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Volumn 2, Issue 9, 2011, Pages 692-697

Synthesis of 4′-ethynyl-2′-deoxy-4′-thioribonucleosides and discovery of a highly potent and less toxic NRTI

Author keywords

4 Thionucleosides; anti HIV 1 activity; electrophilic glycosidation; glycal; nucleoside reverse transcriptaseinhibitors

Indexed keywords

4' ETHYNYL 2' DEOXY 4' THIORIBONUCLEOSIDE; ADENINE; CYTOSINE; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 80052616126     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml2001054     Document Type: Article
Times cited : (19)

References (18)
  • 2
    • 0035038033 scopus 로고    scopus 로고
    • Sugar-modified nucleosides in past 10 years, a review
    • Ichikawa, E.; Kato, K. Sugar-modified nucleosides in past 10 years, a review Curr. Med. Chem. 2001, 8, 385-423 (Pubitemid 32409787)
    • (2001) Current Medicinal Chemistry , vol.8 , Issue.4 , pp. 385-423
    • Ichikawa, E.1    Kato, K.2
  • 4
    • 0033745425 scopus 로고    scopus 로고
    • Synthesis and biological activity of thionucleosides
    • For a review, see
    • For a review, see Yokoyama, M. Synthesis and biological activity of thionucleosides Synthesis 2000, 1637-1655
    • (2000) Synthesis , pp. 1637-1655
    • Yokoyama, M.1
  • 6
    • 41149166259 scopus 로고    scopus 로고
    • Synthesis and anti-HIV activity of 4′-substituted 4′-thiothymidines: A new entry based on nucleophilic substitution of the 4′-acetoxy group
    • DOI 10.1021/jm070824s
    • Haraguchi, K.; Shimada, H.; Tanaka, H.; Hamasaki, T.; Baba, M.; Gullen, E. A.; Dutschman, G. E.; Cheng, Y.-C. Synthesis and anti-HIV activity of 4′-substituted 4′-thiothymidines: A new entry based on nucleophilic substitution of the 4′-acetoxy group J. Med. Chem. 2008, 5, 1885-1893 (Pubitemid 351438870)
    • (2008) Journal of Medicinal Chemistry , vol.51 , Issue.6 , pp. 1885-1893
    • Haraguchi, K.1    Shimada, H.2    Tanaka, H.3    Hamasaki, T.4    Baba, M.5    Gullen, E.A.6    Dutschman, G.E.7    Cheng, Y.-C.8
  • 8
    • 1542504084 scopus 로고    scopus 로고
    • An Improved One-pot Procedure for the Synthesis of Alkynes from Aldehydes
    • Müller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. An improved one-pot procedure for the synthesis of alkynes from aldehydes Synlett 1996, 521-522 (Pubitemid 126426703)
    • (1996) Synlett , vol.1996 , Issue.6 , pp. 521-522
    • Muller, S.1    Liepold, B.2    Roth, G.J.3    Bestmann, H.J.4
  • 10
    • 46549088790 scopus 로고    scopus 로고
    • Stereoselective synthesis of 4′-selenonucleosides using the Pummerer glycosylation reaction
    • Jayakanthan, K.; Johnston, B. D.; Pinto, B. M. Stereoselective synthesis of 4′-selenonucleosides using the Pummerer glycosylation reaction Carbohydr. Res. 2008, 343, 1790-1800
    • (2008) Carbohydr. Res. , vol.343 , pp. 1790-1800
    • Jayakanthan, K.1    Johnston, B.D.2    Pinto, B.M.3
  • 12
    • 33748990073 scopus 로고    scopus 로고
    • Stereoselective functionalization of the 1′-position of 4′-thionucleosides
    • For another method for the synthesis of 17, see
    • For another method for the synthesis of 17, see Guana, P.; Kim, H. O.; Lee, H. W.; Tosh, D. K.; Ryu, J.-S.; Choi, S.; Jeong, L. S. Stereoselective functionalization of the 1′-position of 4′-thionucleosides Org. Lett. 2006, 19, 4267-4270
    • (2006) Org. Lett. , vol.19 , pp. 4267-4270
    • Guana, P.1    Kim, H.O.2    Lee, H.W.3    Tosh, D.K.4    Ryu, J.-S.5    Choi, S.6    Jeong, L.S.7
  • 13
    • 14544289555 scopus 로고    scopus 로고
    • Stereoselective synthesis of conformationally constrained 2′-deoxy-4′-thia β-anomeric spirocyclic nucleosides featuring either hydroxyl configuration at C5′
    • DOI 10.1021/jo048071u
    • Dong, S.; Paquette, L. A. Stereoselective synthesis of conformationally constrained 2′-deoxy-4′-thia-β-anomeric spirocyclic nucleosides featuring either hydroxyl configuration at C5′ J. Org. Chem. 2006, 70, 1580-1596 (Pubitemid 40300116)
    • (2005) Journal of Organic Chemistry , vol.70 , Issue.5 , pp. 1580-1596
    • Dong, S.1    Paquette, L.A.2
  • 14
    • 85045799450 scopus 로고
    • High-yield regioselective synthesis of 9-glycosyl guanine nucleosides and analogues via coupling with 2-N-acetyl-6-O-diphenylcarbamoylguanine
    • Zou, R.; Robins, M. J. High-yield regioselective synthesis of 9-glycosyl guanine nucleosides and analogues via coupling with 2- N -acetyl-6- O -diphenylcarbamoylguanine Can. J. Chem. 1987, 65, 1436-1437 (Pubitemid 17127318)
    • (1987) Canadian Journal of Chemistry , vol.65 , Issue.6 , pp. 1436-1437
    • Zou, R.1    Robins, M.J.2
  • 17
    • 0034676266 scopus 로고    scopus 로고
    • Synthesis of 4′- C -ethynyl-β- d - Arabino - and 4′- C -ethynyl-2′-deoxy-β- d - Ribo -pentofuranosylpyrimidines and -purines and evaluation of their anti-HIV activity
    • Ohrui, H.; Kohgo, S.; Kitano, K.; Sakata, S.; Kodama, E.; Yoshimura, K.; Matsuoka, M.; Shigeta, S; Mitsuya, S. Synthesis of 4′- C -ethynyl-β- d-arabino-and 4′- C -ethynyl-2′-deoxy-β- d-ribo -pentofuranosylpyrimidines and -purines and evaluation of their anti-HIV activity J. Med. Chem. 2000, 43, 4516-4525
    • (2000) J. Med. Chem. , vol.43 , pp. 4516-4525
    • Ohrui, H.1    Kohgo, S.2    Kitano, K.3    Sakata, S.4    Kodama, E.5    Yoshimura, K.6    Matsuoka, M.7    Shigeta, S.8    Mitsuya, S.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.