220510-58-7

Upstream product

• 141874-26-2 N-Boc-(S)-proline chloride 
• 62-53-3 aniline 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 1294505-65-9 (S)-1-tert-butyl 2-((R)-1-(2-methoxyphenyl)prop-2-yn-1-yl)pyrrolidine-1,2-dicarboxylate 
• 1294505-63-7 (S)-1-tert-butyl 2-((R)-1-phenylprop-2-yn-1-yl)-pyrrolidine-1,2-dicarboxylate 
• 15761-39-4 N-tert-butoxycarbonyl-proline 
• 37784-17-1 N-(tert-butoxycarbonyl)-D-proline 
• 64411-39-8 1-tert-butyl 2-phenyl pyrrolidine-1,2-dicarboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 103-71-9 phenyl isocyanate 
• 147-85-3 L-proline 

Downstream Products

• 1078162-90-9 (S)-N-phenylpyrrolidine-2-carboxamide hydrochloride 
• 132139-15-2 (S)-N,N-diphenyl-2-pyrrolidinecarboxamide 

Relevant academic research and scientific papers

Balancing interactions in proline-based receptors for chiral recognition of l-/d-DOPA

Proline based receptors (1-14) attached with phenylboronic acid and benzaldehyde binding groups at the N-/C-or C-/N-termini of the proline residue were created for chiral recognition of l-/d-DOPA, in an attempt to examine if balancing the two binding even

CAL-B-mediated efficient synthesis of a set of valuable amides by direct amidation of phenoxy- and aryl-propionic acids

An efficient, easy and sustainable amidation of a set of non-activated carboxylic acids with anilines, assisted by CAL-B, as biodegradable catalyst, is reported. The enzymatic amidation reactions are performed on set of nonsteroidal anti-inflammatory drugs (NSAIDs), phenoxypropionic acid and protected-prolines by direct condensation of one equivalent of carboxylic acids and two equivalents of anilines derivatives in heptane after 72?h of reaction at 80?°C. The obtained carboxylic amides are recovered with isolated chemical yields varied between moderate and excellent. Fourteen from them are reported for the first time, and an X-ray crystal is obtained for: N-(4-iodophenyl)-2-(4-isobutylphenyl)propanamide 1d.

SAR of novel benzothiazoles targeting an allosteric pocket of DENV and ZIKV NS2B/NS3 proteases

In recent years, dengue virus (DENV) and Zika virus (ZIKV), both mosquito-borne members of the Flaviviridae family, have emerged as intercontinental health issues since their vectors have spread from their tropical origins to temperate climate zones due to climate change and increasing globalization. DENV and ZIKV are positive-sense, single-stranded RNA viruses, whose genomes consist of three structural (capsid, membrane precursor, envelope) and seven non-structural (NS) proteins, all of which are initially expressed as a single precursor polyprotein. For virus maturation, the polyprotein processing is accomplished by host proteases and the viral NS2B/NS3 protease complex, whose inhibitors have been shown to be effective antiviral agents with loss of viral pathogenicity. In this work, we elucidate new structure–activity relationships of benzo[d]thiazole-based allosteric NS2B/NS3 inhibitors. We developed a new series of Y–shaped inhibitors, which, with its larger hydrophobic contact surface, should bind to previously unaddressed regions of the allosteric NS2B/NS3 binding pocket. By scaffold-hopping, we varied the benzo[d]thiazole core and identified benzofuran as a new lead scaffold shifting the selectivity of initially ZIKV-targeting inhibitors to higher activities towards the DENV protease. In addition, we were able to increase the ligand efficiency from 0.27 to 0.41 by subsequent inhibitor truncation and identified N-(5,6-dihydroxybenzo[d]thiazol-2-yl)-4-iodobenzamide as a novel sub-micromolar NS2B/NS3 inhibitor. Utilizing cell-based assays, we could prove the antiviral activity in cellulo. Overall, we report new series of sub-micromolar allosteric DENV and ZIKV inhibitors with good efficacy profile in terms of cytotoxicity and protease inhibition selectivity.

Design, synthesis, and insecticidal activities of novel diamide derivatives with alpha-amino acid subunits

A series of diamide derivatives containing α-amino acids were designed and synthesized. These compounds were evaluated for their insecticidal activities against Plutella xylostella, Mythimna separate, Myzus persicae, and Tetranychus cinnabarinus. Most of the title compounds containing an l-phenylglycine skeleton were endowed with good activities at the concentration of 500 mg·L?1. Compounds (R)-A6 showed a potential value for further optimization as an insecticidal lead with the LC50 value of 86.8 mg·L?1.

New small γ-turn type: N -primary amino terminal tripeptide organocatalyst for solvent-free asymmetric aldol reaction of various ketones with aldehydes

New small γ-turn type N-primary amino terminal tripeptides were synthesized and their functionality as an organocatalyst was examined in the asymmetric aldol reaction of various ketones with different aromatic aldehydes under solvent-free neat conditions to afford the desired chiral anti-aldol products in good to excellent chemical yields, diastereoselectivities and enantioselectivities (up to 99%, up to syn?:?anti/13?:?87 dr, up to 99% ee). This journal is

Double-chiral binaphthalene O-N-N tridentate ligand and preparation method thereof

The invention discloses a bis-chiral binaphthalene O-N-N tridentate ligand and a preparation method thereof. The ligand has the structural formula shown in formula (L). The preparation method comprises the following steps: (1) taking chiral 2 - methyl -2 - methoxy -binaphthalene as a raw material and replacing the reaction with an aromatic ring. As an alternative to the hydroxy protecting group, a brominated derivative (compound IV) is obtained by bromination. (2) Starting from protected chiral proline, a variety of diamine structures are obtained by conversion (Compound B). (3) Compound IV and Compound B are coupled in the presence of a catalyst in the presence of a catalyst to obtain a binaphthalene O-N-N tridentate ligand with bichirality. The ligand preparation method is simple in raw material, and has important significance for asymmetric organic synthesis.

Modular synthesis of new bicyclic carbene precursors

A series of new N-heterocyclic carbene (NHC) precursors, containing bicyclic pyrrolo[1,2-c]imidazole framework, were prepared from N-(tert-butoxycarbonyl)-L-proline (1-Boc-L-proline). The sequential attachment of nitrogen nucleophiles and subsequent ring

Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages

The construction of amide bonds and peptide linkages is one of the most fundamental transformations in all life processes and organic synthesis. The synthesis of structurally ubiquitous amide motifs is essential in the assembly of numerous important molecules such as peptides, proteins, alkaloids, pharmaceutical agents, polymers, ligands and agrochemicals. A method of SO2F2-mediated direct clickable coupling of carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in greater than 99% purity and excellent yields.

Chiral azo-heterocyclic carbene precursor compound with bicyclic framework and preparation method thereof

The invention discloses a chiral azo-heterocyclic carbene precursor compound with a bicyclic framework and a preparation method thereof. A series of the chiral azo-heterocyclic carbene precursor compound with the bicyclic framework is obtained by taking c

Synthesis and anticancer activity of conformationally constrained Smac mimetics containing pseudo β turns

Herein, we report synthesis and in vitro anticancer activity of conformationally constrained Smac mimetics containing reverse turn inducing motifs “Ant-Pro” and “sAnt-Pro”. The synthesis of Smac analogs with diverse hydrophobic groups at the C-