54609-08-4Relevant articles and documents
One-pot synthesis of cyclohexylamine and: N -aryl pyrroles via hydrogenation of nitroarenes over the Pd0.5Ru0.5-PVP catalyst
Chaudhari, Chandan,Sato, Katsutoshi,Ikeda, Yasuyuki,Terada, Kenji,Abe, Naoya,Nagaoka, Katsutoshi
supporting information, p. 9743 - 9746 (2021/06/15)
The direct synthesis of cyclohexylamine via the hydrogenation of nitrobenzene over monometallic (Pd, Ru or Rh) and bimetallic (PdxRu1-x) catalysts was studied. The Pd0.5Ru0.5-PVP catalyst was the most effective catalyst for this reaction. The catalyst can be reused and applied for the synthesis of N-aryl pyrroles and quinoxalines from nitrobenzenes.
Method for preparing N-aryl pyrrole compound
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Paragraph 0021; 0046, (2020/09/09)
The present invention relates to a method for preparing an N-aryl pyrrole compound. Furan containing different substituents, aromatic amine containing different substituents and a solid Lewis acid catalyst are mixed and placed in a closed reactor, and an N-aryl pyrrole compound with different substituents is prepared under certain catalytic conditions. The reaction temperature of the catalytic reaction condition is 140-210 DEG C. The solid Lewis acid catalyst is prepared by a sol-gel method, Hf is used as a core metal element, and a mesoporous molecular sieve SBA-15 is used as a carrier. According to the method, the catalyst is simple to prepare, low in cost, high in reaction activity, good in water resistance and structural stability and high in catalytic reaction yield; meanwhile, the Lewis acid type catalyst does not generate acid protons, the corrosion of the catalyst to equipment at high temperature is avoided, the post-reaction treatment is convenient, and the catalyst is renewable and environment-friendly.
Superbase-promoted multi-molecular acetylene/arylamine self-organization to 1-arylpyrroles
Schmidt, Elena Yu.,Semenova, Nadezhda V.,Ivanova, Elena V.,Bidusenko, Ivan A.,Trofimov, Boris A.
, p. 109 - 111 (2020/02/29)
A new superbase-promoted reaction of acetylene involves self-organization of its three molecules with one molecule of arylamine in KOH/DMSO system to afford 1-aryl-2,5- dimethylpyrroles in up to 63% yields. The key step of this reaction cascade is assumed to be the nucleophilic addition of acetylene to the C = N bond of the intermediate aldimine (aza-Favorsky reaction).
Synthesis, structure and in vitro anti-trypanosomal activity of non-toxic arylpyrrole-based chalcone derivatives
Hoppe, Heinrich C.,Isaacs, Michelle,Khanye, Setshaba D.,Kruger, Cuan,Oderinlo, Ogunyemi O.,Smith, Vincent J.,Veale, Clinton G. L.,Zulu, Ayanda I.
supporting information, (2020/04/10)
With an intention of identifying chalcone derivatives exhibiting anti-protozoal activity, a cohort of relatively unexplored arylpyrrole-based chalcone derivatives were synthesized in moderate to good yields. The resultant compounds were evaluated in vitro for their potential activity against a cultured Trypanosoma brucei brucei 427 strain. Several compounds displayed mostly modest in vitro anti-trypanosomal activity with compounds 10e and 10h emerging as active candidates with IC50 values of 4.09 and 5.11 μM, respectively. More importantly, a concomitant assessment of their activity against a human cervix adenocarcinoma (HeLa) cell line revealed that these compounds are non-toxic.
Improving the Potency of N-Aryl-2,5-dimethylpyrroles against Multidrug-Resistant and Intracellular Mycobacteria
Touitou, Meir,Manetti, Fabrizio,Ribeiro, Camila Maringolo,Pavan, Fernando Rogerio,Scalacci, Nicolò,Zrebna, Katarina,Begum, Neelu,Semenya, Dorothy,Gupta, Antima,Bhakta, Sanjib,Mchugh, Timothy D.,Senderowitz, Hanoch,Kyriazi, Melina,Castagnolo, Daniele
supporting information, p. 638 - 644 (2020/01/11)
A series of N-phenyl-2,5-dimethylpyrrole derivatives, designed as hybrids of the antitubercular agents BM212 and SQ109, have been synthesized and evaluated against susceptible and drug-resistant mycobacteria strains. Compound 5d, bearing a cyclohexylmethylene side chain, showed high potency against M. tuberculosis including MDR-TB strains at submicromolar concentrations. The new compound shows bacteriostatic activity and low toxicity and proved to be effective against intracellular mycobacteria too, showing an activity profile similar to isoniazid.
ANDROGEN RECEPTOR ANTAGONISTS
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Paragraph 0204-0206, (2019/08/26)
Compounds that inhibit the androgen receptor, pharmaceutical compositions comprising one or more of the compounds, as well as methods of treating cancer using such compounds are described.
Grinding solvent-free paal-knorr pyrrole synthesis on smectites as recyclable and green catalysts
Marvi, Omid,Nahzomi, Hossein Taherpour
, p. 139 - 147 (2018/04/23)
An environmentally benign method for the synthesis of N-substituted pyrroles from one-pot solvent-free condensation reaction of 2,5-hexanedione with various primary amines (Paal-Knorr pyrrole synthesis) on smectite clays as green and reusable heterogeneous Lewis acid catalysts is presented. The use of nontoxic, inexpensive, easily available and reusable catalysts under solvent-free conditions make this protocol practical, environmentally friendly and economically attractive.
In vivo potent BM635 analogue with improved drug-like properties
Poce, Giovanna,Cocozza, Martina,Alfonso, Salvatore,Consalvi, Sara,Venditti, Giulia,Fernandez-Menendez, Raquel,Bates, Robert H.,Barros Aguirre, David,Ballell, Lluis,De Logu, Alessandro,Vistoli, Giulio,Biava, Mariangela
supporting information, p. 539 - 550 (2018/01/17)
BM635 is the hit compound of a promising anti-TB compound class. Herein we report systematic variations around the central pyrrole core of BM635 and we describe the design, synthesis, biological evaluation, pharmacokinetic analysis, as well as in vivo TB mouse efficacy studies of novel BM635 analogues that show improved physicochemical properties. This hit-to-lead campaign led to the identification of a new analogue, 4-((1-isopropyl-5-(4-isopropylphenyl)-2-methyl-1H-pyrrol-3-yl)methyl)morpholine (17), that shows excellent activity (MIC = 0.15 μM; SI = 133) against drug-sensitive Mycobacterium tuberculosis strains, as well as efficacy in a murine model of TB infection.
One-pot synthesis of: N -substituted pyrroles from nitro compounds and 2,5-hexadione over a heterogeneous cobalt catalyst
Gong, Zheng,Lei, Yu,Zhou, Peng,Zhang, Zehui
, p. 10613 - 10618 (2017/10/05)
In this study, the one-pot heterocyclization of nitro compounds with 2,5-hexadione was studied for the synthesis of N-substituted pyrroles via a Paal-Knorr condensation process. The heterogeneous cobalt-nitrogen catalyst (Co-Nx/C-800-AT) was found to be active for this reaction with formic acid. Formic acid served as a hydrogen donor for the transfer hydrogenation, and also acted as an acid catalyst. More importantly, this method was tolerant of other functional groups, and hence various N-substituted pyrroles were produced with good to excellent yields. The Co-Nx/C-800-AT catalyst was highly stable, and could be reused several times without loss of its catalytic activity.
Efficient synthesis of substituted pyrroles through Pd(OCOCF3)2-catalyzed reaction of 5-hexen-2-one with primary amines
Chen, Xi,Yang, Meng,Zhou, Min
supporting information, p. 5215 - 5218 (2016/11/11)
An efficient and facile Pd(OCOCF3)2-catalyzed one-pot cascade protocol has been developed for the synthesis of multiple substituted pyrroles in good to excellent yields. Unlike the reported method starting from the 2-alkenal-1,3-carbonyl compounds, the process utilizes the less reactive 5-hexen-2-one and the method has great potential as a complement to the current developed methods.
