- Pharmacophore mapping, molecular docking, chemical synthesis of some novel pyrrolyl benzamide derivatives and evaluation of their inhibitory activity against enoyl-ACP reductase (InhA) and Mycobacterium tuberculosis
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In an effort to produce new lead antimycobacterial compounds, herein we have reported the synthesis of a sequence of new pyrrolyl benzamide derivatives. The new chemical entities were screened to target enoyl-ACP reductase enzyme, which is one of the key enzymes of M. tuberculosis that are involved in type II fatty acid biosynthetic pathway. Compound 3q exhibited H-bonding interactions with Tyr158, Thr196 and co-factor NAD+ that binds the active site of InhA. All the pyrrolyl benzamide compounds were evaluated as inhibitors of M. tuberculosis H37Rv as well as inhibitors of InhA. Among them, few representative compounds were tested for mammalian cell toxicity on the human lung cancer cell-line (A549) and MV cell line that presented no cytotoxicity. Five of these compounds exhibited a good activity against InhA.
- Joshi, Shrinivas D.,Dixit, Sheshagiri R.,Basha, Jeelan,Kulkarni,Aminabhavi, Tejraj M.,Nadagouda, Mallikarjuna N.,Lherbet, Christian
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Read Online
- Utilization of caffeine carbon supported cobalt catalyst in the tandem synthesis of pyrroles from nitroarenes and alkenyl diols
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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.
- Balasubramaniam, Bhuvaneshwari,Dhara, Partha,Gupta, Raju K.,Kundu, Sabuj,Panja, Dibyajyoti,Sau, Anirban
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p. 244 - 254
(2021/09/07)
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- Green synthesis method of aromatic acid
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The invention discloses a green synthesis method of aromatic acid. Nickel-catalyzed carbonyl insertion is carried out on aryl iodine in the presence of formate, acid anhydride, a phosphine ligand andan organic solvent by using a nickel catalyst to obtain the aromatic acid. Efficient catalytic conversion is realized by utilizing the cheap nickel catalyst, the reaction conditions are mild, and theoperation is simple.
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Paragraph 0048-0122; 0261-0265; 0271-0272
(2020/05/01)
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- Nickel-catalyzed carboxylation of aryl iodides with lithium formate through catalytic CO recycling
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A protocol for the Ni-catalyzed carboxylation of aryl iodides with formate has been developed with good functional group compatibility for the synthesis of a variety of aromatic carboxylic acids under mild conditions. The reaction tolerates other functionalities for cross-coupling, such as aryl bromide, aryl chloride, aryl tosylate, and aryl pinacol boronate. The reaction proceeds through a carbonylation process with in situ generated carbon monoxide in the presence of a catalytic amount of acetic anhydride and lithium formate, avoiding the use of gaseous CO. The strategy of CO recycling in catalytic amounts is critical for the success of the reaction.
- Fu, Ming-Chen,Fu, Yao,Shang, Rui,Wu, Ya-Nan
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supporting information
p. 4067 - 4069
(2020/04/20)
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- Palladium-catalyzed carbonylative synthesis of acylstannanes from aryl iodides and hexamethyldistannane
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In this communication, we describe a new method for the carbonylative synthesis of acylstannanes from aryl iodides and hexamethyldistannane. With Pd(PPh3)4 as the catalyst and toluene as the solvent at 60 °C under 10 bar CO for 16 h, the desired acylstannanes were obtained in good to excellent yields. In order to facilitate isolation and analysis, the obtained acylstannanes were transformed into the corresponding benzoic acids by simply stirring under air for 5 h.
- Chen, Bo,Franke, Robert,Wu, Xiao-Feng,Xu, Jian-Xing,Yuan, Yang
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- KDM1A INHIBITORS FOR THE TREATMENT OF DISEASE
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Disclosed herein are new compounds and compositions and their application as pharmaceuticals for the treatment of diseases. Methods of inhibition of KDM1A, methods of increasing gamma globin gene expression, and methods to induce differentiation of cancer cells in a human or animal subject are also provided for the treatment of diseases such as acute myelogenous leukemia.
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- An efficient heterogeneous catalytic method for the N-arylation of pyrrole and other N-heterocycles
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Abstract 4 ? molecular sieve modified with copper(0) or copper(II) is an efficient heterogeneous catalyst for the arylation of pyrrole and some other heterocycles with iodo- or bromoarenes, Cs2CO3 base and pyrrole (or DMF) solvent. The catalysts can be easily prepared and are reusable.
- Nmeth, Jnos,Debreczeni, Nra,Gresits, Ivn,Blint, Mria,Hell, Zoltn
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p. 1113 - 1119
(2015/08/06)
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- Benzoic acid derivatives with improved antifungal activity: Design, synthesis, structure-activity relationship (SAR) and CYP53 docking studies
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Previously, we identified CYP53 as a fungal-specific target of natural phenolic antifungal compounds and discovered several inhibitors with antifungal properties. In this study, we performed similarity-based virtual screening and synthesis to obtain benzo
- Berne, Sabina,Kova?i?, Lidija,Sova, Matej,Kra?evec, Nada,Gobec, Stanislav,Kri?aj, Igor,Komel, Radovan
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p. 4264 - 4276
(2015/08/03)
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- Synthesis and screening of antimicrobial activity of novel pyrrole derivatives
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A new series of substituted N-substituted phenyl-4-(1H-pyrrol-1-yl) benzamides 4(a-g) have been synthesized by reaction of 4-(1H-pyrrol-1-yl) benzoyl chloride (3) with substituted primary amines. The purity of the compounds was confirmed by melting point
- Hallikeri,Joshi,More, Uttam A.,Kulkarni
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p. 249 - 252
(2019/01/21)
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- Two Component Recyclable Heterogeneous Catalyst, Process for Preparation Thereof and its Use for Preparation of Amines
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The invention describes the development of highly efficient, recyclable two component system, CuAl-hydrotalcite/rac 1,1′-Binaphthalene-2,2′-diol catalytic system for the N-alkylation of electron deficient aryl chlorides in presence of potassium carbonate as a base at room temperature in 3-6 h, wherein the process is provided for the preparation of various secondary amines via C—N coupling reaction of aliphatic amines(aliphatic open chain, acyclic, benzyl amines and heterocyclic amines) with various aryl chlorides.
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Page/Page column 8
(2012/01/13)
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- Copper ferrite nanoparticle-mediated N-arylation of heterocycles: A ligand-free reaction
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The synergistic effects of iron and copper in copper ferrite nanoparticles for the N-arylation of heterocycles with aryl halides were demonstrated. The magnetic nature of the catalyst facilitates its removal from the reaction medium for further use. Negligible leaching of Cu and Fe in consecutive cycles makes the catalyst economical and environmentally benign for C-N cross-coupling reactions.
- Panda, Niranjan,Jena, Ashis Kumar,Mohapatra, Sasmita,Rout, Smruti Ranjan
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supporting information; experimental part
p. 1924 - 1927
(2011/04/25)
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- Design, synthesis, and biological evaluation of N-carboxyphenylpyrrole derivatives as potent HIV fusion inhibitors targeting gp41
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On the basis of the structures of small-molecule hits targeting the HIV-1 gp41, N-(4-carboxy-3-hydroxy)phenyl-2,5-dimethylpyrrole (2, NB-2), and N-(3-carboxy-4-chloro)phenylpyrrole (A1, NB-64), 42 N-carboxyphenylpyrrole derivatives in two categories (A and B series) were designed and synthesized. We found that 11 compounds exhibited promising anti-HIV-1 activity at micromolar level and their antiviral activity was correlated with their inhibitory activity on gp41 six-helix bundle formation, suggesting that these compounds block HIV fusion and entry by disrupting gp41 core formation. The structure-activity relationship and molecular docking analysis revealed that the carboxyl group could interact with either Arg579 or Lys574 to form salt bridges and two methyl groups on the pyrrole ring were favorable for interaction with the residues in gp41 pocket. The most active compound, N-(3-carboxy-4-hydroxy)phenyl-2,5-dimethylpyrrole (A12), partially occupied the deep hydrophobic pocket, suggesting that enlarging the molecular size of A12 could improve its binding affinity and anti-HIV-1 activity for further development as a small-molecule HIV fusion and entry inhibitor.
- Liu, Kun,Lu, Hong,Hou, Ling,Qi, Zhi,Teixeira, Cátia,Barbault, Florent,Fan, Bo-Tao,Liu, Shuwen,Jiang, Shibo,Xie, Lan
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experimental part
p. 7843 - 7854
(2009/11/30)
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- Solvent and ligand effects on selective mono- and dilithiation of 1-(chlorophenyl)pyrroles and 1-(methoxyphenyl)pyrroles
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Novel methods for site-selective lithiation of 1-(chlorophenyl)pyrroles and 1-(methoxyphenyl)pyrroles are described. Mono- or dilithiations are governed by change of both the temperature and the solvent from tetrahydrofuran to diethyl ether. Regioselectiv
- Fogassy, Katalin,Kovacs, Krisztina,Keseru, Gyoergy M.,Toke, Laszlo,Faigl, Ferenc
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p. 1039 - 1043
(2007/10/03)
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