81477-91-0

Usage

Uses

Used in Pharmaceutical Industry:
N-(Diphenylmethylene)glycine, phenylmethyl ester is used as a reagent for the synthesis of (-)-Lepadiformine, a marine cytotoxic alkaloid that exhibits activity towards lung carcinoma cell lines. This makes it a valuable compound in the development of anticancer drugs.
Used in Pharmaceutical Industry:
N-(Diphenylmethylene)glycine, phenylmethyl ester is also used as a reagent to prepare (+)-Cylindricine C, another marine alkaloid that shows activity against tumor cell lines. This further highlights its potential in contributing to the discovery and development of novel anticancer agents.

InChI:InChI=1/C22H19NO2/c24-21(25-17-18-10-4-1-5-11-18)16-23-22(19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-15H,16-17H2

Upstream product

• 1013-88-3 Benzophenone imine 
• 63366-76-7 (toluene-4-sulfonylamino)acetic acid benzyl ester 
• 81167-39-7 methyl N-(diphenylmethylene)glycinate 
• 100-39-0 benzyl bromide 
• 1738-76-7 glycine benzyl ester p-toluenesulfonic acid salt 
• 2462-31-9 benzyl 2-aminoacetate hydrochloride 

Downstream Products

• 130712-41-3 2-(Benzhydrylidene-amino)-5-benzyloxycarbonylamino-3-hydroxy-pentanoic acid benzyl ester 
• 98379-08-9 2-(Benzhydrylidene-amino)-3-fluoro-3-phenyl-propionic acid benzyl ester 
• 98379-08-9 2-(Benzhydrylidene-amino)-3-fluoro-3-phenyl-propionic acid benzyl ester 
• 127153-49-5 (+/-)-4-<(1,1-dimethylethoxy)carbonyl>-α-<(diphenylmethylene)amino>benzenepropanoic acid phenylmethyl ester 
• 127152-70-9 (+/-)-4-<(1,1-dimethylethoxy)-2-oxoethyl>-α-<(diphenylmethylene)amino>benzenepropanoic acid phenylmethyl ester 
• 127152-71-0 (+/-)-4-<2-(1,1-dimethylethyl)-2H-tetrazol-5-yl>-α-<(diphenylmethylene)amino>benzenepropanoic acid phenylmethyl ester 
• 127152-72-1 (+/-)-4-<<2-(1,1-dimethylethyl)-2H-tetrazol-5-yl>methyl>-α-<(diphenylmethylene)amino>benzenepropanoic acid phenylmethyl ester 
• 127152-73-2 4-<1,1-difluoro-2-(1,1-dimethylethoxy)-2-oxoethyl>-α-<(diphenylmethylene)amino>benzenepropanoic acid phenylmethyl ester 
• 207803-72-3 2-(Benzhydrylidene-amino)-3-[4-(tert-butoxycarbonyl-difluoro-methoxy)-phenyl]-propionic acid benzyl ester 
• 500695-43-2 3',5'-di-tert-butyltyrosine benzyl ester 
• 138892-10-1 (S)-2-(Benzhydrylidene-amino)-3-phenyl-propionic acid benzyl ester 
• 827628-66-0 [(diphenylmethylene)amino]cyclopropyl benzyl ester 

Relevant academic research and scientific papers

Synthesis of Chiral Spin-Labeled Amino Acids

Spin-labeled amino acids (SLAAs) are often used to determine intermolecular distances and conformations in proteins via double electron-electron resonance. Currently available SLAAs can be difficult to incorporate selectively and have little resemblance to natural side chains in proteins. Enantioselective synthesis of three spin-labeled l-amino acids is described, starting from readily available 2,2,6,6-tetramethyl-4-piperidinone. These SLAAs better replicate canonical residues in proteins and aim for biological incorporation via genetic incorporation or solid-phase peptide synthesis.

Discovery of novel hepatoselective HMG-CoA reductase inhibitors for treating hypercholesterolemia: A bench-to-bedside case study on tissue selective drug distribution

The design of drugs with selective tissue distribution can be an effective strategy for enhancing efficacy and safety, but understanding the translation of preclinical tissue distribution data to the clinic remains an important challenge. As part of a discovery program to identify next generation liver selective HMG-CoA reductase inhibitors we report the identification of (3R,5R)-7-(4-((3-fluorobenzyl)carbamoyl)-5-cyclopropyl-2-(4-fluorophenyl) -1H-imidazol-1-yl)-3,5-dihydroxyheptanoic acid (26) as a candidate for treating hypercholesterlemia. Clinical evaluation of 26 (PF-03491165), as well as the previously reported 2 (PF-03052334), provided an opportunity for a case study comparison of the preclinical and clinical pharmacokinetics as well as pharmacodynamics of tissue targeted HMG-CoA reductase inhibitors.

Solution versus fluorous versus solid-phase synthesis of 2,5-disubstituted 1,3-azoles. Preliminary antibacterial activity studies

(Chemical Equation Presented) A small library of compounds with an oxa(thia)zole scaffold and structural diversity in both positions 2 and 5 has been synthesized. Double acylation of a protected glycine affords intermediate α-amido-β-ketoesters, which in turn can be dehydrated to afford 1,3-oxazoles or reacted with Lawesson's reagent to furnish 1,3-thiazoles. This procedure was designed with its adaptation to fluorous techniques in mind. Thus, when a protected glycine with a fluorous tag in the ester moiety is used as a starting material, the synthesis can be easily completed without column chromatography purification of intermediate compounds with good to excellent yields, thus affording a suitable entry to the preparation of small libraries of these bioactive compounds. The prepared oxa(thia)zoles were assayed for their antibacterial activity, and several of them were active against Staphylococcus aureus.

Oxazole cyclopeptides for chirality transfer in C3-symmetric octahedral metal complexes

A straightforward synthesis of C3-symmetric oxazole-containing macrocyclic peptide scaffolds is presented. This type of macrocycles bears three functional groups on the oxazole rings, which allows fixing of various receptor arms on them in an easy manner. The chiral backbone of the macrocycle proved to be a powerful tool for chirality induction, thus predetermining the configuration of helically coordinated metal centres. The diastereoselective formation of CoII, NiII, CuII and Zn II complexes with tripodal bipyridyl ligand 4 was proved by UV- and CD-absorption spectrophotometric titration experiments. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Antiinfective Lipopeptides

The present invention relates to novel depsipeptide compounds. The invention also relates to pharmaceutical compositions of these compounds and methods of using these compounds as antibacterial compounds. The invention also relates to methods of producing these novel depsipeptide compounds and intermediates used in producing these compounds.

Preparation of a HMG-CoA reductase inhibitor via an optimized imidazole-forming condensation reaction

Development work toward an enabling synthesis of preparative scale batches of an imidazole-based HMG-CoA reductase inhibitor is described. The desired target was synthesized in 16% yield over 7 steps, highlighted by an imidazole-forming condensation reaction in which the yield was improved from 20% to >70% via modification of the solvent, acid, and amine equivalents. The step 2 acylation was improved, and a problematic benzyl ester in step 4 was converted into the corresponding benzyl amide to decrease trans-amidation during the step 5 imidazole formation. A highly effective salt formation and crystallization protocol was also developed.

Configurationally stable propeller-like triarylphosphine and triarylphosphine oxide

Configurationally stable, propeller-like triarylphosphine and triarylphosphine oxide can be synthesized; a chiral scaffold based on Lissoclinum-cyclopeptides linked via three peptide bonds with a triphenylphosphine and triphenylphosphine oxide moiety, respectively, prevents effectively epimerization at the chiral phosphorus atom. The Royal Society of Chemistry.

CRYSTAL FORM OF SODIUM; (3R,5R)-7-[4-BENZYLCARBAMOYL-2-(4-FLUOROPHENYL)-5-ISOPROPYL-IMIDAZOL-1-YL]-3,5-DIHYDROXY-HEPTANOATE

A crystal form A of sodium; (3R, 5R)-7-[4-benzylcarbamoyl-2-(4-fluoropheynl)-5-isopropyl- imidazol-1-yl]-3,5-dihydroxy-heptanoate is provided.

Novel imidazoles

Novel imidazoles are provided. The compounds are useful as HMGCo-A Reductase Inhibitor. Also provided are pharmaceutical compositions of the compounds. Methods of making and methods of using the compounds are also provided.

Convenient synthesis and isolation of 1-aminocyclopropane-1-carboxylic acid (ACC) and N-protected ACC derivatives

A convenient route to 1-aminocyclopropane-1-carboxylic acid (1, ACC) and N-protected derivatives was developed. This route utilizes a bisalkylation of an O-benzyl glycine derived imine followed by global deprotection via hydrogenation. Direct isolation of ACC from a non-aqueous stream or efficient conversion to N-protected derivatives in a single flask is described.