- Bioinspired Total Synthesis of Bussealin e
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The first total synthesis of bussealin E, a natural product with a unique cycloheptadibenzofuran scaffold, is reported. A strategy inspired by a proposed biosynthesis was employed whereby a diphenylpropane derivative underwent an oxidative phenolic coupling to forge the tetracyclic ring system. The synthesis of the diphenylpropane featured a key sp2-sp3 Hiyama coupling between a vinyldisiloxane and a benzylic bromide.
- Twigg, David G.,Baldassarre, Leonardo,Frye, Elizabeth C.,Galloway, Warren R. J. D.,Spring, David R.
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p. 1597 - 1599
(2018/03/23)
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- The synthesis of methylated epigallocatechin gallate
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Synthesis of methylated epigallocatechin gallate from (-)-epigallocatechin gallate and propylgallate was accomplished using a benzyl (Bn) group as a protecting group for phenols. This methodology provided (-)-epigallocatechin-3-(4-O-methylgallate), which
- Lai, Ronghui,Zhao, Wenfang,Huang, Yahui,Zhou, Wen,Wu, Chunlan,Lai, Xingfei,Zhao, Wenxia,Zhang, Ming
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p. 472 - 475
(2015/12/26)
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- Total synthesis of (±)-megistophylline I
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(±)-Megistophylline I (1), carrying a dienone residue in the acridone framework, was synthesized using the Claisen rearrangement to introduce a prenyl group as a key step.
- Nishihama, Yuko,Ishikawa, Yuichi,Nishiyama, Shigeru
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scheme or table
p. 2801 - 2804
(2009/09/28)
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- Synthesis, crystal structure, and growth inhibition of human hepatoma cell (HepG2) of polyphenolic compounds based on gallates
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Seven compounds (1-7) based on gallate were synthesized and characterized by elemental analysis, 1H NMR, and MS spectra. 2-(3,5-Dibenzyloxy-4- methoxy)phenyl-2-propanol (6) was a new compound. Methyl 3,5-dihydroxy-4- methoxybenzoate (3), methyl 3,5-dibenzyloxy-4-methoxybenzoate (4), 3,5-dibenzyloxy-4-methoxybenzyl alcohol (5), and compound 6 were structurally determined by single-crystal X-ray diffraction for the first time. Crystallography data for 3: space group P21212 1; a = 4.0750(8) A, b = 7.5880(15) A, c = 29.802(6) A; V = 921.5(3) A3 Z = 4. 4: space group P-1; a = 10.068(2) A b = 10.499(2) A, c = 11.388(2) A; α = 76.84(3)°, β= 66.79(3)°, γ = 64.10(3)°; V = 993.0(3) A3, Z = 2. 5: space group P-1; a = 8.1410(16) A, b = 8.7590(18) A, c = 12.879(3) A; α = 91.66(3)°, β= 94.69(3)°, γ = 91.73(3)°; V = 914.4(3) A3; Z = 2. 6: space group P21/c; a = 5.8100(12) A, b = 15.778(3) A, c = 23.237(5) A; β= 96.09(3)°; V = 2118.1(7) A3; Z = 4. All of the seven compounds were evaluated for the inhibition of growth of human hepatoma (HepG2) cells. Comparison with the positive-control 5-fluorouracil (IC50 51.6 μmol/L), 5 showed stronger cytotoxic activity with an IC50 around 15.3 μmol/L, while IC50 value of 3 was 90.3 μmol/L. The effect of slight structural variations in this series of compounds was found to cause a marked change in their activity against HepG2 cells.
- Xiao, Zhu-Ping,Fang, Rui-Qin,Shi, Lei,Ding, Hui,Xu, Chen,Zhu, Hai-Liang
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p. 951 - 957
(2008/03/28)
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- Synthesis and PAF antagonist activity of some 2,5-diaryltetrahydrofurans incorporating PAF-like functional groups
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This paper describes the synthesis and structure-activity relationships of a series of 2,5-diaryltetrahydrofurans, as specific and potent antagonists at the rabbit washed platelet activating factor (PAF) receptor. The methoxyl groups in the known PAF antagonist L-652,731 were replaced with functional groups present in PAF and in the 'PAF-like' antagonists. Activity was generally retained or enhanced when one aryl ring in L-652,731 was elaborated; however incorporation of these functional groups into both of the aryl rings greatly reduced or abolished activity. These results are discussed in relation to a putative model for the PAF receptor.
- Smith,Blackwell,Demaine,Garland,Hodson,Hyde,Parke,Rose,Sawyer,Tilling
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p. 347 - 358
(2007/10/03)
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- N,N'-Heptamethylenebis(4-methoxybenzamide)
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4-(Q-O)-4'-R1 -N,N'-alkylenebis(benzamides), N,N'-alkylenebis(3,4-methylenedioxybenzamides) or N,N'-alkylenebis[4-(lower-alkoxy)benzamides], having endocrinological properties, where Q is lower-alkyl, lower-alkoxyalkyl, lower-alkenyl, halo-lower-alkyl, halo-lower-alkenyl, lower-cycloalkyl, phenyl and BN-(lower-alkyl) where BN is di-(lower-alkyl)amino or a saturated N-heteromonocyclic radical having from five to seven ring atoms and alkylene has at least five carbon atoms between its two connecting linkages and R1 is Q-O-, hydrogen, lower-alkoxy, lower-alkyl, halo, benzyloxy, hydroxy, di-(lower-alkyl)amino, nitro, amino or trihalomethyl are prepared preferably by reacting the appropriate diamine or N-(aminoalkyl)-benzamide with two or one molar equivalents, respectively, of the appropriate benzoyl halide.
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