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Dihydroseselin Sale

(Synonyms: 二氢邪蒿内酯) 目录号 : GC60777

Dihydroseselin是7-hydroxycoumarin的衍生物。7-hydroxycoumarin是是香豆素家族的天然产物,是一种荧光化合物,可用作防晒剂。

Dihydroseselin Chemical Structure

Cas No.:2221-66-1

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1mg
¥900.00
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产品描述

Dihydroseselin is a 7-hydroxycoumarin derivative. 7-hydroxycoumarin is a natural product of the coumarin family, is a fluorescing compound which can be used as a sunscreen agent[1]

[1]. Jetter, M. M., et al. Novel syntheses of dihydroxanthyletin and dihydroseselin derivatives. Journal of Heterocyclic Chemistry, 1990:27(4), 995-997.

Chemical Properties

Cas No. 2221-66-1 SDF
别名 二氢邪蒿内酯
Canonical SMILES O=C1C=CC2=CC=C3C(CCC(C)(C)O3)=C2O1
分子式 C14H14O3 分子量 230.26
溶解度 储存条件 Store at -20°C
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1 mM 4.3429 mL 21.7146 mL 43.4292 mL
5 mM 0.8686 mL 4.3429 mL 8.6858 mL
10 mM 0.4343 mL 2.1715 mL 4.3429 mL
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Research Update

Anti-AIDS agents. 15. Synthesis and anti-HIV activity of dihydroseselins and related analogs

J Med Chem 1994 Nov 11;37(23):3947-55.PMID:7525962DOI:10.1021/jm00049a014.

Forty-two dihydroseselins based on the structure of suksdorfin (1) were synthesized in order to evaluate their anti-HIV activity. These synthetic derivatives include 3',4'-di-O-acyl- and 3'- or 4'-O-acyl-cis-dihydroseselins (8-21) and 3',4'-trans-dihydroseselins with O-acyl and/or O-alkyl groups at the 3' and 4' positions (6, 22-43). Two 4'-azido (44, 45) and three 4'-alkylamido (46, 48, 49) derivatives were also prepared. By using optically pure reagents, three pairs of diastereoisomers were synthesized and separated as optically pure compounds (14, 15; 16, 17; 38, 39). Together with the above synthetic derivatives, seselin (3) and (+/-)-cis-(4), (+)-cis- (5), and (+/-)-trans-dihydroseselin-3',4'-diol (7) were also tested for their in vitro anti-HIV activity. An optically pure compound, 3',4'-di-O-(-)-camphanoyl-(+)-cis-khellactone (16), showed potent inhibitory activity and remarkable selectivity against HIV replication. The EC50 value and in vitro therapeutic index (TI) of 16 are 4 x 10(-4) microM and 136,719, respectively, which are better than those shown by AZT in the same assay. In addition, compound 16 is also active against HIV replication in a monocytic cell line and in peripheral blood mononuclear cells (PBMCs). Our in vitro assay indicated that, like compound 1, compound 16 is not an inhibitor of HIV-1 reverse transcriptase. Moreover, the anti-HIV activity of 16 is stereoselective as its three diastereoisomers (17, 38, 39) are at least 10,000 times less active. Since other synthetic Dihydroseselin derivatives with different substituents or without any substituents are inactive or are active only at much higher concentration, the antiviral potency of 16 could be associated with the camphanoyl moieties of its structure. Therefore, compound 16 represents a unique coumarin structure with promising anti-HIV activity.

Suksdorfin: an anti-HIV principle from Lomatium suksdorfii, its structure-activity correlation with related coumarins, and synergistic effects with anti-AIDS nucleosides

Bioorg Med Chem 1994 Oct;2(10):1051-6.PMID:7773621DOI:10.1016/s0968-0896(00)82054-4.

Suksdorfin (1), which is isolated from the fruit of Lomatium suksdorfii, was found to be able to inhibit HIV-1 replication in the T cell line, H9, with an average EC50 value of 2.6 +/- 2.1 microM. In addition, suksdorfin was also suppressive during acute HIV-1 infections of peripheral blood mononuclear cells, monocyte/macrophages and the promonocytic cell line, U937. Combinations of 1 and the anti-HIV nucleosides ddI and ddC demonstrated statistical synergy in inhibiting HIV-1 replication (ddC > ddI). However, the viral inhibition mediated by combining 1 with AZT was not statistically synergistic. Furthermore, the presence of suksdorfin did not antagonize the suppression mediated by the three nucleoside reverse transcriptase inhibitors. Comparison of the structure and activity of 1 with those of ten related compounds indicated that the Dihydroseselin type of pyranocoumarin possessing a 4'-isovaleryl group is important to suksdorfin's enhanced anti-HIV activity.