Some Novel Types of Nitrosugars

Tronchet, J. M. J.; Pallie, K. D.; Barbalat-Rey, Françoise

doi:10.1080/07328308508062947

Cited by 20 publications

(5 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Tronchet and co-workers [80] described the synthesis of novel types of nitrosugars with potentially reactive functionality in the vicinity of the nitro group. Starting from the aldehydosugar 166, the E-configured Michael acceptor 167 was obtained in two steps (nitro aldol reaction and dehydratisation).…”

Section: Olefinic Acceptors Bearing a Nitro Groupmentioning

confidence: 99%

The Phospha‐Michael Addition in Organic Synthesis

et al. 2005

View full text Add to dashboard Cite

Phosphorus is essential for many reagents in organic synthesis, for ligands of late-transition metals and for phosphonoand phosphanylamino acids, the latter being important isosteres of amino acids. Similar to the Michaelis-Arbuzov and the Michaelis-Becker reaction the phospha-Michael addition, i. e. the addition of a phosphorus nucleophile to an acceptor-substituted alkene or alkyne, certainly represents one of the most versatile and powerful tools for the formation of P-C bonds since many different electrophiles and P nu-

show abstract

Section: Olefinic Acceptors Bearing a Nitro Groupmentioning

confidence: 99%

The Phospha‐Michael Addition in Organic Synthesis

et al. 2005

View full text Add to dashboard Cite

show abstract

“…19 Moreover, the substrate scope is not further investigated, and to date, the synthesis of other N-alkylated nitroaziridines has not been described. 18,19 Scheme 6. Aziridination of nitroalkene (21)…”

Section: Aziridination Of Trichloromethylated Nitroalkenesmentioning

confidence: 99%

Chemistry of Nitroaziridines

Nishiwaki¹,

Hao²

2019

HETEROCYCLES

View full text Add to dashboard Cite

This review article introduced synthetic procedures for the preparation of structurally diverse nitroaziridines. In addition, this article also summarized reactivity of nitroaziridines caused by the inherent strain and high electrophilicity of the small ring. These properties facilitate their use as a functionalized building blocks in synthetic and medicinal chemistry. INTRODUCTION Aziridines are an important class of nitrogen-containing heterocycles that can be found in a number of biologically active compounds, such as mitomycin, porfiromycin, and azinomycin. 1 Due to the inherent ring strain and high electrophilicity, they undergo ring-opening reactions with various nucleophiles to produce a wide range of nitrogen-containing compounds such as amino acids, amino sugars and alkaloids. 2 In contrast to epoxides, aziridines can be readily metalated and reacted with electrophiles, 3 leading to a broader range of functionalized derivatives, which serve as versatile building blocks in organic synthesis. 1,4 Indeed, a substantial number of functionalized aziridines have been transformed into useful products such as an HIV protease inhibitor, 5 communesin, 6 ceramide, 7 and oseltamivir 8 via rearrangement, cycloaddition, and ring expansion reactions. 4 Among various functional groups, the nitro group is highly attractive in synthetic chemistry owing to the strongly electron-withdrawing ability and its versatility for obtaining diverse functionalized compounds by chemical conversion. 9 Considering the above features, we focused our attention on nitroaziridines, which are important synthetic intermediates. 10 Hence, the chemistry of nitroaziridines is reviewed here. This article is dedicated to Professor Tohru Fukuyama on the occasion of his 70th birthday.

show abstract

“…2, 3A, 3C, 3D). Such a stereoselectivity is commonly observed in nucleophilic addition on the carbonyl group of aldehydo-sugars bearing these types of sugar moieties (see, for example, [15]). …”

Section: Regioselectivitymentioning

confidence: 99%

Structure-activity relationship between the 3D distribution of the electrophilicity of sugar derivatives and their cytotoxic and antiviral properties

Ricca¹,

Tronchet²,

Weber³

1992

J Computer-Aided Mol Des

Self Cite

View full text Add to dashboard Cite

The cytotoxic activities of a series of sugar derivatives bearing electrophilic groups (1-cyanovinyl, 4-cyanochromen-2-yl and 3-nitrochromen-2-yl) have been correlated with their electrophilic properties. To this end, an electrophilic index was defined as an isovalue surface where the interaction energy with an incoming model nucleophile (H-) was equal to a predefined value. This index, calculated from extended Hückel wave functions, allows one to quantify the electrophilic character of the substrates and to describe its spatial localization within the molecular volume (at Michael acceptor sites or on other parts of the molecules). Only sugars for which Michael acceptor reactivity was predicted were retained, and they were subdivided into two groups: those showing antiviral activity against a retrovirus and those devoid of such activity. Under these conditions, good correlations between cytotoxic activity and electrophilic reactivity--positive for the first group, negative for the second--were found. In addition, the ratio electrophilicity/sum of the absolute value of the dipole plus its projection along the principal axis of inertia, Z, of the molecule allows one to predict to which of these groups a sugar derivative belongs.

show abstract

Some Novel Types of Nitrosugars

Cited by 20 publications

References 21 publications

The Phospha‐Michael Addition in Organic Synthesis

The Phospha‐Michael Addition in Organic Synthesis

Chemistry of Nitroaziridines

Structure-activity relationship between the 3D distribution of the electrophilicity of sugar derivatives and their cytotoxic and antiviral properties

Contact Info

Product

Resources

About