Globoidnan A

Globoidnan A
Names

IUPAC name (2R)-(3,4-dihydroxyphenyl)-2-{[4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-2-naphthoyl]oxy}propanoic acid
Identifiers
CAS Number	827322-48-5^Y
3D model (Jmol)	Interactive image
ChemSpider	26333277^N
PubChem	3013628
InChI InChI=1S/C26H20O10/c27-18-3-1-12(5-20(18)29)6-24(25(33)34)36-26(35)15-7-14-10-22(31)23(32)11-17(14)16(8-15)13-2-4-19(28)21(30)9-13/h1-5,7-11,24,27-32H,6H2,(H,33,34)/t24-/m1/s1^N Key: DHZIDIIBBCIIEG-XMMPIXPASA-N^N InChI=1/C26H20O10/c27-18-3-1-12(5-20(18)29)6-24(25(33)34)36-26(35)15-7-14-10-22(31)23(32)11-17(14)16(8-15)13-2-4-19(28)21(30)9-13/h1-5,7-11,24,27-32H,6H2,(H,33,34)/t24-/m1/s1 Key: DHZIDIIBBCIIEG-XMMPIXPABS
SMILES c1cc(c(cc1C[C@H](C(=O)O)OC(=O)c2cc3cc(c(cc3c(c2)c4ccc(c(c4)O)O)O)O)O)O
Properties
Chemical formula	C₂₆H₂₀O₁₀
Molar mass	492.44 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Globoidnan A is a lignan found in Eucalyptus globoidea, a tree native to Australia.

The molecule has been found to inhibit the action of HIV integrase,^[1] an enzyme which is responsible for the introduction of HIV viral DNA into a host's cellular DNA. It is not known that globoidnan A inhibits the action of other retroviral integrases.

References

↑ Ovenden SP, Yu J, Wan SS, et al. (2004). "Globoidnan A: a lignan from Eucalyptus globoidea inhibits HIV integrase". Phytochemistry. 65 (24): 3255–59. doi:10.1016/j.phytochem.2004.10.006. PMID 15561191.

Antiviral drugs: antiretroviral drugs used against HIV (primarily J05)

Entry/fusion inhibitors
(Discovery and development)

gp41 (Enfuvirtide (ENF, T-20))
CCR5 (Maraviroc (MVC)
Vicriviroc^†, Cenicriviroc^†, PRO 140^†)
CD4 (Ibalizumab^†)
gp120 (Fostemsavir^†)

Reverse-transcriptase
inhibitors (RTIs)

Nucleoside and nucleotide (NRTI)	Nucleoside analogues/NRTIs: Abacavir (ABC)°^# Didanosine (ddI) Emtricitabine (FTC)° Lamivudine (3TC)°^# Stavudine (d4T)^# Zidovudine (AZT, ZDV)^# Amdoxovir^† Apricitabine^† Censavudine^† Elvucitabine^† Racivir^† Stampidine^† Zalcitabine (ddC)^◊ Nucleotide analogues/NtRTIs: Tenofovir disoproxil (TDF)°^# Tenofovir alafenamide (TAF)

Non-nucleoside (NNRTI) (Discovery and development)	(1st generation) Efavirenz (EFV)°^# Nevirapine (NVP)^# Delavirdine (DLV)^◊ (2nd generation) diarylpyrimidines (Etravirine (ETR) Rilpivirine (RPV)°) Doravirine

Integrase inhibitors
(Integrase strand transfer inhibitors (INSTI))

Dolutegravir (DTG)°
Elvitegravir (EVG)°
Raltegravir (RAL)°
BI 224436^†
Globoidnan A (experimental)
Cabotegravir^†
Bictegravir^†
MK-2048^†

Maturation inhibitors

Bevirimat^†
BMS-955176^§

Protease Inhibitors (PI)
(Discovery and development)

1st generation	Amprenavir (APV)^◊ Fosamprenavir (FPV) Indinavir (IDV)^◊ Lopinavir (LPV) Nelfinavir (NFV) Ritonavir (RTV)^# Saquinavir (SQV)^#

2nd generation	Atazanavir (ATV)°^# Darunavir (DRV)°^# Tipranavir (TPV)

Combined formulations

Abacavir/lamivudine°^#
Abacavir/dolutegravir/lamivudine°
Abacavir/lamivudine/zidovudine
Atazanavir/cobicistat
Darunavir/cobicistat
Efavirenz/emtricitabine/tenofovir°^#
Elvitegravir/cobicistat/emtricitabine/tenofovir alafenamide
Elvitegravir/cobicistat/emtricitabine/tenofovir°
Emtricitabine/tenofovir alafenamide
Emtricitabine/rilpivirine/tenofovir alafenamide
Emtricitabine/rilpivirine/tenofovir°
Lamivudine/raltegravir
Lamivudine/zidovudine^#
Lopinavir/ritonavir°^#
Tenofovir/emtricitabine°^#

Pharmacokinetic boosters

Experimental agents

Uncoating inhibitors	TRIM5alpha (gene)

Transcription inhibitors	Tat antagonists

Translation inhibitors	Trichosanthin

Other	Abzyme BIT225^† Calanolide A Ceragenin Cyanovirin-N Diarylpyrimidines Epigallocatechin gallate (EGCG) KP-1461^† Foscarnet Fosdevirine^† Griffithsin Hydroxycarbamide Miltefosine Portmanteau inhibitors Scytovirin Seliciclib^† Synergistic enhancers Tre recombinase Zinc finger protein transcription factor

Failed agents	Aplaviroc Atevirdine Brecanavir Capravirine Dexelvucitabine Droxinavir Lasinavir Emivirine Lersivirine Lodenosine Loviride Mozenavir Palinavir Telinavir

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

°DHHS recommended initial regimen options. ^◊Formerly or rarely used agent.

Types of lignans

Lignans	Arboreol Arctigenin Chamaecypanone A and B Eudesmin Globoidnan A Gmelanone Gmelinol Gummadiol Isootobanone Lyoniresinol Macelignan Matairesinol Obtulignolide Pinoresinol Pluviatilol Podophyllotoxin Secoisolariciresinol Sesamin Sesamolin Steganacin

Lignan glycosides	Arctiin Aviculin (isolariciresinol-9'-rhamnopyranoside) Secoisolariciresinol diglucoside

Mammalian lignans (enterolignans)	Enterodiol Enterolactone Lariciresinol Hydroxymatairesinol Syringaresinol

Neolignans	Balanophonin Eusiderin Honokiol Linderin A Magnolol Megaphone 4-O-Methylhonokiol Rhaphidecursinol A Rhaphidecursinol B

Flavonolignans	Cinchonain-Ib Dehydrosilybin Deoxysilycistin Deoxysilydianin Hydnocarpin Hydnowightin Neosilyhermin Palstatin Rhodiolin Salcolin A Salcolin B Scutellaprostin A, B, C, D, E and F Silandrin Silyamandin Silibinin Silybinome Silicristin Silydianin Silyhermin Tricin 4'-O-(erythro-beta-guaiacylglyceryl) ether Tricin 4'-O-(threo-beta-guaiacylglyceryl) ether

This article is issued from Wikipedia - version of the 8/31/2015. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.