58786-39-3

Basic information

• Product Name: Eupolauridine
• Synonyms: Eupolauridine;Canangine;Indeno[1,2,3-ij][2,7]naphthyridine
• CAS NO: 58786-39-3
• Molecular Formula: C₁₄H₈N₂
• Molecular Weight: 204.23
• Mol File: 58786-39-3.mol

Chemical Properties

• Melting Point: 153-155 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 399.9°C at 760 mmHg
• Flash Point: 181.6°C
• Appearance: /
• Density: 1.375g/cm³
• Vapor Pressure: 3.05E-06mmHg at 25°C
• Refractive Index: 1.892
• PKA: 4.00±0.10(Predicted)
• CAS DataBase Reference: Eupolauridine(CAS DataBase Reference)
• NIST Chemistry Reference: Eupolauridine(58786-39-3)
• EPA Substance Registry System: Eupolauridine(58786-39-3)

Safety Data

• Hazardous Substances Data: 58786-39-3(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
Eupolauridine is used as a pharmaceutical compound for its potential therapeutic properties. The alkaloid nature of Eupolauridine suggests that it may have bioactive properties, which could be harnessed for the development of new drugs or treatments.
2. Used in Traditional Medicine:
Eupolauridine may be used in traditional medicine practices, as it is derived from natural sources like Cananga odorata and Eupomatia laurina. These plants have been used in traditional medicine for various purposes, and Eupolauridine could potentially contribute to their therapeutic effects.
3. Used in Chemical Research:
As an uncharacterized alkaloid, Eupolauridine can be used in chemical research to better understand its structure, properties, and potential applications. This could lead to the discovery of new compounds or the development of novel applications for Eupolauridine in various industries.
4. Used in Cosmetics Industry:
Eupolauridine may have potential applications in the cosmetics industry due to its natural origin and potential bioactive properties. It could be used as an ingredient in skincare products, hair care products, or other cosmetic formulations for its potential benefits to the user.
5. Used in Agricultural Industry:
Eupolauridine's potential bioactive properties may also make it useful in the agricultural industry, where it could be used as a natural pesticide or for other applications related to crop protection and enhancement.

References

Beboeuk, Cave, Ann. Pharm. Fr., 33, 43 (1975)

InChI:InChI=1/C14H8N2/c1-2-4-11-10(3-1)13-12-9(5-7-15-13)6-8-16-14(11)12/h1-8H

Upstream product

• 98-88-4 benzoyl chloride 
• 351031-95-3 ethyl 2-benzoyl-3-methyl-5-oxo-pentanoate 
• 58787-04-5 onychine 
• 96889-95-1 eupolauridine N-oxide 
• 58787-21-6 ethyl 2-phenyl-4-methyl-3-pyridinecarboxylate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 

Relevant articles and documents

The synthesis and biological evaluation of alkyl and benzyl naphthyridinium analogs of eupolauridine as potential antimicrobial and cytotoxic agents

Eupolauridine, an indenonaphthyridine alkaloid, has been previously reported by us to exhibit antifungal activity. This study describes the synthesis of new alkyl and benzyl naphthyridinium/pyridinium analogs of eupolauridine as potential antifungal agent

SESQUITERPENES AND ALKALOIDS FROM CLEISTOPHOLIS PATENS

Key Word Index - Cleistopholis patens; Annonaceae; sesquiterpenes; methyl-(-)-(trans)-(trans)-10,11-dihydroxyfarnesoate; methyl-(+)-(trans)- 10-hydroxy-6,11-cyclofarnes-7(14)-enoate; aza-polycyclic alkaloids; onychine; cleistopholine; naphthyridine alkaloids; eupolauridine; eupolauridine N-oxides. The root bark of Cleistopholis patens collected in Ghana yielded two sesquiterpenes and five alkaloids.The sesquiterpenes have beencharacterised as the acyclic methyl-(-)-(trans)-(trans)-10,11-dihydroxyfarnesoate and its monocyclic derivative methyl-(+)-(trans)-10-hydroxy-6,11-cyclofarnes-7(14)-enoate.The alkaloids were of the unusual aza-polycyclic and naphthyridine groups and included one new member of both classes.Examination of stem bark samples from the same source and from Sierre Leone showed the presence of the sesquiterpenes and oxoaporphine alkaloid liriodenine but neither of the rarer alkaloid types.

Synthesis of eupolauridine and its benzo-annulated derivative

The unique diazafluoranthene alkaloid eupolauridine (1) was synthesized by a three-step routine utilizing as the initial step the thermal rearrangement of the oxime O-crotyl ether 12, which afforded onychine (2). Bracher pyridine synthesis procedure subsequently converted 2 into 1. On the other hand, Friedlander reaction was employed for the synthesis of 3, which is a benzo-annulated derivative of eupolauridine (1).

Polycyclic Aromatic Alkaloids, II: Synthesis of Onychine and Eupolauridine

The total synthesis of onychine (5) is improved by a new approach to the biaryl 4.Eupolauridine (7) is prepared from 5 in a one pot synthesis via the enamine 6.