55708-65-1Relevant articles and documents
Nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones with the liberation of H2
Landge, Vinod G.,Yadav, Vinita,Subaramanian, Murugan,Dangarh, Pragya,Balaraman, Ekambaram
supporting information, p. 6130 - 6133 (2019/06/03)
A nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones to access various terminal and internal olefins with the liberation of hydrogen gas is reported.
Synthesis of C- and O-prenylated tetrahydroxystilbenes and O-prenylated cinnamates and their action towards cancer cells
Koolaji, Nooshin,Abu-Mellal, Abdallah,Tran, Van H.,Duke, Rujee K.,Duke, Colin C.
, p. 415 - 422 (2013/07/27)
Synthesis of the naturally occurred C- and O-prenylated tetrahydroxystilbenes and O-prenylated cinnamates was carried out by decarbonylative Heck reaction and selenium dioxide catalysed oxidation, respectively. In the decarbonylative Heck synthetic route, fusion of benzoyl chloride and styrene derivatives was catalysed by an N-heterocyclic carbene system generated in situ by palladium acetate and 1,3-bis(2,6-diisopropylphenyl) imidazolinium chloride to form a E-tetrahydroxystilbene derivative. Formation of allyl ether was subsequently carried out by reaction of the deprotected OH in the A phenyl ring of the stilbene with 3,3-dimethylallyl bromide and a base (sodium hydride) to form O-prenylated tetrahydroxystilbene derivatives. [1,5]-Rearrangement of the isoprenyl unit from O- to C-position in the A ring was carried out at elevated temperature in the presence of magnesium silicate (Florisil) to form the corresponding C-prenylated tetrahydroxystilbene. Formation of O-prenylated cinnamate was first carried out by base catalysed allyl ether formation between 3,3-dimethylallyl bromide and hydroxycinnamic acid methyl ester. The methyl group of the isoprenyl unit was subsequently oxidized using selenium dioxide to form a terminal hydroxyl group. The prenylated tetrahydroxystilbenes and cinnamate synthesized in this study were novel derivatives of piceatannol and methyl 4-(3′-methylbut-2′-enyloxy) cinnamate isolated from propolis in Kangaroo Island, South Australia. The synthetic compounds were tested against K562 cancer cells and potent growth inhibitory activity was observed for E-1-[5-hydroxy-3-methoxy-2-(3-methyl-2- butenyl)phenyl]-2-[4-hydroxy-3-methoxyphenyl]ethene, IC50 = 0.10 μM.
PRENYLATED HYDROXYSTILBENES
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, (2012/11/14)
Prenylated stilbene compounds and the use of such compounds in the treatment of diseases and medical disorders, for example cancer, skin ageing, inflammation, bacterial or fungal infection and immunosuppression.
Synthesis of diarylheptanoids, (5S)-5-acetoxy-1,7-bis(4-hydroxy-3- methoxyphenyl)-3-heptanone and (3S,5S)-3,5-diacetoxy-1,7-bis(4-hydroxy-3- methoxyphenyl)heptane
Sabitha, Gowravaram,Chandrashekhar, Gajangi,Yadagiri, Kurra,Yadav, Jhillu Singh
, p. 1729 - 1735 (2012/01/14)
The total syntheses of the first examples of diarylheptanoid natural products (5S)-5-acetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone 1, and (3S,5S)-3,5-diacetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane 2 isolated from the rhizomes of Zingiber officinale were accomplished using Sharpless epoxidation and cross-metathesis reactions as the key steps.
Synthesis and biological evaluation of isosteric analogs of mandipropamid for the control of oomycete pathogens
Su, Na,Wang, Zhen-Jun,Wang, Li-Zhong,Zhang, Xiao,Dong, Wei-Li,Wang, Hong-Xue,Li, Zheng-Ming,Zhao, Wei-Guang
, p. 101 - 111 (2012/06/01)
A series of isosteric analogs of mandipropamid were designed and synthesized via 'click chemistry'. The amide bond of mandipropamid was substituted by a 1,2,3-triazole functional group. The bioassay results have indicated that some of the title compounds exhibited moderate fungicidal activity against Pseudoperonospora cubensis, and the activity has been systematically studied as a function of molecular structure. The low activity of the mandipropamid analog that contains a lipid chain is likely due to the presence of a weak hydrogen bond donor in the 1,2,3-triazole. Furthermore, we have performed the molecular modeling and found that N-methylamide could be more effective than amide as the surrogates to 1,2,3-triazole, which ultimately leads to a longer distance (1.1A longer) between the two substitutes in the 1,4-disubstituted 1,2,3-triazole compound.
Total synthesis and biological evaluation of viscolin, a 1,3-diphenylpropane as a novel potent anti-inflammatory agent
Su, Chung-Ren,Shen, Yuh-Chiang,Kuo, Ping-Chung,Leu, Yann-Lii,Damu, Amooru G.,Wang, Yea-Hwey,Wu, Tian-Shung
, p. 6155 - 6160 (2007/10/03)
Total synthesis of viscolin, an anti-inflammatory 1,3-diphenylpropane isolated from Viscum coloratum, employing the Wittig reaction is reported. Key steps in the synthesis of viscolin depend on the selection of protecting groups to maintain the para hydroxyl group that is the most critical chemical structure influencing the biological activity of viscolin and the utilization of microwave-assisted Wittig olefination reaction. Anti-inflammatory potency of the synthetic viscolin, its precursor product 16, and its analogue 17, through their effects on reactive oxygen species (ROS), nitric oxide (NO), and pro-inflammatory cytokine production in leukocytes and microglial cells were evaluated. Excellent inhibition of ROS and NO production in inflammatory cells could confer the synthetic viscolin to be a potent anti-inflammatory agent for the treatment of oxidative stress-induced diseases.
