Bruceantin

Source: Wikipedia, the free encyclopedia.
Bruceantin
Names
IUPAC name
Methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
Other names
Bruceantine
Identifiers
3D model (
JSmol
)
UNII
  • InChI=1S/C28H36O11/c1-11(2)12(3)7-17(30)39-20-22-27-10-37-28(22,25(35)36-6)23(33)19(32)21(27)26(5)9-15(29)18(31)13(4)14(26)8-16(27)38-24(20)34/h7,11,14,16,19-23,31-33H,8-10H2,1-6H3/b12-7+/t14-,16+,19+,20+,21+,22+,23-,26-,27+,28-/m0/s1
    Key: IRQXZTBHNKVIRL-GOTQHHPNSA-N
  • CC1=C(C(=O)C[C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@H]4[C@H](C(=O)O3)OC(=O)/C=C(\C)/C(C)C)(OC5)C(=O)OC)O)O)C)O
Properties
C28H36O11
Molar mass 548.585 g·mol−1
Melting point 225–226 °C (437–439 °F; 498–499 K)[1]
Hazards
Lethal dose or concentration (LD, LC):
mouse (male, IV) 1.95 mg/kg
mouse (female, IV) 2.58 mg/kg[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bruceantin is a chemical compound that was first isolated from the plant Brucea antidysenterica in 1973.[2] Chemically, it is classified as a secotriterpenoid and a quassinoid.

Bucreantin has attracted interest as a potential antitumor drug because of its

antineoplastic activity.[3] It inhibits the peptidyl transferase elongation reaction, resulting in decreased protein and DNA synthesis.[3] Bruceantin also has antibiotic, antiamoebic,[4] and antimalarial activity.[3]

Phase I and II clinical trials were conducted for the treatment of metastatic breast cancer and malignant melanoma, but tumor regression was not observed and clinical development was terminated.[5][6]

References

  1. ^ a b Merck Index, 12th Edition, 1475
  2. PMID 4682660.{{cite journal}}: CS1 maint: multiple names: authors list (link
    )
  3. ^ a b c "Bruceantin". NCI Cancer Dictionary. National Institutes of Health.
  4. PMID 6100431.{{cite journal}}: CS1 maint: multiple names: authors list (link
    )
  5. PMID 14987068
    .
  6. ^ "Bruceantin". Inxsight Drugs.


Stub icon

This article about an organic compound is a stub. You can help Wikipedia by expanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Bruceantin&oldid=1165994302"