Anti-AIDS agents 87. New bio-isosteric dicamphanoyl-dihydropyranochromone (DCP) and dicamphanoyl-khellactone (DCK) analogues with potent anti-HIV activity.
Publication
, Journal Article
Liu, H-S; Xu, S-Q; Cheng, M; Chen, Y; Xia, P; Qian, K; Xia, Y; Yang, Z-Y; Chen, C-H; Morris-Natschke, SL; Lee, K-H
Published in: Bioorg Med Chem Lett
October 1, 2011
Six 3'R,4'R-di-O-(S)-camphanoyl-2',2'-dimethyldihydropyrano[2,3-f]chromone (DCP) and two 3'R,4'R-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) derivatives were designed, synthesized, and evaluated for inhibition of HIV-1(NL4-3) replication in TZM-bl cells. 2-Ethyl-2'-monomethyl-1'-oxa- and -1'-thia-DCP (5a, 6a), as well as 2-ethyl-1'-thia-DCP (7a) exhibited potent anti-HIV activity with EC(50) values of 30, 38 and 54 nM and therapeutic indexes of 152.6, 48.0 and 100.0, respectively, which were better than or comparable to those of the lead compound 2-ethyl-DCP in the same assay. 4-Methyl-1'-thia-DCK (8a) also showed significant inhibitory activity with an EC(50) of 128 nM and TI of 237.9.
Duke Scholars
Published In
Bioorg Med Chem Lett
DOI
EISSN
1464-3405
Publication Date
October 1, 2011
Volume
21
Issue
19
Start / End Page
5831 / 5834
Location
England
Related Subject Headings
- Virus Replication
- Structure-Activity Relationship
- Stereoisomerism
- Medicinal & Biomolecular Chemistry
- Lymphocytes
- Inhibitory Concentration 50
- Hydroxylation
- Humans
- HIV-1
- HIV Infections
Citation
APA
Chicago
ICMJE
MLA
NLM
Liu, H.-S., Xu, S.-Q., Cheng, M., Chen, Y., Xia, P., Qian, K., … Lee, K.-H. (2011). Anti-AIDS agents 87. New bio-isosteric dicamphanoyl-dihydropyranochromone (DCP) and dicamphanoyl-khellactone (DCK) analogues with potent anti-HIV activity. Bioorg Med Chem Lett, 21(19), 5831–5834. https://doi.org/10.1016/j.bmcl.2011.07.105
Liu, Hong-Shan, Shi-Qing Xu, Ming Cheng, Ying Chen, Peng Xia, Keduo Qian, Yi Xia, et al. “Anti-AIDS agents 87. New bio-isosteric dicamphanoyl-dihydropyranochromone (DCP) and dicamphanoyl-khellactone (DCK) analogues with potent anti-HIV activity.” Bioorg Med Chem Lett 21, no. 19 (October 1, 2011): 5831–34. https://doi.org/10.1016/j.bmcl.2011.07.105.
Liu H-S, Xu S-Q, Cheng M, Chen Y, Xia P, Qian K, et al. Anti-AIDS agents 87. New bio-isosteric dicamphanoyl-dihydropyranochromone (DCP) and dicamphanoyl-khellactone (DCK) analogues with potent anti-HIV activity. Bioorg Med Chem Lett. 2011 Oct 1;21(19):5831–4.
Liu, Hong-Shan, et al. “Anti-AIDS agents 87. New bio-isosteric dicamphanoyl-dihydropyranochromone (DCP) and dicamphanoyl-khellactone (DCK) analogues with potent anti-HIV activity.” Bioorg Med Chem Lett, vol. 21, no. 19, Oct. 2011, pp. 5831–34. Pubmed, doi:10.1016/j.bmcl.2011.07.105.
Liu H-S, Xu S-Q, Cheng M, Chen Y, Xia P, Qian K, Xia Y, Yang Z-Y, Chen C-H, Morris-Natschke SL, Lee K-H. Anti-AIDS agents 87. New bio-isosteric dicamphanoyl-dihydropyranochromone (DCP) and dicamphanoyl-khellactone (DCK) analogues with potent anti-HIV activity. Bioorg Med Chem Lett. 2011 Oct 1;21(19):5831–5834.
Published In
Bioorg Med Chem Lett
DOI
EISSN
1464-3405
Publication Date
October 1, 2011
Volume
21
Issue
19
Start / End Page
5831 / 5834
Location
England
Related Subject Headings
- Virus Replication
- Structure-Activity Relationship
- Stereoisomerism
- Medicinal & Biomolecular Chemistry
- Lymphocytes
- Inhibitory Concentration 50
- Hydroxylation
- Humans
- HIV-1
- HIV Infections