Names | |
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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)
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ChEMBL | |
ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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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).
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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]
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]
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]
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]