Michellamine

Last updated
Michellamine B
Michellamine.svg
Names
Preferred IUPAC name
(1R,1′R,3R,3′R)-5,5′-(1,1′-Dihydroxy-8,8′-dimethoxy-6,6′-dimethyl[2,2′-binaphthalene]-4,4′-diyl)bis(1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,8-diol)
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C46H48N2O8/c1-19-9-25-27(41-31-13-21(3) 47-23(5)39(31)33(49)17-35(41)51)15-29(45(53)43(25)37(11-19)55-7)30-16-28(26-10-20(2)12-38(56-8)44(26)46(30)54)42-32-14-22(4)48-24(6)40(32)34(50)18-36(42)52/h9-12,15-18,21-24,47-54H,13-14H2,1-8H3/t21-,22-,23-,24-/m1/s 1
  • Oc1c8c(c(c(O)c1)c2cc(c(O)c3c2cc(cc3OC)C)c7c(O)c4c(cc(cc4OC)C)c(c5c(O)cc(O)c6c5C[C@H](N[C@@H]6C)C)c7)C[C@H](N[C@@H]8C)C
Properties
C46H48N2O8
Molar mass 756.896 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Michellamines are a group of atropisomeric alkaloid which have been found to be HIV viral replication inhibitors in vitro . It was discovered in the leaves of Ancistrocladus korupensis . [1] There are three michellamines represented as A, B, and C; however, michellamine B is the most active against the NID-DZ strain of HIV-2. [2]

Contents

Occurrence

Michellamine A and B occur naturally in Ancistrocladus korupensis leaves. Other chemical substances including alkaloids, tannins, and saponins are found in the roots, leaves, stems, flowers, or bark.[ citation needed ]

Synthesis

There are two methods explored to synthesize michellamines A and B. The first one, originally synthesized in 1994, is a retrosynthesis that leads to a biomimetic pathway that uses the construction of naphthalene/isoquinoline bonds before the naphthalene/naphthalene axis. The second method, originally synthesized only a few montes after the first method, is a complementary pathway that would use the naphthalene/naphthalene axis after it is created and add the two isoquinoline moieties. [3]

Research

Michellamines inhibit protein kinase C and virus-induced cellular fusion. [4] They have a broad range of effectiveness in vitro across most HIV strains, particularly the HIV-2 strain, which is found primarily in and around Cameroon. [4]

References

  1. ↑ Schlauer, Jan; et al. (1 February 1998). "Characterization of Enzymes fromAncistrocladus (Ancistrocladaceae) and Triphyophyllum (Dioncophyllaceae) Catalyzing Oxidative Coupling of Naphthylisoquinoline Alkaloids to Michellamines". Archives of Biochemistry and Biophysics. 350 (1): 87–94. doi:10.1006/abbi.1997.0494. PMID   9466824.
  2. ↑ Zhang, Heping; Zembower, David; Chen, Zhidong (October 1997). "Structural analogues of the michellamine anti-HIV agents. Importance of the tetrahydroisoquinoline rings for biological activity". Bioorganic & Medicinal Chemistry Letters. 7 (20): 2687–2690. doi:10.1016/S0960-894X(97)10057-9.
  3. ↑ Bringmann, Gerhard; Götz, Roland; Keller, Paul A.; Walter, Rainer; Boyd, Michael R.; Lang, Fengrui; Garcia, Alberto; Walsh, John J.; Tellitu, Imanol; Bhaskar, K. Vijaya; Kelly, T. Ross (January 1998). "A Convergent Total Synthesis of the Michellamines". The Journal of Organic Chemistry. 63 (4): 1090–1097. doi:10.1021/jo971495m.
  4. 1 2 White, E.; Chao, W. R.; Ross, L. J.; Borhani, D. W.; Hobbs, P. D.; Upender, V.; Dawson, M. I. (1999). "Michellamine Alkaloids Inhibit Protein Kinase C". Archives of Biochemistry and Biophysics. 365 (1): 25–30. doi:10.1006/abbi.1999.1145. PMID   10222035.
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