53560-33-1Relevant academic research and scientific papers
Synthesis and biological evaluation of 1-(benzofuran-3-yl)-4-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazole derivatives as tubulin polymerization inhibitors
Qi, Zhi-Yuan,Hao, Shu-Yi,Tian, Heng-Zhi,Bian, Hong-Li,Hui, Ling,Chen, Shi-Wu
, (2020)
The key functions of microtubules and the mitotic spindle in cell division make them attractive targets for cancer therapy. In this study, a series of 1-(benzofuran-3-yl)-4-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazole derivatives was synthesized, and their
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.
De Novo Synthesis of Tricyclic 5,5-Benzannulated Spiroketals
Rao, Maddali L. N.,Islam, Sk Shamim
, p. 3944 - 3948 (2021/05/29)
The synthesis of tricyclic 5,5-benzannulated spiroketal scaffolds was accomplished from 2′-hydroxyacetophenones and gem-dibromoalkenes involving a one-pot domino strategy. The hitherto unknown transformation afforded the tricyclic 5,5-benzannulated spirok
Tuning the Molecular Packing of Self-Assembled Amphiphilic PtII Complexes by Varying the Hydrophilic Side-Chain Length
Herkert, Lorena,Selter, Philipp,Daniliuc, Constantin G.,B?umer, Nils,Palakkal, Jasnamol P.,Fernández, Gustavo,Hansen, Michael Ryan
supporting information, p. 4617 - 4626 (2021/02/09)
Understanding the relationship between molecular design and packing modes constitutes one of the major challenges in self-assembly and is essential for the preparation of functional materials. Herein, we have achieved high precision control over the supramolecular packing of amphiphilic PtII complexes by systematic variation of the hydrophilic side-chain length. A novel approach of general applicability based on complementary X-ray diffraction and solid-state NMR spectroscopy has allowed us to establish a clear correlation between molecular features and supramolecular ordering. Systematically increasing the side-chain length gradually increases the steric demand and reduces the extent of aromatic interactions, thereby inducing a gradual shift in the molecular packing from parallel to a long-slipped organization. Notably, our findings highlight the necessity of advanced solid-state NMR techniques to gain structural information for supramolecular systems where single-crystal growth is not possible. Our work further demonstrates a new molecular design strategy to modulate aromatic interaction strengths and packing arrangements that could be useful for the engineering of functional materials based on PtII and aromatic molecules.
Copper-catalyzed domino synthesis of ynamines
Dasgupta, Priyabrata,Islam, Sk Shamim,Rao, Maddali L. N.
, p. 7855 - 7860 (2021/09/28)
The hitherto unexploredN-alkynylation of electron-withdrawing or protecting group free N-heteroarenes such as indole, carbazole and pyrrole was developed usinggem-dibromoalkenes to synthesize ynamines under ligand-free copper-catalyzed domino conditions. The development methodology of ynamines was also applied in the synthesis of enynamines, multi-coupled bis-ynamines, tris-ynamines, and the natural product peyonine, demonstrating its broad synthetic scope and applications.
Synthesis of alkynes under dry reaction conditions
Rao, Maddali L.N.,Shamim Islam, Sk
supporting information, (2021/04/19)
An easy synthetic method was developed under dry reaction conditions for the preparation of terminal alkynes from 1,1-dibromoalkenes and in the presence of succinimide which acts as a nucleophile and proton donor. It was demonstrated with the synthesis of a broad spectrum of terminal alkynes and extended to synthesize internal alkynes under tandem reaction conditions.
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.
DBU-Mediated Synthesis of Aryl Acetylenes or 1-Bromoethynylarenes from Aldehydes
Thummala, Yadagiri,Karunakar, Galla V.,Doddi, Venkata Ramana
supporting information, p. 611 - 616 (2019/01/04)
Two well known synthetic organic reactions Ramirez olefination and Corey-fuchs reactions are integrated in one-pot sequential manner for the synthesis of arylacetylenes and 1,3-enynes starting directly from commercially available aldehydes. The bicyclic amidine 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) along with additive NaOH not only exclusively afforded the terminal alkynes directly from the aldehydes, but also enhanced the reaction rate. The dynamic nature of DBU also facilitated the isolation of 1-bromoalkynes intermediate products. Selection of additive from NaOH and H2O served as a switch for the synthesis of terminal alkyne and 1-bromoalkynes, respectively. (Figure presented.).
Design, synthesis and amplified spontaneous emission of 1,2,5-benzothiadiazole derivatives
Martín, Raúl,Prieto, Pilar,Carrillo, José R.,Rodríguez, Ana M.,De Cozar, Abel,Boj, Pedro G.,Díaz-García, María A.,Ramírez, Manuel G.
supporting information, p. 9996 - 10007 (2019/08/21)
The design, synthesis and evaluation of the amplified spontaneous emission (ASE) properties of a series of arylalkynyl-benzo[c][1,2,5]thiadiazole (BTD) and [1,2,5]thiadiazolo[3,4-g]quinoxaline (TDQ) derivatives are described. The synthetic strategy entailed the use of Sonogashira and Stille reactions based on the different aromatic natures of the two cores. The ASE properties were measured in thin polystyrene (PS) films doped with different concentrations of the synthesised compounds. BTD derivatives showed narrowing of the photoluminescence spectra (PL), thus revealing their potential laser applications. Only one TDQ derivative showed ASE. X-ray diffraction analysis was carried out to understand the observed results and to establish structure-property relationships. Molecules that showed strong molecular packing quenched the PL emission, thus giving rise to higher ASE thresholds. This is the first study in which ASE has been studied in BTD and TDQ derivatives and it represents a step forward in understanding this class of compounds for laser applications.
One-pot synthesis of unsymmetrical 1,3-butadiyne derivatives and their application in the synthesis of unsymmetrical 2,5-diarylthiophenes
Andrade, Camila B.,Carvalho, Diego B.,Trefzger, Ozildéia S.,Kassab, Najla M.,Guerrero, Palimécio G.,Barbosa, Sandro L.,Shiguemoto, Cristiane Y. K.,Baroni, Adriano C. M.
, p. 696 - 704 (2019/01/04)
A one-pot protocol was developed for the synthesis of unsymmetrical 1,3-butadiynes. The procedure is based on two sequential reactions: deprotection of R–C≡C–C≡C– C(Me)2OH derivatives in a retro-Favorskii reaction to furnish a terminal 1,3-butadiyne compound, which reacted with aryl iod-ides in a Sonogashira-type cross-coupling reaction catalyzed by Pd(PPh3)4 and CuI, using TBAOH as activator and toluene as solvent under reflux for 10 min. We also studied in situ thiocycli-zation of 1,3-butadiynes, leading to unsymmetrical 2,5-diaryl-thiophenes. The principal features of this method are operational simplicity, good substrate scope, very fast reaction, and high yields.
