71277-13-9Relevant articles and documents
Iron-Catalyzed ?±,?-Dehydrogenation of Carbonyl Compounds
Zhang, Xiao-Wei,Jiang, Guo-Qing,Lei, Shu-Hui,Shan, Xiang-Huan,Qu, Jian-Ping,Kang, Yan-Biao
supporting information, p. 1611 - 1615 (2021/03/03)
An iron-catalyzed α,β-dehydrogenation of carbonyl compounds was developed. A broad spectrum of carbonyls or analogues, such as aldehyde, ketone, lactone, lactam, amine, and alcohol, could be converted to their α,β-unsaturated counterparts in a simple one-step reaction with high yields.
One-Pot Preparation of (E)-α,β-Unsaturated Aldehydes by a Julia-Kocienski Reaction of 2,2-Dimethoxyethyl PT Sulfone Followed by Acid Hydrolysis
Ando, Kaori,Watanabe, Haruka,Zhu, Xiaoxian
, p. 6969 - 6973 (2021/05/06)
(E)-α,β-Unsaturated aldehydes were synthesized by the Julia-Kocienski reaction of 2,2-dimethoxyethyl 1-phenyl-1H-tetrazol-5-yl (PT) sulfone 3 with various aldehydes, followed by acid hydrolysis. The reaction could be carried out in one pot, and various (E)-α,β-unsaturated aldehydes were obtained in a short time and with high yields.
Structure–Activity Relationship Studies on 6,7-Dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline Derivatives as Multidrug Resistance Reversers
Teodori, Elisabetta,Dei, Silvia,Bartolucci, Gianluca,Perrone, Maria Grazia,Manetti, Dina,Romanelli, Maria Novella,Contino, Marialessandra,Colabufo, Nicola Antonio
, p. 1369 - 1379 (2017/09/01)
A series of derivatives were synthesized and studied with the aim to investigate the structure–activity relationships of the two P-glycoprotein (P-gp) modulators elacridar and tariquidar. Then, different aryl-substituted amides were inserted, and to explore the effects of varying the amide function, the corresponding isosteric ester derivatives and some alkylamine analogues were synthesized. The new compounds were studied to evaluate their P-gp interaction profile and selectivity toward the two other ABC transporters, multidrug-resistance-associated protein-1 (MRP-1) and breast cancer resistance protein (BCRP). Investigation of the chemical stability of the amide and ester derivatives toward spontaneous or enzymatic hydrolysis showed that these compounds were stable in phosphate-buffered saline and human plasma. This study allowed us to evaluate the selectivity of the three series on the three efflux pumps and to propose the structural requirements that define the P-gp interaction profile. We identified two P-gp substrates, a P-gp inhibitor, and three ester derivatives that were active on BCRP, which opens a new scenario in the development of ligands active toward this pump.
Expanding the scope of the Babler–Dauben oxidation: 1,3-oxidative transposition of secondary allylic alcohols
Killoran, Patrick M.,Rossington, Steven B.,Wilkinson, James A.,Hadfield, John A.
supporting information, p. 3954 - 3957 (2016/08/09)
We report the catalytic chromium-mediated oxidation of secondary allylic alcohols to give α,β-unsaturated aldehydes with exclusive (E)-stereoselectivity. This facile procedure employs catalytic PCC (5?mol?%) and periodic acid (H5IO6) as a co-oxidant. This transformation occurs specifically with aromatic substituted allyl alcohols containing both electron withdrawing and electron donating substituents as well as a range of functional groups.
Solvolysis, Electrochemistry, and Development of Synthetic Building Blocks from Sawdust
Nguyen, Bichlien H.,Perkins, Robert J.,Smith, Jake A.,Moeller, Kevin D.
, p. 11953 - 11962 (2016/01/09)
Either aldehyde or cinnamyl ether products can be selectively extracted from raw sawdust by controlling the temperature and pressure of a solvolysis reaction. These materials have been used as platform chemicals for the synthesis of 15 different synthetic substrates. The conversion of the initial sawdust-derived materials into electron-rich aryl substrates often requires the use of oxidation and reduction chemistry, and the role electrochemistry can play as a sustainable method for these transformations has been defined.
Synthesis and assessment of the antioxidant and antitumor properties of asymmetric curcumin analogues
Li, Qingyong,Chen, Jian,Luo, Shuyue,Xu, Jialin,Huang, Qiaoxian,Liu, Tianyu
, p. 461 - 469 (2015/03/04)
In this study, 12 asymmetric curcumin (CUR) analogues and 5 symmetric curcumin derivatives were synthesized, the antioxidant activity of these derivatives were evaluated by radicals 1,1-diphenyl-2- picryl-hydrazyl (DPPH) assay, 2,2-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) assay, ROO. (TRAP) assay and O2-. (NET) assay and anti-proliferative activities of these analogues were assessed against the human hepatoma cell line (SMMC-7721), the human breast cancer cell line (MCF-7) and the human prostate cancer cell lines (PC-3). Most of the asymmetric compounds showed stronger antioxidant activities than Vitamin C (Vc). Curcumin analogues reducing free radicals contain two reaction mechanisms: H-atom and electron transfer mechanisms. Compound 14 showed the most significant antioxidant activity compared with curcumin and other derivatives. Shorted the carbon chain of 14 can reduce the OeH bond dissociation enthalpy (BED) to improve the antioxidant activity. The antioxidant activity of 25 was similar to curcumin. All of the compounds performed better in an anti-proliferate assay than curcumin, especially compound 25, which exhibited the preferential cytotoxic activity against MCF- 7 cells(25, IC50 = 9.11 μM, curcumin, IC50 = 70.2 μM). Considering these data, future studies should be performed to assess the therapeutic values of these asymmetric curcumin analogues.
Silicon-directed rhenium-catalyzed allylic carbaminations and oxidative fragmentations of γ-silyl allylic alcohols
Chavhan, Sanjay W.,Cook, Matthew J.
supporting information, p. 4891 - 4895 (2014/05/06)
A highly regioselective allylic substitution of β-silyl allylic alcohols has been achieved that provides the branched isomer as a single product. This high level of regiocontrol is achieved through the use of a vinyl silane group that can perform a Hiyama coupling providing 1,3-disubstituted allylic amines. An unusual oxidative fragmentation product was also observed at elevated temperature that appears to proceed by a Fleming-Tamao-type oxidation-elimination pathway.
Development of a robust reagent for the two-carbon homologation of aldehydes to (E)-α,β-unsaturated aldehydes in water
Mcnulty, James,Zepeda-Velazquez, Carlos,McLeod, David
supporting information, p. 3146 - 3149 (2013/11/06)
Synthesis of a new pinacolacetal-phosphonium salt and its reaction with aldehydes to give homologated acetals and two-carbon homologated unsaturated aldehydes is presented. The chemistry takes place in water under mild conditions and the sequence can be performed in one-flask operation.
Rhodium-catalyzed hydroformylation of alkynes employing a self-assembling ligand system
Agabekov, Vladislav,Seiche, Wolfgang,Breit, Bernhard
, p. 2418 - 2422 (2013/07/11)
Hydroformylation of alkynes is an underdeveloped atom-economic and redox-neutral method to prepare enals. Applying a new electron poor self-assembling ligand system provides the first general rhodium-catalyst for the chemo- and stereoselective hydroformylation of dialkyl- as well as diaryl-substituted alkynes to furnish enals in excellent chemo- and stereoselectivity.
Synthesis of methoxylated goniothalamin, aza-goniothalamin and γ-pyrones and their in vitro evaluation against human cancer cells
Barcelos, Rosimeire Coura,Pastre, Julio Cezar,Caixeta, Vanessa,Vendramini-Costa, Débora Barbosa,De Carvalho, Jo?o Ernesto,Pilli, Ronaldo Aloise
experimental part, p. 3635 - 3651 (2012/07/27)
The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the γ-pyrones and the aza-goniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin (1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds.
