Rugulovasine

Rugulovasine
Names
	IUPAC name A: (4S,5R)-4'-methyl-4-(methylamino)-3,4-dihydro-1H,5'H-spiro[benzo[cd]indole-5,2'-furan]-5'-one; B: (4R,5R)-4'-methyl-4-(methylamino)-3,4-dihydro-1H,5'H-spiro[benzo[cd]indole-5,2'-furan]-5'-one; ;
Identifiers
CAS Number	A: 26909-33-1; 26909-34-2;
3D model (JSmol)	A: Interactive image; B: Interactive image;
ChemSpider	A: 103037; B: 106408;
PubChem CID	A: 115153; B: 119088;
	InChI A: InChI=1/C16H16N2O2/c1-9-7-16(20-15(9)19)11-4-3-5-12-14(11)10(8-18-12)6-13(16)17-2/h3-5,7-8,13,17-18H,6H2,1-2H3/t13-,16+/s2 Key: QTWQJTORJVFWAQ-WKTCHCBJNA-N; B: InChI=1/C16H16N2O2/c1-9-7-16(20-15(9)19)11-4-3-5-12-14(11)10(8-18-12)6-13(16)17-2/h3-5,7-8,13,17-18H,6H2,1-2H3/t13-,16-/s2 Key: QTWQJTORJVFWAQ-AYSIPDSENA-N;
	SMILES A: O=C1OC2(C=C1C)C=3C=CC=C4NC=C(C43)CC2NC; B: O=C1OC2(C=C1C)C=3C=CC=C4NC=C(C43)CC2NC;
Properties
Chemical formula	C16H16N2O2
Molar mass	268.316 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

Rugulovasines are bio-active alkaloids made by Penicillium.^[1] Rugulovasine A and B bind strongly to the 5-HT_1A, 5-HT_2A, and 5-HT_2C receptors, but lack meaningful binding affinity towards the α₁ adrenergic and dopamine receptors.^[2] Little is known about the in vivo activity of Rugulovasine A and B, although they have hypotensive effects in cats.^[3]

References

^ Dorner, JW; Cole, RJ; Hill, R; Wicklow, D; Cox, RH (September 1980). "Penicillium rubrum and Penicillium biforme, new sources of rugulovasines A and B." Applied and Environmental Microbiology. 40 (3): 685–7. doi:10.1128/aem.40.3.685-687.1980. PMC 291639. PMID 7425621.
^ Bartoccini, Francesca; Regni, Alessio; Retini, Michele; Piersanti, Giovanni (6 May 2022). "Asymmetric Total Synthesis of All Rugulovasine Stereoisomers and Preliminary Evaluation of Their Biological Properties". European Journal of Organic Chemistry. 2022 (17). doi:10.1002/ejoc.202200315. hdl:11576/2701930. ISSN 1434-193X. S2CID 248080578.
^ Nagaoka, A; Kikuchi, K (January 1972). "Pharmacological studies of new indole alkaloids, rugulovasine A and B hydrochloride. II. Hypotensive mechanism of both alkaloids in the anesthetized cats". Arzneimittel-Forschung. 22 (1): 143–6. PMID 5066989.

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[1] Dorner, JW; Cole, RJ; Hill, R; Wicklow, D; Cox, RH (September 1980). "Penicillium rubrum and Penicillium biforme, new sources of rugulovasines A and B." Applied and Environmental Microbiology. 40 (3): 685–7. doi:10.1128/aem.40.3.685-687.1980. PMC 291639. PMID 7425621.

[2] Bartoccini, Francesca; Regni, Alessio; Retini, Michele; Piersanti, Giovanni (6 May 2022). "Asymmetric Total Synthesis of All Rugulovasine Stereoisomers and Preliminary Evaluation of Their Biological Properties". European Journal of Organic Chemistry. 2022 (17). doi:10.1002/ejoc.202200315. hdl:11576/2701930. ISSN 1434-193X. S2CID 248080578.

[3] Nagaoka, A; Kikuchi, K (January 1972). "Pharmacological studies of new indole alkaloids, rugulovasine A and B hydrochloride. II. Hypotensive mechanism of both alkaloids in the anesthetized cats". Arzneimittel-Forschung. 22 (1): 143–6. PMID 5066989.

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