Asperlicin

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Asperlicin
Asperlicin structure.svg
Names
Preferred IUPAC name
(7S)-7-{[(2S,9S,9aS)-9-Hydroxy-2-(2-methylpropyl)-3-oxo-2,3,9,9a-tetrahydro-1H-imidazo[1,2-a]indol-9-yl]methyl}-6,7-dihydroquinazolino[3,2-a][1,4]benzodiazepine-5,13-dione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C31H29N5O4/c1-17(2)15-22-29(39)36-25-14-8-5-11-20(25)31(40,30(36)34-22)16-23-26-32-21-12-6-3-9-18(21)28(38)35(26)24-13-7-4-10-19(24)27(37)33-23/h3-14,17,22-23,30,34,40H,15-16H2,1-2H3,(H,33,37)/t22-,23-,30-,31-/m0/s1 Yes check.svgY
    Key: MGMRIOLWEROPJY-FPACPZPDSA-N Yes check.svgY
  • InChI=1/C31H29N5O4/c1-17(2)15-22-29(39)36-25-14-8-5-11-20(25)31(40,30(36)34-22)16-23-26-32-21-12-6-3-9-18(21)28(38)35(26)24-13-7-4-10-19(24)27(37)33-23/h3-14,17,22-23,30,34,40H,15-16H2,1-2H3,(H,33,37)/t22-,23-,30-,31-/m0/s1
    Key: MGMRIOLWEROPJY-FPACPZPDBR
  • O=C1c7ccccc7/N=C3\N1c2ccccc2C(=O)N[C@H]3C[C@]6(O)c4c(cccc4)N5C(=O)[C@@H](N[C@@H]56)CC(C)C
Properties
C31H29N5O4
Molar mass 535.593 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Asperlicin is a mycotoxin, derived from the fungus Aspergillus alliaceus . It acts as a selective antagonist for the cholecystokinin receptor CCKA, [1] [2] [3] and has been used as a lead compound for the development of a number of novel CCKA antagonists with potential clinical applications. [4] [5] [6] [7] He et al. 1998 present a synthesis from aryl iodide and vinyl iodide. [8]

References

  1. ↑ Chang, RS; Lotti, VJ; Monaghan, RL; Birnbaum, J; Stapley, EO; Goetz, MA; Albers-Schönberg, G; Patchett, AA; Liesch, JM; Hensens, OD; et al. (Oct 1985). "A potent nonpeptide cholecystokinin antagonist selective for peripheral tissues isolated from Aspergillus alliaceus". Science. 230 (4722): 177–9. PMID   2994227.
  2. ↑ Goetz, MA; Lopez, M; Monaghan, RL; Chang, RS; Lotti, VJ; Chen, TB (Dec 1985). "Asperlicin, a novel non-peptidal cholecystokinin antagonist from Aspergillus alliaceus. Fermentation, isolation and biological properties". Journal of Antibiotics (Tokyo). 38 (12): 1633–7. PMID   3005212.
  3. ↑ Liesch, JM; Hensens, OD; Springer, JP; Chang, RS; Lotti, VJ (Dec 1985). "Asperlicin, a novel non-peptidal cholecystokinin antagonist from Aspergillus alliaceus. Structure elucidation". Journal of Antibiotics (Tokyo). 38 (12): 1638–41. PMID   3841533.
  4. ↑ Bock, MG; DiPardo, RM; Rittle, KE; et al. (October 1986). "Cholecystokinin antagonists. Synthesis of asperlicin analogues with improved potency and water solubility". J. Med. Chem. 29 (10): 1941–5. PMID   3761313.
  5. ↑ Evans, BE; Rittle, KE; Bock, MG; DiPardo, RM; Freidinger, RM; Whitter, WL; Gould, NP; Lundell, GF; Homnick, CF; Veber, DF; et al. (Jul 1987). ""Design of nonpeptidal ligands for a peptide receptor " cholecystokinin antagonists". Journal of Medicinal Chemistry. 30 (7): 1229–39. PMID   2885419.
  6. ↑ Van der Bent, A; Ter Laak, AM; IJzerman, AP; Soudijn, W (August 1992). "Molecular modelling of asperlicin derived cholecystokinin A receptor antagonists". Eur. J. Pharmacol. 226 (4): 327–34. PMID   1397061.
  7. ↑ Lattmann, E; Billington, DC; Poyner, DR; Howitt, SB; Offel, M (2001). "Synthesis and evaluation of asperlicin analogues as non-peptidal cholecystokinin-antagonists". Drug Design and Discovery. 17 (3): 219–30. PMID   11469752.
  8. ↑ Nakamura, Itaru; Yamamoto, Yoshinori (2004-02-21). "Transition-Metal-Catalyzed Reactions in Heterocyclic Synthesis". Chemical Reviews . 104 (5). American Chemical Society (ACS): 2127–2198. doi:10.1021/cr020095i. ISSN   0009-2665. PMID   15137788.
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