- Alpha,beta-unsaturated ketone derivatives, preparation method of derivatives and application of derivatives as medicines
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The invention relates to the technical field of medicine, and proposes alpha,beta-unsaturated ketone derivatives and a preparation method thereof. The derivatives have a structural general formula represented by a formula I shown in the specification, whe
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Paragraph 0073-0074; 0077-0078
(2019/12/15)
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- KOtBu-Mediated Domino Isomerization and Functionalization of Aromatic Allylic Alcohols
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Transition-metal- as well as ligand-free base-mediated domino isomerization and alkylation of allylic alcohols is presented. This protocol features the conversion of simple allylic alcohols into the corresponding ketones through isomerization in the presence of a simple base. Significantly, these in situ generated ketones subsequently undergo alkylation with styrenes as electrophiles, in a domino one-pot fashion, as an atom- and step-economical chemical process.
- Suchand, Basuli,Satyanarayana, Gedu
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p. 3886 - 3895
(2017/07/22)
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- Synthesis, Evaluation, and Mechanism Study of Novel Indole-Chalcone Derivatives Exerting Effective Antitumor Activity Through Microtubule Destabilization in Vitro and in Vivo
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Twenty-nine novel indole-chalcone derivatives were synthesized and evaluated for antiproliferative activity. Among them, 14k exhibited most potent activity, with IC50 values of 3-9 nM against six cancer cells, which displayed a 3.8-8.7-fold increase in activity when compare with compound 2. Further investigation revealed 14k was a novel tubulin polymerization inhibitor binding to the colchicine site. Its low cytotoxicity toward normal human cells and nearly equally potent activity against drug-resistant cells revealed the possibility for cancer therapy. Cellular mechanism studies elucidated 14k arrests cell cycle at G2/M phase and induces apoptosis along with the decrease of mitochondrial membrane potential. Furthermore, good metabolic stability of 14k was observed in mouse liver microsomes. Importantly, 14k and its phosphate salt 14k-P inhibited tumor growth in xenograft models in vivo without apparent toxicity, which was better than the reference compound CA-4P and 2. In summary, 14k deserves consideration for cancer therapy.
- Yan, Jun,Chen, Jie,Zhang, Shun,Hu, Jinhui,Huang, Ling,Li, Xingshu
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p. 5264 - 5283
(2016/07/06)
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- Magnesium salt promoted tandem nucleophilic addition-Oppenauer oxidation of aldehydes with organozinc reagents
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A magnesium salt promoted synthesis of ketones via tandem nucleophilic addition-Oppenauer oxidation of aldehydes using organozinc chemistry was demonstrated. Magnesium salts concomitantly generated via magnesium metal mediated organohalide zincation exhibit high efficacy for nucleophilic addition of organozinc reagents to aromatic aldehydes and thereafter Oppenauer oxidation whereby ketones are formed in high to excellent yields.
- Fu, Ying,Zhao, Xing Ling,Hügel, Hulmet,Huang, Danfeng,Du, Zhengyin,Wang, Kehu,Hu, Yulai
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supporting information
p. 9720 - 9724
(2016/10/31)
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- Efficient synthesis of alkyl aryl ketones & ketals via palladium-catalyzed regioselective arylation of vinyl ethers
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The combination of Pd(OAc)2 with 1,3-bis(diphenylphosphino) propane (dppp) in ethylene glycol constitutes a high-performance catalytic system for highly regioselective arylation of a range of electron-rich vinyl ethers by aryl bromides to provide, upon hydrolysis, alkyl aryl ketones and cyclic ketals in good yields with up to 3.75 × 105 TON and 15625 h-1 TOF.
- Liu, Mingcui,Hyder, Zeynab,Sun, Yawei,Tang, Weijun,Xu, Lijin,Xiao, Jianliang
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supporting information; experimental part
p. 2012 - 2015
(2010/07/04)
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- NEW ANALOGS OF POLYSPHORIN AND USES THEREOF FOR TREATING OR PREVENTING MALARIA
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The present invention discloses new analogs of polysphorin and their uses as antimalarial drugs which are highly effective in the hepatic phase of the disease. The present invention further discloses a new method for preparing these compounds.
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Page/Page column 23-24
(2010/04/28)
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- Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity
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The α-methyl chalcone SD400 is a potent inhibitor of tubulin assembly and possesses potent anticancer activity. Various chalcone analogues were synthesized and evaluated for their cell growth inhibitory properties against the K562 human chronic myelogenous leukemia cell line (SD400, IC50 0.21 nM; combretastatin A4 CA4, IC50 2.0 nM). Cell cycle analysis by flow cytometry indicated that these agents are antimitotic (SD400, 83% of the cells are in G2/M phase; CA4 90%). They inhibit tubulin assembly at low concentration (SD400, IC50 0.46 μM; CA4, 0.10 μM) and compete with [3H]colchicine for binding to tubulin (8% [3H]colchicine remained bound to tubulin after competition with SD400 or CA4). Upon treatment with SD400, remarkable cell shape changes were elicited in HUVEC cells, consistent with vasculature damaging activity.
- Ducki, Sylvie,Rennison, David,Woo, Meiko,Kendall, Alexander,Chabert, Jeremie Fournier Dit,McGown, Alan T.,Lawrence, Nicholas J.
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experimental part
p. 7698 - 7710
(2010/03/24)
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- Application of the McMurry coupling reaction in the synthesis of tri- and tetra-arylethylene analogues as potential cancer chemotherapeutic agents
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Structural redesign of selected non-steroidal estrogen receptor binding compounds has previously been successful in the discovery of new inhibitors of tubulin assembly. Accordingly, tetra-substituted alkene analogues (21-30) were designed based in part on combinations of the structural and electronic components of tamoxifen and combretastatin A-4 (CA4). The McMurry coupling reaction was used as the key synthetic step in the preparation of these tri- and tetra-arylethylene analogues. The structural assignment of E, Z isomers was determined on the basis of 2D-NOESY experiments. The ability of these compounds to inhibit tubulin polymerization and cell growth in selected human cancer cell lines was evaluated. Although the compounds were found to be less potent than CA4, these analogues significantly advance the known structure-activity relationship associated with the colchicine binding site on β-tubulin.
- Tanpure, Rajendra P.,Harkrider, Amanda R.,Strecker, Tracy E.,Hamel, Ernest,Trawick, Mary Lynn,Pinney, Kevin G.
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experimental part
p. 6993 - 7001
(2009/12/24)
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- Biocatalytic promiscuity of lipase in chemoselective oxidation of aryl alcohols/acetates: a unique synergism of cal-b and [hmim]br for the metal-free h2o2 activation
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A unique synergistic combination of lipase and Ionic liquid [hmlm]Br Is reported for metal-free H2O2 activation, which is the first example of blocatalytlc promiscuity of CAL-B for chemoselectlve oxidation of aryl alcohols/acetates. The catalytic system exhibits excellent functional group compatibility under neutral conditions besides reusability up to ten cycles thereby making the process economically and environmentally viable.
- Sharma, Upendra K.,Sharma, Nandini,Kumar, Rakesh,Kumar, Rajesh,Sinha, Arun K.
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supporting information; experimental part
p. 4846 - 4848
(2010/01/16)
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- An efficient and chemoselective deprotection of aryl- and styrenyldithioketals (acetals)
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In this Letter, an efficient and chemoselective deprotection of aryl- and styrenyldithioketals (acetals) is described. After being carefully examined, 10% Pd/C and Amberlite 120 in refluxing methanol was found to be an excellent condition for the chemoselective deprotection of aryl- and styrenyldithioketals (acetals) in good yields. Under this condition, no deprotection and no reduction of alkyldithioketals (acetals) was observed.
- Wang, Eng-Chi,Wu, Chien-Huang,Chien, Shih-Chang,Chiang, Wen-Chang,Kuo, Yueh-Hsiung
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p. 7706 - 7708
(2008/03/30)
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- Unexpected formation of aryl dialkyl carbinol as a side product from the reaction of methoxyarylaldehydes with Grignard reagents
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In the attempted formation of secondary aryl alkyl carbinols from the reaction of methoxyarylaldehydes with Grignard reagents, aryl dialkyl carbinols were formed as unexpected side products. A mechanism for their formation is proposed.
- Sharma, Anuj,Joshi, Bhupendra P.,Singh, Narendra P.,Sinha, Arun K.
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p. 847 - 851
(2007/10/03)
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- Microwave- and ultrasound-assisted semisynthesis of natural methoxylated propiophenones from isomeric mixture of phenylpropenes in minutes
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A rapid and practical semisynthesis of natural methoxylated propiophenones (3a-3f) is realized by reacting stereo- and regio-isomeric mixture of phenylpropenes (1a-1f) with a catalytic amount of palladium chloride - sodium formate in formic acid, methanol, and water (2:1:2) into single product phenylpropanes (2a-2f) followed by its oxidation with 2,3-dichloro-5,6- dicyanobenzoquinone (DDQ) in wet dioxane, containing a few drops of formic acid. Conventional, ultrasound, and microwave heating were compared through these studies.
- Joshi, Bhupendra P.,Sharma, Anuj,Sinha, Arun K.
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p. 1826 - 1832
(2007/10/03)
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- Ultrasound-assisted convenient synthesis of hypolipidemic active natural methoxylated (E)-arylalkenes and arylalkanones
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An ultrasound-assisted convenient method was developed for the conversion of toxic methoxylated cis-isomer of arylalkenes into its hypolipidemic active trans-isomer. Treatment of cis-isomer or mixture of all three isomers (1a-1j) with ammonium formate and 10% Pd/C gave arylalkanes (2a-2j), which upon oxidation with DDQ in anhydrous dioxane containing a little amount of silica gel, provided (E)-arylalkenes (3a-3g) in 42-72% yield depending upon the substituents attached at the aryl ring. The same method, upon addition of a few drops of water, provided hypolipidemic active arylalkanones (3h-3j) in 59-65% yield.
- Joshi, Bhupendra P.,Sharma, Anuj,Sinha, Arun K.
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p. 3075 - 3080
(2007/10/03)
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- Potent antimitotic and cell growth inhibitory properties of substituted chalcones
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A series of substituted chalcones was synthesised and screened for cytotoxic activity against the K562 human leukaemia cell line. (E)-3-(3'- Hydroxy-4'-methoxyphenyl)-2-methyl-1-(3',4',5'-trimethoxyphenyl)-prop-2-en- 1-one [IC50 (K562) 0.21 nM] was found to be the most active. A relationship between the conformation and cytotoxicity of the chalcones is discussed.
- Ducki, Sylvie,Forrest, Richard,Hadfield, John A.,Kendall, Alex,Lawrence, Nicholas J.,McGown, Alan T.,Rennison, David
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p. 1051 - 1056
(2007/10/03)
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- A New Synthesis of 1-n-Alkyl-3,5-dimethoxybenzenes (Olivetol Dimethyl Ether and Homologs)
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An efficient method is reported for the synthesis of 1-n-alkyl-3,5-dimethoxybenzenes, useful intermediates in the synthesis of cannabinoids, from the readily available and cheap 3,4,5-trimethoxybenzoic acid.The key step is the electron-transfer induced highly regioselective demethoxylation of 1-n-alkyl-3,4,5-trimethoxybenzenes.
- Azzena, Ugo,Denurra, Teresa,Fenude, Emma,Melloni, Giovanni,Rassu, Gloria
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