705-87-3

Basic information

• Product Name: N-(2-THIAZOLYL)ACETOACETAMIDE
• Synonyms: 3-keto-N-thiazol-2-yl-butyramide
• CAS NO: 705-87-3
• Molecular Formula: C₇H₈N₂O₂S
• Molecular Weight: 184.218
• Mol File: 705-87-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 165-168 °C
• Appearance: /
• Density: 1.361g/cm³
• Refractive Index: 1.599
• PKA: 8.16±0.50(Predicted)
• CAS DataBase Reference: N-(2-THIAZOLYL)ACETOACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-THIAZOLYL)ACETOACETAMIDE(705-87-3)
• EPA Substance Registry System: N-(2-THIAZOLYL)ACETOACETAMIDE(705-87-3)

Safety Data

• Hazardous Substances Data: 705-87-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H8N2O2S/c1-5(10)4-6(11)9-7-8-2-3-12-7/h2-3H,4H2,1H3,(H,8,9,11)

Upstream product

• 96-50-4 2-thiazolylamine 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 112664-63-8 2-[1-(4-Nitro-phenyl)-meth-(E)-ylidene]-3-oxo-N-thiazol-2-yl-butyramide 
• 3673-34-5 thiazole-2-ylcarbamic acid ethyl ester 

Relevant articles and documents

Synthesis of new 2-aminothiazolyl/benzothiazolyl-based 3,4-dihydropyrimidinones and evaluation of their effects on adenocarcinoma gastric cell migration

Abstract: Gastric cancer is one of the malignant tumors of the gastrointestinal tract that, despite its decrease in recent years, is still the fourth most common cancer and the second leading cause of cancer-related death. Various strategies including chemotherapy are used to keep cancer cells from spreading and induce apoptotic death in them. Recent studies have shown that dihydropyrimidinones (DHPMs) are privileged structures in medicinal chemistry due to their pharmacological effects. A number of new 2-aminothiazolyl/benzothiazolyl derivatives of 3,4-DHPMs (3–8) were synthesized and structurally identified, and then their effects on the migration behavior of human AGS cells (gastric cancer cells) were investigated. Molecular docking and molecular dynamics (MD) simulations were applied to explore binding potential and realistic binding model of the assessed derivatives through identification of key amino acid residues within L5/α2/α3 allosteric site of kinesin 5 (Eg5) as a validated microtubule-dependent target for monastrol as a privileged DHPM derivative. Graphical abstract: [Figure not available: see fulltext.].

Expedient synthesis of a 72-membered isoxazolino-β-ketoamide library by a 2·3-component reaction

An efficient 2·3-component reaction (2·3CR; a 2-component reaction followed, in one pot, by a3-component reaction) is presented for the synthesis of isoxazolino-β-ketoamides. This 2·3CR proceeds by (i) a Meldrum's acid-generated acyl ketene, which is trapped by an amine to form a β-ketoamide intermediate in a 2CR followed, in one pot, by (ii) a Mannich reaction followed by elimination of dimethyl amine·HCl to generate an α,β-unsaturated β-ketoamide dipolarophile that reacts in a nitrile oxide 1,3-dipolar cycloaddition reaction. This one-pot 2·3CR process delivers the targeted isoxazolino-β-ketoamide product. A total of 72 compounds are presented, all of which have been submitted to the NIH Molecular Libraries Small Molecule Repository for high-throughput biological screening.