Fascaplysin

Fascaplysin
Names
	IUPAC name 13-Oxo-12,13-dihydrobenzo[2,3]indolizino[8,7-b]indol-5-ium
	Other names LSM-4272
Identifiers
CAS Number	114719-57-2 [[1]];
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:93765;
ChEMBL	ChEMBL602937;
ChemSpider	66033;
IUPHAR/BPS	5969;
PubChem CID	73293;
	InChI InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H 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;
	SMILES C1=CC=C2C(=C1)C3=C(N2)C4=[N+](C=C3)C5=CC=CC=C5C4=O;
Properties
Chemical formula	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). Infobox references

Fascaplysin is a marine alkaloid based on 12H-pyrido[1–2-a:3,4-b′]diindole ring system.^[2] 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.^[3] Fascaplysin possesses a broad range of in vitro biological activities including analgesic,^[4] antimicrobial, antifungal, antiviral, antimalarial, anti-angiogenic, and antiproliferative activity against numerous cancer cell lines.^[2]

Synthesis

The first total synthesis of fascaplysin was performed in seven steps from indole in 1990.^[5] Fascaplysin and its derivatives can be synthesized from tryptamine,^[6]^[7]^[8]^[9] beta-carboline,^[10] indoleketones,^[11]^[12] and indigo.^[13]

References

^ "KNApSAcK Metabolite Information - C00026567". www.knapsackfamily.com.
^ ^a ^b 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[1] "KNApSAcK Metabolite Information - C00026567". www.knapsackfamily.com.

[Bharate-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.

[Johnson_Milan-Lobo_Che_Ferwerda_pp._473–485-4] 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.

[Radchenko_Novikov_Elyakov_1997_pp._5339–5342-6] 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.

[Zhu_Liu_Cai_Jia_pp._10132–10137-7] 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.

[Dighe_Samanta_Kolle_Batra_2017_pp._2455–2467-8] 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.

[Bharate_Manda_Joshi_Singh_2012_p=1098-9] 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.

[Zhidkov_Kaminskii_2013_pp._3530–3532-10] 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.

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]