S
    5. Molecular Weight: 262.71
    6. EINECS: N/A
    7. 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
    8. Mol File: 19749-93-0.mol
  • Chemical Properties

    1. Melting Point: 146-148 °C(lit.)
    2. Boiling Point: °Cat760mmHg
    3. Flash Point: °C
    4. Appearance: /
    5. Density: 1.413g/cm3
    6. Refractive Index: 1.586
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: ETHYL 2-(2-CHLOROACETAMIDO)-4-THIAZOLEACETATE(CAS DataBase Reference)
    10. NIST Chemistry Reference: ETHYL 2-(2-CHLOROACETAMIDO)-4-THIAZOLEACETATE(19749-93-0)
    11. EPA Substance Registry System: ETHYL 2-(2-CHLOROACETAMIDO)-4-THIAZOLEACETATE(19749-93-0)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 19749-93-0(Hazardous Substances Data)

19749-93-0 Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 2-(2-CHLOROACETAMIDO)-4-THIAZOLEACETATE is used as a building block in the synthesis of various pharmaceuticals, playing a crucial role in the development of new drugs and agrochemicals.
Used in Medicinal Chemistry and Drug Discovery:
In the field of medicinal chemistry and drug discovery, ETHYL 2-(2-CHLOROACETAMIDO)-4-THIAZOLEACETATE serves as an intermediate, facilitating the creation of novel compounds with potential therapeutic properties.
Used in Research and Development:
ETHYL 2-(2-CHLOROACETAMIDO)-4-THIAZOLEACETATE is available for purchase from various chemical suppliers, making it accessible for research and development purposes, where it can be utilized to explore its properties and applications further.

Check Digit Verification of cas no

The CAS Registry Mumber 19749-93-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,7,4 and 9 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 19749-93:
(7*1)+(6*9)+(5*7)+(4*4)+(3*9)+(2*9)+(1*3)=160
160 % 10 = 0
So 19749-93-0 is a valid CAS Registry Number.
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)

19749-93-0 Well-known Company Product Price

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  • Aldrich

  • (445436)  Ethyl2-(2-chloroacetamido)-4-thiazoleacetate  98%

  • 19749-93-0

  • 445436-10G

  • 1,272.96CNY

  • Detail

19749-93-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl 2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]acetate

1.2 Other means of identification

Product number -
Other names 2-chloroacetamido-4-thiazolyl-acetic acid ethyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:19749-93-0 SDS

19749-93-0Relevant 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

Alt?ntop, Mehlika Dilek,Ciftci, Halil Ibrahim,Radwan, Mohamed O.,Sever, Belgin,Kaplanc?kl?, Zafer As?m,Ali, Taha F. S.,Koga, Ryoko,Fujita, Mikako,Otsuka, Masami,Zdemir, Ahmet

, (2018)

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.

Design, synthesis, and bioassay of 4-thiazolinone derivatives as influenza neuraminidase inhibitors

Xiao, Mengwu,Xu, Lvjie,Lin, Ding,Lian, Wenwen,Cui, Manying,Zhang, Meng,Yan, Xiaowei,Li, Shuishi,Zhao, Jun,Ye, Jiao,Liu, Ailin,Hu, Aixi

, (2021/02/09)

A series of 4-thiazolinone derivatives (D1-D58) were designed and synthesized. All of the derivatives were evaluated in vitro for neuraminidase (NA) inhibitory activities against influenza virus A (H1N1), and the inhibitory activities of the five most pot

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

-

Paragraph 0035; 0038; 0039, (2016/10/10)

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.

Synthesis and in vitro kinetic evaluation of N-thiazolylacetamido monoquaternary pyridinium oximes as reactivators of sarin, O-ethylsarin and VX inhibited human acetylcholinesterase (hAChE)

Valiveti, Aditya Kapil,Bhalerao, Uma M.,Acharya, Jyotiranjan,Karade, Hitendra N.,Acharya, Badri Narayan,Raviraju,Halve, Anand K.,Kaushik, Mahabir Parshad

, p. 4899 - 4910 (2015/08/03)

Presently available medications for treatment of organiphosphorus poisoning are not sufficiently effective due to various pharmacological and toxicological reasons. In this regard, herein we report the synthesis of a series of N-thiazolylacetamide monoquaternary pyridinium oximes and its analogs (1a-1b to 6a-6b) with diversely substituted thiazole ring and evaluation of their in vitro reactivation efficacies against nerve agent (sarin, O-ethylsarin and VX) inhibited human erythrocyte acetylcholinesterase (hAChE). Reactivation kinetics was performed to determine dissociation constant (KD), reactivity rate constant (kr) and the second order rate constant (kr2) for all the compounds and compared their efficacies with commercial antidotes viz. 2-PAM and obidoxime. All the newly synthesized oximes were evaluated for their physicochemical parameters (pKa) and correlated with their respective reactivation efficacies to assess the capability of the oxime reactivator. Three of these novel compounds showed promising reactivation efficacies toward OP inhibited hAChE. Molecular docking studies were performed in order to correlate the reactivation efficacies with their interactions in the active site of the AChE.

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

Makena, Anne,Van Berkel, Sander S.,Lejeune, Clarisse,Owens, Raymond J.,Verma, Anil,Salimraj, Ramya,Spencer, James,Brem, Juergen,Schofield, Christopher J.

, p. 1923 - 1929 (2014/01/06)

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

Synthesis and evaluation of antimicrobial and anticonvulsant activities of some new 3-[2-(5-aryl-1,3,4-oxadiazol-2-yl/4-carbethoxymethylthiazol-2-yl)imino- 4-thiazolidinon-5-ylidene]-5-substituted/nonsubstituted 1H-indole-2-ones and investigation of their

Altintas, Handan,Ates, Oeznur,Uydes-Dogan, B. Soenmez,Alp, F. Ilkay,Kaleli, Deniz,Oezdemir, Osman,Birteksoez, Seher,Oetuek, Guelten,Satana, Dilek,Uzun, Meltem

, p. 239 - 248 (2007/10/03)

In the present study, 20 new compounds having 3-[2-(5-aryl-1,3,4-oxadiazol- 2-yl) imino-4-thiazolidinon-5-ylidene]-5-substituted/nonsubstituted 1H-indole-2-one (I-XII) and 3-[2-(4-carbethoxymethylthiazol-2-yl)imino-4- thiazolidinon-5-ylidene]-5-substitute

Synthesis, characterization and evaluation of antimicrobial activity of Mannich bases of some 2-[(4-carbethoxymethylthiazol-2-yl)imino]-4- thiazolidinones

Altintas, Handan,Ates, Oeznur,Kocabalkanli, Ayse,Birteksoez, Seher,Oetuek, Guelten

, p. 585 - 590 (2007/10/03)

A series of 5-(N,N-disubstituted aminomethyl)-2-[(4- carbethoxymethylthiazol-2-yl)imino]-4-thiazolidinones 4a-m have been synthesized. Their structures are confirmed by elemental analyses and spectral data (IR, 1H NMR, EIMS). The antibacterial activities of the compounds against Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC 12228, Escherichia coli ATCC 8739, Klebsiella pneumoniae ATCC 4352, Pseudomonas aeruginosa ATCC 1539, Salmonella typhi, Shigella flexneri, Proteus mirabilis ATCC 14153 and antifungal activity against Candida albicans ATCC 10231 are tested using disk diffusion method. Some of the compounds are found to have significant activity against S. aureus ATCC 6538.

Synthesis and antimicrobial activity of 4-phenyl/cyclohexyl-5-(1- phenoxyethyl)-3-[N-(2-thiazolyl)acetamido]thio-4H-1,2,4-triazole derivatives

Turan-Zitouni, Guelhan,Kaplancikli, Zafer Asim,Yildiz, Mehmet Taha,Chevallet, Pierre,Kaya, Demet

, p. 607 - 613 (2007/10/03)

The increasing clinical importance of drug-resistant fungal and bacterial pathogens has lent additional urgency to microbiological research and new antimicrobial compound development. For this purpose, new thiazole derivatives of triazoles were synthesize

Aminothiazole derivatives with antidegenerative activity on cartilage

Panico, Anna Maria,Geronikaki, Athina,Mgonzo, Remi,Cardile, Venera,Gentile, Barbara,Doytchinova, Irini

, p. 2983 - 2989 (2007/10/03)

A series of 2-dialkylamino-N-(4-substituted thiazolyl-2)acetamides and 3-dialkylamino-N-(4-substituted thiazolyl-2)propionamides were synthesized and evaluated for their anti-inflammatory activity. Encouraging results led us to investigate the effect of t

Synthesis and antimicrobial activity of {2-[2-(N,N-disubstituted thiocarbamoyl-sulfanyl)-acylamino]thiazol-4-yl}acetic acid ethyl esters

Ates, Oeznur,Guersoy, Aysel,Altintas, Handan,Oetuek, Guelten,Birteksoez, Seher

, p. 39 - 46 (2007/10/03)

{2-[2-(N,N-Disubstituted thiocarbamoyl-sulfanyl)acylamino]thiazol-4-yl}acetic acid ethyl esters (3 a-x) were synthesized by the reaction of potassium salts of N,N-di-substituted dithiocarbamoic acids with [2-(2-chloroalkanoyl)amino-thiazol-4-yl]acetic acid ethyl esters. The structures of the synthesized compounds were confirmed by elemental analyses, UV, IR, 1H-NMR, and EI mass spectral data. The antimicrobial activities of all the compounds were investigated by microbroth dilution technique using Mueller-Hinton broth and Mueller-Hinton agar. In this study, Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC 12228, Escherichia coli ATCC 8739, Klebsiella pneumoniae ATCC 4352, Pseudomonas aeruginosa ATCC 1539, Salmonella typhi, Shigella flexneri, Proteus mirabilis ATCC 14153 and Candida albicansATCC 10231 were used as test microorganisms. Among the tested compounds 3 a, d, e, f, h, k, w showed activity against S. epidermidis ATCC 12228 (MIC: 156 mg/L, 78 mg/L, 62.5 mg/L, 78 mg/L, 62.5 mg/L, 312 mg/L, 250 mg/L, respectively), compound 3 d also had some activity against S. aureus ATCC 6538 (MIC: 156 mg/L) and C. albicans ATCC 10231 (MIC: 156 mg/L). Compounds 3 I, 3 x were also evaluated for antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system and BACTEC 12B medium. The preliminary results indicated that all of the tested compounds were inactive against the test organism.

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