90923-99-2

Basic information

• Product Name: propargyl anthranilate
• Synonyms: propargyl anthranilate
• CAS NO: 90923-99-2
• Molecular Weight: 175.187
• Mol File: 90923-99-2.mol

Chemical Properties

• CAS DataBase Reference: propargyl anthranilate(CAS DataBase Reference)
• NIST Chemistry Reference: propargyl anthranilate(90923-99-2)
• EPA Substance Registry System: propargyl anthranilate(90923-99-2)

Safety Data

• Hazardous Substances Data: 90923-99-2(Hazardous Substances Data)

Upstream product

• 118-48-9 isatoic anhydride 
• 107-19-7 propargyl alcohol 

Downstream Products

• 1415326-75-8 C₂₄H₂₈N₄O₁₁ 
• 1383577-44-3 prop-2-yn-1-yl 2-(4-([(2-azidophenyl)carbonyloxy]methyl)-1H-1,2,3-triazol-1-yl)benzoate 
• 1383577-58-9 [1-(2-([(1-(2-[(prop-2-yn-1-yloxy)carbonyl]phenyl)-1H-1,2,3-triazol-4-yl)methoxy]carbonyl)phenyl)-1H-1,2,3-triazol-4-yl]methyl 2-(4-([(2-azidophenyl)carbonyloxy]methyl)-1H-1,2,3-triazol-1-yl)benzoate 
• 1383577-57-8 [1-(2-([(1-(2-[(prop-2-yn-1-yloxy)carbonyl]phenyl)-1H-1,2,3-triazol-4-yl)methoxy]carbonyl)phenyl)-1H-1,2,3-triazol-4-yl]methyl 2-(4-([(2-aminophenyl)carbonyloxy]methyl)-1H-1,2,3-triazol-1-yl)benzoate 
• 1383577-56-7 2-(4-[((2-[4-(([2-(4-([(2-aminophenyl)carbonyloxy]methyl)-1H-1,2,3-triazol-1-yl)phenyl]carbonyloxy)methyl)-1H-1,2,3-triazol-1-yl]phenyl)carbonyloxy)methyl]-1H-1,2,3-triazol-1-yl)benzoic acid 
• 1383577-53-4 (1-{2-[(prop-2-yn-1-yloxy)carbonyl]phenyl}-1H-1,2,3-triazol-4-yl)methyl 2-(4-{[(2-aminophenyl)carbonyloxy]methyl}-1H-1,2,3-triazol-1-yl)benzoate 
• 1383577-47-6 2-(4-([(2-aminophenyl)carbonyloxy]methyl)-1H-1,2,3-triazol-1-yl)benzoic acid 
• 1383577-52-3 2-[4-(([2-(4-([(2-aminophenyl)carbonyloxy]methyl)-1H-1,2,3-triazol-1-yl)phenyl]carbonyloxy)methyl)-1H-1,2,3-triazol-1-yl]benzoic acid 

Relevant articles and documents

Propargyl anthranilate derivatives and their application in the synthesis of rings containing 1,2,3-triazolo motifs

Propargyl anthranilate, a simple and less studied molecule with several reactive sites, is widely applicable in organic synthesis. An optimized synthesis of this compound and its derivatives and the preparation of azide derivatives are described. The optimized process of the known intramolecular cyclization is described, and the unknown intermolecular cyclizations of these azido derivatives and formation of a macrocycle are discussed.

Synthesis and cytotoxicity of some d-mannose click conjugates with aminobenzoic acid derivatives

Two sets of new conjugates obtained from d-mannose derivatives and o-, m-, and p-substituted benzoic acid esters interconnected through a triazole ring were synthesized by Cu(I) catalyzed azide-alkyne cycloaddition. All synthesized compounds were tested for their in vitro cytotoxic activity against seven cancer cell lines with/without multidrug resistance phenotype as well as non-tumor MRC-5 and BJ fibroblasts. Butyl ester of 4-aminobenzoic acid 6c showed the highest activity among all tested compounds, however, it was active only against K562 myeloid leukemia cells. N-Glycosyltriazole conjugates, both acetylated and nonacetylated at mannose moiety, were almost completely inactive. In contrast, some of the acetylated O-glycosyl conjugates showed cytotoxic activity which was cell line dependent and strongly affected by position of benzoic acid substitution as well as a length of its ester alkyl chain; the most potent compound was acetylated mannoside conjugated with octyl ester of m-substituted benzoic acid. However, deacetylation resulting in hydrophilicity increase of the glycosides almost completely abolished their cytotoxic potency.

SYNTHESIS OF -TRIAZOLOBENZOXAZEPINES via INTRAMOLECULAR AZIDE CYCLOADDITION

Starting from isatoic anhydride and propargyl alcohols, we developed a synthetic approach to the title compounds, were the key step is an intramolecular cycloaddition of the azido group onto the acetylenic bond.