- Concise synthesis of (+)-serinolamide A
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Serinolamide A, isolated from a species of marine cyanobacteria, exhibits a moderate agonist effect and selectivity for the CB1 cannabinoid receptor, which is unusual for marine natural products. Herein, we reported a highly efficient enantiospecific first total synthesis of (+)-serinolamide A from l-serine in nine steps with 30% overall yield. The synthesis method provides a facile, practicable, and economical approach for the preparation of other similar endocanabinoid lipids.
- Gao, Ya-Ru,Guo, Shi-Huan,Zhang, Zhuan-Xiang,Mao, Shuai,Zhang, Yan-Lei,Wang, Yong-Qiang
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Read Online
- Incorporation and visualization of azido-functionalized: N -oleoyl serinol in Jurkat cells, mouse brain astrocytes, 3T3 fibroblasts and human brain microvascular endothelial cells
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The synthesis and biological evaluation of azido-N-oleoyl serinol is reported. It mimicks biofunctional lipid ceramides and has shown to be capable of click reactions for cell membrane imaging in Jurkat and human brain microvascular endothelial cells.
- Walter,Collenburg,Japtok,Kleuser,Schneider-Schaulies,Müller,Becam,Schubert-Unkmeir,Kong,Bieberich,Seibel
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supporting information
p. 8612 - 8614
(2016/07/13)
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- Synthesis and antibacterial activities of Yanglingmycin analogues
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The synthesis of Yanglingmycin and its enantiomer, along with eighteen Yanglingmycin analogues is reported. The structures were confirmed mainly by analyses of NMR spectral data. Antibacterial activity assays showed that Yanglingmycin and some of its analogues exhibited significant antibacterial activities against two important agricultural pathogenic bacteria, Ralstonia solanacearum and Pseudomonas syringae pv. actinidiae, with minimum inhibitory concentration (MIC) values ranging from 3.91 to 15.62 μg/mL. The antibacterial activities exhibited by Yanglingmycin and its analogues are promising, suggesting potential in the development of compounds for novel bactericides.
- Li, Long-Bo,Dan, Wen-Jia,Tan, Fang-Fang,Cui, Li-Hui,Yuan, Zhi-Peng,Wu, Wen-Jun,Zhang, Ji-Wen
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- I2-Catalyzed C-O Bond Formation and Dehydrogenation: Facile Synthesis of Oxazolines and Oxazoles Controlled by Bases
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A general method for the synthesis of oxazolines and oxazoles was developed through I2-catalyzed C-O bond formation and dehydrogenation with the same oxidant, TBHP. By simply tuning reaction bases, either oxazolines or oxazoles were selectively
- Gao, Wen-Chao,Hu, Fei,Huo, Yu-Ming,Chang, Hong-Hong,Li, Xing,Wei, Wen-Long
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supporting information
p. 3914 - 3917
(2015/08/18)
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- Synthesis of protected α-alkyl lanthionine derivatives
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Protected α-alkyl lanthionine derivatives were synthesized in five steps starting from a known phenyloxazoline precursor. This approach involved the synthesis of a family of substituted cyclic sulfamidates and their regioselective opening by nucleophilic attack with a protected cysteine. This efficient multistep strategy affords various α-alkylated lanthionine derivatives in high yields.
- Deno?l, Thibaut,Zervosen, Astrid,Lemaire, Christian,Plenevaux, Alain,Luxen, André
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p. 4526 - 4533
(2014/06/10)
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- Pd(ii)-catalyzed direct C5-arylation of azole-4-carboxylates through double C-H bond cleavage
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The first palladium-catalyzed direct C5-arylation of azole-4-carboxylates with simple unactivated arenes through double C-H bond cleavage is realized. This protocol provided a straightforward access to diverse 5-arylsubstituted azole-4-carboxylic derivatives with good functional group tolerance. The Royal Society of Chemistry 2012.
- Li, Ziyuan,Ma, Ling,Xu, Jinyi,Kong, Lingyi,Wu, Xiaoming,Yao, Hequan
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supporting information; scheme or table
p. 3763 - 3765
(2012/06/15)
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- Synthesis of 2-oxazolines and related N-containing heterocycles using [Et2NSF2]BF4 as a cyclodehydration agent
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The preparation of 2-oxazolines and related N-containing heterocycles from the corresponding hydroxyamides using XtalFluor-E ([Et2NSF 2s]BF4) as a cyclodehydration agent is described. A wide range of heterocycles are obtai
- Pouliot, Marie-France,Angers, Laetitia,Hamel, Jean-Denys,Paquin, Jean-Fran?ois
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p. 4121 - 4123
(2012/08/28)
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- COMPOUNDS FOR TREATMENT OF CANCER
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The present invention relates to novel compounds having anti-cancer activity, methods of making these compounds, and their use for treating cancer and drug-resistant tumors, e.g. melanoma, metastatic melanoma, drug resistant melanoma, prostate cancer and drug resistant prostate cancer.
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Paragraph 0034; 00263
(2011/10/03)
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- Catalytic asymmetric hydrogenation of N-Boc-imidazoles and oxazoles
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Substituted imidazoles and oxazoles were respectively hydrogenated into the corresponding chiral imidazolines and oxazolines (up to 99% ee). The highly enantioselective hydrogenation was achieved by using the chiral ruthenium catalyst, which is generated
- Kuwano, Ryoichi,Kameyama, Nao,Ikeda, Ryuhei
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experimental part
p. 7312 - 7315
(2011/06/24)
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- Solid-phase synthesis of α-alkylserines via phase-transfer catalytic alkylation of polymer-supported 2-phenyl-2-oxazoline-4-carboxylate
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Described is the development of a new solid-phase synthetic method for α-alkylserines in which phase-transfer catalytic alkylation of polymer-supported 2-phenyl-2-oxazoline-4-carboxylate (12) is the key step. The easy preparation of the polymer-supported
- Lee, Jihye,Ha, Min Woo,Kim, Taek-Soo,Kim, Mi-Jeong,Ku, Jin-Mo,Jew, Sang-sup,Park, Hyeung-geun,Jeong, Byeong-Seon
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experimental part
p. 8839 - 8843
(2009/12/26)
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- The use of phosphonium anhydrides for the synthesis of 2-oxazolines, 2-thiazolines and 2-dihydrooxazine under mild conditions
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β-Hydroxy amides 6 and 7 were treated with triphenylphosphonium anhydride trifluoromethane sulfonate (3), or the cyclic analogue 4, to generate 2-oxazolines 5 and 8 under mild conditions. The reaction was optimised by examining the number of equivalents of reagents 3 or 4, or diisopropylethyl amine required to best effect cyclisation. The effects of altering the reaction temperature, reaction time, concentration, solvent, and addition rate also were investigated. However, it was found that use of a trityl group to block reaction at the hydroxyl or thiol group of the starting amides, and subsequent in situ detritylation, in the absence of base, led to greatly improved yields. Reagent 4 offered significant advantages in the purification of products and was used to dehydrate a range of trityl derivatives to form simple oxazolines, thiazolines, and a dihydro-1,3-oxazine, in high yield (85-99%), as well as a tetrahydro-1,3-oxazepine (31%).
- Petersson, Maria J.,Jenkins, Ian D.,Loughlin, Wendy A.
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experimental part
p. 739 - 746
(2009/06/20)
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- Modular phosphite-oxazoline/oxazine ligand library for asymmetrie Pd-catalyzed allylic substitution reactions: scope and limitations - origin of enantioselectivity
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A library of phosphite-oxazoline/oxazine ligands L1-L15a-h has been synthesized and screened in the Pd-catalyzed allylic substitution reactions of several substrate types. These series of ligands can be prepared efficiently from easily accessible hydroxyl amino acid derivatives. Their modular nature enables the substituents/configurations in the oxazoline/oxazine moiety, alkyl backbone chain and in the biaryl phosphite moiety to be easily and systematically varied. By carefully selecting the ligand components, therefore, high regio- and enantioselectivities (ee values up to 99%) and good activities have been achieved in a broad range of mono- and disubstituted linear hindered and unhindered liner and cyclic substrates. The NMR studies on the Pd-π-allyl intermediates provide a deeper understanding about the effect of the ligand parameters on the origin of enantioselectivity. It also indicates that the nucleophilic attack takes place predominantly at the allylic terminal carbon atom located trans to the phosphite moiety.
- Dieguez, Montserrat,Pamies, Oscar
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experimental part
p. 3653 - 3669
(2009/04/23)
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- A flexible synthetic approach to the hennoxazoles
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Three advanced intermediates corresponding to the carbon skeleton of the hennoxazoles have been prepared. Central to the strategy is the synthesis of the oxazoles prior to coupling with the other fragments and a dithiane addition to allow for the generati
- Zylstra, Eric J.,She, Miles W.-L.,Salamant, Walter A.,Leahy, James W.
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p. 623 - 627
(2007/10/03)
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- IMMUNOMODULATORY COMPOUNDS AND METHODS OF USE THEREOF
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The present invention is directed to methods of treating diseases and disorders related to immune responses by administering one or more immunomodulatory compounds. In particular, the invention is directed to methods of stimulating and reducing immune responses, treating autoimmune conditions, treating allergic reactions and asthma, and preventing ischemic damage and asthma by administering one or more immunomodulatory compounds.
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- NOVEL ALIPHATIC COMPOUNDS, PROCESS FOR THEIR PREPARATION AND THEIR USAGE
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The present invention provides an aliphatic compound represented by the following formula (I) or pharmacologically acceptable salts thereof: ???where n denotes an integer of 1 to 11, and l denotes an integer of 1 to 16, the aliphatic compound being an opt
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- Benzamide bioisosteres incorporating dihydroheteroazole substructures: EPC synthesis and SAR leading to a selective dopamine D4 receptor partial agonist (FAUC 179)
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Conformationally restricted benzamide bioisosteres were investigated when the chiral phenyldihydroimidazole derivative 4e (FAUC 179) showed strong and highly selective dopamine D4 receptor binding (Kihigh = 0.95 nM). Mitogenesis experiments indicated partial agonist properties (42%). EPC syntheses of the target compounds of type 4 were performed starting from α-amino acids.
- Einsiedel, Juergen,Huebner, Harald,Gmeiner, Peter
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p. 2533 - 2536
(2007/10/03)
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- Synthesis of functionalized oxazolines and oxazoles with DAST and Deoxo-Fluor.
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[formula: see text] A mild and highly efficient cyclization of beta-hydroxy amides to oxazolines is described using DAST and Deoxo-Fluor reagents. A one-pot protocol for the synthesis of oxazoles from beta-hydroxy amides is also presented.
- Phillips,Uto,Wipf,Reno,Williams
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p. 1165 - 1168
(2007/10/03)
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- Electrophilic ring opening of oxazolines derived from serine and threonine: A practical entry to N(N)-protected β-halogeno α-aminoesters
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Treatment of oxazolines 4a-c derived from serine or threonine with chloroformates, leads to the oxazoline ring opening and to the formation of N,N-protected β-chloro-α-aminoesters la-e in 30-88% isolated yields. In the presence of NaI (0.9 equiv), oxazolines 4a,b,d react with ethyl chloroformate to afford the N,N-protected β-iodo α-amino esters 1f-h (67-89% yields), whereas the reaction of 4a,b with trimethylsilyl halide gives the analogous N-benzoyl β-halogeno derivatives 1i,k with 30-86% yields.
- Laaziri, Abdelhamid,Uziel, Jacques,Juge, Sylvain
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p. 437 - 447
(2007/10/03)
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- The efficient, enantioselective synthesis of aza sugars from amino acids. 1. The polyhydroxylated pyrrolidines
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Beginning with (+)-serine or (-)-serine, as appropriate, convenient, high-yield, enantioselective synthesis of all eight stereoisomeric 2-hydroxymethyl-3,4-dihydroxypyrrolidines (the enantiomeric pairs of iminoribitol, -arabinitol, -xylitol, and -lyxitol) can be effected. The absolute configuration of the starting amino acid defines the set of azasugars produced.
- Huang, Yifang,Dalton, David R.,Carroll, Patrick J.
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p. 372 - 376
(2007/10/03)
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- Oxidation of oxazolines and thiazolines to oxazoles and thiazoles. Application of the Kharasch-Sosnovsky reaction
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Using a modification of the Kharasch-Sosnovsky reaction, the oxidation of oxazolines and thiazolines bearing a variety of 2-alkyl substituents (chiral and achiral) were smoothly oxidized to their corresponding oxazoles and thiazoles, respectively. The key feature involved in the successful implementation of this important oxidation was the use of a mixture of Cu(I) and Cu(II) salts to enhance the oxidation of the intermediate captodative radical, 24. The main limitation of this method was shown when the oxidation failed with oxazolines/thiazolines lacking the carboalkoxy group at C-4.
- Meyers,Tavares, Francis X.
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p. 8207 - 8215
(2007/10/03)
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- Stereoselective Cycloaddition of Nitrile Oxides to 4-Vinyl-Oxazolines and -Oxazolidines
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Cycloaddition of nitrile oxides to 4-vinyl-2-oxazoline 1 and to 4-vinyloxazolidine 2 afford diastereomeric mixtures of 2-isoxazolines in which the erythro product predominates (32-64percent d.e.).In contrast, the corresponding reactions with acyclic analogue 3 favoured the threo-adducts and were less selective (8-20percent d.e.).Key Words: 1,3-dipolar cycloaddition; nitrile oxides; isoxazolines
- Boyd, Ewan C.,Paton, R. Michael
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p. 3169 - 3172
(2007/10/02)
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- Asymmetric addition to chiral aromatic and unsaturated oxazolines using a novel chiral auxillary
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By utilizing S-serine, both enantiomers of the reduced methoxyamino alcohol (12) were efficiently prepared. The corresponding oxazolines, prepared from these auxiliaries, showed favorable properties toward additions to naphthalenes 22 and cyclohexene, 27.
- Meyers,Schmidt,McKennon
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p. 250 - 262
(2007/10/02)
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- Synthesis and Biological Activity of the Isomers and Analogs of (4E,8E,2S,3R,2'R)-N-2'-Hydroxyhexadecanoyl-9-methyl-4,8-sphingadienine, the Ceramide Portion of the Fruiting-inducing Cerebroside in a Basidiomycete Schizophyllum commune
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The title compounds were synthesized by employing 2-aminohexadecanoic acid and serine as the chiral sources, and served for an assay of fruiting-inducing activity on Schizophyllum commune.The structure-bioactivity relationship among closely related synthetic ceramides is discussed.
- Funaki, Yuji,Kawai, Genshiro,Mori, Kenji
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p. 615 - 624
(2007/10/02)
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- A MILD PROCEDURE FOR THE PREPARATION OF 2-OXAZOLINES
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A general procedure using triphenylphosphine and diethylazodicarboxylate to prepare 2-oxazolines is described.
- Roush, David M.,Patel, Manorama M.
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p. 675 - 680
(2007/10/02)
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- Von der basenkatalysierten Ringoeffnung von 2H-Azirinen zu einer α-Alkylierungsmethode von primaeren Aminen
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It is shown than fluorene-9'-spiro-2-(3-phenyl-2H-azirine) (1) on treatment with various alcohols in the presence of the corresponding alkoxide ions yields N-(9'-fluorenyl)benzimidates 2a-d (Scheme 1). 2,2,3-Triphenyl-2H-aziridine (3) reacts with methanol in a similar manner (Scheme 2).Benzimidates 2a (Scheme 3), 8 (Scheme 4) and 10 (Scheme 5) can easily be deprotonated by butyllithium (BuLi) or lithium diisopropylamide (LDA) in tetrahydrofuran (THF) to 1-methoxy-2-aza-allylanions, that can be alkylated, at C(3), exclusively, by various electrophiles (e.g.R-X (X = I, Br), RCHO or methyl acrylate (see also Scheme 6)).As the acidic hydrolyses (1 N HCl) of benzimidates 9 and 11 leads to the corresponding α-alkylated free amines 15 and 18 (Scheme 7 and 8), benzoyl derivatives 16 and 19 are obtained from the hydrolysis under basic conditions.On the other hand it is observed that a catalyzed Chapman rearrangement of 9 and 11 results in the formation of N-benzoyl-N-methyl derivatives 17 and 20 (Scheme 7 and 8).The described reactions offer a simple method for the α-alkylation of actived primary amines.
- Schulthess, Adrian Heinz,Hansen, Hans-Juergen
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p. 1322 - 1336
(2007/10/02)
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