3945-69-5Relevant academic research and scientific papers
4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4-methyl-morpholinium chloride (DMTMM): A valuable alternative to PyBOP for solid phase peptide synthesis
Falchi, Alessandro,Giacomelli, Giampaolo,Porcheddu, Andrea,Taddei, Maurizio
, p. 275 - 277 (2000)
The salt formed from 2-chloro-4,6-dimethoxy[1,3,5]triazine and N- methylmorpholine (DMTMM) is an effective coupling agent for solid phase peptide synthesis that can be used as economical alternative to PyBOP. Several oligopeptides were prepared on a Wang type resin using this reagent and the yields and purity of the products were always comparable with those obtained with PyBOP as the coupling agent.
Synthesis and Properties of Functional Glycomimetics through Click Grafting of Fucose onto Chondroitin Sulfates
Fan, Fei,Zhang, Ping,Wang, Lihao,Sun, Tiantian,Cai, Chao,Yu, Guangli
, (2019)
Fucosylated chondroitin sulfate (fCS), a representative marine polysaccharide isolated from sea cucumber, possesses diverse biological functions especially as a promising anticoagulant. However, its supply suffers from the challenges of high-cost materials, different species, and batch-to-batch variability. In the present study, we designed a concise route for the synthesis of functional glycomimetics by natural fCS as a template. 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride-mediated amidation was applied on chondroitin sulfates for site-selective alkynylation with controllable ratios between 0.15 and 0.78. A small library of 12 fCS glycomimetics with specific sulfation patterns and fucose branches was prepared through copper-catalyzed azide-alkyne cycloaddition, which was fully characterized by nuclear magnetic resonance spectroscopy and size-exclusion chromatography with multiangle light scattering and refractive index. Through screening of their biological activities, CSE-F1 and CSE-SF1 exhibited anticoagulant activities through intrinsic pathway and inhibition of factor Xa by antithrombin III. The concise approach developed herein supplies novel glycopolymers to mimic the distinct functions of natural polysaccharides and promote the development of marine carbohydrate-based drugs.
Kinetically driven intra-and interchain association of hydrophobically and hydrophilically modified poly(acrylic acid) in dilute aqueous solutions
Hao, Jinkun,Li, Zhiyong,Cheng, He,Wu, Chi,Han, Charles C.
, p. 9534 - 9540 (2010)
Effects of pH, dodecyl, and PEO contents as well as the method of preparing the solution on the formation of the unimolecular micelles (unimer micelle) or aggregates made of poly(acrylic acid)-graftpoly( ethylene oxide)-graft-dodecyl (PAA-g-PEO-g-dodecyl) and PAA-g-dodecyl have been studied by a combination of static and dynamic laser light scattering (SLS and DLS). It revealed that: in most cases, these copolymers tend to form interchain associates; while low pH value, proper high dodecyl content and fast switch rate of solvent quality promote intrachain association. These phenomena of the system being trapped in a metastable state can be mainly attributed to its kinetic pathway: the factors mentioned earlier can enhance the initial intrachain contraction, leading to τc (interaction time) e (entanglement time) for the two interaction intrachain globules. So they behave like tiny "elastic balls" and their further merge/fusion become nearly impossible during their interaction time (τc). In this way, the copolymer system is trapped in the metastable, unimer micelle state. The interplay of τc and τe in the formation of metastable unimer micelles or stable aggregates has been discussed in detail.
Bifunctional copper(II) chelators from the coupling of the encapsulating ligand 1-methyl-8-amino-3,13,16-trithia-6,10,19-triazabicyclo[6.6.6]icosane (AMN3S3sar) with carboxylic acids; Applications of the coupling agent DMT-MM
Lee, Hui Hui,Lim, Peiying Alinia,Vu, Hoan,Poulsen, Sally-Ann,Gahan, Lawrence R.
, p. 627 - 634 (2015)
Reaction of 1-methyl-8-amino-3,13,16-trithia-6,10,19-triazabicyclo[6.6.6]icosane (AMN3S3sar) with the amide coupling agent 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) and 4-nitrobenzoic acid, the protected amine 4-(1,3-dioxoisoindolin-2-yl)benzoic acid and the tricarboxylic acid, benzene-1,3,5-tricarboxylic acid (trimesic acid) resulted in the three new ligands N3S3amideSarArNO2, N3S3amideSarAr, and (AMN3S3sar)3TMA. Two of the respective copper(II) complexes have been isolated and characterized.
Synthesis and Antimicrobial Evaluation of Bis-morpholine Triazine Quaternary Ammonium Salts
Morandini, Andrea,Leonetti, Benedetta,Riello, Pietro,Sole, Roberto,Gatto, Vanessa,Caligiuri, Isabella,Rizzolio, Flavio,Beghetto, Valentina
supporting information, p. 3172 - 3176 (2021/08/03)
Efficient, environmentally and economically sustainable, and nontoxic antibacterial products are of global relevance in the fight against microorganism contamination. In this work, an easy and straightforward method for the synthesis of bis-morpholino triazine quaternary ammonium salts (bis-mTQAS) is reported, starting from 2,4,6-trichloro-1,3,5-triazine or 2,4-dichloro-6-methoxy-1,3,5-triazine and various N-alkylmorpholines. Bis-mTQAS were tested as antimicrobials against Gram-negative and Gram-positive bacterial strains. The best-performing bis-mTQAS were found to achieve total disinfection against Staphylococcus aureus ATCC 25923 and Escherichia coli ATCC 25922 at 50 and 400 μg/mL, respectively. Distinctively, bis-mTQAS with the highest antimicrobial efficiency had lowest cytotoxicity.
Phosphorus-Based Organocatalysis for the Dehydrative Cyclization of N-(2-Hydroxyethyl)amides into 2-Oxazolines
Foo, Siong Wan,Mori, Shogo,Ogawa, Saeko,Saito, Susumu,Soleymani Movahed, Farzaneh
, (2021/12/17)
A metal-free, biomimetic catalytic protocol for the cyclization of N-(2-hydroxyethyl)amides to the corresponding 2-oxazolines (4,5-dihydrooxazoles), promoted by the 1,3,5,2,4,6-triazatriphosphorine (TAP)-derived organocatalyst tris(o-phenylenedioxy)cyclotriphosphazene (TAP-1) has been developed. This approach requires less precatalyst compared to the reported relevant systems, with respect to the phosphorus atom (the maximum turnover number (TON) ～30), and exhibits a broader substrate scope and higher functional-group tolerance, providing the functionalized 2-oxazolines with retention of the configuration at the C(4) stereogenic center of the 2-oxazolines. Widely accessible β-amino alcohols can be used in this approach, and the cyclization of N-(2-hydroxyethyl)amides provides the desired 2-oxazolines in up to 99% yield. The mechanism of the reaction was studied by monitoring the reaction using spectral and analytical methods, whereby an 18O-labeling experiment furnished valuable insights. The initial step involves a stoichiometric reaction between the substrate and TAP-1, which leads to the in situ generation of the catalyst, a catechol cyclic phosphate, as well as to a pyrocatechol phosphate and two possible active intermediates. The dehydrative cyclization was also successfully conducted on the gram scale.
Site-Selective Modification of Peptides and Proteins via Interception of Free-Radical-Mediated Dechalcogenation
Griffiths, Rhys C.,Smith, Frances R.,Long, Jed E.,Williams, Huw E. L.,Layfield, Robert,Mitchell, Nicholas J.
supporting information, p. 23659 - 23667 (2020/10/21)
The development of site-selective chemistry targeting the canonical amino acids enables the controlled installation of desired functionalities into native peptides and proteins. Such techniques facilitate the development of polypeptide conjugates to advance therapeutics, diagnostics, and fundamental science. We report a versatile and selective method to functionalize peptides and proteins through free-radical-mediated dechalcogenation. By exploiting phosphine-induced homolysis of the C?Se and C?S bonds of selenocysteine and cysteine, respectively, we demonstrate the site-selective installation of groups appended to a persistent radical trap. The reaction is rapid, operationally simple, and chemoselective. The resulting aminooxy linker is stable under a variety of conditions and selectively cleavable in the presence of a low-oxidation-state transition metal. We have explored the full scope of this reaction using complex peptide systems and a recombinantly expressed protein.
POLYPEPT(O)ID-BASED GRAFT COPOLYMERS FOR IN VIVO IMAGING BY TETRAZINE TRANSCYCLOOCTENE CLICK CHEMISTRY
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Page/Page column 11, (2020/01/24)
There is provided novel polypeptide-based carrier systems, which make it possible to label polymeric nanoparticles in the living organism. This enables new approaches in tumor diagnostics (high signal to background ratio) and radiotherapy (radiotherapy of solid tumors). The polypeptide-based carrier system comprises a polypept(o)idic comb (graft) copolymer, and one or more tetrazine bioorthogonal functional groups each linked to a diagnostic agent.
Heparin alendronate sodium conjugate synthetic method and drugs
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Paragraph 0009; 0030-0032, (2019/10/01)
The invention relates to a heparin alendronate sodium conjugate synthetic method and drugs in the field of medicine. The heparin alendronate sodium conjugate synthetic method comprises the steps: step1, firstly, dissolving 2-chloro-4,6-dimethoxy-1,3,5-triazine in tetrahydrofuran, adding 4-methylmorpholine, stirring for 1-2 h at room temperature, collecting by filtration and washing a precipitatefive times with THF, and thus then obtaining a DMT-MM condensation agent after 48 h of vacuum drying; and step 2, adding heparin and the condensation agent into ultra-pure water, stirring for 1 h, then adding an alendronate sodium solution into the mixed solution of heparin and the condensation agent, carrying out reaction for 24-48 h, pouring the solution into a dialysis bag, dialysing for 48-72h, changing water once every 4 h, finally, freeze-drying the product obtained from dialysis, and thus obtaining the heparin alendronate sodium conjugate drugs. In the method, alendronate sodium is modified by heparin, so the solubility of the drugs is increased, the bioavailability is improved, the cytotoxicity is reduced and the formation of osteoclasts is effectively inhibited.
Indole and quinoline derivatives and its preparation method and application
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Paragraph 0112; 0114, (2017/02/28)
The invention provides an indoloquinoline derivative, a preparation method and application thereof in preparing antitumor drugs and antiviral drugs. The chemical structure of the indoloquinoline derivative is shown as a formula I. Experiments show that a partly-boric-acid-modified indoloquinoline derivative and a non-boric-acid-modified indoloquinoline derivative have strong inhibition effect on various tumor cell strains, thereby being capable of being used for preparation of the antitumor drugs, and have strong antiviral activity, thereby being capable of being used for preparation of the antiviral drugs.
