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Usage

Uses

Used in Pharmaceutical Industry:
4-Ethoxy-3-(4-pyridinyl)-3-buten-2-one is used as an impurity in Milrinone, a drug with cardiotonic properties. It is important to monitor and control the levels of this impurity to ensure the safety and efficacy of Milrinone as a treatment for heart conditions.

InChI:InChI=1/C11H13NO2/c1-3-14-8-11(9(2)13)10-4-6-12-7-5-10/h4-8H,3H2,1-2H3/b11-8+

Upstream product

• 6304-16-1 pyridin-4-yl-propan-2-one 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 116228-69-4 3-Cyan-6-methyl-5-(pyrid-4-yl)-1,2-dihydro-pyrid-2-thion 
• 78415-72-2 1,6-dihydro-2-methyl-6-oxo-(3,4'-bipyridine)-5-carbonitrile 

Relevant academic research and scientific papers

Potential cardiotonic agents. 4. Synthesis, cardiovascular activity, molecular and crystal structure of 5-phenyl- and 4-(4-pyridinyl)-substituted 2(1H)-pyridinethiones

Cyclisation of the vinylogous amidinium salt 1 or the 4-ethoxy- and 4-morpholino-3-butene-2-ones, respectively, 4 and 6 with cyano-thioacetamide yielded the 5-(4-pyridinyl)-, 6-methyl-5-(4-pyridinyl)- and 6-methyl-5-phenyl-, respectively, substituted 3-cyano-2(1H)-pyridinethiones 3, 5 and 7. The 2(1H)-pyridinethiones 3, 5 and 7a as well as the in 3-position unsubstituted or carbamoyl substituted derivatives 8 and 9 were obtained from the corresponding 2-chloro-pyridines and potassium sulfide, too. Especially compound 5 showed remarkable positive inotropic potency and, additionally, vasodilator activity. The molecular and crystal structure of 5 have been determines by X-ray structure analysis. Based on the molecular structure charge distribution and electrostatic potential were evaluated. The results are discussed in comparison with those of milrinone.

A NOVEL SYNTHESIS OF 1,6-DIHYDRO-2-METHYL-6-OXO-5-CARBONITRILE (MILRINONE)

Milrinone (3) was prepared either by reacting ethoxymethylenemalononitrile with 1-(4-pyridinyl)-2-propanone or malononitrile with 4-ethoxy-3-(4-pyridinyl)-3-buten-2-one.