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Piperolactam A

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Piperolactam A
Names
Preferred IUPAC name 1-Hydroxy-2-methoxydibenzoindol-4(5H)-one
Other names Aristolactam FI
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C16H11NO3/c1-20-12-7-10-13-11(17-16(10)19)6-8-4-2-3-5-9(8)14(13)15(12)18/h2-7,18H,1H3,(H,17,19)Key: KBGNBPGXVKPRQI-UHFFFAOYSA-N
SMILES
  • COC1=CC2=C3C(NC2=O)=CC2=C(C=CC=C2)C3=C1O
Properties
Chemical formula C16H11NO3
Molar mass 265.268 g·mol
Melting point 313 °C (595 °F; 586 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Piperolactam A is a natural product alkaloid found in many plants and first isolated from roots of Piper longum (long pepper). As a group, such compounds are called aristolactams, and are related to aristolochic acid.

History

Piperolactam A was first reported in 1988 after isolation from an extract of Piper longum. Many closely related natural product alkaloids are known including aristolochic acid and its lactam derivatives. In some reports, piperolactam A is called aristolactam FI.

Synthesis

Biosynthesis

Main article: Aristolochic_acid § Biosynthesis

It has been suggested that piperolactam A and related compounds are biosynthesised from aporphine precursors.

Chemical synthesis

Aristolactams including piperolactam A have been the subject of chemical synthesis studies, which have been reviewed.

Natural occurrence

Piperolactam A and related compounds are found in Aristolochiaceae (birthwort), Annonaceae (custard apple), Piperaceae (pepper), and Saururaceae plant families.

References

  1. Desai, Sanjay J.; Prabhu, Bharathi R.; Mulchandani, Newand B. (1988). "Aristolactams and 4,5-dioxoaporphines from Piper longum". Phytochemistry. 27 (5): 1511–1515. doi:10.1016/0031-9422(88)80226-7.
  2. ^ Kumar, Vineet; Poonam; Prasad, Ashok K.; Parmar, Virinder S. (2003). "Naturally occurring aristolactams, aristolochic acids and dioxoaporphines and their biological activities". Natural Product Reports. 20 (6): 565–83. doi:10.1039/B303648K. PMID 14700200.
  3. Michl, Johanna; Ingrouille, Martin J.; Simmonds, Monique S. J.; Heinrich, Michael (2014). "Naturally occurring aristolochic acid analogues and their toxicities". Natural Product Reports. 31 (5): 676–93. doi:10.1039/c3np70114j. PMID 24691743.
  4. ^ Kim, Joa Kyum; Kim, Young Ha; Nam, Ho Tae; Kim, Bum Tae; Heo, Jung-Nyoung (2008). "Total Synthesis of Aristolactams via a One-Pot Suzuki−Miyaura Coupling/Aldol Condensation Cascade Reaction". Organic Letters. 10 (16): 3543–3546. doi:10.1021/ol801291k. PMID 18642834.
  5. Dos Santos, Anderson R.; Vaz, Nelissa P. (2019). "Isoquinoline Alkaloids and Chemotaxonomy". Biodiversity and Chemotaxonomy. Sustainable Development and Biodiversity. Vol. 24. pp. 167–193. doi:10.1007/978-3-030-30746-2_8. ISBN 978-3-030-30745-5. S2CID 209712699.
  6. ^ Reddy, Mallu Chenna; Jeganmohan, Masilamani (2017). "Total synthesis of aristolactam alkaloids via synergistic C–H bond activation and dehydro-Diels–Alder reactions". Chemical Science. 8 (5): 4130–4135. doi:10.1039/c7sc00161d. PMC 6100235. PMID 30155216.
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