• Title/Summary/Keyword: Efficient synthetic route

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Cross-Coupling Reaction of 2-halo1-methyl-1H-imidazo[4,5-b]pyridine Offers a New Synthetic Route to Mutagenic Heterocyclic Amine-PHIP and DMIP

  • Sajith, Ayyiliath M.;Muralidharan, Arayambath;Karuvalam, Ranjith P.;Haridas, Karickal R.
    • Journal of the Korean Chemical Society
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    • v.57 no.3
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    • pp.361-364
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    • 2013
  • A modified synthetic approach to the synthesis of heterocyclic food mutagens, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PHIP) and 2-amino-1,6-dimethylimidazo[4,5-b]pyridine (DMIP) is reported. This route highlights an optimized palladium catalysed Buchwald cross-coupling of 2-halo-1-methyl-imidazo[4,5-b]pyridine with benzophenoneimine followed by acidic hydrolysis to yield compound 7. Using finely tailored conditions, Suzuki cross-coupling reactions with highly efficient catalytic systems were performed as the final step on 8 to introduce the aryl group and methyl group on the heterocyclic core.

A Highly Efficient Synthesis of Itraconazole Intermediates and Their Analogues (Itraconazole 중간체의 효율적 합성법과 그 유사체의 합성)

  • Ahn, Chong Il;Myoung, Young Chan;Choi, Ha Young;Kim, Seung Jin
    • Journal of the Korean Chemical Society
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    • v.43 no.6
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    • pp.676-681
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    • 1999
  • Itraconazole is an important drug for oral treatment of histoplasmosis and blastomycosis. ltraconazole has been the targets of many synthetic efforts due to their diverse antifungal activities. ln this study, an efficient synthetic route for Itraconazole intermediates has been developed using new procedures. Also, ltraconazole analogues introducing 2- and 3-methoxy group instead of ltraconazole intermediates with 4-methoxy group were synthesized.

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Synthesis of Novel 2'-Spirocyclopropanoid 4'-Deoxythreosyl Phosphonic Acid Nucleoside Analogues

  • Shen, Guang Huan;Hong, Joon Hee
    • Bulletin of the Korean Chemical Society
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    • v.34 no.3
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    • pp.868-874
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    • 2013
  • Efficient synthetic route to novel 2'-spirocyclopropanoid 4'-deoxythreosyl phosphonic acid nucleosides was described from 1,4-dihydroxy-2-butene. Cyclopropane moiety was prepared via ester enolate alkylation using (2-chloroethyl)dimethylsulfonium iodide. Synthesized nucleoside analogues 16, 19, 23 and 26 were tested for anti-HIV activity as well as cytotoxicity. However, none of them showed any anti-HIV activity or cytotoxicity up to 100 ${\mu}M$.

Synthesis of Carbocycles Using Metal Catalyst(I) -Stereoselective Synthesis of Cyclopentane Using Pd(0) Catalyst- (금속 촉매를 이용한 Carbocycle의 합성(I) -Pd(0) 촉매를 이용한 Cyclopentane의 입체선택적 합성-)

  • Suh, Young-Ger;Lee, Gi-Ho;Cho, Youn-Sang
    • YAKHAK HOEJI
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    • v.34 no.5
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    • pp.287-290
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    • 1990
  • An efficient stereoselective synthetic route to carbocycle is described. 1,1,2-Trisubstituted cyclopentane was synthesized from allylic carbonate by Pd(0) catalyzed cyclization.

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Synthesis of 4'α-C Phenyl-Branched Carbocyclic Nucleoside Using Ring-Closing Metathesis

  • Hong, Joon-Hee;Ko, Ok-Hyun
    • Bulletin of the Korean Chemical Society
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    • v.24 no.9
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    • pp.1289-1292
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    • 2003
  • An efficient synthetic route for preparing novel $4'{\alpha}$-C phenyl branched carbocyclic nucleoside is described. The installation of phenyl group at the $4'$-position of carbocyclic nucleoside was successfully accomplished via a sequential [3,3]-sigmatropic rearrangement and ring-closing metathesis (RCM) beginning from simple ketone such as 2-hydroxy acetophenone.

Synthesis of 4′$\alpha$-C Methyl Branched Novel Adenine and Uracil Carbocyclic Nucleosides Using Ring-Closing Metathesis (Ring-Closing Metathesis 반응을 이용한 새로운 4-메칠 아데닌 및 유라실 카보사이클릭 뉴크레오사이드의 합성)

  • 홍준희
    • YAKHAK HOEJI
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    • v.47 no.5
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    • pp.271-275
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    • 2003
  • Easy and efficient synthetic route of novel 4'-C methyl branched carbocyclic nucleosides is described. The installation of alkyl and aryl groups at 4'-position of carbocyclic nucleosides were successfully made via sequential [3,3]-sigmatropic rearrangement and ring-closing metathesis (RCM) starting from simple ketones such as acetol. Adenine and uracil were coupled via Pd(0) catalyzed reaction, followed by desilylation to give novel compounds 13 and 14, respectively.

Approach to the Total Synthesis of Acanthoside-D

  • Ngoc, Thyen-Truong;Park, Hae-Il
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.186.4-187
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    • 2003
  • Acanthoside-D, one of major components of Acanthopanacis Cortex, is known as a ginseng-like substance. it has been known to possess diverse biological effects. Acanthoside-D has a furofuran lignan structure and the synthesis of which poses interesting and often unsolved proplems of stereocontrol. Although a few interesting syntheses providing this natural product have been reported, an intermolecular McMurry coupling - intramolecular Mitsunobu cyclization route has not yet been explored. We report here a short and efficient synthetic pathway to the total synthesis of Acanthoside-D from aryl aldehydes and methyl acrylates via Baylis-Hillman reaction, intermolecular McMurry coupling and intramolecular Mitsunobu cyclization as key reaction.

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Synthesis of N-Aryl Phenylglycine Ο-Alkyl Esters Using Hydrolysis of 1,5-Diphenylhydantoins (1,5-Diphenylhydantoins의 가수분해에 의한 N-Aryl Phenylglycine Ο-Alkyl Esters의 합성)

  • 박해선;최희전;권순경;박명숙
    • YAKHAK HOEJI
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    • v.47 no.3
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    • pp.130-134
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    • 2003
  • For the development of new synthetic method for unnatural amino acid esters, N-aryl phenylglycine Ο-alkyl esters 4a∼i were synthesized through base-catalyzed hydrolysis of 1,5-diphenylhydantoins 1a∼b and Ο-alkylation in 16∼87% yield. An efficient and practical route for final 4a∼i was that the starting materials 1a∼b were heated in dil-methanol for 30 minute using sodium hydroxide or potassium hydroxide and evaporated. In addition, reaction mixture were refluxed for 1 h in DMF. All synthetic process from hydantoin to N-aryl phenylglycine Ο-alkyl esters 4a∼i could be carried out in one-pot without isolation of intermediates.

Efficient Synthesis and in vitro PDT Effect of Purpurin-18-N-Aminoimides

  • Cui, Bing Cun;Cha, Min-Uk;Li, Jia Zhu;Park, Ho-Sung;Yoon, Il;Shim, Young-Key
    • Bulletin of the Korean Chemical Society
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    • v.31 no.11
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    • pp.3313-3317
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    • 2010
  • A simple and efficient synthetic route for making purpurin-18-N-aminoimides is described. The purpurin-18-Naminoimides are obtained by treatment of purpurin-18 methyl ester with various amines. These new compounds have long wavelength absorptions in the range of 706 - 711 nm. In preliminary screening, the purpurin-18-N-aminoimides have shown promising photosensitizing activity for the cancer cell by in vitro study in photodynamic therapy.