Lavendamycin

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Lavendamycin
Names
Preferred IUPAC name
1-(7-Amino-5,8-dioxo-5,8-dihydroquinolin-2-yl)-4-methyl-9H-pyrido[3,4-b]indole-3-carboxylic acid
Identifiers
3D model (
JSmol
)
ChemSpider
UNII
  • InChI=1S/C22H14N4O4/c1-9-16-10-4-2-3-5-13(10)24-20(16)19(26-17(9)22(29)30)14-7-6-11-15(27)8-12(23)21(28)18(11)25-14/h2-8,24H,23H2,1H3,(H,29,30)
    Key: IGQJRDIREIWBQP-UHFFFAOYSA-N
  • InChI=1/C22H14N4O4/c1-9-16-10-4-2-3-5-13(10)24-20(16)19(26-17(9)22(29)30)14-7-6-11-15(27)8-12(23)21(28)18(11)25-14/h2-8,24H,23H2,1H3,(H,29,30)
    Key: IGQJRDIREIWBQP-UHFFFAOYAD
  • Cc1c2c3ccccc3[nH]c2c(nc1C(=O)O)c4ccc5c(n4)C(=O)C(=CC5=O)N
Properties
C22H14N4O4
Molar mass 398.378 g·mol−1
Appearance Dark red crystals[1]
Melting point >300 °C[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lavendamycin is a naturally occurring

analogs designed to overcome these liabilities has been an area of research.[3]

Discovery

Lavendamycin was first discovered in 1981 by Doyle et al., who isolated it from Streptomyces lavendulae.

β-carboline unit and a quinolinequinone unit.[citation needed
]

Total syntheses

The attractive biological properties and complex structure of lavendamycin have made it the target of a large number of

total syntheses.[4] Within a few years after the structural elucidation by Doyle et al., the research groups of Kende,[5] Hibino,[6] Rao,[7] and Boger[8] had already developed total syntheses for the compound independently of one another. The discovery that analogs of lavendamycin are potent inhibitors of HIV reverse transcriptase led to further attempts in the 90s to develop efficient routes to lavendamycin.[9][10][11][12] However, large numbers of steps, low overall yields (0.5–2%) or poorly available starting materials make these syntheses unattractive for further systematic development of lavendamycin and its analogs. Notably, total syntheses by Behforouz[13] and Nissen[14]
offer flexible construction of the lavendamycin scaffold at high yields.

References

  1. ^ a b "Lavendamycin". Römpp's Chemistry Lexicon (in German).
  2. PMID 7076573
    .
  3. ^
    PMID 18457384
    .
  4. doi:10.1016/j.tet.2004.02.060
    .
  5. doi:10.1016/S0040-4039(01)80063-0
    .
  6. ISSN 0385-5414.{{cite journal}}: CS1 maint: DOI inactive as of February 2024 (link
    )
  7. doi:10.1016/S0040-4020(01)88058-3
    .
  8. ISSN 0022-3263
    .
  9. ISSN 0022-4936
    .
  10. doi:10.1016/S0040-4039(00)78888-5
    .
  11. doi:10.1016/S0040-4039(00)76244-7
    .
  12. doi:10.1016/S0040-4039(00)60486-0
    .
  13. ISSN 0022-3263
    .
  14. doi:10.1002/ejoc.201100131
    .
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