Ageliferin

Last updated
Ageliferin
Ageliferin.png
Names
Preferred IUPAC name
N,N′-{[(4R,5R,6S)-2-Amino-4-(2-amino-1H-imidazol-5-yl)-4,5,6,7-tetrahydro-1H-1,3-benzimidazole-5,6-diyl]bis(methylene)}bis(4-bromo-1H-pyrrole-2-carboxamide)
Other names
Ageliferine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C22H24Br2N10O2/c23-10-2-14(27-5-10)19(35)29-4-9-1-13-18(34-22(26)32-13)17(16-8-31-21(25)33-16)12(9)7-30-20(36)15-3-11(24)6-28-15/h2-3,5-6,8-9,12,17,27-28H,1,4,7H2,(H,29,35)(H,30,36)(H3,25,31,33)(H3,26,32,34)/t9-,12-,17-/m1/s1 X mark.svgN
    Key: DMMLTRAQSJWUHT-OGTWGDGJSA-N X mark.svgN
  • InChI=1/C22H24Br2N10O2/c23-10-2-14(27-5-10)19(35)29-4-9-1-13-18(34-22(26)32-13)17(16-8-31-21(25)33-16)12(9)7-30-20(36)15-3-11(24)6-28-15/h2-3,5-6,8-9,12,17,27-28H,1,4,7H2,(H,29,35)(H,30,36)(H3,25,31,33)(H3,26,32,34)/t9-,12-,17-/m1/s1
    Key: DMMLTRAQSJWUHT-OGTWGDGJBG
  • C1[C@@H]([C@H]([C@@H](C2=C1NC(=N2)N)C3=CN=C(N3)N)CNC(=O)C4=CC(=CN4)Br)CNC(=O)C5=CC(=CN5)Br
Properties
C22H24Br2N10O2
Molar mass 620.310 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ageliferin is a chemical compound produced by some sponges. It was first isolated from Caribbean and then Okinawan marine sponges in the genus Agelas . [1] [2] [3] It often co-exists with the related compound sceptrin and other similar compounds. It has antibacterial properties and can cause biofilms to dissolve. [4] Total syntheses have been independently accomplished by the research groups of Phil S. Baran at the Scripps Research Institute, [5] [6] Chuo Chen at UT Southwestern Medical Center, [7] [8] Patrick Harran at UCLA, [9] and Daisuke Urabe at Toyama Prefectural University. [10]

See also

References

  1. ↑ Rinehart, Kenneth L; et al. (1990). "Bioactive Compounds from Aquatic and Terrestrial Sources". Journal of Natural Products. 53 (4): 771–792. Bibcode:1990JNAtP..53..771R. doi:10.1021/np50070a001. PMID   2095373.
  2. ↑ Keifer, Paul A.; et al. (1991). "Bioactive Bromopyrrole Metabolites from the Caribbean Sponge Agelas conifera". J. Org. Chem. 56 (9): 2965–75. doi:10.1021/jo00009a008.
  3. ↑ Kobayashi, Junichi; et al. (1990). "Ageliferins, potent actomyosin ATPase activators from the Okinawan marine sponge Agelas sp". Tetrahedron. 46 (16): 5579–86. doi:10.1016/S0040-4020(01)87756-5.
  4. ↑ Laura Sanders (2009). "Sponge's secret weapon restores antibiotics' power: Bacteria treated with compound lose their resistance" . Science News. 175 (6): 16. doi:10.1002/scin.2009.5591750616.
  5. ↑ Baran, Phil S.; O'Malley, Daniel P.; Zografos, Alexandros L. (2004). "Sceptrin as a Potential Biosynthetic Precursor to Complex Pyrrole–Imidazole Alkaloids: The Total Synthesis of Ageliferin". Angewandte Chemie International Edition. 43 (20): 2674–2677. doi:10.1002/anie.200453937. ISSN   1521-3773.
  6. ↑ Baran, Phil S.; Li, Ke; O'Malley, Daniel P.; Mitsos, Christos (2006). "Short, Enantioselective Total Synthesis of Sceptrin and Ageliferin by Programmed Oxaquadricyclane Fragmentation". Angewandte Chemie International Edition. 45 (2): 249–252. doi:10.1002/anie.200503374. ISSN   1521-3773.
  7. ↑ Wang, Xiao; Ma, Zhiqiang; Lu, Jianming; Tan, Xianghui; Chen, Chuo (2011-10-05). "Asymmetric Synthesis of Ageliferin". Journal of the American Chemical Society. 133 (39): 15350–15353. doi:10.1021/ja207386q. ISSN   0002-7863. PMC   3183238 . PMID   21888421.
  8. ↑ Wang, Xiao; Wang, Xiaolei; Tan, Xianghui; Lu, Jianming; Cormier, Kevin W.; Ma, Zhiqiang; Chen, Chuo (2012-11-14). "A Biomimetic Route for Construction of the [4+2] and [3+2] Core Skeletons of Dimeric Pyrrole–Imidazole Alkaloids and Asymmetric Synthesis of Ageliferins". Journal of the American Chemical Society. 134 (45): 18834–18842. doi:10.1021/ja309172t. ISSN   0002-7863. PMC   3498534 . PMID   23072663.
  9. ↑ Ding, Hui; Roberts, Andrew G.; Harran, Patrick G. (2012-11-29). "Total synthesis of ageliferin via acyl N-amidinyliminium ion rearrangement". Chemical Science. 4 (1): 303–306. doi:10.1039/C2SC21651E. ISSN   2041-6539. PMC   3653441 . PMID   23687567.
  10. ↑ Fujino, Yudai; Fukaya, Keisuke; Urabe, Daisuke (2025-09-24). "Automated Reactivity Prediction of Complex Molecules and Its Application to Total Synthesis of Ageliferin". Journal of the American Chemical Society. 147 (38): 34556–34563. doi:10.1021/jacs.5c09045. ISSN   0002-7863.
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