10022-35-2Relevant articles and documents
A new approach to sesquiterpene arenes of the 9,11-drimenyl type (=[(1E,2RS,4aRS,8aRS)-octahydro-2,5,5,8a-tetramethylnaphthalen-1(2H)-ylidene] methyl type)
Bernet, Andreas,Seifert, Karlheinz
, p. 784 - 796 (2006)
A new reaction sequence for the synthesis of the sesquiterpene arenes (±)-wiedendiol B ((±)-1) and the siphonodictyal B derivative (±)- 21 consists in the coupling of (±)-drimanoyl chloride ((±)-3) with lithiated and appropriately substituted aromatic synthons to furnish the ketones (±)-7 and (±)-17 which were reduced to the benzyl alcohols (±)-8a,b and (±)-18a,b, respectively (Schemes 5, 4, and 12). The 9,11-double bond of the drimenes (±)-9 and (±)-19 was formed by elimination of H2O from the benzyl alcohols (±)-8a,b and (±)-18a,b (Schemes 6 and 12). New alternatives were applied to this elimination reaction involving either the pyridine · SO3 complex or chloral as reagents.
Unified syntheses of gramniphenols F and G, cicerfuran, morunigrol C and its derivative
Damodar, Kongara,Kim, Jin-Kyung,Jun, Jong-Gab
, p. 1183 - 1186 (2016/03/09)
The first syntheses of natural benzofurans, gramniphenols F and G, morunigrol C and its 3′,5′-di-O-methyl analogue along with the synthesis of cicerfuran are achieved by a unified synthetic sequence using 7-hydroxycoumarin, 5-bromoresorcinol, 2,4-dihydroxybenzaldehyde, and sesamol as building blocks. Ramirez gem-dibromoolefination, Miyaura borylation, Suzuki coupling have been successfully exploited in the synthesis. Additionally, their anti-inflammatory effects were also investigated in lipopolysaccharide (LPS)-induced RAW-264.7 macrophages. The compounds exhibited significant inhibition of iNOS mediated nitric oxide (NO) production with no cytotoxicity at 10 μM concentration and IC50 values are found in the range from 9.1 to 25.2 μM.
The first total synthesis of Cicerfuran utilizing a one-pot synthesis of hydroxylated benzofurans
Novák, Zoltán,Timári, Géza,Kotschy, András
, p. 7509 - 7513 (2007/10/03)
A simple one-pot procedure was elaborated for the preparation of hydroxylated benzofurans from halogenated phenols and was successfully applied to the first total synthesis of Cicerfuran, a natural defence agent of wild chickpea.
Total Synthesis of Carpacin and Its Geometric Isomer as a Cancer Chemopreventer
Tseng, Tsui-Hwa,Tsheng, Yen-Min,Lee, Yean-Jang,Hsu, Hsing-Ling
, p. 1165 - 1170 (2007/10/03)
Carpacin (1a), an antidepressant in Asiatic folk medicine from the Carpano tree, is achieved in which the longest linear sequence is only four steps in over all yield 67 percent from commercially available Sesamol. The key transformations in the synthesis are the selective palladium-catalyzed coupling reactions of aryl bromide with Grignard reagents. The first preparation of its geometric isomer (1b) is described. Highlights of the synthesis include Pd-ctalyzed coupling, selective hydrogenation, and Wittig reactions. Carpacin was examined as a potential inhibitor of carcinogenesis.
Synthesis of Alkoxy-Substituted Diaryl Compounds and Correlation of Ring Separation with Inhibition of Tubulin Polymerization: Differential Enhancement of Inhibitory Effects under Suboptimal Polymerization Reaction Conditions
Getahun, Zelleka,Jurd, Leonard,Chu, Ping S.,Lin, Chii M.,Hamel, Ernest
, p. 1058 - 1067 (2007/10/02)
A number of cytostatic compounds (2-4, 7, and 8), which can be described as "diaryl", inhibit tubulin polymerization, cause cells to accumulate in mitotic arrest, and competitively inhibit the binding of colchicine to tubuline.They differ, however, in the separation of the two aryl moieties.To attempt to understand this variability we prepared a series of analogues modeled on 3 and 4 ("benzodioxole series") and on 7 and 8 ("combretastatin series") which differed only in the number of methylene units (ranging from none to four) separating the aryl moieties.These compounds were evaluated for their effects on tubulin polymerization, colchicine binding, and the growth of L1210 murine leukemia cells.In terms of inhibitory effects on tubulin polymerization, for the combretastatin series there was an optimal separation of the two phenyl rings by a two-carbon bridge (compound 24), with progressively decreasing inhibitory activity when the separation was by one carbon (20), three carbons (25), or four carbons (28) (the biphenyl analogue 16 was inactive).The benzodioxole series, however, did not permit us to generalize this finding, because the least active agents prepared (39 and 40) had a two-carbon bridge, while those with one- (5 and 6) and three-carbon (46 and 47) bridges were nearly equivalent in potency.Submicromolar (IC50 values for inhibition of L1210 cell growth were only obtained for compounds 20 (IC50 0.2 μM), 24 (0.07 μM), and 25 (0.4 μM).While evaluating the effects of these agents on tubulin polymerization, we noted with the combretastatin series and with several standard agents that apparent potency (in terms of IC50 values) was always lower if the reaction was performed at 30 deg C, with 0.25 mM MgCl2, than at 37 deg C, with 1.0 mM MgCl2.This enhancement of IC50 values in the former system as compared with the latter was particularly dramatic for the less active agents (e.g., 28) as compared with the more active (e.g., 24).
