Novel desosamine-modified 14- and 15-membered macrolides without antibacterial activity

Jakopović, Ivana Palej; Krajačić, Mirjana Bukvić; Škugor, Maja Matanović; Štimac, Vlado; Pešić, Dijana; Vujasinović, Ines; Alihodžić, Sulejman; Paljetak, Hana Čipčić; Kragol, Goran

doi:10.1016/j.bmcl.2012.03.076

Cited by 13 publications

(7 citation statements)

References 18 publications

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“…Exposure of 29 to ferrous sulfate in methanol20 subsequently provided the 7′ N ‐demethyl‐7′ N ‐ethylapramycin derivative 30 in 40 % yield (Scheme ). In an alternative approach to modification at the 7′‐position, the secondary amine 6 was subjected to iodine and sodium methoxide in the presence of Tris buffer,21 resulting in the formation of the 7′ N ‐desmethyl derivative 31 in 58 % yield. Standard reductive amination with benzyloxyacetaldehyde then afforded the 7′ N ‐desmethyl‐7′ N ‐benzyloxyethyl derivative 32 in 63 % yield (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

The structure and evolution of lower stratospheric frontal zones. Part II: The influence of tropospheric ascent on lower stratospheric frontal development

Lang

Martin

2013

Quart J Royal Meteoro Soc

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The intensification of frontal characteristics in the region above the mid-latitude jet core within the lower stratospheric portion of an upper-level jet front system (ULJF) is known as lower stratospheric frontogenesis. Four recent cases of lower stratospheric frontogenesis in southwesterly flow are examined in order to elucidate the interaction between lower stratospheric dynamical processes and tropospheric ascent that characterizes such developments. In all of the cases examined the lower stratospheric front was (1) characterized by lower stratospheric quasi-geostrophic forcing for ascent on its cold side, and (2) parallel to a surface cold front.As latent heating associated with ascent along the surface cold front redistributed the potential temperature field within the upper troposphere, the stability of the near-tropopause upper troposphere decreased, thus intensifying the response to lower stratospheric frontal forcing by enhancing the frontogenetic ascent within the upper troposphere. It is therefore suggested that ascent originating in the lower troposphere is able to influence the development of lower stratospheric fronts and substantially alter the structure of the mid-latitude tropopause and its associated horizontal potential vorticity gradient at and above the jet core. The implications of lower stratospheric frontogenetic processes on facilitating tropical-extratropical interactions is discussed.Key Words: lower stratospheric fronts; convection; stability reduction

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Section: Resultsmentioning

confidence: 99%

The structure and evolution of lower stratospheric frontal zones. Part II: The influence of tropospheric ascent on lower stratospheric frontal development

Lang

Martin

2013

Quart J Royal Meteoro Soc

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“…The crucial ethynylbenzyl moieties were installed at either the desosamine sugar (azithromycin and clarithromycin) or N10 position of azithromycin to furnish the requisite alkynyl-macrolides 4, 7 12, 13 and 14 following the literature procedure. 14,15,16,17 Subsequently, copper (I) catalyzed azide-alkyne-cycloaddition (AAC) 18 reaction between TBS-protected azidohydroxamates 51a–f and compounds 4, 7 and 12–14 , followed by removal of TBS-group 19 afforded the final compounds 5a–d, 8a–f, 15a–b, 16a–b , and 17a–d (Scheme 1). …”

Section: Chemistrymentioning

confidence: 99%

A structure–activity relationship of non-peptide macrocyclic histone deacetylase inhibitors and their anti-proliferative and anti-inflammatory activities

Tapadar

Fathi

Raji

et al. 2015

Bioorganic & Medicinal Chemistry

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Inhibition of the enzymatic activity of histone deacetylase (HDAC) is a promising therapeutic strategy for cancer treatment and several distinct small molecule histone deacetylase inhibitors (HDACi) have been reported. We have previously identified a new class of non-peptide macrocyclic HDACi derived from 14- and 15-membered macrolide skeletons. In these HDACi, the macrocyclic ring is linked to the zinc chelating hydroxamate moiety through a para-substituted aryl-triazole cap group. To further delineate the depth of the SAR of this class of HDACi, we have synthesized series of analogous compounds and investigated the influence of various substitution patterns on their HDAC inhibitory, anti-proliferative and anti-inflammatory activities. We identified compounds 25b and 38f with robust anti-proliferative activities and compound 26f (IC50 47.2 nM) with superior anti-inflammatory (IC50 88 nM) activity relative to SAHA.

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“…These compounds are also interesting in the synthesis of new biological targeting agents, in the polymer chemistry as the functional group of polyurethanes, and in agricultural chemistry as active ingredients of insecticides, fungicides, and herbicides . Moreover, they are products resulting from the processes of CO 2 removal using amines and alcohol amines …”

Section: Introductionmentioning

confidence: 99%

Kinetic study of the formation reaction of N-chloro-2-oxazolidinone

Pastoriza

Antelo

Amoedo

et al. 2015

J. Phys. Org. Chem.

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The chlorination reactions of 2-oxazolidinone with hypochlorous acid (HOCl), tert-butyl hypochlorite ( t BuOCl) and N-chlorosuccinimide (NCS) were studied at 25°C, constant ionic strength, and under isolation conditions. The kinetic results obtained in the formation processes of the N-chloro-2-oxazolidinone are summarized in this paper. The kinetics studied showed a first order with respect to the concentration of the each reactant and a complex dependence of the pH on the rate constant. The reactivity order with respect to the chlorinating agent found is k(HOCl) > k( t BuOCl) > k(NCS).

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Novel desosamine-modified 14- and 15-membered macrolides without antibacterial activity

Cited by 13 publications

References 18 publications

The structure and evolution of lower stratospheric frontal zones. Part II: The influence of tropospheric ascent on lower stratospheric frontal development

The structure and evolution of lower stratospheric frontal zones. Part II: The influence of tropospheric ascent on lower stratospheric frontal development

A structure–activity relationship of non-peptide macrocyclic histone deacetylase inhibitors and their anti-proliferative and anti-inflammatory activities

Kinetic study of the formation reaction of N-chloro-2-oxazolidinone

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