5-[(1E)-2-nitroethenyl]-1,3-benzodioxole

5-[(1E)-2-nitroethenyl]-1,3-benzodioxole is a versatile small molecule scaffold and pharmaceutical intermediate supplied by Cosperpharm for both drug discovery and organic synthesis applications. As a key intermediate for the synthesis of the blockbuster antidepressant paroxetine, 5-[(1E)-2-nitroethenyl]-1,3-benzodioxole provides the indispensable 1,3-benzodioxole framework that characterizes the final API, enabling the efficient construction of the pharmacophore in a multi-step synthetic sequence. Beyond its role as a synthetic building block, 5-[(1E)-2-nitroethenyl]-1,3-benzodioxole (MNS) is a well-documented bio-active molecule that acts as a selective inhibitor of Syk and Src tyrosine kinases, exhibiting potent anti-platelet, anti-inflammatory, and anti-cancer properties. As a fragment molecule, 5-[(1E)-2-nitroethenyl]-1,3-benzodioxole serves as an important scaffold for molecular linking, expansion, and modification, providing a structural basis for the design and screening of novel drug candidates. At Cosperpharm, each batch of 5-[(1E)-2-nitroethenyl]-1,3-benzodioxole is manufactured under strict quality control and supplied with comprehensive analytical documentation to support both research and production.

Product Parameters

Synthetic Route

The synthesis of 5-[(1E)-2-nitroethenyl]-1,3-benzodioxole typically proceeds via a Henry (nitroaldol) reaction followed by dehydration. Piperonal (3,4-methylenedioxybenzaldehyde) is condensed with nitromethane in the presence of a base catalyst, typically ammonium acetate in acetic acid or alternatively using primary amines as organocatalysts. The reaction proceeds through the formation of a β-nitrostyrene intermediate, which undergoes base-catalyzed dehydration to yield the desired trans-nitroethenyl product. The trans (E) isomer is predominantly formed due to thermodynamic stability and can be isolated by recrystallization from ethanol or other suitable solvents. The product is obtained as a yellow crystalline solid with a characteristic melting point of 159-163°C. Cosperpharm can provide non-confidential process details under a mutual confidentiality agreement.

Frequently Asked Questions (FAQ)

Q1: How does this compound compare to paroxetine?

A: This compound is an intermediate, not the final API. It provides the 1,3-benzodioxole ring system that is ultimately incorporated into the paroxetine molecule. Several additional synthetic steps are required to convert this intermediate to paroxetine.

Q2: What is the (E)-configuration and why is it important?

A: The (E) notation indicates that the two substituents (the benzodioxole ring and the nitro group) are on opposite sides of the double bond. This trans configuration is the thermodynamically more stable isomer and is the predominant form isolated during synthesis. Both the chemical reactivity and biological activity of the compound are influenced by this stereochemistry.

Product Applications

1.Paroxetine API synthesis – A key intermediate for the production of paroxetine, a widely prescribed selective serotonin reuptake inhibitor (SSRI) for the treatment of depression, anxiety disorders, and other neurological conditions.

2.Kinase inhibitor research – As MNS, it serves as a selective Syk and Src tyrosine kinase inhibitor for studying platelet aggregation, thrombosis, inflammatory responses, and cancer cell proliferation.

3.Fragment-based drug discovery (FBDD) – The compact 1,3-benzodioxole core functions as an ideal fragment for molecular linking and expansion, enabling the design and screening of novel drug candidates.

4.Anti-platelet drug development – Used in preclinical research to evaluate the inhibition of platelet aggregation induced by various stimulators including thrombin, ADP, collagen, and arachidonic acid.

5.Anti-inflammatory research – Investigated for its ability to modulate inflammatory signaling pathways through Syk and Src kinase inhibition.

6.Medicinal chemistry SAR studies – Serves as a scaffold for synthesizing β-nitrostyrene derivatives with varied substitution patterns to explore structure-activity relationships for kinase inhibition and anti-cancer activity.

7.Analytical method development – Used as a reference standard for HPLC and GC method validation in quality control of paroxetine API and related intermediates.

8.Antimicrobial research – Investigated for potential anti-bacterial and anti-fungal properties due to the electrophilic nature of the β-nitrostyrene moiety.

Contact Us

Ready to incorporate 5-[(1E)-2-nitroethenyl]-1,3-benzodioxole into your research or production program? Contact Cosperpharm today for a competitive quotation, sample request, or technical consultation with our experienced team.