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Synthesis of the polyketide (E)-olefin of the jamaicamides

The jamaicamides, isolated in Jamaica from the cyanobacterium Lyngbya majuscula, are new mixed polyketide-peptides that are known to be sodium channel blockers. The polyketide moiety contains an (E)-vinyl chloride, an undetermined methyl stereocenter (C9), and an (E)-olefin. Herein, we report the synthesis of the (E)-olefin moiety of the polyketide of the jamaicamides utilizing a Kocienski-Julia coupling. Supplemental materials are available for this article. Go to the publisher’s online edition of Synthetic Communications to view the free supplemental file.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H2071NO – PubChem

 

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Studies towards a novel synthesis of tubulysins: Highly asymmetric aza-Michael reactions of 2-enoylthiazoles with metalated chiral oxazolidinones

Herein we report the highly asymmetric aza-Michael reactions of alpha,beta-enones (2-enoylthiazoles) with metalated chiral oxazolidinones under different reaction conditions and for different substituents at the beta-position of the Michael acceptor. The reaction proceeds with complete diastereoselectivity to give exclusively one of the two diastereomers. The significance of the reaction is that no catalyst has been used; the steric requirements of the chiral Michael nucleophile drive the stereospecificity of the reaction and the reaction time is much less compared to the reported procedures. This methodology might be useful for an improved total synthesis of the highly cytotoxic peptides known as the tubulysins. Georg Thieme Verlag Stuttgart.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2012NO – PubChem

 

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Investigation of the noncovalent binding mode of covalent proteasome inhibitors around the transition state by combined use of cyclopropylic strain-based conformational restriction and computational modeling

To develop potent covalent inhibitors, the noncovalent interactions around the transition state to form covalent bonding should be optimized because the potency of the inhibitor can be depending on the energy of the transition state. Here, we report an efficient analysis of the noncovalent binding mode of a potent covalent proteasome inhibitor 3a around the transition state by a combined use of the chemical approach, i.e., the cyclopropylic strain-based conformational restriction, and the computational docking approach. Furthermore, we calculated the binding energy of a series of salinosporamide derivatives in the predicted noncovalent complex around the transition state with the simulation model of proteasome constructed in this study, which was well correlated to their pIC50. Thus, the proposed docking methods to predict the noncovalent binding mode around the transition state of covalent inhibitors will be helpful toward the development of covalent inhibitors.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1879NO – PubChem

 

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HYDROXAMIC ACID DERIVATIVES OF ANILINE USEFUL AS THERAPEUTIC AGENTS FOR TREATING ANTHRAX POISONING

Compounds having the formula (I), wherein the symbols have the meaning described in the specification are hydroxamic acid derivatives of aniline and capable of inhibiting the lethal effects of infection by anthrax bacteria and are useful in the treatment of poisoning by anthrax.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1614NO – PubChem

 

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Copper salt-catalyzed azide-[3 + 2] cycloadditions of ynamides and bis-ynamides

A one-pot synthesis of amide-substituted triazoles from alkyl bromides and ynamides is described here along with syntheses of novel bis-ynamidesand their applications in [3 + 2] cycloadditions with azides to construct unique bis-triazoles.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2105NO – PubChem

 

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THIOARYL DERIVATIVES AS GPR120 AGONISTS

The present invention relates to thioaryl derivatives of Formula 1 as defined in the specification, a method for preparing the same, a pharmaceutical composition comprising the same and use thereof. The thioaryl derivatives of Formula 1 according to the present invention promote GLP-1 formation in the gastrointestinal tract and improve insulin resistance in macrophages, pancreas cells, etc. due to anti-inflammatory action, and can accordingly be effectively used for preventing or treating diabetes, complications of diabetes, inflammation, obesity, non-alcoholic fatty liver, steatohepatitis or osteoporosis.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1621NO – PubChem

 

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NOVEL ANTIVIRAL PYRROLOPYRIDINE DERIVATIVE AND A PRODUCTION METHOD FOR SAME

The present invention relates to a pyrrolopyridine derivative represented by the Chemical Formula I, and a racemate or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, and relates to an antiviral composition including the same as an active ingredient. The compound of the Chemical Formula I has excellent antiviral activity and selectivity for wild type and resistant HIV-1, and thereby is useful as a therapeutic agent for acquired immune deficiency syndrome (AIDS).

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Oxazolidine – Wikipedia,
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Collective synthesis of 4-hydroxy-2-pyridone alkaloids and their antiproliferation activities

A collective synthesis of 4-hydroxy-2-pyridone alkaloids – specifically, pretenellin B, prebassianin B, farinosone A, militarione D, pyridovericin, and torrubiellone C – has been achieved. Key steps include using a strategic convergent method to synthesize the densely substituted pyridone key intermediate by Suzuki-Miyaura cross-coupling reaction, a divergent synthesis approach of target molecules by aldol condensation of pyridone intermediate with homologous aldehydes, and an iterative synthesis of homologous aldehydes with all-trans-polyene backbones. Interestingly, among the six tumor cell lines investigated, torrubiellone C was found to induce potent and apoptotic inhibitory activities on Jurkat T cells with IC50 values of 7.05 muM. Hence, this approach could potentially contribute to the synthesis of bioactive small-molecule libraries as well as drug discovery.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1800NO – PubChem

 

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Synthetic studies on lytophilippine A: Synthesis of the proposed structure

Chemical equations presented. Synthesis of the proposed structure of lytophilippine A was accomplished employing SmI2-mediated 5-exo cyclization of an aldehydo beta-alkoxyvinyl sulfoxide and ring-closing metathesis reaction.

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Oxazolidine – Wikipedia,
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Asymmetric synthesis of unusual amino acids: An efficient synthesis of optically pure isomers of beta-methylphenylalanine

Substitution of the diastereotopic beta-hydrogens of many alpha-amino acids provides an approach to the three dimensional topographic control of peptide structure. Asymmetric synthesis of the desired amino acids is needed to facilitate these studies. All four individual isomers of beta-methylphenylalanine, (2S,3S)-, (2R,3%)-, (2S,3R)- and (2R,3S)-beta-methylphenylalanine have been synthesized in high optical purity. The stereochemistry at the beta-center was set by the choice of starting material, either (+)- or (-)-3-phenylbutyric acid. These acids were attached to the appropriate D- or L-auxiliary (a 4-phenylmethyl-2-oxazolidinone) to give a 3′-phenylbutanoyl-4-phenylmethyl-2-oxazolidinone. Asymmetric bromination was accomplished via the chiral imide enolate bromination methodology of Evans and co-workers (J. Am. chem. Soc. 1990, 112, 4011-40). Evidence for asymmetric induction was obtained from the X-ray structure of one of the intermediate bromides. The bromide was converted to the diastereoisomeric azide by S(N)2 displacement using tetramethylguanidinium azide. After recovery of the chiral auxiliary by catalyzed hydrolysis, the chiral amino acid was obtained by catalytic hydrogenation over 10% Pd/C. All four isomers were obtained in enantiomeric purities of 95:5 to 99:1.

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Oxazolidine – Wikipedia,
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