Ageliferin

Ageliferin
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
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 markN
    Key: DMMLTRAQSJWUHT-OGTWGDGJSA-N X markN
  • 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. It often co-exists with the related compound sceptrin and other similar compounds. It has antibacterial properties and can cause biofilms to dissolve. Total syntheses have been independently accomplished by the research groups of Phil S. Baran at the Scripps Research Institute, Chuo Chen at UT Southwestern Medical Center, Patrick Harran at UCLA, Daisuke Urabe at Toyama Prefectural University,and Evanno Laurent at Université Paris-Saclay.

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. Bibcode:1991JOrgC..56.2965K. 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. Bibcode:2004ACIE...43.2674B. doi:10.1002/anie.200453937. ISSN 1521-3773. PMID 18629987.
  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. Bibcode:2006ACIE...45..249B. doi:10.1002/anie.200503374. ISSN 1521-3773. PMID 16317782.
  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. Bibcode:2011JAChS.13315350W. 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. Bibcode:2012JAChS.13418834W. 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. ↑ Ding, Hui; Roberts, Andrew G.; Chiang, Rocky; Harran, Patrick G. (2018). "Cascading Auto-oxidative Biproline Guanylations Form Optically Active Dispacamide Dimers and Permit an Eight-Step Synthesis of (−)-Ageliferin". The Journal of Organic Chemistry. 83 (13): 7231–7238. doi:10.1021/acs.joc.8b00631. PMID 29708748.
  11. ↑ 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. Bibcode:2025JAChS.14734556F. doi:10.1021/jacs.5c09045. ISSN 0002-7863. PMID 40931967.
  12. ↑ Fujino, Yudai; Amano, Ayami; Matoba, Taisei; Fukaya, Keisuke; Urabe, Daisuke (2026-10-20). "Further Insights into the Stereoselective Total Synthesis of Ageliferin via Dearomatizing Diels–Alder Cycloaddition". The Journal of Organic Chemistry. doi:10.1021/acs.joc.6c02174. ISSN 0022-3263.
  13. ↑ Latrache, Mohammed; Sesay, Amina; Oger, Samuel; Montaner, Mireia Benito; Mellah, Mohamed; Poupon, Erwan; Hilton, Stephen T.; Arseniyadis, Stellios; Evanno, Laurent (2026). "Bioinspired total synthesis of (dibromo)sceptrin and (dibromo)ageliferin". Chemical Communications. 62 (41): 10418–10422. doi:10.1039/D6CC01851C. ISSN 1359-7345.