title: Synthesis of seven-membered iminosugars fused thiazolidin-4-one and benzthiazinan-4-one and their HIV-RT inhibitory activity.
abstract: Novel seven-membered iminosugars fused thiazolidin-4-one and benzthiazinan-4-one were conveniently synthesized by the tandem Staudinger/aza-Wittig/cyclization reaction under microwave radiation. Benzoyl group (Bz) migrations were found in the synthesis of 8c and 9b using D-galactoside or D-mannoside as starting materials, respectively, which was suggested by HMBC and X-ray. The new bi/tricyclic iminosugars 3~4(a-d) and 5(b-d) were examined for their HIV reverse transcriptase (RT) inhibitory activities. The result showed that all compounds except 5b could effectively inhibit RT activity. Among them, compounds 3c and 4c were the best ones with the IC50 values of RT inhibitory activities of 2.11 µM and 2.73 µM, respectively. Structure-activity relationship analysis suggested that the phenyl group in the tricyclic azasugars was beneficial for their anti-HIV RT activity.
authors.affiliation: Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China.
authors.forename: Yuheng
authors.initials: Y
authors.lastname: Hou
authors.affiliation: Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China.
authors.forename: Shunkai
authors.initials: S
authors.lastname: Xing
authors.affiliation: Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China.
authors.forename: Jie
authors.initials: J
authors.lastname: Shao
authors.affiliation: Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China.
authors.forename: Zhuqing
authors.initials: Z
authors.lastname: Yin
authors.affiliation: Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China.
authors.forename: Le
authors.initials: L
authors.lastname: Hao
authors.affiliation: Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China.
authors.forename: Tianyu
authors.initials: T
authors.lastname: Yang
authors.affiliation: Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China.
authors.forename: Hongzhi
authors.initials: H
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China.
authors.forename: Mo
authors.initials: M
authors.lastname: Zhu
authors.affiliation: Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China; National Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, China. Electronic address: hua-todd@163.com.
authors.forename: Hua
authors.initials: H
authors.lastname: Chen
authors.affiliation: Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China; National Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, China. Electronic address: lixl@hbu.cn.
authors.forename: Xiaoliu
authors.initials: X
authors.lastname: Li
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D057075:Enzyme Assays; D005697:Galactosides / Q000737:chemistry; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D054303:HIV Reverse Transcriptase / Q000037:antagonists & inhibitors / Q000737:chemistry*; D015497:HIV-1 / Q000737:chemistry / Q000187:drug effects / Q000201:enzymology; D050111:Imino Sugars / Q000737:chemistry*; D008362:Mannosides / Q000737:chemistry; D008872:Microwaves; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013843:Thiazines / Q000737:chemistry*; D013844:Thiazoles / Q000737:chemistry*
chemical_list: C543931:1,3-benzthiazinan-4-one; D019380:Anti-HIV Agents; D005697:Galactosides; D006001:Glycoconjugates; D050111:Imino Sugars; D008362:Mannosides; D018894:Reverse Transcriptase Inhibitors; D013843:Thiazines; D013844:Thiazoles; D054303:HIV Reverse Transcriptase
keywords: Anti-HIV RT activity; Benzthiazinan-4-one; Seven-membered iminosugar; Staudinger/aza-Wittig; Thiazolidin-4-one