4.1 Article

Synthesis and antiviral activity of some 2-substituted 3-formyl-and 3-cyano-5,6-dichloroindole nucleosides

期刊

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
卷 24, 期 10-12, 页码 1613-1626

出版社

TAYLOR & FRANCIS INC
DOI: 10.1080/15257770500265836

关键词

indole nucleoside; nucleoside analog; TCRB; antiviral; human cytomegalovirus (HCMV)

资金

  1. NATIONAL INSTITUTE OF ALLERGY AND INFECTIOUS DISEASES [U19AI031718, P01AI046390] Funding Source: NIH RePORTER
  2. NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [T32GM007767] Funding Source: NIH RePORTER
  3. NIAID NIH HHS [U19-AI31718, P01-AI46390] Funding Source: Medline
  4. NIGMS NIH HHS [T32-GM07767] Funding Source: Medline

向作者/读者索取更多资源

A series of dichlorinated indole nucleosides has been synthesized and tested for activity against human cytomegalovirus (HCMV) and herpes simplex virus type-1 (HSV-1) and for cytotoxicity. The isopropylidene-protected analogs of the previously reported 3-formyl-2,5,6-trichloro-1-(beta-D-ribofuranosyl)indole (FTCRI) and 3-cyano-2,5,6-trichloro-1-(beta-D-ribofuranosyl)indole (CTCRI) were modified by nucleophilic displacement of the 2-chloro substituent using secondary amines. Deprotection of the intermediates provided 2-substituted analogs of FTCRI and CTCRI in good yield. There was a significant difference in reactivity between the isopropylidene-protected and the fully deprotected FTCRI and CTCRI with respect to nucleophilic displacement of the 2-chloro substituent using dialkylamines. This difference in reactivity was not observed with monoalkylamines or with alkoxides, and the corresponding 2-alkylamino- and 2-methoxy substituted analogs were synthesized from FTCRI and CTCRI directly. None of the synthesized analogs demonstrated potent antiviral activity without some corresponding cytotoxicity.

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