5145-71-1Relevant academic research and scientific papers
An expeditious synthesis of n-substituted pyrroles via microwave-induced iodine-catalyzed reactions under solventless conditions
Bandyopadhyay, Debasish,Mukherjee, Sanghamitra,Banik, Bimal K.
, p. 2520 - 2525 (2010)
An expeditious synthesis of N-substituted pyrroles has been developed by reacting 2,5-dimethoxy tetrahydrofuran and several amines using a microwave-induced molecular iodine-catalyzed reaction under solventless conditions. Copyright
Metal-Free Synthetic Shortcut to Octahydro-Dipyrroloquinoline Skeletons from 2,5-Cyclohexadienone Derivatives and l -Proline
Zhang, Can,Li, Jianbin,Wang, Xin,Shen, Xuan,Zhu, Dunru,Shen, Ruwei
, p. 10397 - 10406 (2021)
The tandem decarboxylative condensation-dimerization reaction of l-proline with 2,5-cyclohexadienones including p-quinone monoacetals, p-quinol ethers, and p-quinols is reported to provide a concise and rapid synthesis of octahydro-dipyrroloquinoline comp
A facile synthesis of diaryl pyrroles led to the discovery of potent colchicine site antimitotic agents
Romagnoli, Romeo,Oliva, Paola,Salvador, Maria Kimatrai,Manfredini, Stefano,Padroni, Chiara,Brancale, Andrea,Ferla, Salvatore,Hamel, Ernest,Ronca, Roberto,Maccarinelli, Federica,Rruga, Fatlum,Mariotto, Elena,Viola, Giampietro,Bortolozzi, Roberta
, (2021/02/09)
Three different series of cis-restricted analogues of combretastatin A-4 (CA-4), corresponding to thirty-nine molecules that contained a pyrrole nucleus interposed between the two aryl rings, were prepared by a palladium-mediated coupling approach and evaluated for their antiproliferative activity against six human cancer cell lines. In the two series of 1,2-diaryl pyrrole derivatives, results suggested that the presence of the 3′,4′,5′-trimethoxyphenyl moiety at the N-1 position of the pyrrole ring was more favorable for antiproliferative activity. In the series of 3,4-diarylpyrrole analogues, three compounds (11i-k) exhibited maximal antiproliferative activity, showing excellent antiproliferative activity against the CA-4 resistant HT-29 cells. Inhibition of tubulin polymerization of selected 1,2 pyrrole derivatives (9a, 9c, 9o and 10a) was similar to that observed with CA-4, while the isomeric 3,4-pyrrole analogues 11i-k were generally from 1.5- to 2-fold more active than CA-4. Compounds 11j and 11k were the only compounds that showed activity as inhibitors of colchicine binding comparable to that CA-4. Compound 11j had biological properties consistent with its intracellular target being tubulin. This compound was able to block the cell cycle in metaphase and to induce significant apoptosis at a concentration of 25 nM, following the mitochondrial pathway, with low toxicity for normal cells. More importantly, compound 11j exerted activity in vivo superior to that of CA-4P, being able to significantly reduce tumor growth in a syngeneic murine tumor model even at the lower dose tested (5.0 mg/kg).
The remarkable selectivity of the 2-arylquinoline-based acyl hydrazones toward copper salts: Exploration of their catalytic applications in the copper catalysed: N -arylation of indole derivatives and C1-alkynylation of tetrahydroisoquinolines via the A
Echeverry-Gonzalez, Carlos A.,Ortiz Villamizar, Marlyn Catalina,Kouznetsov, Vladimir V.
supporting information, p. 243 - 250 (2021/01/11)
Ligands promoting copper-catalysed coupling reactions have received increasing attention because of their ability to enhance the catalytic activity of copper, making these reactions applicable in different fields such as drugs, pharmaceutically interestin
Echeverry-Gonzalez, Carlos A.,Ortiz Villamizar, Marlyn Catalina,Kouznetsov, Vladimir V.
supporting information, p. 243 - 250 (2021/01/11)
Ligands promoting copper-catalysed coupling reactions have received increasing attention because of their ability to enhance the catalytic activity of copper, making these reactions applicable in different fields such as drugs, pharmaceutically interestin
Utilization of caffeine carbon supported cobalt catalyst in the tandem synthesis of pyrroles from nitroarenes and alkenyl diols
Balasubramaniam, Bhuvaneshwari,Dhara, Partha,Gupta, Raju K.,Kundu, Sabuj,Panja, Dibyajyoti,Sau, Anirban
, p. 244 - 254 (2021/09/07)
Employing bio-waste caffeine carbon-supported heterogeneous cobalt catalyst, synthesis of various substituted pyrrole derivatives is reported. In this methodology, pyrroles were synthesized through coupling between nitroarenes and alkenyl diols in a tandem manner. Among all the heterogeneous catalysts Co(OAc)2-CC-800 displayed the highest catalytic activity. Preparative scale synthesis of pyrroles and synthesis of anti-tubercular agent 5-(4-(1H-pyrrol-1-yl)phenyl)-1,3,4-oxadiazole-2-thiol revealed the practical applicability of this protocol. Several kinetic experiments and Hammett studies were conducted to understand the probable mechanism and electronic effects on this transformation.
N -Arylation of (hetero)arylamines using aryl sulfamates and carbamates via C-O bond activation enabled by a reusable and durable nickel(0) catalyst
Dindarloo Inaloo, Iman,Majnooni, Sahar,Eslahi, Hassan,Esmaeilpour, Mohsen
, p. 13266 - 13278 (2020/10/07)
An effective and general aryl amination protocol has been developed using a magnetically recoverable Ni(0) based nanocatalyst. This new stable catalyst was prepared on Fe3O4@SiO2 modified by EDTA and investigated by FT-IR, EDX, TEM, XRD, DLS, FE-SEM, XPS, NMR, TGA, VSM, ICP and elemental analysis techniques. The reaction proceeded via carbon-oxygen bond cleavage of (hetero)aryl carbamates and sulfamates under simple and mild conditions without the use of any external ligands. This method demonstrated functional group tolerance in the N-arylation of various nitrogen-containing compounds as well as aliphatic amines, anilines, pyrroles, pyrazoles, imidazoles, indoles, and indazoles with good to excellent yields. Furthermore, the catalyst could be easily recovered by using an external magnetic field and directly reused at least six times without notable reduction in its activity. This journal is
Ligand and Cu freeN-arylation of indoles, pyrroles and benzylamines with aryl halides catalyzed by a Pd nanocatalyst
Paul, Abhijit,Chatterjee, Debnath,Banerjee, Srirupa,Yadav, Somnath
supporting information, p. 14447 - 14452 (2020/09/21)
Herein, theN-arylation of aromatic heterocycles like indoles and pyrroles is reported by a Pd nanocatalyst under ligand- and Cu-free conditions. The reaction conditions tolerate several functional groups and work very efficiently for aryl iodides and bromides. Aryl chlorides are also successful as the coupling partners albeit with lower yields. The methodology is also applicable for theN-arylation of aliphatic primary amines as demonstrated by the reactions of benzylamine with several aryl iodides as well as bromides. The recyclable Pd nanocatalyst catalyzes the reaction by a heterogeneous mechanism, which has been demonstrated by several techniques including the three phase test and thein situICP-MS analysis of the reaction mixture.
Sulphonic acid functionalized porphyrin anchored with a: Meso -substituted triazolium ionic liquid moiety: A heterogeneous photo-catalyst for metal/base free C-C cross-coupling and C-N/C-H activation using aryl chloride under visible light irradiation
Bhansali, Karan,Raut, Subodh,Barange, Shital,Bhagat, Pundlik
, p. 19690 - 19712 (2020/12/04)
We report an easy process to synthesize sulphonic acid functionalized porphyrin, anchored with a meso-substituted triazolium ionic liquid moiety (SAFPTILM) for metal/base free C-C cross-coupling and C-N/C-H activation using aryl chloride under visible light irradiation. The acid strength has been measured based on the Hammett indicator. The SAFPTILM photocatalyst comprising 18 π-conjugated electronic systems with the chromophore substituents in the meso-position can provide rapid electronic conducting channels during photocatalysis under the irradiation of visible light. It was found that SAFPTILM is an efficient photocatalyst for the Heck, Sonogashira, Buchwald, Ullmann/Fittig coupling and C-H activation of phenols with different aryl chlorides in the absence of a base/noble metal, using 5 W LED (yellow) light under ambient conditions. The photocatalyst with low band gap (1.55 eV) comprising conjugation, favors coupling reaction of unactivated aryl chlorides, by easy excitation of electrons and transfer to the conjugated benzimidazolium based phenylenediamine support delaying the recombination of photoinduced electron-hole pairs.
Lactam derivatives and preparation method and application thereof
-
Paragraph 0048-0052; 0076; 0078, (2020/02/10)
The invention relates to lactam derivatives and a preparation method and application thereof. Compared with the prior art, the invention provides lactam compounds with a novel structure. The compoundsand compositions thereof have remarkable activity in inhibition of the proliferation of cancer cells (including, but not limited to, the liver cancer cell line HepG2 and the lung cancer cell line A549), and the activity of multiple compounds is in the same order of magnitude as the activity of the commercial drug adriamycin or superior to the activity of adriamycin. The compounds of the inventioncan be prepared from N-substituted pyrrole compounds through a reaction, and the preparation method is convenient, rapid and efficient.
A facile synthesis of 1-aryl pyrroles by clauson-Kaas reaction using oxone as a catalyst under microwave irradiation
Gullapelli, Kumaraswamy,Brahmeshwari,Ravichander
, p. 143 - 148 (2019/03/21)
A new and efficient methodology to synthesize N-substituted pyrrole derivatives by Clauson Kaas reaction employing Oxone as catalyst was developed. The transformation was performed in acetonitrile under microwave irradiation. This procedure has several advantages such as high yield, clean product formation, and short reaction time.
