Eupolauridine | CAS#58786-39-3 | azafluoranthene alkaloid

MedKoo Cat#: 145692 | Name: Eupolauridine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Eupolauridine is an azafluoranthene alkaloid. The major target of eupolauridine for fungal cell killing is DNA topoisomerase II.

Chemical Structure

Eupolauridine

CAS#58786-39-3

Theoretical Analysis

MedKoo Cat#: 145692

Name: Eupolauridine

CAS#: 58786-39-3

Chemical Formula: C14H8N2

Exact Mass: 204.0700

Molecular Weight: 204.23

Elemental Analysis: C, 82.33; H, 3.95; N, 13.72

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Eupolauridine; Canangine;

IUPAC/Chemical Name

indeno[1,2,3-ij][2,7]naphthyridine

InChi Key

KIVUUVOREYMMFE-UHFFFAOYSA-N

InChi Code

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

SMILES Code

C1=CC=C2C(=C1)C3=NC=CC4=C3C2=NC=C4

Appearance

To be determined

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 204.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Khan SI, Nimrod AC, Mehrpooya M, Nitiss JL, Walker LA, Clark AM. Antifungal activity of eupolauridine and its action on DNA topoisomerases. Antimicrob Agents Chemother. 2002 Jun;46(6):1785-92. doi: 10.1128/AAC.46.6.1785-1792.2002. PMID: 12019091; PMCID: PMC127229. 2: Pan E, Cao S, Brodie PJ, Callmander MW, Randrianaivo R, Rakotonandrasana S, Rakotobe E, Rasamison VE, TenDyke K, Shen Y, Suh EM, Kingston DG. Isolation and synthesis of antiproliferative eupolauridine alkaloids of Ambavia gerrardii from the Madagascar Dry Forest. J Nat Prod. 2011 May 27;74(5):1169-74. doi: 10.1021/np200093n. Epub 2011 Apr 19. PMID: 21504145; PMCID: PMC3103620. 3: Hufford CD, Liu S, Clark AM, Oguntimein BO. Anticandidal activity of eupolauridine and onychine, alkaloids from Cleistopholis patens. J Nat Prod. 1987 Sep-Oct;50(5):961-4. doi: 10.1021/np50053a037. PMID: 3325614. 4: Taghavi-Moghadam S, Kwong CD, Secrist JA 3rd, Khan SI, Clark AM. The synthesis and biological evaluation of alkyl and benzyl naphthyridinium analogs of eupolauridine as potential antimicrobial and cytotoxic agents. Bioorg Med Chem. 2016 Dec 1;24(23):6119-6130. doi: 10.1016/j.bmc.2016.02.028. Epub 2016 Feb 23. PMID: 27769668. 5: Tripathi SK, Xu T, Feng Q, Avula B, Shi X, Pan X, Mask MM, Baerson SR, Jacob MR, Ravu RR, Khan SI, Li XC, Khan IA, Clark AM, Agarwal AK. Two plant-derived aporphinoid alkaloids exert their antifungal activity by disrupting mitochondrial iron-sulfur cluster biosynthesis. J Biol Chem. 2017 Oct 6;292(40):16578-16593. doi: 10.1074/jbc.M117.781773. Epub 2017 Aug 18. PMID: 28821607; PMCID: PMC5633121. 6: Bracher F. Polycyclische aromatische Alkaloide. 9. Mitteilung: Synthese und antimykotische Wirksamkeit von Diazafluoranthen-Alkaloiden [Polycyclic aromatic alkaloids. 9. Synthesis and antifungal activity of diazafluoroanthene alkaloids]. Pharmazie. 1993 Jul;48(7):521-3. German. PMID: 8415849. 7: Fostel JM, Montgomery DA, Shen LL. Characterization of DNA topoisomerase I from Candida albicans as a target for drug discovery. Antimicrob Agents Chemother. 1992 Oct;36(10):2131-8. doi: 10.1128/AAC.36.10.2131. PMID: 1332588; PMCID: PMC245467. 8: Leboeuf M, Cavé A. Alcaloides des annonacees. XIV. Identite de la canangine et de l'eupolauridine, nouvel alcaloide a noyau naphtyridine [Alkaloids of Annonaceae. XIV. Identification of canangine and eupolauridine, new alkaloids with a naphthyridine nucleus]. Lloydia. 1976 Nov-Dec;39(6):459-60. French. PMID: 1026846. 9: Liu SC, Oguntimein B, Hufford CD, Clark AM. 3-Methoxysampangine, a novel antifungal copyrine alkaloid from Cleistopholis patens. Antimicrob Agents Chemother. 1990 Apr;34(4):529-33. doi: 10.1128/AAC.34.4.529. PMID: 2188584; PMCID: PMC171638.