Stereoselective synthesis and anti-HCV activity of conformationally restricted 2′-C-substituted carbanucleosides

Choi, Won Jun; Ko, Yun Jung; Chandra, Girish; Lee, Hyuk Woo; Kim, Hea Ok; Koh, Hyo Jung; Moon, Hyung Ryong; Jung, Young Hoon; Jeong, Lak Shin

doi:10.1016/j.tet.2011.11.052

Cited by 8 publications

(3 citation statements)

References 38 publications

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“…The native glycans were found to have limitations like low binding affinities due to their characteristic high polarity and low pharmacokinetics. Fluorination by replacement of the -OH group has been found to solve a few of the above problems (Choi et al 2012).…”

Section: Brief Outlook Of Fluoro Compoundsmentioning

confidence: 99%

Fluorine-a small magic bullet atom in the drug development: perspective to FDA approved and COVID-19 recommended drugs

et al. 2023

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During the last twenty years, organic fluorination chemistry established itself as an important tool to get a biologically active compound. This belief can be supported by the fact that every year, we are getting fluorinated drugs in the market in extremely significant numbers. Last year, also ten fluorinated drugs have been approved by FDA and during the COVID-19 pandemic, fluorinated drugs played a very crucial role to control the disease and saved many lives. In this review, we surveyed all ten fluorinated drugs approved by FDA in 2021 and all fluorinated drugs which were directly-indirectly used during the COVID-19 period, and emphasis has been given particularly to their synthesis, medicinal chemistry, and development process. Out of ten approved drugs, one drug pylarify, a radioactive diagnostic agent for cancer was approved for use in positron emission tomography imaging. Also, very briefly outlined the significance of fluorinated drugs through their physical, and chemical properties and their effect on drug development.

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Section: Brief Outlook Of Fluoro Compoundsmentioning

confidence: 99%

Fluorine-a small magic bullet atom in the drug development: perspective to FDA approved and COVID-19 recommended drugs

et al. 2023

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“…Some of them are depicted on Scheme 11 including the access to (±)‐grandifloracin 78 , [105] (−)‐valiolamine 81 , [106] cochlearenine 83 , [107–108] paniculamine 84 , [107–108] pseudo‐β‐fructopyranose 87 , [109] koningic acid derivative 89 , [110] 13α,16α,17‐tri‐hydroxy‐ ent ‐kaur‐19‐oic acid 91 , [111] africane‐9,15‐diol 93 , [112] and trichodermin derivative 95 [113] . Moreover, this strategy has been employed in the synthesis of diverse intermediates which serve as building blocks for further synthesis [114–119] …”

Section: Synthesismentioning

confidence: 99%

Design, Synthesis, and Evaluation of α‐(Hydroxymethyl)cycloalkanols

Nassar

Piva

2021

Eur J Org Chem

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α‐(Hydroxymethyl)cycloalkanols are pervasive structural scaffolds found in natural products and synthetic intermediates with varied biochemical and physicochemical properties. These profiles have driven numerous research groups to the synthesis of such motifs using innovative methodologies. The presence of vicinal diols attached to a cycloalkane makes from these motifs excellent synthetic intermediates for the synthesis of diverse ring systems. This investigation takes an overview of the literature for the occurrence and synthesis of α‐(hydroxymethyl)cycloalkanol derivatives, concentrating on advances in the last two decades.

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“…These were obtained efficiently via stereoselective conversion of the ketone into an epoxide coupled with stereoselective opening of the epoxide with a range of nucleophiles (OAc, N 3 , F, etc.). All synthesized nucleosides were assayed for their activity against the hepatitis C virus 38. Moon and co‐workers used trityl‐protected cyclopentenone intermediate 16 b in the synthesis of iodoneplanocin A and its analogues 39a.…”

Section: Ring‐closing Metathesis In Nucleoside Chemistrymentioning

confidence: 99%

Synthesis of Ar‐BINMOL Ligands by [1,2]‐Wittig Rearrangement to Probe Their Catalytic Activity in 1,2‐Addition Reactions of Aldehydes with Grignard Reagents

et al. 2012

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We have demonstrated a highly diastereoselective synthesis of optically pure Ar‐BINMOL‐derived diols and their analogues. The present study demonstrates a unique cascade chirality transfer in a [1,2]‐Wittig rearrangement that leads to chiral diols with three stereogenic centers, which include a chiral sp3 center at the alcohol and C2‐axial chirality. Screening these ligands in the arylation of aromatic aldehydes with Grignard reagents shows that the naphthyl‐substituted BINMOL promotes the aryl transfer reaction in good yields (70–92 %) and moderate‐to‐good enantioselectivities (up to 72 % ee), and a series of control experiments substantiates that the axial chirality and the chiral sp3 center at the alcohol of the Ar‐BINMOLs are the pivotal enantioselectivity‐controlling structure elements. In addition, this study demonstrated the importance of the chiral sp3 center at the alcohol on Ar‐BINMOL for the aryl transfer reaction. Finally, we found that the chiral Ar‐BINMOL ligand 2h mediated the titanium‐promoted 1,2‐addition of MeMgBr to aldehydes to give the desired products in good yields with excellent enantioselectivities (up to 92 % ee).

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Stereoselective synthesis and anti-HCV activity of conformationally restricted 2′-C-substituted carbanucleosides

Cited by 8 publications

References 38 publications

Fluorine-a small magic bullet atom in the drug development: perspective to FDA approved and COVID-19 recommended drugs

Fluorine-a small magic bullet atom in the drug development: perspective to FDA approved and COVID-19 recommended drugs

Design, Synthesis, and Evaluation of α‐(Hydroxymethyl)cycloalkanols

Synthesis of Ar‐BINMOL Ligands by [1,2]‐Wittig Rearrangement to Probe Their Catalytic Activity in 1,2‐Addition Reactions of Aldehydes with Grignard Reagents

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