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Synthesis and stereoselective C-C bond-forming reactions of peptide aldehydes

The reaction of the activated form of N-protected amino acids 6 and 10 or peptides 14 and 18 with chiral amino alcohols derived from the corresponding alpha-amino acids affords peptide alcohols which can be oxidized under Swern conditions to produce the corresponding peptide aldehydes 9, 12, 16 and 20. The rational synthesis of diastereomeric di- and tripeptide aldehydes, e.g., (S,S)- or (R,S)-dipeptides as well as (S,S,S)- or (R,S,S)-tripeptides is possible by proper choice of the respective building blocks [(S)- versus (R)-amino acids]. The compounds can be prepared without any undesired alpha-epimerization. However, the long-term configurational stability depends upon the configuration at the remote stereogenic center, e.g., (R,S)-dipeptide aldehydes epimerize faster than the (S,S) diastereomers. Di- and tripeptide aldehydes 9, 12, 16 and 20 undergo chelation-controlled Grignardtype additions with Me2CuLi that involve little or no undesired alpha-epimerization. The (S,S)- and (R,S)-dipeptide aldehydes 9 and 12 undergo chelation-controlled pinacol reactions induced by the low-valent vanadium reagent [V2Cl3(THF)6]2[Zn2Cl 6]. The major products in both cases are the corresponding C2-symmetric diols 33 and 36, respectively, which are of interest as potential HIV-protease inhibitors. The degree of stereoselectivity is significantly higher in the case of the (S,S)-dipeptide aldehydes relative to the (R,S) analogs, an observation which can be explained on the basis of three-point binding of the peptides to vanadium. VCH Verlagsgesellschaft mbH, 1996.

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Reference：
Pyridazine – Wikipedia,
Pyridazine | C4H4N2725 – PubChem

 

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INHIBITORS OF NAAA AND METHODS THEREOF

Compounds and pharmaceutical compositions are contemplated that inhibit N-acyl-ethanolamine-hydrolyzing acidamidase (NAAA) to so increase the concentration of the substrate of NAAA, palmitoylethanolamide (PEA). NAAA inhibition is contemplated to be effective to alleviate conditions associated with a reduced concentration of PEA. Among other uses, various NAAA inhibitors are especially contemplated as therapeutic agents in the treatment of inflammatory diseases.

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Reference：
Pyridazine – Wikipedia,
Pyridazine | C4H4N2561 – PubChem

 

20375-65-9, Name is 3-Phenyl-6-chloropyridazine, belongs to pyridazine compound, is a common compound. Formula: C10H7ClN2In an article, once mentioned the new application about 20375-65-9.

Dipeptides with 3-(trimethylstannyl)alanine building blocks: Synthesis, characterization, and reactivity

3-(Trimethylstannyl)alanine esters containing a free amino group react with different N-benzoyloxycarbonyl amino acids in the presence of N,N?-dicyclohexylcarbodiimide to yield new dipeptides with beta-(trimethylstannyl)alanine building blocks. Reactions at the stannyl group were studied in more detail in two glycyl alaninates. Their reaction with Me3SnCl without solvent yields the chlorostannyl-substituted compounds. The glycyl alaninates react with two equivalents of bromine to give the dibromostannylated compounds.

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Reference：
Pyridazine – Wikipedia,
Pyridazine | C4H4N2615 – PubChem

 

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Synthesis of phenyl substituted valinomycins

The synthesis is described of a modified valinomycin, which incorporates phenyl groups located around the exterior belt. The synthesis is accomplished by a build up of linear fragments using both dicyclohexylcarbodiimide- and pentafluoroester- methods of coupling. The final cyclisation is accomplished using the pentafluoroester protocol. The modified valinomycin is shown to be an effective ligand for complexation with potassium ion. Both nmr and electrochemical studies show that the modified valinomycin has similar properties to the parent valinomycin, and hence phenyl substitution around the periphery does not disrupt the network of hydrogen bonds which influence the conformation of valinomycins.

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Pyridazine – Wikipedia,
Pyridazine | C4H4N2616 – PubChem

 

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PAPAIN-ASSISTED RESOLUTION OF NATURAL AND XENOBIOTIC alpha-AMINO ACIDS

A new and convenient method for the preparation of pure enantiomers of alpha-amino acids is described.Industrial papain, catalyzes the synthesis of L-Z-amino acid ethyl esters in ethanolic medium, with good yields.These esters are obtained from DL-Z-amino acids with 100percent optical purity.Unreactive D-Z-amino acids are readily isolated from reaction medium.Physical constants of natural and xenobiotic L-Z-amino acid esters and D-Z-amino acids are described.

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Pyridazine – Wikipedia,
Pyridazine | C4H4N2707 – PubChem

 

Chemistry is traditionally divided into organic and inorganic chemistry. Product Details of 20375-65-9, The former is the study of compounds containing at least one carbon-hydrogen bonds.In a patent，Which mentioned a new discovery about 20375-65-9

A 2,3-butanedione protected chiral glycine equivalent–a new building block for the stereoselective synthesis of enantiopure N-protected alpha-amino acids.

A new chiral glycine equivalent 7 has been synthesised from glycidol using a chiral memory protocol, and its use in the synthesis of N-Z protected alpha-amino acids was demonstrated in a series of diasteroselective lithium enolate alkylation reactions and subsequent acid hydrolyses.

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Reference：
Pyridazine – Wikipedia,
Pyridazine | C4H4N2614 – PubChem

 

Chemistry is an experimental science, and the best way to enjoy it and learn about it is performing experiments. Quality Control of 3-Phenyl-6-chloropyridazine. Introducing a new discovery about 20375-65-9, Name is 3-Phenyl-6-chloropyridazine

Analgesic and/or opiate antagonist tripeptide amides and processes for preparation and compositions thereof

A genus of tripeptide amides and fifteen species thereof of Examples 4-18, which are useful as analgesics and/or opiate antagonists, three processes for preparation thereof, pharmaceutical compositions thereof, and the three tripeptide amide species of Examples 1-3, which are not within the genus and are useful as analgesics and/or opiate antagonists, are disclosed.

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Pyridazine – Wikipedia,
Pyridazine | C4H4N2574 – PubChem

 

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Small multivalent architectures mimicking homotrimers of the TNF superfamily member CD40L: Delineating the relationship between structure and effector function

Synthetic multivalent ligands, owing to the presence of multiple copies of a recognition motif attached to a central scaffold, can mediate clustering of cell surface receptors and thereby function as effector molecules. This paper dissects the relationship between structure and effector function of synthetic multivalent ligands targeting CD40, a cell surface receptor of the tumor necrosis factor receptor (TNF-R) superfamily. Triggering CD40 signaling in vivo can be used to enhance immunity against intracellular pathogens or tumors. A series of multimeric molecules has been prepared by systematically varying the shape and the valency of the central scaffold, the nature and the length of the linker as well as the sequence of the receptor binding motif. The data reported here (i) suggest that radial distribution of CD40-binding units and C 3-symmetry are preferred for optimal binding to CD40 and signaling, (ii) underscore the importance of choosing an appropriate linker to connect the receptor binding motif to the central scaffold, and (iii) show the versatility of planar cyclic alpha- and beta-peptides as templates for the design of CD40L mimetics. In particular, the (Ahx)3-B trimeric scaffold-linker combination equally accommodated binding elements derived from distinct CD40L hot-spot regions including AA? loop and beta-strand E. The use of miniCD40Ls such as those reported here is complementary to other approaches (recombinant ligands, agonistic anti-receptor antibodies) and may find interesting therapeutic applications. Furthermore, the results disclosed in this paper provide the basis for future design of other TNF family member mimetics.

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Reference：
Pyridazine – Wikipedia,
Pyridazine | C4H4N2760 – PubChem

 

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Compounds for enzyme inhibition

One aspect of the invention relates to inhibitors that preferentially inhibit immunoproteasome activity over constitutive proteasome activity. In certain embodiments, the invention relates to the treatment of immune related diseases, comprising administering a compound of the invention. In certain embodiments, the invention relates to the treatment of cancer, comprising administering a compound of the invention.

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Pyridazine – Wikipedia,
Pyridazine | C4H4N2565 – PubChem

 

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Selectivity and Specificity in Substrate Binding to Proteases: Novel Hydrolytic Reactions Catalysed by alpha-Chymotrypsin Suspended in Organic Solvents with Low Water Content and Mediated by Ammonium Hydrogen Carbonate

alpha-Chymotrypsin suspended in organic solvents with low water content catalysed hydrolytic reactions in the presence of ammonium hydrogen carbonate.Molecular modelling studies were carried out and structure-reactivity relationships were established by studying the hydrolysis of amino acid derivatives and analogues.The enzyme was found to be stereoselective with respect to the hydrolysis of L-amino acid derivatives, but no stereoselectivity was observed when alpha-hydroxy esters were used as substrates.A general procedure for the resolution of aromatic amino acid esters is given.The results are interpreted in terms of molecular modelling based on X-ray crystallographic data and literature data.

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Reference：
Pyridazine – Wikipedia,
Pyridazine | C4H4N2728 – PubChem