Fascaplysin

Fascaplysin
Chemical structure of fascaplysin
Names
IUPAC name
13-Oxo-12,13-dihydrobenzo[2,3]indolizino[8,7-b]indol-5-ium
Other names
LSM-4272
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
  • InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H checkY
    Key: WYQIPCUPNMRAKP-UHFFFAOYSA-O
  • InChI=1S/C18H10N2O/c21-18-13-6-2-4-8-15(13)20-10-9-12-11-5-1-3-7-14(11)19-16(12)17(18)20/h1-10H/p+1
    Key: WYQIPCUPNMRAKP-UHFFFAOYSA-O
  • C1=CC=C2C(=C1)C3=C(N2)C4=[N+](C=C3)C5=CC=CC=C5C4=O
Properties
C18H11N2O+
Molar mass 271.298 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Fascaplysin is a marine alkaloid based on 12H-pyrido[1–2-a:3,4-b′]diindole ring system. It was first isolated as a red pigment from the marine sponge Fascaplysinopsis reticulata that was collected in the South Pacific near Fiji in 1988. Fascaplysin possesses a broad range of in vitro biological activities including analgesic, antimicrobial, antifungal, antiviral, antimalarial, anti-angiogenic, and antiproliferative activity against numerous cancer cell lines.

Synthesis

The first total synthesis of fascaplysin was performed in seven steps from indole in 1990. Fascaplysin and its derivatives can be synthesized from tryptamine, beta-carboline, indoleketones, and indigo.

References

  1. ↑ "KNApSAcK Metabolite Information - C00026567". www.knapsackfamily.com.
  2. 1 2 B. Bharate, S.; Manda, S.; Mupparapu, N.; Battini, N.; A. Vishwakarma, R. (1 May 2012). "Chemistry and Biology of Fascaplysin, a Potent Marine-Derived CDK-4 Inhibitor". Mini-Reviews in Medicinal Chemistry. 12 (7): 650–664. doi:10.2174/138955712800626719. PMID 22512549.
  3. ↑ Roll, D. (1988). "Fascaplysin, an unusual antimicrobial pigment from the marine sponge Fascaplysinopsis sp". J. Org. Chem. 53 (14): 3276–3278. doi:10.1021/jo00249a025.
  4. ↑ Johnson, Tyler A.; Milan-Lobo, Laura; Che, Tao; Ferwerda, Madeline; Lambu, Eptisam; McIntosh, Nicole L.; Li, Fei; He, Li; Lorig-Roach, Nicholas; Crews, Phillip; Whistler, Jennifer L. (2016-11-22). "Identification of the First Marine-Derived Opioid Receptor "Balanced" Agonist with a Signaling Profile That Resembles the Endorphins". ACS Chemical Neuroscience. 8 (3). American Chemical Society (ACS): 473–485. doi:10.1021/acschemneuro.6b00167. ISSN 1948-7193. PMC 5352491. PMID 27744679.
  5. ↑ Pelcman, Benjamin; Gribble, Gordon (1990). "Total synthesis of the marine sponge pigment fascaplysin". Tetrahedron Letters. 31 (17): 2381–2384. doi:10.1016/S0040-4039(00)97367-2.
  6. ↑ Radchenko, Oleg S.; Novikov, Vyacheslav L.; Elyakov, George B. (1997). "A simple and practical approach to the synthesis of the marine sponge pigment fascaplysin and related compounds". Tetrahedron Letters. 38 (30). Elsevier BV: 5339–5342. doi:10.1016/s0040-4039(97)01167-2. ISSN 0040-4039.
  7. ↑ Zhu, Yan-Ping; Liu, Mei-Cai; Cai, Qun; Jia, Feng-Cheng; Wu, An-Xin (2013-06-20). "A Cascade Coupling Strategy for One-Pot Total Synthesis of β-Carboline and Isoquinoline-Containing Natural Products and Derivatives". Chemistry - A European Journal. 19 (31). Wiley: 10132–10137. doi:10.1002/chem.201301734. ISSN 0947-6539. PMID 23788489.
  8. ↑ Dighe, Shashikant U.; Samanta, Surya K.; Kolle, Shivalinga; Batra, Sanjay (2017). "Iodine-mediated oxidative Pictet-Spengler reaction using terminal alkyne as the 2-oxoaldehyde surrogate for the synthesis of 1-aroyl-β-carbolines and fused-nitrogen heterocycles". Tetrahedron. 73 (17). Elsevier BV: 2455–2467. doi:10.1016/j.tet.2017.03.031. ISSN 0040-4020.
  9. ↑ Bharate, Sandip B.; Manda, Sudhakar; Joshi, Prashant; Singh, Baljinder; Vishwakarma, Ram A. (2012). "Total synthesis and anti-cholinesterase activity of marine-derived bis-indole alkaloid fascaplysin". MedChemComm. 3 (9). Royal Society of Chemistry (RSC): 1098. doi:10.1039/c2md20076g. ISSN 2040-2503.
  10. ↑ Zhidkov, Maxim E.; Kaminskii, Vladimir A. (2013). "A new method for the synthesis of the marine alkaloid fascaplysin based on the microwave-assisted Minisci reaction". Tetrahedron Letters. 54 (27). Elsevier BV: 3530–3532. doi:10.1016/j.tetlet.2013.04.113. ISSN 0040-4039.
  11. ↑ Dubovitskii, Sergey (1996). "Method for synthesis of 12H-pyrido[1,2-a:3,4-b']diindoles. Total synthesis of homofascaplysin C". Tetrahedron Letters. 37 (29): 5207–5208. doi:10.1016/0040-4039(96)01052-0.
  12. ↑ Zhidkov, M. (2010). "A new method for the synthesis of the marine alkaloid fascaplysin". Tetrahedron Letters. 51 (50): 6498–6499. doi:10.1016/j.tetlet.2010.09.120.
  13. ↑ Zhidkov, M. (2018). "Syntheses of the marine alkaloids 6-oxofascaplysin, fascaplysin and their derivatives". Tetrahedron Letters. 59 (8): 708–711. doi:10.1016/j.tetlet.2018.01.023.