118017-13-3Relevant articles and documents
4-(Dimethylamino)pyridinium Chlorochromate, a New Selective Reagent for the Oxidation of Allylic and Benzylic Alcohols
Guziec, Frank S.,Luzzio, Frederick A.
, p. 1787 - 1789 (1982)
4-(Dimethylamino)pyridinium chlorochromate (3) is a mild selective reagent for the oxidation of complex allylic and benzylic alcohols to the corresponding carbonyl compounds.
Design, Synthesis, and Activity Evaluation of Novel Acyclic Nucleosides as Potential Anticancer Agents in Vitro and in Vivo
Hao, Er-Jun,Li, Gong-Xin,Liang, Yu-Ru,Xie, Ming-Sheng,Wang, Dong-Chao,Jiang, Xiao-Han,Cheng, Jia-Yi,Shi, Zhi-Xian,Wang, Yang,Guo, Hai-Ming
, p. 2077 - 2109 (2021)
In the present work, 103 novel acyclic nucleosides were designed, synthesized, and evaluated for their anticancer activities in vitro and in vivo. The structure-activity relationship (SAR) studies revealed that most target compounds inhibited the growth of colon cancer cells in vitro, of which 3-(6-chloro-9H-purin-9-yl)dodecan-1-ol (9b) exhibited the most potent effect against the HCT-116 and SW480 cells with IC50 values of 0.89 and 1.15 μM, respectively. Furthermore, all of the (R)-configured acyclic nucleoside derivatives displayed more potent anticancer activity compared to their (S)-counterparts. Mechanistic studies revealed that compound 9b triggered apoptosis in the cancer cell lines via depolarization of the mitochondrial membrane and effectively inhibited colony formation. Importantly, compound 9b inhibited the growth of the SW480 xenograft in a mouse model with low systemic toxicity. These results indicated that acyclic nucleoside compounds are viable as potent and effective anticancer agents, and compound 9b may serve as a promising lead compound that merits further attention in future anticancer drug discovery.
Total syntheses of melodienones by redox isomerization of propargylic alcohols
Dong, Chunmao,Peng, Weiwei,Wang, Huan,Zhang, Xiao,Zhang, Jun,Tan, Guishan,Xu, Kangping,Zou, Zhenxing,Tan, Haibo
, p. 5077 - 5081 (2021/06/21)
A remarkable base-promoted methodology for the rapid construction of the (E)- and (Z)-γ-oxo-α,β-alkenoic ester skeletons from readily accessible vinyl propargylic alcohols through modified redox isomerization was uncovered. This approach manifested its hi
Preparation method of anti-tumor natural medicine melodienones and analogues thereof
-
, (2021/09/04)
The invention discloses a preparation method of anti-tumor natural medicine melodienones and analogues thereof. The preparation method comprises the following steps: reacting benzoyl chloride (9) and cis-1, 2-dimethylol ethylene (10) under a strong alkali
Sequencing cross-metathesis and non-metathesis reactions to rapidly access building blocks for synthesis
Sirasani, Gopal,Paul, Tapas,Andrade, Rodrigo B.
experimental part, p. 2197 - 2205 (2011/04/22)
The olefin cross-metathesis reaction has been sequenced with four common organic transformations in a one- or two-pot manner to rapidly access useful building blocks. Those reactions are: (1) phosphorus-based olefination (e.g., Wittig and Horner-Wadsworth-Emmons); (2) hydride reduction; (3) Evans propionate aldol reaction; (4) Brown allyl- and Roush crotyl-boration. The products of these reactions include stereodefined 2,4-dienoates, trans allylic alcohols, syn-propionate aldols, and chiral non-racemic homoallylic alcohols, respectively. Many of these intermediates have been carried further to natural products, demonstrating the utility of the methodology.
Nazarov approach to 4-benzoyloxymethyl-cyclopent-2-enone, a precursor to the helminthosporols
Belardi, Justin K.,Curtis, Lindsay A.,Clareen, Steven S.,Shimp, Heidi L.,Leimkuhler, Catherine E.,Simonowicz, Nicole L.,Casillas, Eduard
, p. 1633 - 1640 (2007/10/03)
A short, scalable route to 4-hydroxymethylcyclopent-2-enone, based upon a silicon-directed Nazarov cyclization, is described. Noteworthy in this study is the success of the cyclization with an oxygenated substrate. Copyright Taylor & Francis, Inc.
Applications of olefin cross metathesis to commercial products
Pederson, Richard L.,Fellows, Ingrid M.,Ung, Thay A.,Ishihara, Hiroki,Hajela, Sharad P.
, p. 728 - 735 (2007/10/03)
In this paper, we will demonstrate the value of olefin cross metathesis as an effective synthetic tool for applications in the agrochemical and pharmaceutical industries. First, we will demonstrate the usefulness of cross metathesis reactions in the efficient synthesis of the major component of the Peach Twig Borer pheromone and the of Omnivorous Leafroller pheromone, insect pheromones are environmentally friendly pest-controlling agents. Second, we will demonstrate highly efficient cross metathesis routes into novel α,β-unsaturated carbonyl intermediates. These novel α,β-unsaturated carbonyl intermediates can be further functionalized into pharmaceutical compounds that are difficult to prepare by the traditional synthetic methodologies. This paper highlights key catalyst-substrate reactivity variations with different ruthenium olefin metathesis catalysts, highlights cross metathesis reactions and techniques and highlights an efficient ruthenium catalyst removal technique.
Palladium(II)-catalyzed synthesis of α-alkylidene-γ-butyrolactams from N-allylic 2-alkynamides. Total synthesis of (±)-isocynodine and (±)-isocynometrine
Xie,Lu,Liu,Xu
, p. 6545 - 6550 (2007/10/03)
An efficient method for preparing α-alkylidene-γ-butyrolactams via the Pd(II)-catalyzed cyclization of acyclic N-allylic 2-alkynamides via halopalladation, intramolecular olefin insertion, and β-heteroatom elimination was developed. The reaction is less influenced by the leaving group and the concentration of the halide ions in comparison with the cyclization of acyclic alkynoates. The total syntheses of (±)-isocynodine and (±)-isocynometrine were realized using this method.
Synthetic research on hepoxilins. 7.* Divergent total synthesis of hepoxilins and related eicosanoids
Mel'nikova,Vasil'eva,Pivnitsky
, p. 1199 - 1208 (2007/10/03)
A new synthetic strategy for hydroxy-epoxy eicosanoids formed through the lipoxygenase pathway is developed. It makes use of a single synthon of the central functionalized fragment of the target molecules, namely racemic (E)-CICH2C≡CCHOHCH=CHCH2OBz. Elongation of the carbon chain of the synthon by successive condensations at both ends altenatively with hept-1-yne and hex-5-ynoic acid followed by enantioselective double bond epoxidation and partial hydrogenation of the triple bonds resulted in the syntheses of hepoxilins B3, their potential 8-lipoxygenase analogs, or their enantiomers, depending on the sequence of carbon chain elongations and the chirality of the epoxidation controller used.
