63353-51-5

Upstream product

• 79-08-3 bromoacetic acid 
• 105-13-5 4-Methoxybenzyl alcohol 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 536726-20-2 thiocyanato-acetic acid 4-methoxy-benzyl ester 

Relevant academic research and scientific papers

Synthesis, antiinflammatory activity, and molecular docking studies of bisphosphonic esters as potential MMP-8 and MMP-9 inhibitors

Bisphosphonic acids (or bisphosphonates) have been successfully used in the clinic treatment of bone diseases for over decades. Additionally, the antiinflammatory activity of these compounds has been gaining attention. In our previous work, we synthesized and in vivo evaluated the bisphosphonic esters 1 and 2, finding a moderate edema inhibition upon oral and topical administration on BALB/c mice. Thus, in this work, the bioisosteric replacement of an amide functional group for an ester afforded the new bisphosphonates 3–6, which had a moderate oral edema inhibition (25 mg/kg dose) and a significant topical antiinflammatory activity (2 mg/ear) on BALB/c mice, with 6 being the most active hit (55.9% edema inhibition), comparable to the positive control (55.5% edema inhibition) on a TPA topical model. Next, to assess the acute toxicity of the synthesized derivatives, test animals were administered with 50–100 mg/kg of 3–6, respectively, by an oral route, and after 14 days, neither lethality nor a significative weight loss were observed. Finally, a structure–activity relationship (SAR) and a molecular docking analysis of 3–6 helped us to explain the trend observed in biological tests. Considering all these aspects, we propose the inhibition of MMP-8 and MMP-9 as a possible action mechanism of the synthesized derivatives.

A General Catalytic Route to Enantioenriched Isoindolinones and Phthalides: Application in the Synthesis of (S)-PD 172938

Chiral Br?nsted acid catalyzed enantioselective syntheses of isoindolinones and phthalides have been accomplished via tandem Mannich-lactamization and aldol-lactonization reactions, respectively. A variety of enantioenriched isoindolinones (up to 99% ee) and phthalides (up to 85% ee) containing α-diazoesters were afforded in excellent yields. Furthermore, a concise synthesis of (S)-PD 172938 has been demonstrated by using this protocol.

A General Catalytic Route to Enantioenriched Isoindolinones and Phthalides: Application in the Synthesis of (S)-PD 172938

Chiral Br?nsted acid catalyzed enantioselective syntheses of isoindolinones and phthalides have been accomplished via tandem Mannich-lactamization and aldol-lactonization reactions, respectively. A variety of enantioenriched isoindolinones (up to 99% ee) and phthalides (up to 85% ee) containing α-diazoesters were afforded in excellent yields. Furthermore, a concise synthesis of (S)-PD 172938 has been demonstrated by using this protocol.

Sulfinate-Engaged Nucleophilic Addition Induced Allylic Alkylation of Allenoates

A strategically novel Pd-catalyzed nucleophilic addition induced allylic alkylation reaction (NAAA) of allenoates has been successfully accomplished. By judiciously integrating ZnCl2-promoted Michael addition with Pd-catalyzed allylic alkylation, allenoates readily undergo allyl-sunfonylation at the internal double bond, thus providing a straightforward avenue for the rapid assembly of a host of structurally diversified α-allyl-β-sufonylbut-3-enoate derivatives. The success of this transformation profits from a delicate control of the reaction kinetic of each elementary step, thanks to the synergistic interaction of Pd/Zn bimetallic system, thus suppressing either direct allylic sulfonylation or premature quenching of therein in situ generated ester enolate intermediate. Furthermore, by expanding the scope of workable Michael acceptor beyond those previously required doubly activated ones, such as methylenemalononitrile, the present work substantially enriches the repertoire of NAAA reactions.

Organo-Cation Catalyzed Asymmetric Homo/Heterodialkylation of Bisoxindoles: Construction of Vicinal All-Carbon Quaternary Stereocenters and Total Synthesis of (-)-Chimonanthidine

A novel chiral spirocyclic amide (SPA)-derived triazolium organocatalyst has been designed and demonstrated to effect asymmetric homo- and heterodialkylations of various bisoxindoles, enabling enantioselective construction of vicinal all-carbon quaternary stereocenters. These reactions feature excellent enantio- and diastereoselectivities (up to 99% ee and >20:1 dr) as well as good to high yields (up to 89% over two steps). As an application of this methodology, the first asymmetric total synthesis of (-)-chimonanthidine has been achieved.

Convenient synthesis, antimalarial and antimicrobial potential of thioethereal 1,4-disubstituted 1,2,3-triazoles with ester functionality

This paper elicits the synthesis of twenty five 1,4-disubstituted 1,2,3-triazole analogs (5a–5y) comprising thioether and ester linkages from aryl(prop-2-yn-1-yl)sulfanes and benzyl 2-azidoacetates employing Cu(I) catalyzed Huisgen 1,3-dipolar cycloaddition. Structures of synthesized compounds were elucidated by spectroscopic techniques like FTIR, 1H NMR, 13C NMR, and HRMS. Newly synthesized compounds were screened for in vitro antimalarial evaluation against P. falciparum strain and microbicidal potential against B. subtilis, S. epidermidis, E. coli, P. aeruginosa, C. albicans, and A. niger. Some of synthesized triazoles displayed moderate antimalarial activity against tested strain, while, the compounds 5i and 5n were found to exhibit significant inhibitory activity against most of the tested microbial strains.

A chiral Br?nsted acid-catalyzed highly enantioselective Mannich-type reaction of α-diazo esters with in situ generated N -acyl ketimines

A chiral phosphoric acid-catalyzed asymmetric Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines, derived from 3-hydroxyisoindolinones has been demonstrated in this communication. A variety of isoindolinone-based α-amino diazo esters bearing a quaternary stereogenic center were afforded in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). Furthermore, the synthetic utility of the products has been depicted by the hydrogenation of the diazo moiety of adducts.

Synthesis and Antimicrobial Evaluation of (1-(2-(Benzyloxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl Benzoate Analogues

A convenient one pot synthesis of 20 (1-(2-(benzyloxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl benzoate analogues (5a–5t) with ester functionality was carried out via Cu(I) catalyzed click reaction between prop-2-yn-1-yl benzoates and benzyl 2-azidoacetates. The structure of synthesized triazoles were explicated by various spectral techniques like FT-IR, 1H NMR, 13C NMR, and high-resolution mass spectrometry and evaluated for in vitro antimicrobial potential against Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Enterobacter aerogenes, Candida albicans, and Aspergillus niger. Most of synthesized triazole derivatives exhibited average to excellent activity against tested microbial strains.

Photoinduced Intermolecular [4+2] Cycloaddition Reaction for Construction of Benzobicyclo[2.2.2]octane Skeletons

A novel and efficient method for the synthesis of highly substituted benzobicyclo[2.2.2]octane skeletons has been explored. Under UV-light irradiation, o-divinylbenzenes underwent a pericyclic reaction to form the cyclic o-quinodimethane intermediates which were subsequently reacted with olefins through [4+2] addition to construct the benzobicyclo[2.2.2]octane skeletons in mild conditions. Gram scale reactions demonstrated the synthetic potential application of this protocol.

Click synthesis of some mono/bis 1,2,3-triazoles with ester linkage and their microbicidal activity

Synthesis of some new 1,4-disubstituted 1,2,3-triazoles with ester functionality is reported employing Cu(I) catalyzed Huisgen [3+2] cycloaddition reaction of prop-2-yn-1-yl benzoates with 1,4-phenylenebis(methylene) bis(2-azidoacetate) and benzyl 2-azidoacetates. The synthesized compounds were well characterized through FTIR, 1H NMR, 13C NMR and HRMS. Further, the synthesized triazole derivatives were accessed for in vitro antimicrobial activity against one Gram-positive bacterial strain Staphylococcus aureus, three Gram-negative bacterial strains Escherichia coli, Klebsiella pneumoniae, Enterobacter aerogenes and two fungi Candida albicans and Aspergillus niger. Few of the synthesized disubstituted 1,2,3-triazoles displayed moderate to good inhibitory activity against tested microbial strains.