Lamellarin D

Last updated
Lamellarin D
LamellarinD.png
Names
Preferred IUPAC name
3,11-Dihydroxy-14-(4-hydroxy-3-methoxyphenyl)-2,12-dimethoxy-6H-[1]benzopyrano[4′,3′:4,5]pyrrolo[2,1-a]isoquinolin-6-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C28H21NO8/c1-34-21-9-14(4-5-17(21)30)24-25-16-11-23(36-3)19(32)12-20(16)37-28(33)27(25)29-7-6-13-8-18(31)22(35-2)10-15(13)26(24)29/h4-12,30-32H,1-3H3 Yes check.svgY
    Key: ATHLLZUXVPNPAW-UHFFFAOYSA-N Yes check.svgY
  • InChI=1S/C28H21NO8/c1-34-21-9-14(4-5-17(21)30)24-25-16-11-23(36-3)19(32)12-20(16)37-28(33)27(25)29-7-6-13-8-18(31)22(35-2)10-15(13)26(24)29/h4-12,30-32H,1-3H3
    Key: ATHLLZUXVPNPAW-UHFFFAOYSA-N
  • COC1=C(C=CC(=C1)C2=C3C4=CC(=C(C=C4C=CN3C5=C2C6=CC(=C(C=C6OC5=O)O)OC)O)OC)O
Properties
C28H21NO8
Molar mass 499.475 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lamellarins are a group of pyrrole alkaloids first isolated in 1985 from the marine mollusk Lamellaria in the waters of Palau. Over 70 lamellarins and similar compounds were subsequently isolated. Other similar compounds include ningalins, lukianols, polycitones, and storniamides. [1]

Contents

Biological activity

These compounds have shown a wide variety of biological activity, including reversal of multidrug resistance, HIV-1 integrase inhibition, and antibiotic activity. Lamellarin D, for example, displays strong cytotoxic activity against tumor cell lines, and is a potent topoisomerase I inhibitor. [2]

Structure

The lamellarins all contain a central pyrrole ring, substituted at the 3 and 4 positions by polyhydroxy- or methoxyphenyls. They are divided into two groups, depending on whether the pyrrole ring is fused or unfused. [3]

Synthesis

The lamellarins have been synthesized by a number of groups, including Isibashi, Steglich, Ruchirawat, Banwell, Alvarez, Gupton, Boger, and Handy. [4]

Steglich synthesis of lamellarin G trimethyl ether

The Steglich synthesis features an oxidative coupling of two benzylic carbons, as well as a Paal-Knorr pyrrole synthesis. [5] [6]

Banwell synthesis of lamellarin K

The Banwell group’s synthesis of lamellarin K includes an intramolecular azomethine ylide cyclization. [7]

1997 - Lamellarin K synthesis by Banwell: (i) nBuLi, THF, -78 degC, 0.83 h; ZnCl2, -78 degC -> 18 degC, 1 h; aryliodide, Pd(PPh3), 18 degC, 4 h (ii) ClCH2CH2Cl, 18 degC, 7 h; Hunig's base, 83 degC, 32 h (iii) AlCl3, CH2Cl2, 18 degC, 2 h LamellarinK Banwell synthesis.png
1997 - Lamellarin K synthesis by Banwell: (i) nBuLi, THF, -78 °C, 0.83 h; ZnCl2, -78 °C -> 18 °C, 1 h; aryliodide, Pd(PPh3), 18 °C, 4 h (ii) ClCH2CH2Cl, 18 °C, 7 h; Hunig’s base, 83 °C, 32 h (iii) AlCl3, CH2Cl2, 18 °C, 2 h
1997 Lamellarin G Trimethyl Ether Synthesis by Steglich: (i) 1. -70 degC, 2 eq. nBuLi; 2. 0.5 eq. I2, -70 degC -> RT (ii) Mol sieves, 12h, RT (iii) EtOAc, 1 eq. Pb(OAc)4, reflux (iv) CH3CN, PPh3, NEt3, Pd(OAc)2 Lamellarin G Trimethyl Ether Steglich.png
1997 Lamellarin G Trimethyl Ether Synthesis by Steglich: (i) 1. -70 °C, 2 eq. nBuLi; 2. 0.5 eq. I2, -70 °C -> RT (ii) Mol sieves, 12h, RT (iii) EtOAc, 1 eq. Pb(OAc)4, reflux (iv) CH3CN, PPh3, NEt3, Pd(OAc)2

See also

References

  1. ↑ Bailly, Christian; Newman, David J. (2015-02-19). "Download Limit Exceeded" (PDF). Marine Drugs. 13 (3). Pierre Fabre Research Institute: 1105–1123. doi: 10.3390/md13031105 . ISSN   1660-3397. PMC   4377975 . PMID   25706633.
  2. ↑ Reddy, Venkata M.; Rao, Rama M.; Rhodes, Denise; Hansen, Mark S.; Rubins, Kathleen; Bushman, Frederic D.; Venkateswarlu, Yenamandra; Faulkner, John D. (November 24, 1999). "Lamellarin r 20-Sulfate, an Inhibitor of HIV-1 Integrase Active against HIV Virus in Cell Culture" (PDF). Journal of Medicinal Chemistry . 42 (11). Indian Institute of Chemical Technology: 1901–1907. doi:10.1021/jm9806650. eISSN   1520-4804. ISSN   0022-2623. PMID   10354398. Archived (PDF) from the original on 2022-08-11. Retrieved 2022-08-11.
  3. ↑ Bailly, Christian (2004-07-04). "Lamellarins, from A to Z: a family of anticancer marine pyrrole alkaloids". Current Medicinal Chemistry. Anti-Cancer Agents. 4 (4): 363–378. doi:10.2174/1568011043352939. ISSN   1568-0118. PMID   15281908. Archived from the original on 2022-08-11.
  4. ↑ Ruchirawat, Somsak; Mutarapat, Thumnoon; Sahakitpichan, Poolsak; Bhavakul, Vanida; Mahidol, Chulabhorn (1997-11-13). "The Syntheses of Lamellarins and Isoindolobenzazepine Alkaloids" (PDF). International Conference on Biodiversity and Bioresources . 70 (11). Phuket, Thailand: 6. Archived (PDF) from the original on 2022-08-11. Retrieved 2022-08-11– via IUPAC.
  5. ↑ "Paal-Knorr Pyrrole Synthesis", Comprehensive Organic Name Reactions and Reagents, Hoboken, NJ, USA: John Wiley & Sons, Inc., pp. conrr475, 2010-09-15, doi:10.1002/9780470638859.conrr475, ISBN   978-0-470-63885-9, archived from the original on August 11, 2022, retrieved 2022-08-11
  6. ↑ "Hantzsch Pyrrole Synthesis", Comprehensive Organic Name Reactions and Reagents, Hoboken, NJ, USA: John Wiley & Sons, Inc., pp. conrr295, 2010-09-15, doi:10.1002/9780470638859.conrr295, ISBN   978-0-470-63885-9, archived from the original on August 11, 2022, retrieved 2022-08-11
  7. ↑ Padwa, Albert (2017-11-29). "Use of nitrogen and oxygen dipole ylides for alkaloid synthesis" (PDF). The Free Internet Journal for Organic Chemistry . 5 (1) (published 2018-02-06): 23–49. doi: 10.24820/ark.5550190.p010.416 . Retrieved 2022-08-11– via ARKAT USA.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.