2079-53-0Relevant academic research and scientific papers
Safe, convenient ortho-Claisen thermal rearrangement using a flow reactor
Rincon, Juan A.,Barberis, Mario,Gonzalez-Esguevillas, Maria,Johnson, Martin D.,Niemeier, Jeffry K.,Sun, Wei-Ming
, p. 1428 - 1432 (2011)
The [3,3] Claisen rearrangement is a well-known reaction that has been very useful for the synthesis of o-allyl phenols. The thermally induced rearrangement could present safety and operational issues at large batch scale. Herein, we report a process that
Making the family portrait complete: Synthesis of Electron Withdrawing Group activated Hoveyda-Grubbs catalysts bearing sulfone and ketone functionalities
Arlt, Dieter,Bieniek, Micha?,Bujok, Robert,Grela, Karol,Kajetanowicz, Anna,Milewski, Mariusz
, (2020)
Synthesis of five Electron Withdrawing Group (EWG) activated Hoveyda-Grubbs’ catalysts containing thioperfluoroalkyl, sulfone and ketone functions is reported. The catalytic activity of these catalysts was well correlated with the σp values of
Total Synthesis and Anti-inflammatory Evaluation of Penchinone A and Its Structural Analogues
Oh, Yongguk,Jang, Yeon Jeong,Jeon, Mijin,Kim, Hyung Sik,Kwak, Jong Hwan,Chung, Kyu Hyuck,Pyo, Suhkneung,Jung, Young Hoon,Kim, In Su
, p. 11566 - 11572 (2017)
The first total synthesis and biological evaluation of penchinone A and its structural analogues are described. The key steps for the preparation of penchinone A derivatives involve the oxime-directed palladium(II)-catalyzed oxidative acylation, Claisen r
Design and synthesis of C3-symmetric molecules containing oxepine and benzofuran moieties via Metathesis
Gupta, Naveen Kumar,Kotha, Sambasivarao,Solanke, Balaji. U.
, (2021/07/17)
We report a new synthetic strategy to C3-symmetric star-shaped phenyl and triazine central cores bearing oxepine and benzofuran ring systems. In this regard, we have explored the application of metathetic strategy to construct C3-sym
Synthesis, molecular modelling studies of indolyl chalcone derivatives and their antimalarial activity evaluation
Jyoti,Gaur, Rashmi,Kumar, Yogesh,Cheema, Harveer Singh,Kapkoti, Deepak Singh,Darokar, Mahendra P.,Khan, Feroz,Bhakuni, Rajendra Singh
, p. 3261 - 3268 (2019/12/11)
Twenty one chalcone derivatives were synthesized using Claisen-Schmidt condensation, their antimalarial activity against Plasmodium falciparum was determined and quantitative structure–activity relationship (QSAR) was developed. Condensation of substituted acetophenones with various aromatic aldehydes at room temperature gave chalcones in 75–96% yield. Chalcones are secondary metabolites of terrestrial plants, precursors for the biosynthesis of flavonoids and exhibit various biological activities. Antiplasmodial IC50 (half-maximal inhibitory concentration) activity of a compound against malaria parasites in?vitro provides a good first screen for identifying the antimalarial potential of the compound. The most active compound was Trans-3-(1H-indol-3-yl)-1-(2’-hydroxyphenyl)-2-propen-1-one(1b) with IC50 of 2.1 μM/L. Molecular mechanism was explored through in silico docking & ADMET studies for the active compounds.
Highly regioselective O-allylation of phenol derivatives using MMZCu(I)Y catalyst
Thangapriya, Cheirmakani,Ilaamirthamani, Simsonrubarathinam,Kumarraja, Mayilvasagam
, p. 361 - 367 (2019/12/11)
A clean and effective method has been developed for the regioselective of O-allylation of phenol derivatives using a recyclable Cu(I)-exchanged multi-size porous material. Ease of preparation of catalyst through simple solid-state exchange and its compatibility in producing excellent amount of O-allylated products and a plausible mechanistic pathway for the regioselectivity are highlighted. This reported procedure is not requiring any external stabilizing ligand for Cu(I) species and further purification of products.
Design, synthesis, biological evaluation and inhibition mechanism of 3-/4-alkoxy phenylethylidenethiosemicarbazides as new, potent and safe tyrosinase inhibitors
Liao, Bing,Mai, Yuliang,Shi, Huahong,Song, Senchuan,Wang, Fei
, p. 369 - 379 (2020/05/14)
Tyrosinase plays important roles in many different disease related processes, and the development of its inhibitors is particularly important in biotechnology. In this study, thirty-nine 3-/4-alkoxyphenylethyli-denethiosemicarbazides were synthesized as novel tyrosinase inhibitors based on structure-based molecular design. Our experimental results demonstrated that thirty-one of them possess remarkable tyrosinase inhibitory activities with IC50 value below 1μM, and 5a, 6e, 6g and 6t did not display any toxicity to 293T cell line at the concentration of 1000μmol/L. According to the inhibitory activities, several compounds were selected for detail investigation on the structure–activity relationships (SARs), mechanisms of enzyme inhibition, inhibitory kinetics and cytotoxicity. In particular, the interaction between the selected inhibitors and the active center of tyrosinase was considered and discussed in detail based on their structural characteristics. Taken together, the results presented here demonstrated that the newly designed compounds are promising candidates for the treatment of tyrosinase-related disorders and further development of them may have significant contribution in biomedical science.
Design, synthesis, docking studies and monoamine oxidase inhibition of a small library of 1-acetyl- and 1-thiocarbamoyl-3,5-diphenyl-4,5-dihydro-(1h)-pyrazoles
Guglielmi, Paolo,Carradori, Simone,Poli, Giulio,Secci, Daniela,Cirilli, Roberto,Rotondi, Giulia,Chimenti, Paola,Petzer, Anél,Petzer, Jacobus P.
, (2019/02/03)
New N-acetyl/N-thiocarbamoylpyrazoline derivatives were designed and synthesized in high yields to assess their inhibitory activity and selectivity against human monoamine oxidase A and B. The most important chiral compounds were separated into their single enantiomers and tested. The impact of the substituents at N1, C3 and C5 positions as well the influence of the configuration of the C5 on the biological activity were analyzed. Bulky aromatic groups at C5 were not tolerated. p-Prenyloxyaryl moiety at C3 oriented the selectivity toward the B isoform. The results were also corroborated by molecular modelling studies providing new suggestions for the synthesis of privileged structures to serve as lead compounds for the treatment of mood disorders and neurodegenerative diseases.
A molybdenum based metallomicellar catalyst for controlled and chemoselective oxidation of activated alcohols in aqueous medium
Thiruvengetam, Prabaharan,Chakravarthy, Rajan Deepan,Chand, Dillip Kumar
, p. 123 - 133 (2019/07/19)
A surfactant based oxodiperoxo molybdenum complex, which could activate molecular oxygen, has been employed as a catalyst for controlled oxidation of benzylic alcohols to corresponding carbonyls. The oxidation reactions were carried out under aqueous environment, however, in the absence of any extraneous base or co-catalyst. Sensitive/oxidizable functional groups like cyano, sulfide, hydroxyl, aryl-hydroxyl, alkene (internal/terminal), alkyne (internal/terminal), and acetal were tolerated during the transformations. Such selectivity is attributed to the mild nature of the catalyst. The methodology could also be scaled-up for multi-gram synthesis and the protocol is likely to find practical use since it requires an inexpensive recyclable-catalyst and easily available oxidant (under green conditions). A plausible mechanism is proposed with the help of preliminary computational study.
Thiyl radical promoted chemo- and regioselective oxidation of CC bonds using molecular oxygen: Via iron catalysis
Xiong, Baojian,Zeng, Xiaoqin,Geng, Shasha,Chen, Shuo,He, Yun,Feng, Zhang
supporting information, p. 4521 - 4527 (2018/10/17)
The first example of the thiyl radical promoted ligand-free iron-catalyzed oxidative cleavage of alkenes using molecular oxygen (1 atm) has been developed. The reaction proceeds under mild reaction conditions with high efficiency and high chemo- and regioselectivity. It features a broad substrate scope and excellent functional group compatibility, enabling facile access to valuable molecules for application in medicinal chemistry. Preliminary mechanistic studies reveal that a vital intermediate dioxetane might be involved in the reaction and a thiyl radical plays a synergistic role in facilitating the selective oxidation of the CC bond.
