3357-54-8

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 5-AMINO-2-METHYLOXAZOLE-4-CARBOXYLATE is used as a precursor in the preparation of non-nucleoside reverse transcriptase inhibitors for the treatment of HIV. It plays a crucial role in the development of these life-saving medications.
Used in Agricultural Industry:
ETHYL 5-AMINO-2-METHYLOXAZOLE-4-CARBOXYLATE is used in the production of fungicides and herbicides due to its antimicrobial and pesticidal properties. It helps in controlling the growth of harmful microorganisms and unwanted plants, ensuring better crop yield and protection against diseases.

Upstream product

• 819877-81-1 C₆H₁₀ClNO₃ 
• 5804-85-3 diethylaluminium cyanide 
• 32683-02-6 ethyl-2-aminocyano acetate 
• 3849-21-6 ethyl cyanoglyoxylate-2-oxime 
• 90877-70-6 ethyl 2-acetamido-2-cyanoacetate 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 99419-09-7 5-amino-2-methyl-oxazole-4-carboxylic acid hydrazide 
• 1260861-94-6 ethyl 5-bromo-2-methyloxazole-4-carboxylate 

Relevant academic research and scientific papers

New efficient synthesis of 2,5,6-trisubstituted oxazolo[5,4-d]pyrimidi-7(6H)-ones via an oxazolyliminophosphorane

A new efficient synthesis of 2,5,6-trisubstituted oxazolo[5,4-d]pyrimidi-7(6H)-ones by consecutive aza-Wittig reaction was developed. The sequential three-component reaction of oxazolyliminophosphorane 4, isocyanates and amines produced 2,5,6-trisubstituted oxazolo[5,4-d]pyrimidi-7(6H)-ones 7 in good overall yields in the presence of catalytic amount of EtONa.

2-substituted tricyclic oxazolo[5,4-d]pyrimidine library: Design, synthesis, and cytotoxicity activity

We report the design, synthetic route, and cytotoxicity of a library of 49 newly synthesized tricyclic oxazolo[5,4-d]pyrimidines. The condensed pyrimidinones were constructed from ethyl 5-aminooxazole-4-carboxylate building blocks. A tricyclic ring system was built using the naturally occurring mackinazolinone alkaloid with a focus on the molecular diversity at position C-2 of the oxazole ring. Synthesized compounds were evaluated against a panel of human cancer cell lines including MCF-7 (breast), HeLa (cervical), and A549 (lung) in vitro. The results revealed that substitution of halogen-related aromatic fragments at position C-2 of the oxazole ring may serve as promising anticancer drug candidates.

Dihydrooxazolo[5,4-d]pyrrolo[1,2-a]pyrimidine-9(5H)-one derivative and application thereof

The invention relates to a dihydrooxazolo[5,4-d]pyrrolo[1,2-a]pyrimidine-9(5H)-one derivative and application. The preparation method comprises the following steps: by taking ethyl cyanoacetate as an initial raw material, generating a hydroxylamine compound (A) under the action of sodium nitrite and phosphoric acid, reducing with sodium hydrosulfite to obtain ethyl 2-aminocyanoacetate (B), reacting with different substituted acyl chlorides respectively under an alkali condition, generating different substituted oxazole compounds D1-D48 of 5-amino-4-formate under the action of trifluoroacetic acid, and reacting with pyrrolidone under the action of phosphorus oxychloride to obtain a dihydrooxazolo[5,4-d]pyrrolo[1,2-a]pyrimidine-9(5H)-one compound E1-E48. According to the invention, the inhibition activity of 48g of the compounds on Hela cervical cancer cells, MCF7 breast cancer cells and A549 lung cancer cells is investigated, and results show that the compounds E5, E10, E13, E16, E18, E19, E24, E42 and E43 have inhibition activity on Hela cervical cancer cells, the compounds E22, E24, E47 and E48 have inhibitory activity on MCF7 breast cancer cells, and the compounds E18 and E20 have inhibitory activity on A549 lung cancer cells.

Oxazolo[5,4-d]pyrido[1,2-a]pyrimidone derivative and application thereof

The invention relates to an oxazolo[5,4-d]pyrido[1,2-a]pyrimidone derivative and application thereof. Ethyl cyanoacetate is used as a raw material, a hydroxylamine compound (A) is generated under the action of sodium nitrite and phosphoric acid, 2-amino ethyl cyanoacetate (B) is obtained through reduction with sodium hydrosulfite, the 2-amino ethyl cyanoacetate (B) reacts with different substituted acyl chlorides under alkali conditions, and oxazole compounds (D1-D48) of different substituted 5-amino-4-formate are generated under the action of trifluoroacetic acid, and then react with valerolactam under the action of phosphorus oxychloride to obtain the oxazolo[5,4-d]pyrido[1,2-a]pyrimidone compounds (E1-E48). The inhibitory activity of the 48 compounds on Hela cervical cancer cells, MCF-7 breast cancer cells and A549 lung cancer cells is investigated, and the result shows that 11 compounds have the inhibitory activity on the Hela cervical cancer cells; eight compounds have inhibitory activity on MCF-7 breast cancer cells; and five compounds have inhibitory activity on A549 lung cancer cells. E32, E33, E45, E46 and E47 have inhibitory activity on three tumor cells; and E29 and E42 have inhibitory activity on Hela cervical cancer cells and MCF-7 breast cancer cells.

Tetrahydrooxazolopyridino-oxaazaone derivative and application of tetrahydrooxazolopyridino-oxaazaone derivative

The invention relates to a tetrahydrooxazolopyridino-oxaazaone derivative and application thereof. Specifically, the derivative tetrahydrooxazolo[5',4' : 4,5]pyridino[1, 2-a]oxaaza-11(5H)-one derivatives E1-E48. In anti-tumor activity screening, the positive control of DOX is used; the inhibition effect of the 48 tetrahydrooxazolo[5',4':4,5]pyridino[1, 2-a]oxaaza-11(5H)-one derivatives E1-E48 on Hela human cervical cancer cells, MCF-7 breast cancer cells and A549 lung cancer cells is observed, and the results show that compared with the positive control, the compounds E5, E8, E9, E20, E26, E28, E32, E34, E38, E41, E42, E44, E45, E46, E47 and E48 have the inhibition activity on the Hela cervical cancer cells, the compounds E26, E38, E42, E45, E46 and E47 have inhibitory activity on MCF-7 breast cancer cells; and the compounds E8, E9, E26 and E47 have inhibitory activity on A549 lung cancer cells.

Synthesis of 5-Amino-oxazole-4-carboxylates from α-Chloroglycinates

Aluminum-based Lewis acids are effective promoters of the condensation of α-chloroglycinates with isonitriles or with cyanide ion, leading to the formation of 5-amino-oxazoles.