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Synthesis and Antiviral Activity Evaluation of 5',5'-Difluoro-2'-methylapiosyl Nucleoside Phosphonic Acid Analogs

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  • 발행기관
    조선대학교 기초과학연구원 바로가기
  • 간행물
    통합자연과학논문집(구 조선자연과학논문집) KCI 등재 바로가기
  • 통권
    제8권 3호 (2015.09)바로가기
  • 페이지
    pp.153-163
  • 저자
    Joon Hee Hong
  • 언어
    영어(ENG)
  • URL
    https://www.earticle.net/Article/A254204

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원문정보

초록

영어
Racemic synthesis of novel 5',5'-difluoro-2'-methyl-apiose nucleoside phosphonic acid analogs was achieved as potent antiviral agents. Phosphonation was performed by direct displacement of triflate intermediate with diethyl (lithiodifluoromethyl) phosphonate to give the corresponding (α,α-difluoroalkyl) phosphonate. Condensation successfully proceeded from a glycosyl donor with persilylated bases to yield the nucleoside phosphonate analogs. Deprotection of diethyl phosphonates provided the target nucleoside analogs. An antiviral evaluation of the synthesized compounds against various viruses such as HIV, HSV-1, HSV-2 and HCMV revealed that the pyrimidine analogs (cytosine, uracil, and thymine) have weak anti-HIV or HCMV activity.

목차

Abstract
 1. Introduction
 2. Experimental Section
  2.1. (rel)-(3S,4S)-Dihydro-4-(hydroxymethyl)-3-methylfuran-2(3H)-one (7)
  2.2. (rel)-(3S,4S)-Dihydro-4-(t-butyldimethylsilyloxymethyl)-3-methylfuran-2(3H)-one (8)
  2.3. (rel)-(4R,3S,2R/S)-Tetrahydro-4-(t-butyldimethylsilyloxymethyl)-3-methylfuran-2-ol (9)
  2.4. (rel)-(3R,4S,5R/S)-[(4-Methyl-tetrahydro-5-methoxyfuran-3-yl)methoxy](t-butyl)dimethylsilane(10)
  2.5. (rel)-(3S,4S,5R/S)-(4-Methyl-tetrahydro-5-methoxyfuran-3-yl)methanol (11)
  2.6. (rel)-(3R,4S,5R/S)-(4-Methyl-tetrahydro-5-methoxyfuran-3-yl)methyl trifluoromethanesulfonate (12)
  2.7. (rel)-Diethyl 1,1-difluoro-2-[(3S,4S,5R/S)-4-methyl-tetrahydro-5-methoxyfuran-3-yl] ethylphosphonate(13)
  2.8. (rel)-Diethyl 2-[(3S,4S,5R/S)-5-acetoxy-4-methyl-tetrahydrofuran-3-yl]-1,1-difluoroethylphosphonate(14)
  2.9. (rel)-Diethyl 4-[(1S,2S,3S)-1-(6-chloro-9H-purin-9-yl)-2-methyl-tetrahydrofuran-3-yl]-5,5-difluoroethylphosphonate(15α) an
  2.10. (rel)-Diethyl 4-[(1R,2S,3S)-1-(6-amino-9Hpurin-9-yl)-2-methyl-tetrahydrofuran-3-yl]-5,5-difluoroethylphosphonate (16)
  2.11. (rel)-4-[(1R,2S,3S)-1-(6-Amino-9H-purin-9-yl)-tetrahydrofuran-3-yl]-2-methyl-5,5-difluoroethylphosphonicacid sodium salt (17)
  2.12. (rel)-Diethyl 4-[(1S,2S,3S)-1-(2-fluoro-6-chloro-9H-purin-9-yl)-2-methyl-tetrahydrofuran-3-yl]-5,5-difluoroethylphosphona
  2.13. (rel)-Diethyl 4-[(1R,2S,3S)-1-(2-fluoro-6-amino-9H-purin-9-yl)-2-methyl-tetrahydrofuran-3-yl]-5,5-difluoroethylphosphonate (19) and (rel)-diethyl 4-[(1R,2S,3S)-1-(2-amino-6-chloro-9H-purin-9-yl)-2-methyltetrahydrofuran-3-yl]-5,5-difluoroethylphosphona
  2.14. (rel)-4-[(1R,2S,3S)-1-(2-Amino-6-oxo-9Hpurin-9-yl)-tetrahydrofuran-3-yl]-2-methyl-5,5-difluoroethyl-phosphonic acid sodium salt (21)
  2.15. (rel)-Diethyl 4-[(1S,2S,3S)-1-(N4-benzoylamino-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methyl-tetrahydrofuran-3-yl]-5,5-di
  2.16. (rel)-Diethyl 4-[(1R,2S,3S)-1-(4-amino-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methyl-tetrahydrofuran-3-yl]-5,5-difluoroethylphosphonate (23)
  2.17. (rel)-4-[(1R,2S,3S)-1-(4-Amino-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl]-2-methyl-5,5-difluoroethyl-phosphonic acid sodiumsalt (24)
  2.18. (rel)-Diethyl 4-[(1S,2S,3S)-1-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methyl-tetrahydrofuran-3-yl]-5,5-difluoroethylp
  2.19. (rel)-Diethyl 4-[(1S,2S,3S)-1-(2,4-dioxo-5-methyl-3,4-dihydropyrimidin-1(2H)-yl)-2-methyltetrahydrofuran-3-yl]-5,5-difluo
  2.20. (rel)-4-[(1R,2S,3S)-1-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl]-2-methyl-5,5-difluoroethyl-phosphonic acid sodium salt (27)
  2.21. (rel)-4-[(1R,2S,3S)-1-(2,4-Dioxo-5-methyl-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl]-2-methyl-5,5-difluoroethyl-phosphonic acid sodiumsalt (28)
 3. Results and Discussion
  3.1. Biological Activity Evaluation
 4. Conclusion
 Acknowledgment
 References

키워드

Antiviral Agents 5'-Difluoro-2'-methyl-apiose Nucleoside Phosphonic Acid Analogues Vorbrüggen Reaction 5'

저자

  • Joon Hee Hong [ BK-21 Project Team, College of Pharmacy, Chosun University, Kwangju Korea ] Corresponding author

참고문헌

자료제공 : 네이버학술정보

간행물 정보

발행기관

  • 발행기관명
    조선대학교 기초과학연구원 [The Natural Science Research Institute of Chosun]
  • 설립연도
    2008
  • 분야
    자연과학>자연과학일반
  • 소개
    본 연구원은 기초과학을 진흥하기 위한 연구·교육 및 그 보급을 목적으로 한다. 이 목적을 달성하기 위하여 다음 각 호의 사업을 수행한다. 1. 기초과학 제 분야에 관한 조사와 연구 2. 기초과학에 관한 학술행사(학술대회, 학술세미나, 심포지엄, 초청강연회 등) 개최 3. 학문후속세대 및 일반인을 위한 기초과학 교육 4. 기관지『조선자연과학논문지』 발간 5. 『자연과학연구총서』, 『자연과학번역총서』 등 단행본 발간 6. 기타 본 연구원의 목적과 관련된 사업

간행물

  • 간행물명
    통합자연과학논문집(구 조선자연과학논문집) [Journal of Integrative Natural Science]
  • 간기
    계간
  • pISSN
    2005-1042
  • 수록기간
    2008~2026
  • 등재여부
    KCI 등재
  • 십진분류
    KDC 405 DDC 505

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