• Title/Summary/Keyword: Click reaction

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Synthesis of Multi Hydroxyl Chain-End Functionalized Polyolefin Elastomer with Poly(t-butylstyrene) Graft (Poly(t-butylstyrene) 그라프트를 가지는 수산기 말단 관능화 폴리올레핀 탄성체의 합성)

  • Lee, Hyoung Woo;Cho, Hee Won;Lee, Sang Min;Park, Sat Byeol;Kim, Dong Hyun;Lee, Bum Jae
    • Elastomers and Composites
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    • v.48 no.1
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    • pp.10-17
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    • 2013
  • Polyolefin-g-poly(t-butylstyrene) as one of the high-temperature polyolefin-based thermoplastic elastomers was synthesized by the graft-from anionic living polymerization from the styrene moieties of the linear poly(ethylene-ter-1-hexene-ter-divinylbenzene) as a soft block to form the hard end blocks, poly(t-butylstyrene). The chemistry of the anionic graft-from polymerization involved complete lithiation of the pendant styrene unit of the soft polyolefin elastomer with sec-BuLi/TMEDA followed by the subsequent graft anionic polymerization of 4-tert-butylstyrene with Mn=10,000~30,000 g/mol. The graft-from living anionic polymerization were very effective and the grafting size increased proportionally with increasing monomer concentration and the reaction times. The synthetic methodology for the multi-hydroxyl chain-end modified polyolefin-g-poly(t-butylstyrene) was proposed by using the thiol-ene click reaction between 2-mercaptoethanol and the polyolefin-g-[poly(t-butylstyrene)-b-high vinyl polyisoprene], which was obtained from the subsequent living block copolymerization using polyolefin-g-Poly(t-butylstyrene) with isoprene. The result indicated that this process produced a new well-defined functionalized graft-type polyolefin-based TPE with high $T_g$ hard block(> $145^{\circ}C$).

Facile Synthesis of Fréchet Type Dendritic Benzyl Azides and Dendrimer via Cycloaddition Reaction with Tripodal Core

  • Lee, Jae-Wook;Kim, Byung-Ku;Kim, Jung-Hwan;Shin, Won-Suk;Jin, Sung-Ho
    • Bulletin of the Korean Chemical Society
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    • v.26 no.11
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    • pp.1790-1794
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    • 2005
  • Fréchet-type dendritic benzyl azides were efficiently synthesized using 5-(azidomethyl)-1,3-dihydroxybenzene as an azide focal point functionalized unit by adding a generation to the existing dendron and applied for the construction of dendrimers containing 1,2,3-triazole rings as connectors via click chemistry with a tripodal acetylene core.

Synthesis of Dendrimers from Alkyne-focal Dendrons by Oxidative Homo-coupling of Terminal Acetylene

  • Han, Seung-Choul;Kim, Jong-Sik;Lee, Jae-Wook
    • Bulletin of the Korean Chemical Society
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    • v.32 no.11
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    • pp.3899-3903
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    • 2011
  • General, fast, and efficient fusion methods for the synthesis of dendrimers with 1,3-diynes at a core were developed. The synthetic strategy was employed the oxidative homo-coupling of terminal alkyne. The oxidative homo-coupling reaction of the alkyne-functionalized Frechet-type dendrons 1-Dm was allowed to provide first through fourth generation dendrimers 2-Gm with 1,3-diynes at core. The fusion of the propargylfunctionalized PAMAM dendrons 3-Dm by homo-coupling of terminal alkyne lead to the formation of symmetric PAMAM dendrimers 4-Gm. Their structure of dendrimers was confirmed by $^1H$ and $^{13}C$ NMR spectroscopy, IR spectroscopy, mass spectrometry, and GPC analysis.

Azide/Alkyne Resins for Quick Preparation of 1,4-Disubstituted 1,2,3-Triazoles

  • Sirion, Uthaiwan;Lee, Jae-Hak;Bae, Yu-Jin;Kim, Hee-Jun;Lee, Byoung-Se;Chi, Dae-Yoon
    • Bulletin of the Korean Chemical Society
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    • v.31 no.7
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    • pp.1843-1847
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    • 2010
  • An efficient method for the preparation of 1,4-disubstituted 1,2,3-triazole compounds is described using polymeric quaternary ammonium salts having azide or alkyne functionality to remove unreacted excess starting molecules (azide/alkyne). Copper metal could easily be removed by simple filtration with a short $Na_2SO_4$/silica cartridge, affording highly regioselective products in high yield and excellent purity without the need for work-up, extraction and chromatographic purification.

Nanocrystalline Copper Oxide(II)-Catalyzed Alkyne-Azide Cycloadditions

  • Song, Young-Jin;Yoo, Chung-Yul;Hong, Jong-Tai;Kim, Seung-Joo;Son, Seung-Uk;Jang, Hye-Young
    • Bulletin of the Korean Chemical Society
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    • v.29 no.8
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    • pp.1561-1564
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    • 2008
  • Although the use of Cu(II) salts as catalysts without reductants is limited in the cycloaddition of acetylenes with azides, the catalytic system employing average 10 nm CuO(II) nanoparticles in the absence of reductants shows good catalytic activity to form 1,4-disubstituted 1,2,3-triazoles even in wet THF as well as water. It is also noticeable that CuO(II) nanoparticle catalysts can be recycled with consistent activity. A range of alkynes and azides were subject to the optimized CuO(II) nanoparticle-catalyzed cycloaddition reaction conditions to afford the desired products in good yields.

A Case Report of Surgical Treatment in a Lamed Hunting Dog with Cranial Cruciate Ligament Rupture and Medial Meniscal Injury (사낭견에서 내측반월판 손상을 수반한 전방십자인대단열의 외과적 치유예)

  • 정순욱;김영대;박수현;정월순;이충헌;신영규
    • Journal of Veterinary Clinics
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    • v.16 no.2
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    • pp.497-500
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    • 1999
  • A 4 years old male mixed breed dog, which weighed 25.5 kg, referred to Veterinary Teaching Hospital at College of Veterinary Medicine in Chonnam National University, because of chronic hindleg lameness. Click sound by flexion and extension of stifle joint, positive reaction by cranial drawer movement, fat pad sign and tibial position in cranial drawer position on the lateral radiographic view, medial patellar luxation (grade II), and lameness score 2.5 at standing and 2 at walking in right hindleg were showed. Under general anesthesia with enflurane, after medial arthrotomy, it was performed to remove remnants of cranial cruciate ligament and torn medial menisci and joint closed. In modified retinacular imbrication technique, one lateral fabellar/tuberosity suture, one medial fabellar/tuberosity suture, and one imbrication suture adjacent to the patella were placed. At 9 days after operation, lameness score 0 was observed and general condition was excellent.

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Kojic Acid Derivatives, Have Tyrosinase Inhibitory Activity to Suppress the Production of Melanin in the Biosynthetic Pathway (생체 내 경로에서 멜라닌 생성을 억제하는 타이로신 억제제로서의 코직산 유도체)

  • Park, Jung Youl;Lee, Ha Neul;Hu, Meng Yang;Park, Jeong Ho
    • Journal of Life Science
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    • v.29 no.7
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    • pp.755-761
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    • 2019
  • Kojic acid (KA) is produced by Aspergillus oryzae-sort of like mushrooms, which is commonly called as koji in Japan. KA is used as a chelation agent and a preservative preventing oxidative browning of fruits. KA also shows antibacterial and antifungal properties. Because KA stops the production of melanin by inhibiting tyrosinase in the biosynthetic pathway from tyrosine to melanin in skin, it has been applied as a skin lightening ingredient in cosmetics. Since some animal studies have shown that high amounts of KA had side effects such as in liver, kidney, reproductive, cardiovascular, gastrointestinal, respiratory, brain, and nervous system, more efficient KA derivatives are needed to be developed in order to safely apply as a skin lightening ingredient. A series of KA derivatives via conjugated with triazole by click reaction were synthesized and their in vitro tyrosinase inhibitory activities were evaluated. Most of all KA derivatives have shown in moderate tyrosinase inhibitory activities. In case of KA-hybrid compound, 1~3 have shown tyrosinase inhibitory activities about 50~10,000 times more effective tyrosinase inhibitor compared to KA itself. Specifically, the $IC_{50}$ value of KA-hybrid compound, 2 was $0.0044{\pm}0.74{\mu}M$ against tyrosinase. It is about 10,000 times more effective tyrosinase inhibitor compared to KA itself ($IC_{50}=45.2{\pm}4.6{\mu}M$).

Synthesis and in vitro Assay of New Triazole Linked Decursinol Derivatives Showing Inhibitory Activity against Cholinesterase for Alzheimer’s Disease Therapeutics

  • Park, Jung-Youl;Shin, Sujeong;Park, Kyoung Chan;Jeong, Eunju;Park, Jeong Ho
    • Journal of the Korean Chemical Society
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    • v.60 no.2
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    • pp.125-130
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    • 2016
  • With the goal of developing Alzheimer’s disease therapeutics, we have designed and synthesized new triazole linked decursinol derivatives having potency inhibitory activities against cholinesterase [acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE)]. Since inhibition of cholinesterase (ChE) is still considered to be one of the most effective targets to treat AD patients, many new classes of ChE inhibitors have been synthesized. In an effort of identifying new type of cholinergic drug, decursinol derivatives 11-17 have been synthesized between decursinol and other biological interesting compounds such as lipoic acid, polyphenols, etc by using the click reaction and then evaluated their biological activities. Compound 12 (IC50 = 5.89 ± 0.31 mM against BuChE) showed more effective inhibitory activity against BuChE than galantamine (IC50 = 9.4 ± 2.5 mM). Decursinol derivatives can be considered a new class inhibitor for BuChE and can be applied to be a novel drug candidate to treat AD patients.

Synthesis of Fréchet-type Dendrimers with Tripodal Core via Staudinger/Aza-Wittig Reactions (Staudinger/Aza-Wittig 반응에 의한 삼발이 핵을 갖는 Fréchet-type 덴드리머의 합성)

  • Han, Seung Choul;Lee, Jae Wook;Jin, Sung-Ho
    • Polymer(Korea)
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    • v.38 no.3
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    • pp.386-390
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    • 2014
  • Efficient stitching methods for the synthesis of tripodal Fr$\acute{e}$chet-type dendrimers containing secondary amine as a connector were elaborated. The synthetic strategy involved Staudinger/aza-Wittig reactions (new click reaction) between tripodal tris(azides) and aldehyde-dendrons in toluene in the presence of triphenylphosphine and followed by the reduction of imine intermediates. The tripodal core (1,3,5-tris-(3-azido-propoxy)-benzene) was chosen to serve as the azide functionalities for dendrimer growth. 1,3,5-Tris-(3-azido-propoxy)-benzene was stitched with the aldehyde-functionalized Fr$\acute{e}$chet-type dendrons via Staudinger/aza-Wittig reactions leading to the formation of the corresponding Fr$\acute{e}$chet-type dendrimers in high yields.

Selective tyrosine conjugation with a newly synthesized PCB -TE2A-luminol bifunctional chelator

  • Subramani Rajkumar;Hyun Park;Abhinav Bhise;Seong Hwan Cho;Jung Young Kim;Kyo Chul Lee;Jeongsoo Yoo
    • Journal of Radiopharmaceuticals and Molecular Probes
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    • v.7 no.2
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    • pp.85-91
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    • 2021
  • Selective amino acid conjugation of bulky antibodies is a valuable asset for real-time diagnosis and therapy. However, selective conjugation incorporating a chelate-bearing radioactive atom into an antibody without affecting its immunoreactivity is a challenging task. A bifunctional chelator (BFC), a selective amino acid-targeting probe, and a linker have been developed to overcome this problem. Here, we report the synthesis of a novel propylene cross-bridged chelator (PCB)-1,8-N,N'-bis-(carboxymethyl)-1,4,8,11-tetraazacyclotetradecane (TE2A)-luminol BFC via a click reaction and radiolabel it with a 64Cu ion for tyrosine-selective conjugation of trastuzumab. In the initial optimization study, we tried different oxidative addition conditions such as electro-oxidation, hemin, horseradish peroxidase, iodogen tube, chloramine-T, and iodo beads. In this study, up to 82% of 64Cu-PCB-TE2A-luminol was conjugated with the antibody in an iodo bead-catalyzed oxidative addition reaction with an isolated yield of 24.4%.