Piperolactam A

Piperolactam A
Names
	IUPAC name 15-hydroxy-14-methoxy-10-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,4,6,8,12,14-heptaen-11-one
	Preferred IUPAC name 1-Hydroxy-2-methoxydibenzo[cd,f]indol-4(5H)-one
	Other names Aristolactam FI
Identifiers
CAS Number	112501-42-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:387864 ;
ChEMBL	ChEMBL387864;
ChemSpider	2338707 ;
PubChem CID	3081016;
CompTox Dashboard (EPA)	DTXSID90150083 ;
	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−1
Melting point	313 °C (595 °F; 586 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

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.[1] Many closely related natural product alkaloids are known including aristolochic acid and its lactam derivatives.[2][3]In some reports, piperolactam A is called aristolactam FI.[4]

Synthesis

Biosynthesis

It has been suggested that piperolactam A and related compounds are biosynthesised from aporphine precursors.[5]

Chemical synthesis

Aristolactams including piperolactam A have been the subject of chemical synthesis studies,[4] which have been reviewed.[6]

Natural occurrence

Piperolactam A and related compounds are found in Aristolochiaceae (birthwort), Annonaceae (custard apple), Piperaceae (pepper), and Saururaceae plant families.[2][6]

References

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.
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.
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.
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.
Dos Santos, Anderson R.; Vaz, Nelissa P. (2019). "Isoquinoline Alkaloids and Chemotaxonomy". Biodiversity and Chemotaxonomy. Sustainable Development and Biodiversity. 24. pp. 167–193. doi:10.1007/978-3-030-30746-2_8. ISBN 978-3-030-30745-5.
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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[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.

[Parmar-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.

[Lactamfi-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. 24. pp. 167–193. doi:10.1007/978-3-030-30746-2_8. ISBN 978-3-030-30745-5.

[Synthesis-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.