Flindersine | CAS#523-64-8 | alkaloid

MedKoo Cat#: 149222 | Name: Flindersine

Description:

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

Flindersine is a naturally occurring alkaloid belonging to the class of furoquinoline alkaloids, commonly isolated from plants in the Rutaceae family, such as Flindersia species. It has shown various biological activities, including antimicrobial, anticancer, and insecticidal effects. The mechanism of action of flindersine is thought to involve intercalation with DNA and inhibition of key enzymes involved in cell division and microbial metabolism. Its applications are primarily in natural product research and drug discovery, particularly for developing therapeutic agents against infections and cancer.

Chemical Structure

Flindersine

CAS#523-64-8

Theoretical Analysis

MedKoo Cat#: 149222

Name: Flindersine

CAS#: 523-64-8

Chemical Formula: C14H13NO2

Exact Mass: 227.0946

Molecular Weight: 227.26

Elemental Analysis: C, 73.99; H, 5.77; N, 6.16; O, 14.08

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.

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Related CAS #

No Data

Synonym

Flindersine;

IUPAC/Chemical Name

2,2-dimethyl-2,6-dihydro-5H-pyrano[3,2-c]quinolin-5-one

InChi Key

PXNMNABLQWUMCX-UHFFFAOYSA-N

InChi Code

1S/C14H13NO2/c1-14(2)8-7-10-12(17-14)9-5-3-4-6-11(9)15-13(10)16/h3-8H,1-2H3,(H,15,16)

SMILES Code

CC1(C)OC2=C(C=C1)C(=O)NC3=C2C=CC=C3

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 227.26 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: Irudayaraj SS, Jincy J, Sunil C, Duraipandiyan V, Ignacimuthu S, Chandramohan G, Packiam SM. Antidiabetic with antilipidemic and antioxidant effects of flindersine by enhanced glucose uptake through GLUT4 translocation and PPARγ agonism in type 2 diabetic rats. J Ethnopharmacol. 2022 Mar 1;285:114883. doi: 10.1016/j.jep.2021.114883. Epub 2021 Nov 30. PMID: 34861363. 2: Duraipandiyan V, Ignacimuthu S. Antibacterial and antifungal activity of Flindersine isolated from the traditional medicinal plant, Toddalia asiatica (L.) Lam. J Ethnopharmacol. 2009 Jun 25;123(3):494-8. doi: 10.1016/j.jep.2009.02.020. Epub 2009 Feb 25. PMID: 19481384. 3: Karunai Raj M, Balachandran C, Duraipandiyan V, Agastian P, Ignacimuthu S. Antimicrobial activity of Ulopterol isolated from Toddalia asiatica (L.) Lam.: a traditional medicinal plant. J Ethnopharmacol. 2012 Mar 6;140(1):161-5. doi: 10.1016/j.jep.2012.01.005. Epub 2012 Jan 14. PMID: 22265751. 4: Aly AA, El-Sheref EM, Mourad AE, Bakheet MEM, Bräse S. 4-Hydroxy-2-quinolones: syntheses, reactions and fused heterocycles. Mol Divers. 2020 May;24(2):477-524. doi: 10.1007/s11030-019-09952-5. Epub 2019 Apr 27. PMID: 31030378. 5: Bowman RM, Grundon MF, James KJ. Quinoline alkaloids. XVI. 2,2-Dimethylpyranoquinolines from base-catalysed rearrangement of isoprenyl epoxides. Synthesis and biogenesis of flindersine. J Chem Soc Perkin 1. 1973;10:1055-9. doi: 10.1039/p19730001055. PMID: 4739008. 6: Cantrell CL, Schrader KK, Mamonov LK, Sitpaeva GT, Kustova TS, Dunbar C, Wedge DE. Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii. J Agric Food Chem. 2005 Oct 5;53(20):7741-8. doi: 10.1021/jf051478v. PMID: 16190626. 7: Hanawa F, Fokialakis N, Skaltsounis AL. Photo-activated DNA binding and antimicrobial activities of furoquinoline and pyranoquinolone alkaloids from rutaceae. Planta Med. 2004 Jun;70(6):531-5. doi: 10.1055/s-2004-827153. PMID: 15229804. 8: Gentili PL, Ortica F, Romani A, Favaro G. Effects of proximity on the relaxation dynamics of flindersine and 6(5H)-phenanthridinone. J Phys Chem A. 2007 Jan 18;111(2):193-200. doi: 10.1021/jp0646426. PMID: 17214453. 9: Dugan D, Bell RJ, Brkljača R, Rix C, Taki AC, Gasser RB, Urban S. Phytochemical Profiling Studies of Alkaloids and Coumarins from the Australian Plant Geijera parviflora Lindl. (Rutaceae) and Their Anthelmintic and Antimicrobial Assessment. Metabolites. 2024 Apr 30;14(5):259. doi: 10.3390/metabo14050259. PMID: 38786736; PMCID: PMC11123165. 10: Gentili PL. Boolean and fuzzy logic gates based on the interaction of flindersine with bovine serum albumin and tryptophan. J Phys Chem A. 2008 Nov 27;112(47):11992-7. doi: 10.1021/jp806772m. PMID: 18973319. 11: Varamini P, Javidnia K, Soltani M, Mehdipour AR, Ghaderi A. Cytotoxic activity and cell cycle analysis of quinoline alkaloids isolated from Haplophyllum canaliculatum Boiss. Planta Med. 2009 Nov;75(14):1509-16. doi: 10.1055/s-0029-1185807. Epub 2009 Jun 23. PMID: 19551611. 12: Banbury LK, Shou Q, Renshaw DE, Lambley EH, Griesser HJ, Mon H, Wohlmuth H. Compounds from Geijera parviflora with prostaglandin E2 inhibitory activity may explain its traditional use for pain relief. J Ethnopharmacol. 2015 Apr 2;163:251-5. doi: 10.1016/j.jep.2015.01.033. Epub 2015 Feb 2. PMID: 25656002. 13: Cabral RS, Allard PM, Marcourt L, Young MC, Queiroz EF, Wolfender JL. Targeted Isolation of Indolopyridoquinazoline Alkaloids from Conchocarpus fontanesianus Based on Molecular Networks. J Nat Prod. 2016 Sep 23;79(9):2270-8. doi: 10.1021/acs.jnatprod.6b00379. Epub 2016 Aug 24. PMID: 27557347. 14: Adams DH, Shou Q, Wohlmuth H, Cowin AJ. Native Australian plant extracts differentially induce Collagen I and Collagen III in vitro and could be important targets for the development of new wound healing therapies. Fitoterapia. 2016 Mar;109:45-51. doi: 10.1016/j.fitote.2015.12.010. Epub 2015 Dec 17. PMID: 26705840. 15: Jansen O, Akhmedjanova V, Angenot L, Balansard G, Chariot A, Ollivier E, Tits M, Frédérich M. Screening of 14 alkaloids isolated from Haplophyllum A. Juss. for their cytotoxic properties. J Ethnopharmacol. 2006 Apr 21;105(1-2):241-5. doi: 10.1016/j.jep.2005.11.001. Epub 2005 Dec 2. PMID: 16330172. 16: Nguyen TH, Nguyen THT, Dang TPT, Nguyen PAT, Truong TBN, Phung NKP, Nguyen TAT. Three quinolinone alkaloid - phenylpropanoid adducts from Melicope pteleifolia. Nat Prod Res. 2022 Aug;36(15):3858-3864. doi: 10.1080/14786419.2021.1892669. Epub 2021 Mar 1. PMID: 33648406. 17: Pacher T, Bacher M, Hofer O, Greger H. Stress induced carbazole phytoalexins in Glycosmis species. Phytochemistry. 2001 Sep;58(1):129-35. doi: 10.1016/s0031-9422(01)00186-8. PMID: 11524122. 18: Stephen Irudayaraj S, Sunil C, Duraipandiyan V, Ignacimuthu S. Antidiabetic and antioxidant activities of Toddalia asiatica (L.) Lam. leaves in streptozotocin induced diabetic rats. J Ethnopharmacol. 2012 Sep 28;143(2):515-23. doi: 10.1016/j.jep.2012.07.006. Epub 2012 Jul 27. PMID: 22842651. 19: Ali MS, Pervez MK, Saleem M, Tareen RB. Haplophytin-A and B: the alkaloidal constituents of Haplophyllum acutifolium. Phytochemistry. 2001 Aug;57(8):1277-80. doi: 10.1016/s0031-9422(01)00188-1. PMID: 11454359. 20: Torres Suarez E, Granados-Falla DS, Robledo SM, Murillo J, Upegui Y, Delgado G. Antileishmanial activity of synthetic analogs of the naturally occurring quinolone alkaloid N-methyl-8-methoxyflindersin. PLoS One. 2020 Dec 28;15(12):e0243392. doi: 10.1371/journal.pone.0243392. PMID: 33370295; PMCID: PMC7769561.