Towards chemical libraries of annonaceous acetogenins

1997 ◽  
Vol 69 (3) ◽  
pp. 423-430 ◽  
Author(s):  
E. Keinan ◽  
A. Sinha ◽  
Ahmad Yazbak ◽  
Santosh C. Sinha ◽  
Subhash C. Sinha
Keyword(s):  
Annonaceous Acetogenins ◽  
Chemical Libraries

ChemInform Abstract: Toward Chemical Libraries of Annonaceous Acetogenins. Total Synthesis of Trilobacin.

ChemInform ◽  
2010 ◽  
Vol 28 (11) ◽  
pp. no-no
Author(s):  
S. C. SINHA ◽  
A. SINHA ◽  
A. YAZBAK ◽  
E. KEINAN
Keyword(s):  
Total Synthesis ◽  
Annonaceous Acetogenins ◽  
Chemical Libraries

Toward Chemical Libraries of Annonaceous Acetogenins. Total Synthesis of Trilobacin

1996 ◽  
Vol 61 (22) ◽  
pp. 7640-7641 ◽  
Author(s):  
Subhash C. Sinha ◽  
Anjana Sinha ◽  
Ahmad Yazbak ◽  
Ehud Keinan
Keyword(s):  
Total Synthesis ◽  
Annonaceous Acetogenins ◽  
Chemical Libraries

Oxidative polycyclizations with rhenium(VII) oxides

2002 ◽  
Vol 74 (1) ◽  
pp. 93-105 ◽  
Author(s):  
Ehud Keinan ◽  
Subhash C. Sinha
Keyword(s):  
Antitumor Agents ◽  
Single Step ◽  
Annonaceous Acetogenins ◽  
Chemical Libraries ◽  
Stereogenic Centers

The consecutive oxidative polycyclization reaction with rhenium(VII) oxides represents a highly stereoselective synthetic tool by which polyenes that contain a bis-homoallylic alcohol can be transformed into poly-THF products in a single step. On the basis of a detailed study with model substrates, a set of rules is proposed to predict product configurations in the polycyclization reactions with trifluoroacetylperrhenate. This methodology is exceptionally useful for the synthesis of polyoxygenated carbon skeletons that contain many stereogenic centers, and for the Annonaceous acetogenins in particular. Many of these potent antitumor agents, including solamin, reticulatacin, asimicin, bullatacin, trilobin, trilobacin, squamotacin, rolliniastatin, uvaricin, rollidecins C and D, mucocin, goniocin, and cyclogoniodenin T, as well as chemical libraries of non-natural analogs, were synthesized using the oxidative polycyclization reaction in combination with the Sharpless AD and AE reactions.

Annonaceous acetogenins within extracts: dereplication by HPLC-ESI-LTQ-Orbitrap® using post-column lithium infusion

Planta Medica ◽  
2012 ◽  
Vol 78 (11) ◽  
Author(s):  
J Le Ven ◽  
I Schmitz-Afonso ◽  
G Lewin ◽  
O Laprévote ◽  
A Brunelle ◽  
...  
Keyword(s):  
Annonaceous Acetogenins

A chemoinformatic analysis of atoms, scaffolds and functional groups in natural products

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Joelle Ngo Hanna ◽  
Boris D. Bekono ◽  
Luc C. O. Owono ◽  
Flavien A. A. Toze ◽  
James A. Mbah ◽  
...  
Keyword(s):  
Natural Products ◽  
Drug Discovery ◽  
Physicochemical Properties ◽  
Functional Groups ◽  
Atomic Composition ◽  
Synthetic Compounds ◽  
Chemical Libraries ◽  
Synthetic Drugs ◽  
Drugs Analysis ◽  
Chemical Class

Abstract In the quest to know why natural products (NPs) have often been considered as privileged scaffolds for drug discovery purposes, many investigations into the differences between NPs and synthetic compounds have been carried out. Several attempts to answer this question have led to the investigation of the atomic composition, scaffolds and functional groups (FGs) of NPs, in comparison with synthetic drugs analysis. This chapter briefly describes an atomic enumeration method for chemical libraries that has been applied for the analysis of NP libraries, followed by a description of the main differences between NPs of marine and terrestrial origin in terms of their general physicochemical properties, most common scaffolds and “drug-likeness” properties. The last parts of the work describe an analysis of scaffolds and FGs common in NP libraries, focusing on huge NP databases, e.g. those in the Dictionary of Natural Products (DNP), NPs from cyanobacteria and the largest chemical class of NP – terpenoids.

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