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
3D model (JSmol)
ChemSpider
  • 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
  • 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
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-HT1A, 5-HT2A, and 5-HT2C 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

  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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