30866-42-3

Upstream product

• 3815-86-9 malonic acid dihydrazide 
• 15119-34-3 3-cyanocoumarin 
• 3949-36-8 3-acetylcoumarin 
• 1846-74-8 3-benzoyl-chromen-2-one 
• 1846-76-0 ethyl coumarin-3-carboxylate 
• 89-95-2 2-methyl-benzyl alcohol 
• 1846-91-9 2-oxo-2H-chromene-3-carbohydrazide 
• 90-02-8 salicylaldehyde 
• 30866-24-1 ethyl 3-hydrazino-3-oxopropanoate 
• 531-81-7 2-oxo-2H-chromene-3-carboxylic acid 
• 30866-43-4 2-Imino-2H-chromene-3-carboxylic acid [1-(2-hydroxy-phenyl)-meth-(E)-ylidene]-hydrazide 

Downstream Products

• 853935-02-1 3-(4-acetyl-5-H-5-o-hydroxyphenyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one 

Relevant academic research and scientific papers

Synthesis, antitrypanosomal and antimycobacterial activities of coumarin n-acylhydrazonic derivatives

Background: Near to 5-7 million people are infected with T. cruzi in the world, and about 10,000 people per year die of problems associated with this disease. Method: Herein, the synthesis, antitrypanosomal and antimycobacterial activities of seventeen coumarinic N-acylhydrazonic derivatives have been reported. Results: These compounds were synthesized using methodology with reactions global yields ranging from 46%-70%. T. cruzi in vitro effects were evaluated against trypomastigote and amastigote, forming M. tuberculosis activity towards H37Rv sensitive strain and resistant strains. Discussion: Against T. cruzi, the more active compounds revealed only moderate activity IC50 /96h~20 μM for both trypomastigotes and amastigotes intracellular forms. (E)-2-oxo-N'-(3,4,5-trimethoxybenzylidene)-2H-chromene-3-carbohydrazide showed meaningful activity in INH resistant/RIP resistant strain. Conclusion: These compound acting as multitarget could be good leads for the development of new trypanocidal and bactericidal agents.

The reaction of ethyl 2-oxo-2H-chromene-3-carboxylate with hydrazine hydrate

Although salicylaldehyde azine (3) was reported in 1985 as the single product of the reaction of ethyl 2-oxo-2H-chromene-3-carboxylate (1) with hydrazine hydrate, we identified another main reaction product, besides 3, which was identified as malono-hydrazide (4). In the last two decades, however, some articles have claimed that this reaction afforded exclusively hydrazide 2 and they have reported the use of this hydrazide 2 as a precursor in the syntheses of several heterocyclic compounds and hydrazones 6. We reported herein a study of the formation of 2 and a facile route for the synthesis of the target compounds N'-arylidene-2-oxo-2H-chromene-3-carbohydrazides 6a-f.

Synthesis of novel 3-(4-acetyl-5H/methyl-5-substituted phenyl-4,5-dihydro- 1,3,4-oxadiazol-2-yl)-2H-chromen-2-ones as potential anticonvulsant agents

A series of 3-(4-acetyl-5H/methyl-5-substituted phenyl-4,5-dihydro-1,3,4- oxadiazol-2-yl)-2H-chromene-2-ones (6a-j) were synthesized and evaluated for anticonvulsant activity and neurotoxicity. The structures of the synthesized compounds were confirmed on the basis of their spectral data and elemental analysis. A majority of the compounds was active in MES tests. Compound (6e) was found to be potent and had activity at lower dose of 30 mg/kg in MES-test. All the compounds were less toxic as compared with the standard drug phenytoin.

Conversions of coumarins accompanied by intermediate opening and recyclization of the lactone ring. 2. Study of the interaction of malonic acid hydrazide and amide derivatives with 3-acyl(3-cyano, 3-ethoxycarbonyl)coumarins

Reaction between the N,N′-diisopropylidene and N,N′-diacetyl derivatives of malonic acid dihydrazide and 3-acyl(3-cyano, 3-ethoxycarbonyl) coumarins under the conditions of the Michael reaction lead to the formation of N′-isopropylidene and N′-acetyl derivatives of coumarin-3-carboxylic acid hydrazide. Ethoxycarbonylacethydrazide reacts in an analogous manner. Special features have been studied of the interaction of malonic acid amide derivatives with unsubstituted coumarin and with coumarins containing electron-withdrawing groupings in position 3 of the ring. 2005 Springer Science+Business Media, Inc.

Synthesis of some new 2, 5-disubstituted 1,3,4-oxadiazole derivatives and their biological activity

2-(Coumarin-3-yl)-5-aryl-1,3,4-oxadiazole derivatives 3-5 have been synthesised by condensing hydrazide 2 of 3-carbethoxycoumarin with various aromatic acids. Compound 3 is also synthesized by another route involving synthesis of an intermediate N-2-hydroxy benzylidene coumarin-3-carboxyhydrazide 6 which is prepared by reacting 2 with salicylaldehyde. On refluxing it in presence of chloramine T the desired 1,3,4- oxadiazole derivative 3 is obtained. In another set of experiments, 4-methyl-7-(5-phenyl-1,3,4-oxadiazole-2-yl methoxy) coumarin 10 and 4-methyl-7-(5-amino-1,3,4-oxadiazo-2-yl methoxy) coumarin 11 were prepared by condensing 4-methyl coumarinyl-7-oxyacetic hydrazide 9 with benzoic acid and cyanogen bromide respectively. All the oxadiazole derivatives and the compound 6 have been tested for their antiinflammatory, analgesic and antimicrobial activity with interesting results.

Isomerisation of 2-Aryl-4-oxo-2,3-dihydrobenzopyranopyrimidines to 2-Aryl-4-hydroxy-5H-benzopyranopyrimidines

The base-catalysed condensation of 3-carbamoyl-2-iminochromen with aromatyc aldehydes yields 2-aryl-4-oxo-2,3-dihydrobenzopyranopyrimidines, which isomerise to stable 2-aryl-4-hydroxy-5H-benzopyranopyrimidines.The synthesis of 3-oxo-2H-benzopyranopyrazole is also described.