66338-96-3

Basic information

• Product Name: 2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetic acid
• Synonyms: -2-(hydroxyimino);2-(2-Amino-4-thiazolyl)-2-hydroxyiminoaceticacid;2-(2-aminothiazole-4-yl)-z-hydroxyiminoaceticacid;2-Amino-alpha-(hydroxyimino)-4-thiazoleaceticacid;2-(2-AMINOTHIAZOLE-4-YL)-2-HYDROXYIMINOACETIC ACID;(2-AMINOTHIAZOL-4-YL)HYDROXYIMINO ACETIC ACID;(Z)-2-HYDROXYIMINO-2-(2-AMINOTHIAZOL-4-YL)ACETIC ACID;(Z)-2-HYDROXYIMINO-2-(2-AMINOTHIAZOLE-4-YL)ACETIC ACID
• CAS NO: 66338-96-3
• Molecular Formula: C₅H₅N₃O₃S
• Molecular Weight: 187.18
• Product Categories: Cephalosporins
• Mol File: 66338-96-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 190-192°C
• Boiling Point: 539.4 °C at 760 mmHg
• Flash Point: 280 °C
• Appearance: /
• Density: 1.92 g/cm³
• Vapor Pressure: 1.82E-12mmHg at 25°C
• Refractive Index: 1.798
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility: DMSO (Slightly, Heated)
• PKA: 10.37±0.70(Predicted)
• CAS DataBase Reference: 2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetic acid(66338-96-3)
• EPA Substance Registry System: 2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetic acid(66338-96-3)

Safety Data

• Hazardous Substances Data: 66338-96-3(Hazardous Substances Data)

Usage

Description

2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetic acid is an organic compound with the molecular formula C5H6N4O2S. It features a thiazole ring with an amino group at position 2, and a hydroxyiminoacetic acid moiety attached to the same position. 2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetic acid is known for its potential applications in the pharmaceutical industry, particularly in the synthesis of various drugs.

Uses

Used in Pharmaceutical Industry:
2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetic acid is used as a key intermediate in the synthesis of cephalosporin derivatives and β-lactam antibiotics. These are important classes of antibiotics that are widely used to treat a variety of bacterial infections. 2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetic acid's unique structure allows for the development of new antibiotics with improved properties, such as enhanced potency, broader spectrum of activity, and reduced side effects.
Used in Research and Development:
In addition to its applications in the pharmaceutical industry, 2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetic acid can also be used in research and development for the discovery of new drugs and therapeutic agents. Its unique chemical properties make it a valuable tool for exploring novel chemical reactions and synthetic pathways, which could lead to the development of innovative drugs with improved efficacy and safety profiles.
Used in Drug Synthesis:
2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetic acid is used as a building block in the synthesis of various pharmaceutical compounds. Its versatile structure allows for the creation of a wide range of molecules with different biological activities, making it a valuable asset in the development of new drugs for the treatment of various diseases and conditions.

InChI:InChI=1/C5H5N3O3S/c6-5-7-2(1-12-5)3(8-11)4(9)10/h1,11H,(H2,6,7)(H,9,10)/b8-3+

Upstream product

• 64485-82-1 (Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate 
• 68401-22-9 2-ethoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetic acid 

Downstream Products

• 177703-28-5 (Z)-2-(2-aminothiazol-4-yl)-N-(2-hydroxyethyl)-2-(hydroxyimino)acetamide 
• 68786-47-0 (Z)-2-(trityloxyimino)-2-(2-tritylamino-4-thiazolyl)acetic acid 

Relevant articles and documents

Novel chelate complexes of Co(II), Ni(II), Cu(II), Pd(II) derived from anti- and syn-isomers of 2-(2-aminothiazole-4-yl)-2-hydroxyiminoacetic acid with pro-/antiproliferative actions on endothelial cells

Anti- and syn-isomers of 2-(2-aminothiazole-4-yl)-2-hydroxyiminoacetic acid (anti-A and syn-A respectively) were used as potential biologically active polydentate complexing agent for Co2+, Ni2+, Cu2+ and Pd2+ ions for the synthesis of novel complex compounds with directed angiogenesis-correcting action. It shown that the location of functional groups in ligand molecules, the electronic structure of metal as complexing agent and the synthesis conditions affect the localization of coordination bonds and the structure of formed complexes. The interaction of ethanol solutions of metal salts with anti-A and syn-A in an acidic medium at the component ratios M:L = 1:1 and 1:2 leads to the formation of complexes [Co(anti-A)(H2O)3SO4] (1); [Ni(anti-A)(H2O)3SO4] (2); [Cu(anti-A)2Cl2] (3); [Pd(anti-A)2Cl2] (4); [Cu(syn-A)2Cl2] (5); [Pd(syn-A)Cl2] (6) with different coordination of ligands. Coordination mode of ligands identified by IR, UV-Vis, XPS and 1H (13C) NMR spectra. The structures of salt of the anti-A and complexes 1, 2, 6 were determined by X-ray diffraction study. Anti-A is coordinated to metal ions in a chelate manner by the nitrogen atom of the hydroxylimino group and the oxygen atom of the deprotonated carboxyl group. In this case, the 2-aminothiazole fragment does not involve in complexation. Syn-A is coordinated to the central metal ion in neutral form through the nitrogen atoms of hydroxyimino group and thiazole ring. All synthesized complex compounds form stable solutions in neutral medium, which makes it possible to use them as potential biologically active substances. Investigation of biological effects for syn-A shows mitogenic and antiapoptotic activity against endotheliocytes, while anti-A causes inhibition of proliferation almost in the entire concentration range. Complex compounds of Cu2+ and Pd2+ with anti-A and syn-A (3-6) cause an increase of antiproliferative activity of endothelial cells compared with baseline complexing agents. In this case, the activity of complexes with syn-A is superior to activity of analogues with anti-A. The results of cytotoxicity tests revealed a pronounced cytotoxic action for complexes 3 and 4, cytotoxic and proapoptotic activity for 6 and cytostatic effect for 5. For all compounds investigated, a checkpoint from S to G2 has been established, which may indicate DNA replication disturbance or dysregulation in the endogenous signals of the cell cycle of endotheliocytes.

3-Acetoxymethyl-7-(iminoacetamido)-cephalosporanic acid derivatives

Compounds of the formula STR1 wherein R is hydrogen, R' is selected from the group consisting of alkenyl and alkynyl of 2 to 4 carbon atoms, A is selected from the group consisting of hydrogen, alkali metal and equivalents of an alkaline earth metal or magnesium and an organic amine base and the OR' group is in the syn position having antibiotic activity and process for their preparation.