20839-80-9

Upstream product

• 126079-16-1 N-(4-methoxybenzylidene)glycine methyl ester 
• 123-11-5 4-methoxy-benzaldehyde 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 616-34-2 methoxycarbonylmethylamine 
• 126079-16-1 methyl N-(4-methoxybenzylidene)glycinate 
• 67-56-1 methanol 
• 515158-60-8 N-<4-Methoxy-benzyliden>-glycin 

Downstream Products

• 13155-48-1 {(4-Methoxy-benzyl)-[2-(4-methoxy-benzyloxycarbonylamino)-acetyl]-amino}-acetic acid 
• 161139-28-2 methyl N-(4-methoxybenzyl)-N-diazoacetylglycinate 
• 209627-21-4 N-methoxycarbonylmethyl-N-(4-methoxyphenylmethyl)-3-aminopyrazine-2-carboxamide 
• 344765-15-7 N-(p-methoxybenzyl)-N-chloroacetyl-Gly-OMe 
• 709649-95-6 7-bromo-4-(4-methoxy-benzyl)-1,3,4,5-tetrahydro-pyrido[2,3-e][1,4]diazepin-2-one 
• 709649-96-7 (E)-3-[4-(4-methoxy-benzyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl]acrylic acid tert-butyl ester 
• 709649-93-4 (E)-3-[4-(4-methoxy-benzyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl]acrylic acid hydrochloride 
• 1309208-28-3 (E)-4-(4-methoxybenzyl)-7-(3-oxo-3-(3-(thiophen-2-ylmethoxy)azetidin-1-yl)prop-1-enyl)-4,5-dihydro-1H-pyrido[2,3-e][1,4]diazepin-2(3H)-one 
• 197516-50-0 methyl 2-{N-(methoxycarbonylmethyl)-N-[(4-methoxyphenyl)methyl]aminomethyl}benzoate 
• 217439-29-7 (2S,3R,4S)-2-(2,2-Dimethyl-propionyloxymethyl)-3-hydroxy-4-isopropenyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of 1,4-Oxazepane-2,5-diones via Cyclization of Rotationally Restricted Amino Acid Precursors and Structural Reassignment of Serratin

Several natural products containing a 1,4-oxazepane-2,5-dione-core are known. One example is serratin, isolated from Serratia marcescens. Because of the presence of a carboxylic amide, which has a preference for a trans-conformation, and the presence of a labile lactone in this core, many synthetic methodologies commonly used for the cyclization toward medium-sized heterocycles cannot be applied. As N-acyl amino acids lacking a third substituent at nitrogen failed to undergo ring-closure, several N-protecting groups were evaluated. With the use of the removable PMB-group, an N-unsubstituted 1,4-oxazepane-2,5-dione was synthesized. Via the application of pseudoprolines (i.e. serine-derived oxazolidines as another type of protecting group), a compound with the presumed structure of the natural product serratin was obtained. As a result of the differences in spectral data, the incorrect structural assignment of the natural product serratin was identified. Instead of the predicted seven-membered heterocycle, a symmetrical serratamolide analogue is proposed to be the correct structure of serratin.

A systematic exploration of the effects of flexibility and basicity on sigma (σ) receptor binding in a series of substituted diamines

The sigma-1 receptor (S1R) has attracted a great deal of attention as a prospective drug target due to its involvement in numerous neurological disorders and, more recently, for its therapeutic potential in neuropathic pain. As there was no crystal structure of this membrane-bound protein reported until 2016, ligand generation was driven by pharmacophore refinements to the general model suggested by Glennon and co-workers. The generalised S1R pharmacophore comprises a central region where a basic amino group is preferred, flanked by two hydrophobic groups. Guided by this pharmacophore, S1R ligands containing piperazines, piperazinones, and ethylenediamines have been developed. In the current work, we systematically deconstructed the piperazine core of a prototypic piperazine S1R ligand (vide infra) developed in our laboratories. Although we did not improve the affinity at the S1R compared to the lead, we identified several features important for affinity and selectivity. These included at least one basic nitrogen atom, conformational flexibility and, for S1R, a secondary or tertiary amine group proximal to the anisole. Furthermore, S2R selectivity can be tailored with functional group modifications of the N-atom proximal to the anisole.

Visible light-induced intramolecular dearomative cyclization of α-bromo-N-benzyl-alkylamides: Efficient construction of 2-azaspiro[4.5]decanes

An efficient intramolecular dearomative cyclization via visible light-induced photoredox catalysis allows for a highly regioselective dearomative cyclization of α-bromo-N-benzyl-alkylamides to construct 2-azaspiro[4.5]decanes in the presence of an iridium catalyst.

Mild construction of 3-methyl tetramic acids enabling a formal synthesis of palau'imide

A general method to construct 3-methyl-4-O-methylated tetramic acids displaying a C-5 stereocenter is presented. The synthetic sequence employs a SmI2-mediated cyclization, whereby the chirality of the emerging tetramic acid core is retained from the starting chiral amino acid. Application to palau'imide is discussed.

NOVEL HETEROCYCLIC ACRYLAMIDES AND THEIR USE AS PHARMACEUTICALS

The invention relates to novel heterocyclic acrylamide compounds (I), to the preparation of the compounds and intermediates used therein, to the use of the compounds as antibacterial medicaments and pharmaceutical compositions containing the compounds.

Arylsulfonamido-substituted hydroxamic acid derivatives

α-Amino hydroxamic acid derivative of formula (I), in which R is C2–C7-alkyl, which is mono-, di- or trisubstituted by halogen, nitro, lower acyloxy, trifluoromethoxy, cyano, C3–C5-cycloalkyl or unsubstituted or substituted C3–C4-heteroaryl comprising one or two heteroatoms selected from the group consisting of O, S and N; or C3–C7-alkenyl or C3–C7-alkynyl, which in each case is unsubstituted or mono-, di- or trisubstituted by halogen, nitro, lower acyloxy, trifluoromethoxy, cyano, C3–C5-cycloalkyl or unsubstituted or substituted C3–C6-heteroaryl comprising one or two heteroatoms selected from the group consisting of O, S and N; and the other symbols are as defined in claim 1, are described. These compounds are MMP and in particular MMP2 inhibitors and can be used for treatment of MMP dependent diseases, in particular inflammation conditions, rheumatoid arthritis, osteoarthritis, tumors (tumor growth, metastasis, progression or invasi n) and pulmonary disorders (e.g. emphysema, COPD).

Efficient solid-phase synthesis of highly functionalized 1,4-benzodiazepin-5-one derivatives and related compounds by intramolecular aza-wittig reactions

Due to their widespread biological activities and favorable pharmacokinetic properties, benzodiazepines were among the first classes of small molecules to be synthesized on solid supports. Since then, there have been numerous reports on the synthesis of similar skeletons. We have employed the T1 triazene linker to yield 1,4-benzodiazepin-5-one. Starting from various substituted triazene resins, cleavage in the presence of an azide donor, such as trimethylsilylazide, gave rise to aryl azides. Intramolecular aza-Wittig reactions produced the appropriately functionalized N-heterocycles. By using this route, the natural product deoxyvasicinone and related compounds were prepared.

Synthetic and photochemical studies of N-arenesulfonyl amino acids

Near-UV irradiation of N-arenesulfonyl amino acids in aqueous solution in the presence of a water-soluble 1,5-dialkoxynaphthalene as light absorber and single electron source results in cleavage of the sulfonamide with very sub-stoichiometric release of t