4302-52-7Relevant academic research and scientific papers
Specific features of the chemical behavior of acetylenic derivatives of benzocrown ethers
Klyatskaya,Tretyakov,Vasilevsky
, p. 868 - 873 (2001)
4′-Ethynylbenzo-12-crown-4 (8), 4′-ethynylbenzo-15-crown-5 (9), and 4′-ethynylbenzo-18-crown-6 (10) were synthesized by cross-coupling of the corresponding aryl iodides 1-3 with 2-methylbut-3-yn-2-ol (4a) followed by the retro-Favorsky cleavage of the res
Anti-inflammatory, ulcerogenic and platelet activation evaluation of novel 1,4-diaryl-1,2,3-triazole neolignan-celecoxib hybrids
Felipe, Josyelen L.,Cassamale, Tatiana B.,Louren?o, Leticia D.,Carvalho, Diego B.,das Neves, Amarith R.,Duarte, Rita C.F.,Carvalho, Maria G.,Toffoli-Kadri, Monica C.,Baroni, Adriano C.M.
, (2021/12/27)
This study reports the synthesis of novel neolignans-celecoxib hybrids and the evaluation of their biological activity. Analogs 8–13 (L13-L18) exhibited anti-inflammatory activity, inhibited glycoprotein expression (P-selectin) related to platelet activation, and were considered non– ulcerogenic in the animal model, even with the administration of 10 times higher than the dose used in reference therapy. In silico drug-likeness showed that the analogs are compliant with Lipinski's rule of five. A molecular docking study showed that the hybrids 8–13 (L13-L18) fitted similarly with celecoxib in the COX-2 active site. According to this data, it is possible to infer that extra hydrophobic interactions and the hydrogen interactions with the triazole core may improve the selectivity towards the COX-2 active site. Furthermore, the molecular docking study with P-selectin showed the binding affinity of the analogs in the active site, performing important interactions with amino acid residues such as Tyr 48. Whereas the P-selectin is a promising target to the design of new anti-inflammatory drugs with antithrombotic properties, a distinct butterfly-like structure of 1,4-diaryl-1,2,3-triazole neolignan-celecoxib hybrids synthesized in this work may be a safer alternative to the traditional COX-2 inhibitors.
Palladium-Catalyzed Carbonylative Sonogashira/Annulation Reaction: Synthesis of Indolo[1,2-b]isoquinolines
Li, Lin,Liu, Xin-Lian,Ma, Ai-Jun,Peng, Jin-Bao,Qi, Zhuang,Yang, Ai-Hua
supporting information, (2022/02/14)
A palladium-catalyzed carbonylative Sonogashira/annulation reaction for the synthesis of indolo[1,2-b]isoquinolines has been developed. Tetracyclic 6/5/6/6 indoline skeletons were synthesized in moderate to good yields from easily available 2-bromo-N-(2-i
Thermal decarboxylative Nazarov cyclization of cyclic enol carbonates involving chirality transfer
Kozuma, Akane,Komatsuki, Keiichi,Saito, Kodai,Yamada, Tohru
, p. 60 - 63 (2019/12/12)
Decarboxylative Nazarov cyclization of chiral cyclic enol carbonates proceeded to afford chiral 2-cyclopentenones with excellent chirality transfer under thermal conditions without any catalyst. Interestingly, the thermal decarboxylative Nazarov cyclization furnished the desired product with better chirality transfer than the Lewis acid-catalyzed reaction.
Total Synthesis of Indolizidine Alkaloids via Nickel-Catalyzed (4 + 2) Cyclization
Renner, Jonas,Thakur, Ashish,Rutz, Philipp M.,Cowley, Jacob M.,Evangelista, Judah L.,Kumar, Puneet,Prater, Matthew B.,Stolley, Ryan M.,Louie, Janis
, p. 924 - 928 (2020/02/04)
A Ni-catalyzed (4 + 2) cycloaddition of alkynes and azetidinones toward piperidinones was used as key reaction in the enantioselective synthesis of naturally occurring indolizidine alkaloids. The reaction benefits from the use of an easily accessible azet
Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N -propargylanilines with diverse carbon pronucleophiles: Facile access to functionalized tetrahydroquinolines
Li, Guangzhe,Wang, Chengdong,Li, Yueqing,Shao, Kun,Yu, Guo,Wang, Shisheng,Guo, Xiuhan,Zhao, Weijie,Nakamura, Hiroyuki
supporting information, p. 7333 - 7336 (2020/07/23)
Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N-propargylanilines with two types of carbon pronucleophiles (nitromethane as a sp3 carbon pronucleophile and phenylacetylenes as sp carbon pronucleophiles) proceeded to give the 2-substituted tetrahydroquinolines in good yields with 100percent atomic utilization without any additional external oxidants.
Design, synthesis, antileishmanial, and antifungal biological evaluation of novel 3,5-disubstituted isoxazole compounds based on 5-nitrofuran scaffolds
Trefzger, Ozildéia S.,Barbosa, Natália V.,Scapolatempo, Renata L.,das Neves, Amarith R.,Ortale, Maria L. F. S.,Carvalho, Diego B.,Honorato, Ant?nio M.,Fragoso, Mariana R.,Shuiguemoto, Cristiane Y. K.,Perdomo, Renata T.,Matos, Maria F. C.,Chang, Marilene R.,Arruda, Carla C. P.,Baroni, Adriano C. M.
, (2019/12/27)
Nineteen 3,5-disubstituted-isoxazole analogs were synthesized based on nitrofuran scaffolds, by a [3 + 2] cycloaddition reaction between terminal acetylenes and 5-nitrofuran chloro-oxime. The compounds were obtained in moderate to very good yields (45–91%). The antileishmanial activity was assayed against the promastigote and amastigote forms of Leishmania (Leishmania) amazonensis. Alkylchlorinated compounds 14p–r were active on both the promastigote and amastigote forms, with emphasis on compound 14p, which showed strong activity against the amastigote form (IC50 = 0.6 μM and selectivity index [SI] = 5.2). In the alkyl series, compound 14o stands out with an IC50 = 8.5 μM and SI = 8.0 on the amastigote form. In the aromatic series, the most active compounds were those containing electron-donor groups, such as trimethoxy isoxazole 14g (IC50 = 1.2 μM and SI = 20.2); compound 14h, with IC50 = 7.0 μM and SI = 6.1; and compound 14j containing the 4-SCH3 group, with IC50 = 5.7 μM and SI = 10.2. In addition, the antifungal activity of 19 nitrofuran isoxazoles was evaluated against five strains of Candida (C. albicans, C. parapsilosis, C. krusei, C. tropicalis, and C. glabrata). Eleven isoxazole derivatives were active against C. parapsilosis, and compound 14o was found to be the most active (minimal inhibitory concentration [MIC] = 3.4 μM) for this strain. Compound 14p was active against all the strains tested, with an MIC = 17.5 μM for C. glabrata, lower than that of the fluconazole used as the reference drug.
An efficient synthesis of Nepetoidin B
Xiong, Hangxing,Yang, Sen,Yao, Ming,Zhang, Jingjing
, (2020/09/07)
The synthesis of nepetoidin B from readily and commercially available 3,4-dimethoxybenzaldehyde in an overall yield of 52% is achieved. The present three-step protocol involves Ramirez–Corey–Fuchs reaction, ruthenium-catalyzed anti-Markovnikov addition of a carboxylic acid to a terminal alkyne and demethylation using iodotrimethylsilane (Me3SiI) and quinoline. In this work, the two isomers of (Z, E)- nepetoidin B /(E, E)nepetoidin B and the single isomer of (E, E)- nepetoidin B can be obtained through the demethylation of (Z, E)-5 and (E, E)-5, respectively.
Cs2CO3-Mediated Vicinal Thiosulfonylation of 1,1-Dibromo-1-Alkenes with Thiosulfonates: An Expedient Synthesis of (E)-1,2-Thiosulfonylethenes
Reddy, Raju Jannapu,Kumari, Arram Haritha,Kumar, Jangam Jagadesh,Nanubolu, Jagadeesh Babu
, p. 1587 - 1591 (2019/02/16)
A new and highly efficient vicinal thiosulfonylation of 1,1-dibromo-1-alkenes with thiosulfonates in the presence of cesium carbonate has been developed. The metal-free diheterofunctionalization is an operationally simple to access a wide range of (E)-1,2-thiosulfonylethenes (α-aryl-β-thioarylvinyl sulfones) in moderate to high yields with high levels of stereoselectivities. Further, scalable reactions have been demonstrated for this transformation, thus illustrating its efficiency and practicality. (Figure presented.).
Copper-Mediated Deacylative Coupling of Ynones via C-C Bond Activation under Mild Conditions
Feng, Lili,Hu, Tingjun,Zhang, Saisai,Xiong, Heng-Ying,Zhang, Guangwu
supporting information, p. 9487 - 9492 (2019/12/02)
The intermolecular deacylative coupling of unstrained ynones via C-C bond activation was accomplished by a CuCl-bpy system under mild reaction conditions. This protocol features facile cleavage of the C-C bond at room temperature, broad substrate scope, and efficient construction of important symmetric and unsymmetrical 1,3-diyne adducts through homo or cross coupling of ynones, respectively. The preliminary mechanistic investigations indicated that an acyl copper(III) complex is likely involved in this process.
