• Title/Summary/Keyword: Imine synthesis

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Synthesis of ($\pm$)-Methyl-(1-aryl-4-pyridin-3-yl-but-3-enyl)-amines

  • Jang, Jin-Hee;Sin, Kwan-Seog;Park, Hae-Il
    • Archives of Pharmacal Research
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    • v.24 no.6
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    • pp.503-507
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    • 2001
  • trans-Metanicotine, a subtype (${\alpha}_4{\beta}_2$)-selective ligand for neuronal nicotinic acetylcholine receptor, is under clinical phase for Alzheimer's disease. An efficient synthetic route for ($\pm$)-methyl-(1-aryl-4-pyridin-3-yl-but-3-enyl)-am ices, derivatives of tracts-metanicotine, was explored. Allylation reaction of aryl aldimines with allylmagnesium bromide in THF gave ($\pm$)-methyl-(1-aryl-but-3-enyl)-amines. Protection of the amines with the Boc group and following Heck reaction of the N-Boc amines with 3-bromopyridine gave ($\pm$)-methyl-(1-aryl-4-pyridin-3-yl-but-3-enyl)-carbamic acid tert-butyl esters. Deprotection of the N-Boc group in aqueous 1 N-HCI solution gave the titled amines in good yields. Thus, trans-metanicotine analogues modified at the ${\alpha}-position$ of the methylamino group with amyl groups were obtained in 5 steps.

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Synthesis and Evaluation of Biological activities of New Imine Derivatives of Apicidin

  • Jin, Cheng-Hua;Kim, Hyung-Kyo;Han, Jeong-Whan;Lee, Hyang-Woo;Lee, Yin-Won;Zee, Ok-Pyo;Jung, Young-Hoon
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.253.2-253.2
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    • 2002
  • Apicidin. a natural product HDAC inhibitor. is recently isolated from Fusarium sp. at Merk Research Laboratories, induces therapeutic applications as a broad spectrum antiprotozoal agent to muti-drug resistant malaria and a potential antitumor agent. The biological activity of apicidin appears to be apicocomplexan HDAC at low nanomolar concentrations. (omitted)

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Synthesis, Chemical Characterization and Catalytic Activity of Transition Metal Complexes Having Imine Based Nitrogen Donor Ligand (이민에 기초한 질소주개 리간드의 전이금속 착물 합성, 화학적 특성 및 촉매활성)

  • Hussain, Raja Azadar;Badshah, Amin;Asma, Maliha
    • Journal of the Korean Chemical Society
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    • v.54 no.1
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    • pp.23-26
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    • 2010
  • A Schiff base ligand (Z)-N-((Z)-2-(sec-butylimino)-1,2-diphenylethylidene)butan-2-amine was synthesized by condensation of benzil with sec-butyl amine. Complexation of the ligand was carried out with first row transition elements, manganese(II) and nickel(II). Ligand and complexes were characterized by FTIR, elemental analysis and thermogravimetric analysis in solid state and by NMR ($^1H,\;^{13}C$) in solution form. Both the complexes demonstrate good catalytic activity for butadiene oligomerization under mild conditions with methylaluminoxane (MAO) as co-catalyst.

Synthesis and Charaterization of Photoluminescent and Electrochemical Property for Diruthenium Complex with Diimine Bridge (디이민 가교제를 갖는 이핵 루테늄 착체의 광발광 및 전기화학적 특성)

  • Kim, Dong-Hwan;Kim, Hwa-Seon;Kwak, Ji-Hoon;Lee, Jee-Hoon;An, Ho-Guen;Woo, Myung-Woo;Ruimao, Hua;Jung, Min-Chul
    • Proceedings of the Korean Institute of Electrical and Electronic Material Engineers Conference
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    • 2006.11a
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    • pp.296-297
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    • 2006
  • 유기EL의 발광재료로 쓰일 수 있는 이핵 루테늄착체는 $Ru(bpy)_2Cl_2$와 새롭게 디자인한 가교체 (Bis(-2,2'-dipyridyl ketenylidene)-N,N-1,6-diphenylene diamine)의 반응으로부터 합성하였고, FT-IR, $^1H$-NMR, $^{13}C$-NMR, UV-vis, P.L, C.V를 이용하여 착체의 구조분석, 광학적 특성과 전기화학적인 특성을 측정하였다.

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Synthesis and Tautomerism of Pyrido[2,3-b]pyrazines (Pyriodo[2,3-b]pyrazine류의 합성과 토토머화 현상)

  • Kim, Ho-Sik;Choi, Kyung-Ok;Kurasawa, Yoshihisa
    • Journal of the Korean Chemical Society
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    • v.44 no.5
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    • pp.435-440
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    • 2000
  • The reaction of 2-methoxycarlmethylen-l,2-dihydro-4H-pyrido[2,3-b]pyrazin-3-one(5) with hydrazine hydrate and ethylenediamine gave 2-hydrazinocarbonylmethylene-1,2-dihydro-4H-pyrido[2,3-b]pyrazin-3-one(6) and 2-aminoethylcarbamethylene-1,2-dihydro-4H-pyrido[2,3-b]pyrazin-3-one(7), res-pectively. The reaction of compound 6 or 7 with substituted benzaldehydes or heteroaryl aldehydes afforded pyrido[2,3-b]pyrazines(8-13). Some pyrin the enamine, methylene imine and enaminol forms in solution. The tau-tomer ratios were determined by the H NMR.

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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.

Sol-gel synthesis, computational chemistry, and applications of Cao nanoparticles for the remediation of methyl orange contaminated water

  • Nnabuk Okon Eddy;Rajni Garg;Rishav Garg;Samson I. Eze;Emeka Chima Ogoko;Henrietta Ijeoma Kelle;Richard Alexis Ukpe;Raphael Ogbodo;Favour Chijoke
    • Advances in nano research
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    • v.15 no.1
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    • pp.35-48
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    • 2023
  • Nanoparticles are known for their outstanding properties such as particle size, surface area, optical and electrical properties. These properties have significantly boasted their applications in various surface phenomena. In this work, calcium oxide nanoparticles were synthesized from periwinkle shells as an approach towards waste management through resource recovery. The sol gel method was used for the synthesis. The nanoparticles were characterized using X-Ray diffractometer (XRD), Fourier Transformed Infra-Red Spectrophotometer (FTIR), Brunauer Emmett Teller (BET), scanning electron microscopy (SEM), transmission electron microscopy (TEM) and ultra violet visible spectrophotometer (UV-visible). While DLS and SEM underestimate the particle diameter, the BET analysis reveals surface area of 138.998 m2/g, pore volume = 0.167 m3/g and pore diameter of 2.47 nm. The nanoparticles were also employed as an adsorbent for the purification of dye (methyl orange) contaminated water. The adsorbent showed excellent removal efficiency (up to 97 %) for the dye through the mechanism of physical adsorption. The adsorption of the dye fitted the Langmuir and Temkin models. Analysis of FTIR spectrum after adsorption complemented with computational chemistry modelling to reveal the imine nitrogen group as the site for the adsorption of the dye unto the nanomaterials. The synthesized nanomaterials have an average particle size of 24 nm, showed a unique XRD peak and is thermally and mechanically stable within the investigated temperature range (30 to 70 ℃).

Fabrication of Meso/Macroporous Carbon Monolith and its Application as a Support for Adsorptive Separation of D-Amino Acid from Racemates

  • Park, Da-Min;Jeon, Sang Kwon;Yang, Jin Yong;Choi, Sung Dae;Kim, Geon Joong
    • Bulletin of the Korean Chemical Society
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    • v.35 no.6
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    • pp.1720-1726
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    • 2014
  • (S)-Alanine Racemase Chiral Analogue ((S)-ARCA) was used as an efficient adsorbent for the selective separation of D-amino acids (D-AAs), which are industrially important as chiral building blocks for the synthesis of pharmaceutical intermediates. The organic phase, containing (S)-ARCA adsorbent and phase transfer reagents, such as ionic liquid type molecules (Tetraphenylphosphonium chloride (TPPC), Octyltriphenylphosponium bromide (OTPPBr)), were coated on the surfaces of mesoporous carbon supports. For the immobilization of chiral adsorbents, meso/macroporous monolithic carbon (MMC), having bimodal pore structures with high surface areas and pore volumes, were fabricated. The separation of chiral AAs by adsorption onto the heterogeneous (S)-ARCA was performed using a continuous flow type packed bed reactor system. The effects of loading amount of ARCA on the support, the molar ratio of AA to ARCA, flow rates, and the type of phase transfer reagent (PTR) on the isolation yields and the optical purity of product D-AAs were investigated. D-AAs were selectively combined to (S)-ARCA through imine formation reaction in an aqueous basic solution of racemic D/L-AA. The (S)-ARCA coated MMC support showed a high selectivity, up to 95 ee%, for the separation of D-type phenylalanine, serine and tryptophan from racemic mixtures. The ionic liquids TPPC and OTPPBr exhibited superior properties to those of the ionic surfactant Cetyltrimethyl ammonium bromide (CTAB), as a PTR, showing constant optical purities of 95 ee%, with high isolation yields for five repeated reuses. The unique separation properties in this heterogeneous adsorption system should provide for an expansion of the applications of porous materials for commercial processes.

Synthesis of New Draw Solute Based on Polyethyleneimine for Forward Osmosis (정삼투를 위한 Polyethyleneimine 기반 유도용질 제조)

  • Lee, Hye-Jin;Choi, Jin-Il;Kwon, Sei;Kim, In-Chul
    • Membrane Journal
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    • v.28 no.4
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    • pp.286-295
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    • 2018
  • A novel multi-valent salt based on polyethyleneimine having molecular weight of 800 (PEI 800) has been synthesized and characterized as forward osmosis draws solute. A reaction intermediate was synthesized by the neutralization reaction of polyethyleneimine and methyl acrylate, and was hydrolyzed with potassium hydroxide to synthesize a water soluble carboxylic acid (potassium salt) polyethyleneimine. NMR spectrometry, viscometry measurements and osmometry measurements was performed to characterize the draw solute. Forward osmosis experiments were done to know whether the solute could be used as a draw solute or not. The result shows comparable water flux and lower reverse salt flux compared with NaCl as a draw solute. We have also demonstrated recycling of the draw solute in the FO-NF integrated process.

Synthesis of d- and l-Form of $^{99m}Tc$-HMPAO, and Comparison of Brain Uptake ($^{99m}Tc$-HMPAO의 광학이성체 d-, l-Form의 합성과 뇌섭취율 비교)

  • Kang, Chan-Soon;Chang, Young-Soo;Jeong, Jae-Min;Lee, Dong-Soo;Chung, June-Key;Lee, Kang-Choon;Lee, Myung-Chul
    • The Korean Journal of Nuclear Medicine
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    • v.35 no.1
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    • pp.69-74
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    • 2001
  • Purpose: $^{99m}Tc$-HMPAO is a radiopharmaceutical for imaging cerebral blood flow. HMPAO (RR, SS)-4.8-diaza-3,6,6,9-tetramethylundecan-2,10- dione bisoxime) has three stereoismers such as, meso-. d-, and l-HMPAO. Techentium complexes of meso-HMPAO and d,l-HMPAO are known to have different in vivo brain uptakes. In this study, enantiomers of HMPAO (d-HMPAO and l-HMPAO) were separated from d,l-HMPAO. These enantiomers were labeled with $^{99m}Tc$ and the biodistribution studies were performed in mice. Materials and Methods: An intermediate imine product was produced from 2,3-butanedione monooxime and 2,2-dimethyl-1,3-propanediamine (54% yield) and was reduced into a mixture of three isomers (35% yield). The meso-isomer was separated from d,l-mixture by repeated fractional crystallization (11 % yield). The d- and l-enantiomers were subsequently separated by co-crystallization with optical isomers of tartaric acid (25% and 5% yield. respectively). Each enantiomeric HMPAO was labeled with $^{99m}Tc$ by reacting with $SnCI_2{\cdot}2H_2O\;and\;^{99m}Tc$-pertechnetate. Biodistribution study was performed 1 hr after tail vein injection to ICR mice. Results: Radiochemical purities of each compound were over 80%. In biodistribution study. the brain uptakes of d,l- d- and l-form were 1.34, 1.12 and 1.67% ID/g, respectively. In case of l-lsomer the brain uptake was higher (1.5 fold) than d-isomer. Conclusion: We successfully purified each enantiomeric HMPAO. In biodistribution study of stereoismers of $^{99m}Tc$-HMPAO in mice, l-HMPAO may show better brain image than d,l-HMPAO which was supplied in a commercial kit.

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