- Crystal structure, characterization, Hirshfeld surface analysis and DFT studies of two [propane 3-bromo-1-(triphenyl phosphonium)] cations containing bromide (I) and tribromide (II) anions: The anion (II) as a new brominating agent for unsaturated compounds
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In this study, propane 3-bromo-1- (triphenyl phosphonium) bromide, I, and propane 3-bromo-1- (triphenyl phosphonium) tribromide, II, (II as a new brominating agent) were synthesized and characterized by 1H NMR, 13C NMR, 31P NMR, FT-IR, spectroscopy, Thermogravimetric Analysis, Differential thermal analysis, Differential scanning calorimetry and single crystal X-ray analysis. Density functional theory calculations (energy, structural optimization and frequencies, Natural Bond Orbital, absorption energy and binding energy) were performed by using B3LYP/6-311 G++ (d, p) level of theory. Hirshfeld surface analysis and fingerprint plots were utilized to investigate the role of bromide and tribromide anions on the crystal packing structures of title compounds. The results revealed that the change of accompanying anionic moiety can affect the directional interactions of C-H?Br hydrogen bonds between anionic and cationic units in which the H?Br with a proportion of 53.8% and 40.9% have the major contribution in the stabilization of crystal structures of I and II, respectively. Furthermore, the thermal stability of new brominating agent II with tribromide anion was compared with compound I with bromide anion. Nontoxicity, short reaction time, thermal stability, simple working up and high yield are some of the advantages of these salts.
- Nokhbeh, Seyed Reza,Gholizadeh, Mostafa,Salimi, Alireza,Sparkes, Hazel A.
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p. 542 - 554
(2019/06/18)
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- Pyrrole as a Directing Group: Regioselective Pd(II)-Catalyzed Alkylation and Benzylation at the Benzene Core of 2-Phenylpyrroles
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Pyrrole has been employed for the first time as a directing group in the Pd(II)-catalyzed ortho-functionalization of C(sp2)-H bonds. A variety of substituted 2-phenylpyrroles were successfully methylated, alkylated, or benzylated in the ortho-position of the benzene ring, yielding the respective 2-substituted pyrrol-2-yl benzenes (36 examples, 51-93% yield). Neither additives nor additional ligands were required to perform the reaction, which was routinely conducted with PdBr2 as the catalyst and Li2CO3 as the base. Mechanistically, there is evidence that precoordination of palladium to the pyrrole enables the regioselective ortho-attack. (Chemical Equation Presented).
- Wiest, Johannes M.,P?thig, Alexander,Bach, Thorsten
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supporting information
p. 852 - 855
(2016/03/04)
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- PYRROLO CARBOXAMIDES AS MODULATORS OF ORPHAN NUCLEAR RECEPTOR RAR-RELATED ORPHAN RECEPTOR-GAMMA (ROR?, NR1F3) ACTIVITY AND FOR THE TREATMENT OF CHRONIC INFLAMMATORY AND AUTOIMMUNE DISEASES
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The invention provides modulators for the orphan nuclear receptor ROR? and methods for treating ROR? mediated diseases by administrating these novel ROR? modulators to a human or a mammal in need thereof. Specifically, the present invention provides pyrrolo carboxamide compounds of Formula (1) and the enantiomers, diastereomers, N-oxides, tautomers, solvates and pharmaceutically acceptable salts thereof.
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Page/Page column 122
(2013/06/27)
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- Synthesis and biological evaluation of 3-substituted-indolin-2-one derivatives containing chloropyrrole moieties
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Eighteen novel 3-substituted-indolin-2-ones containing chloropyrroles were synthesized and their biological activities were evaluated. The presence of a chlorine atom on the pyrrole ring was crucial to reduce cardiotoxicity. The presence of a 2-(ethylamino) ethylcarbamoyl group as a substituent at the C-4' position of the pyrrole enhanced the antitumor activities notably. IC 50 values as low as 0.32, 0.67, 1.19 and 1.22 μM were achieved against non-small cell lung cancer (A549), oral epithelial (KB), melanoma (K111) and large cell lung cancer cell lines (NCI-H460), respectively.
- Jin, Yun-Zhou,Fu, Da-Xu,Ma, Nan,Li, Zhan-Cheng,Liu, Quan-Hai,Xiao, Lin,Zhang, Rong-Hua
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experimental part
p. 9368 - 9385
(2012/01/05)
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- Discovery of potent, selective sulfonylfuran urea endothelial lipase inhibitors
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Endothelial lipase (EL) activity has been implicated in HDL catabolism, vascular inflammation, and atherogenesis, and inhibitors are therefore expected to be useful for the treatment of cardiovascular disease. Sulfonylfuran urea 1 was identified in a high-throughput screening campaign as a potent and non-selective EL inhibitor. A lead optimization effort was undertaken to improve potency and selectivity, and modifications leading to improved LPL selectivity were identified. Radiolabeling studies were undertaken to establish the mechanism of action for these inhibitors, which were ultimately demonstrated to be irreversible inhibitors.
- Goodman, Krista B.,Bury, Michael J.,Cheung, Mui,Cichy-Knight, Maria A.,Dowdell, Sarah E.,Dunn, Allison K.,Lee, Dennis,Lieby, Jeffrey A.,Moore, Michael L.,Scherzer, Daryl A.,Sha, Deyou,Suarez, Dominic P.,Murphy, Dennis J.,Harpel, Mark R.,Manas, Eric S.,McNulty, Dean E.,Annan, Roland S.,Matico, Rosalie E.,Schwartz, Benjamin K.,Trill, John J.,Sweitzer, Thomas D.,Wang, Da-yuan,Keller, Paul M.,Krawiec, John A.,Jaye, Michael C.
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supporting information; scheme or table
p. 27 - 30
(2009/05/07)
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- INHIBITORS OF THE HIV INTEGRASE ENZYME
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The present invention is directed to compounds of formula (I), and pharmaceutically acceptable salts and solvates thereof, their synthesis, and their use as modulators or inhibitors of the human immunodeficiency virus (“HIV”) integrase enzyme.
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Page/Page column 54-55
(2010/11/27)
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- Magnetic Circular Dichroism Studies. 66. Synthesis of Demethyl Monosubstituted Porphyrins. The Effect of Substituent Conformation on the Magnetic Circular Dichroism Spectra of Ethoxycarbonyl Porphyrins.
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The synthesis of a series of demethyl monosubstituted (acetyl, vinyl, formyl, cyano, and ethoxycarbonyl) free-base porphyrins (6b-f) is described.The key intermediates, 5-formyl-5'-methyldipyrrylmethanes 16a and 26, used in this synthesis are prepared in high yields by an improved procedure which entails decarboxylation of the 5-carboxy-5'-methyldipyrrylmethanes 15a and 25 in trifluoroacetic acid and subsequent formylation of the decarboxylated dipyrrylmethane with a mixture of dimethylformamide and p-nitrobenzoyl chloride.The preparation of the demethylformylporphyrin 6d from the demethylvinylporphyrin 6c was succesfully accomplished by the use of thallium(III) as a "protecting group" for the macrocycle.This series of monosustituted porphyrins allows, or the first time, the assessment of the electronic and optical consequences of the substituent effects on the porphyrin macrocycle on the same sterically unconstrained basis as now exists for a wide variety of other cyclic ?-electron systems.This is illustrated by comparing the MCD spectra of the methyl and demethyl ethoxycarbonyl free-base porphyrins.The observed sign variations of the MCD bands for these two porphyrins are explained with the perimeter model approach previously elaborated for substituted porphyrins.
- Wee, Andrew G. H.,Shu, Arthur Y. L.,Bunnenberg, Edward,Djerassi, Carl
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p. 3327 - 3336
(2007/10/02)
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- Ambident Electrophilic Character of Thioxophosphoranesulphenyl Bromides =P(S)SBr. A Novel Observation of Electrophilic Addition to a Carbon-Carbon Double Bond
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The thioxophosphoranesulphenyl bromides (1) act as ambident electrophiles towards alkenes and react, depending on the structure of the alkene, to give either the normal addition products -SC(R1)(R2)CR3(R4)(Br) or 1,2-dibromides and -disulphides.
- Lopusinski, Andrzej,Michalski, Jan,Potrzebowski, Mark
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p. 1362 - 1364
(2007/10/02)
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