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Selective deuterium labeling of the sphingoid backbone: Facile syntheses of 3,4,5-trideuterio-d-erythro-sphingosine and 3-deuterio-d-erythro-sphingomyelin

Deuteration at C-4 and C-5 of sphingosine was achieved via a hydrogen-deuterium exchange reaction of a beta-ketophosphonate intermediate catalyzed by ND4Cl in D2O/tetrahydrofuran. To install deuterium at C-3 of sphingosine and sphingomyelin, sodium borodeuteride reduction/cerium(III) chloride reduction of an alpha,beta-enone in perdeuteromethanol was used.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H2495NO – PubChem

 

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ORALLY AVAILABLE SPHINGOSINE 1-PHOSPHATE RECEPTOR AGONISTS AND ANTAGONISTS

The present invention relates to S1P analogs that have activity as S1Preceptor modulating agents and the use of such compounds to treat diseases associated with inappropriate S1P receptor activity. The compounds have the general structure (I) wherein R11 is C5-C18 alkyl or C5-C18 alkenyl; Q is selected from the group consisting of C3-C6 optionally substituted cycloalkyl, C3-C6 optionally substituted heterocyclic, C3-C6 optionally substituted aryl C3-C6 optionally substituted heteroaryl and; R2 is selected from the group consisting of H, C1-C4 alkyl, (C1-C4 alkyl)OH and (C1-C4 alkyl)NH2; R23is H or C1-C4 alkyl, and R15 is a phosphonate ester or a phosphate ester or a pharmaceutically acceptable salt or tautomer thereof.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2566NO – PubChem

 

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Practical Cleavage of Acetals by Using an Odorless Thiol Immobilized on Silica

A practical, efficient and general method was developed for the deprotection of a variety of aromatic and aliphatic acetals to their corresponding catechol or diol derivatives using thiol immobilized on silica gel. This is an application for the well-known commercial solid-supported thiol (SiliaMetS Thiol). The procedure is mild and amenable to scale-up. It does not require inert atmosphere and clean conversions were observed. This method is applicable to substituted 1,3-benzodioxole and aliphatic acetals with different functionalities. It offers the advantage of a general route with high yield, which can be undertaken at ambient temperature.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2503NO – PubChem

 

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Synthesis of novel 2,3,4-trisubstituted-oxazolidine derivatives and in Vitro cytotoxic evaluation

We have previously reported the discovery of cytotoxic and pro-Apoptotic hit compound 1,1-dimethylethyl (S)- 2,2-dimethyl-4-[(3-nitrophenoxy)methyl]-3- oxazolidinecarboxylate 1 against leukemia cells. In the present work we describe the synthesis of 25 derivatives of this hit varying the substituent at ring or stereochemistry of the oxazolidine ring and evaluated them against human cancer cells lines. Six compounds exerted significant activity against HL60 promyelocytic leukemia cells with IC50 in low micromolar range (4-18 muM) and three compounds displayed activity against MDA-MB231 breast cancer cells (25-37 muM). In vitro cytotoxicity on normal cells PBMC (human peripheral blood mononuclear cells) was also evaluated. Compounds 7e (p-NO2, S) and 7m (p-COOCH3, S) showed good antiproliferative activity against HL60 (4 and 5 muM) and MDA-MB231 (37 and 25 muM) without affecting lymphocyte proliferation in PBMC, indicating low toxicity to normal cells. Besides, compound 7e induced DNA fragmentation on about 100% of HL60 cells at 50 muM. In this case, it was more potent than 7m and lead 1. This indicated that compound 7e has a great pro-Apoptotic potential.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2487NO – PubChem

 

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Novel peptidomimetic cysteine protease inhibitors as potential antimalarial agents

The synthesis of a new class of peptidomimetics 1a-j, based on a 1,4-benzodiazepine scaffold and on a C-terminal aspartyl aldehyde building block, is described. Compounds 1a-j provided significant inhibitory activity against falcipains 2A and 2B (FP-2A and FP-2B), two cysteine proteases from Plasmodium falciparum.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2539NO – PubChem

 

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Efficient construction of a doubly functionalized trisoxazole derivative relevant to the synthesis of the novel telomerase inhibitor telomestatin and its analogues

An efficient construction of a suitably functionalized trisoxazole derivative related to telomestatin was developed from L-serine, which involved three sequential oxazoline cyclization-oxidation steps in an overall yield of 11% in a linear sequence of twelve steps. Georg Thieme Verlag Stuttgart.

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Oxazolidine – Wikipedia,
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Total Synthesis and Biological Evaluation of Siladenoserinol A and its Analogues

The total synthesis of siladenoserinol A, an inhibitor of the p53?Hdm2 interaction, has been achieved. AuCl3-catalyzed hydroalkoxylation of an alkynoate derivative smoothly and regioselectively proceeded to afford a bicycloketal in excellent yield. A glycerophosphocholine moiety was successfully introduced through the Horner?Wadsworth?Emmons reaction using an originally developed phosphonoacetate derivative. Finally, removal of the acid-labile protecting groups, followed by regioselective sulfamate formation of the serinol moiety afforded the desired siladenoserinol A, and benzoyl and desulfamated analogues were also successfully synthesized. Biological evaluation showed that the sulfamate is essential for biological activity, and modification of the acyl group on the bicycloketal can improve the inhibitory activity against the p53?Hdm2 interaction.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2565NO – PubChem

 

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Stereocontrolled Total Synthesis of Galactostasin from Serine

An efficient stereoselective total synthesis of (-)-galactostasin (-)-1 from N-tert-butoxycarbonyl-2,3-isopropylidene L-serine methyl ester (21percent overall yield) is described via thiazole intermediates serving as protected aldehydes; the parallel synthesis of the natural antipole (+)-1 starts from D-serine.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2507NO – PubChem

 

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Generation and Cycloadditions of 4,5-Dihydrooxazole- and Oxazolidine-4-carbonitrile N-Oxides

A route to 2-phenyl-4,5-dihydrooxazole-4-carbonitrile N-oxide 7 has been developed starting from (S)-serine methyl ester and involving dehydration of the 4-nitromethyl derivative 13 using m-tolylene diisocyanate and triethylamine.Cycloaddition of the nitrile oxide to styrene afforded a 55:45 mixture of diastereoisomeric dihydroisoxazoles 21 and 22; furazan N-oxides 19 and 20 were also formed in a competing dimerisation.The analogous (R)-oxazolidine-4-carbonitrile oxide 8, also prepared from (S)-serine methyl ester, reacted similarly with styrene, oct-1-ene and diethyl fumarate to afford ca. 1:1 mixtures of adducts.The structures of the dihydrooxazole-dihydroisoxazole adduct 21 and furazan N-oxide 20 were determined by X-ray crystallography.

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Oxazolidine – Wikipedia,
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Synthesis and immobilization of ceramide analogs on silica particles

Ceramides are the major lipid components of the stratum corneum, the major permeability barrier of the skin. Here we report a chemical synthesis of ceramide analogs covalently bonded on the silica particles, that can be used to predict the skin permeability of chemicals via HPLC methods.

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Oxazolidine – Wikipedia,
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