- TRIAZOLE COMPOUNDS AND METHODS OF MAKING AND USING THE SAME
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The present invention provides triazole macrocyclic compounds useful as therapeutic agents. More particularly, these compounds are useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents.
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Page/Page column 151-152
(2018/11/10)
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- Dicyclic clarithromycin derivative and purpose of dicyclic clarithromycin derivative as tumor cells proliferation inhibitor
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The invention belongs to the technical field of medicine, and relates to a dicyclic clarithromycin derivative and a preparation method thereof and an application of the dicyclic clarithromycin derivative as a tumor cells proliferation inhibitor in prepara
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Paragraph 0089; 0090
(2017/05/20)
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- Novel desosamine-modified 14- and 15-membered macrolides without antibacterial activity
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Novel modifications of the desosamine sugar of 14- and 15-membered antibacterial macrolides, in which the desosamine was fused with N-substituted-1,3-oxazolidin-2-ones, were developed in order to completely suppress antibacterial activity and make them pr
- Jakopovi?, Ivana Palej,Kraja?i?, Mirjana Bukvi?,?kugor, Maja Matanovi?,?timac, Vlado,Pe?i?, Dijana,Vujasinovi?, Ines,Alihod?i?, Sulejman,Paljetak, Hana ?ip?i?,Kragol, Goran
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scheme or table
p. 3527 - 3530
(2012/07/03)
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- Synthesis and antibacterial activity of desosamine-modified macrolide derivatives
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Structural factors behind erm macrolide resistance were studied through synthesis of new macrolide derivates possessing truncated desosamine sugar moieties and subsequent determination of their antibacterial activity. Synthesized compounds with 2′-deoxy a
- Letourneau, Nicolas,Vimal, Pavan,Klepacki, Dorota,Mankin, Alexander,Melman, Artem
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scheme or table
p. 4575 - 4578
(2012/08/08)
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- Novel tandem reaction for the synthesis of Na′-substituted 2-imino-1,3-oxazolidines from vicinal (sec- or tert-)amino alcohol of desosamine
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Two one-pot methods, sequential and tandem, for the preparation of Na′-substituted 2-imino-1,3-oxazolidines from the vicinal (sec- or tert)-amino alcohol of desosamine via intermediary alkyl-, aryl-, heteroaryl-, and heteroalkyl-thiourea moieties are described. Particularly interesting is the novel one-pot tandem reaction of the vicinal tert-amino alcohol that involves dealkylation, thiourea formation, and a final cyclization to yield 2-imino-1,3-oxazolidine structures. The yields of both one-pot methods are comparable to the yield of the sequential reaction. A small library of a new class of desosamine-modified 14- and 15-membered macrolides was prepared to demonstrate the variety of substituents that can be easily introduced and thus enable a huge variation of the physicochemical and hence biological properties of these new molecules. Na′-Substituted 2-imino-1,3-oxazolidines have been condensed onto a desosamine amino sugar by two one-pot methods. A novel one-pot tandem reaction of the 2a′,3a′-vicinal tert-amino alcohol of desosamineinvolving dealkylation, thiourea formation, and a final cyclization to yield 2-imino-1,3-oxazolidine structures with a Z configuration around the imine bond has been discovered. Copyright
- Vujasinovic, Ines,Marusic Istuk, Zorica,Kapic, Samra,Bukvic Krajacic, Mirjana,Hutinec, Antun,Dilovic, Ivica,Matkovic-Calogovic, Dubravka,Kragol, Goran
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experimental part
p. 2507 - 2518
(2011/06/10)
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- Non-peptide macrocyclic histone deacetylase inhibitors derived from tricyclic ketolide skeleton
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Inhibition of histone deacetylase (HDAC) function is a validated therapeutic strategy for cancer treatment. Of the several structurally distinct small molecule histone deacetylase inhibitors (HDACi) reported, macrocyclic depsipeptides possess the most complex cap groups and have demonstrated excellent HDAC inhibition potency and isoform selectivity. Unfortunately, the development of macrocyclic depsipeptides has been hampered in part because of development problems characteristic of large peptides and the complex reaction schemes required for their synthesis. Herein we report that tricyclic ketolide TE-802 is an excellent mimetic for the peptide backbone of macrocyclic HDACi. Compounds derived from this template are particularly selective against HDACs 1 and 2 with nanomolar inhibitory activity. Interrogation of the association between a subset of these compounds and key HDAC isoforms, using AutoDock, enables a molecular description of the interaction between the HDAC enzyme's outer rim and the inhibitors' macrocyclic cap group that are responsible for compound affinity and presumably isoform selectivity.
- Mwakwari, Sandra C.,Guerrant, William,Patil, Vishal,Khan, Shabana I.,Tekwani, Babu L.,Gurard-Levin, Zachary A.,Mrksich, Milan,Oyelere, Adegboyega K.
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scheme or table
p. 6100 - 6111
(2010/11/19)
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- Synthesis of an antibacterial compound containing a 1,4-substituted 10-1,2,3-triazole: A scaleable alternative to the click reaction
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The copper-catalyzed click reaction of an azide with an alkyne has become a popular method to build up 1,4-substituted 1H-1,2,3- triazoles in medicinal chemistry and this approach was used on a laboratory scale during the preparation of novel macrolide 1. However, the manufacture of the key azide component, as well as its subsequent use in the presence of a copper catalyst on a large scale, was associated with potential safety concerns. Therefore, a sequence was developed in which construction of the 1,4- substituted 1H-1,2,3-triazole in 1 was accomplished via cyclocon - densation of an a,a-dichloro tosyl hydrazone with an amine.
- Hanselmann, Roger,Job, Gabriel E.,Johnson, Graham,Lou, Rongliang,Martynow, Jacek G.,Reeve, Maxwell M.
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experimental part
p. 152 - 158
(2010/06/13)
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- MACROLIDE DERIVATIVES
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Compounds represented by formula (I) and the formula (IV) have an inhibitory activity of MMP-9 production, therefore, are useful as a medicine agent with fewer side effects than conventional MMP enzyme activity inhibitors, as a prophylactic and therapeuti
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Page/Page column 40
(2009/04/24)
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- Non-peptide macrocyclic histone deacetylase inhibitors
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Inhibition of histone deacetylase inhibitors (HDACi) hold great promise in cancer therapy because of their demonstrated ability to arrest proliferation of nearly all transformed cell types. Of the several structurally distinct small molecule HDACi reporte
- Oyelere, Adegboyega K.,Chen, Po C.,Guerrant, William,Mwakwari, Sandra C.,Hood, Rebecca,Zhang, Yunzhe,Fan, Yuhong
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experimental part
p. 456 - 468
(2009/10/23)
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- 2'-O,3'-N-BRIDGED MACROLIDES
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Novel 2 ' -O, 3 ' -/V-bridged macrolides useful in treatment of inflammatory diseases. More particularly, the invention relates to 2 ' -O, 3 ' -/V-bridged 14- membered macrolides and to 2 ' - O, 3 ' -/V-bridged 15-membered azalide macrolides useful in treatment of neutrophil dominated inflammatory diseases resulting from neutrophilic infiltration and/or diseases associated with altered cellular functionality of neutrophils, to intermediates for their preparation, to the methods for their preparation, to their use as therapeutic agents, and to salts thereof.
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Page/Page column 35
(2009/12/05)
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- MACROLIDE COMPOUNDS AND METHODS OF MAKING AND USING THE SAME
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The present invention provides amide containing macrocyclic compounds useful as therapeutic agents. More particularly, these compounds are useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents.
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Page/Page column 112
(2008/12/07)
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- MACROLIDE DERIVATIVES AS ANTIBACTERIAL AGENTS
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The present invention provides macrolide derivatives, which can be used as antibacterial agents. Compounds disclosed herein can be used for treating or preventing conditions caused by or contributed to by gram positive, gram negative or anaerobic bacteria, more particularly against, for example, Staphylococci, Streptococci, Enterococci, Haemophilus, Moraxella spp., Chlamydia spp., Mycoplasm, Legionella spp., Mycobacterium, Helicobacter, Clostridium, Bacteroides, Corynebacterium, Bacillus, Enterobactericeae or any combination thereof. Also provided, are processes for preparing compounds disclosed herein, pharmaceutical compositions containing compounds disclosed herein, and methods of treating bacterial infections.
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Page/Page column 29
(2008/12/08)
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- TRIAZOLE COMPOUNDS AND METHODS OF MAKING AND USING THE SAME
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The present invention provides triazole macrocyclic compounds useful as therapeutic agents. More particularly, these compounds are useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents.
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Page/Page column 148
(2008/06/13)
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- TRIAZOLE COMPOUNDS AND METHODS OF MAKING AND USING THE SAME
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The present invention provides triazole macrocyclic compounds useful as therapeutic agents. More particularly, these compounds are useful as anti-infective, antiproliferative, anti-inflammatory, and prokinetic agents.
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Page/Page column 302
(2008/06/13)
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- PREPARATION AND UTILITY OF SUBSTITUTED ERYTHROMYCIN ANALOGS
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The present disclosure is directed to novel macrolide antibiotics of Formula 1 and pharmaceutically acceptable salts and prodrugs thereof; and the chemical syntheses and medical uses of these novel macrolide antibiotics for the treatment and/or management of infections caused by various aerobic and anaerobic gram-positive and gram-negative microorganisms as well as various mycobacteria.
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Page/Page column 35
(2008/06/13)
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- MACROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING THE SAME
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The present invention provides macrocyclic compounds useful as therapeutic agents. More particularly, these compounds are useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents.
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Page/Page column 193
(2010/02/14)
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- BIFUNCTIONAL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME
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The invention provides a family of bifunctional heterocyclic compounds useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents. The invention also provides methods of making the bifunctional hetercyclic compounds, and methods of using such compounds as anti-infective, anti-proliferative agents, anti-inflammatory, and/or prokinetic agents.
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Page/Page column 231
(2010/02/06)
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- Synthesis of [N-methyl-13C]clarithromycin
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We describe a simple synthesis of [N-methyl-13C]clarithromycin (3) via the N-desmethylation of clarithromycin. Copyright
- Murase, Tomoko,Kajiwara, Masahiro
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- MACROLIDE COMPOUNDS ENDOWED WITH ANTIINFLAMMATORY ACTIVITY
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Macrolide compounds endowed with antiinflammatory activity are described, and more particularly macrolide derivatives lacking cladinose in position 3, with antiinflammatory activity, pharmaceutically acceptable salts thereof and pharmaceutical composition
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- Nonpeptide Luteinizing Hormone-Releasing Hormone Antagonists Derived from Erythromycin A: Design, Synthesis, and Biological Activity of Cladinose Replacement Analogues
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The design and synthesis of a series of 11,12-cyclic carbamate derivatives of 6-O-methylerythromycin A that are novel, nonpeptide LHRH antagonists, is described. The macrolide antagonist 1, discovered during a screen of our chemical repository, was compar
- Randolph, John T.,Waid, Philip,Nichols, Charles,Sauer, Daryl,Haviv, Fortuna,Diaz, Gilbert,Bammert, Gary,Besecke, Leslie M.,Segreti, Jason A.,Mohning, Kurt M.,Bush, Eugene N.,Wegner, Craig D.,Greer, Jonathan
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p. 1085 - 1097
(2007/10/03)
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- Chemical Modification of Erythromycins. X. Removal of Benzyloxycarbonyl and 2-Chlorobenzyl Groups of Erythromycin Derivatives by Use of Catalytic Transfer Hydrogenation
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The benzyloxycarbonyl and the 2-chlorobenzyl groups of erythromycin derivatives were easily removed by catalytic transfer hydrogenation (CTH).Their deprotection reaction was dependent on both the hydrogen donor and the solvent for use.Application of CTH to removal of the protective groups is discussed.
- Watanabe, Yoshiaki,Kashimura, Masato,Asaka, Toshifumi,Adachi, Takashi,Morimoto, Shigeo
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p. 761 - 768
(2007/10/02)
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