81453-99-8Relevant academic research and scientific papers
Ketorolac impurity C and preparation method and application thereof
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, (2021/06/06)
The invention discloses a ketorolac impurity C and a preparation method and application thereof. According to the method, the ketorolac impurity C is prepared by taking pyrrole as an initial raw material through a series of reactions such as substitution,
Synthesis of three asymmetric N-confused tetraarylporphyrins
Acharya, Rajendra,Paudel, Liladhar,Joseph, Jojo,McCarthy, Claire E.,Dudipala, Venkat R.,Modarelli, Jody M.,Modarelli, David A.
experimental part, p. 6043 - 6050 (2012/09/25)
Two monosubstituted and one tetrasubstituted N-confused porphyrins (1-3) were prepared in ca. 3-5% yields using a [2 + 2] synthesis. The monosubstituted porphyrins have carbomethoxy (1) or nitro (2) substituents on one of the meso-phenyl groups, while the meso-phenyl groups of the third NCP (3) are substituted with nitro, bromo, and methyl groups in an AB2C pattern. The specific regiochemistry of the aryl rings around the macrocycle in each porphyrin was definitively determined using a combination of 1D (1H and 13C) and 2D (gHMBC, gHSQC and ROESY) NMR spectroscopy. The absorption spectra of 1-3 in CH2Cl2 are similar to those of N-confused tetraphenylporphyrin (NCTPP) but have Soret and Q bands that are shifted to lower energies with smaller extinction coefficients in comparison to those for NCTPP.
Antimalarial activity of natural and synthetic prodiginines
Papireddy, Kancharla,Smilkstein, Martin,Kelly, Jane Xu,Shweta,Salem, Shaimaa M.,Alhamadsheh, Mamoun,Haynes, Stuart W.,Challis, Gregory L.,Reynolds, Kevin A.
, p. 5296 - 5306 (2011/10/02)
Prodiginines are a family of linear and cyclic oligopyrrole red-pigmented compounds. Herein we describe the in vitro antimalarial activity of four natural (IC50 = 1.7-8.0 nM) and three sets of synthetic prodiginines against Plasmodium falciparum. Set 1 compounds replaced the terminal nonalkylated pyrrole ring of natural prodiginines and had diminished activity (IC 50 > 2920 nM). Set 2 and set 3 prodiginines were monosubstituted or disubstituted at either the 3 or 5 position of the right-hand terminal pyrrole, respectively. Potent in vitro activity (IC50 = 0.9-16.0 nM) was observed using alkyl or aryl substituents. Metacycloprodiginine and more potent synthetic analogues were evaluated in a P. yoelii murine patent infection using oral administration. Each analogue reduced parasitemia by more than 90% after 25 (mg/kg)/day dosing and in some cases provided a cure. The most favorable profile was 92% parasite reduction at 5 (mg/kg)/day, and 100% reduction at 25 (mg/kg)/day without any evident weight loses or clinical overt toxicity.
1-arylsulfonyl-3-(α-hydroxybenzyl)-1H-pyrroles, a novel class of anti-HIV-1 reverse transcriptase inhibitors
Artico, Marino,Di Santo, Roberto,Costi, Roberta,Massa, Silvio,Scintu, Franca,Loi, Anna Giulia,De Montis, Antonella,La Colla, Paolo
, p. 1931 - 1936 (2007/10/03)
Various 1-arylsulfonyl-3-(α-hydroxybenzyl)-1H-pyrroles were prepared by Friedel-Crafts reaction of 1-arylsulfonyl-1H-pyrroles with aroylchlorides in the presence of aluminum trichloride, followed by reduction of the ketones to the required carbinols. The compounds were identified as a novel class of non-nucleoside HIV-1 reverse transcriptase inhibitors characterized by the presence of a diarylcarbinol moiety, a chemical feature that strictly correlates with the anti-HIV-1 activity.
The regioselective photoinduced aroylation at the 3-position of pyrrole derivatives
Oda, Kazuaki,Hiratsuka, Rin,Machida, Minoru
, p. 463 - 470 (2007/10/03)
Irradiation of arenecarbothioamide with pyrrole or indole derivatives gave regioselectively 3-aroylpyrrole or -indole derivatives, respectively.
Antifungal agents. VIII. Synthesis and antifungal activities of bipyrryl analogues of bifonazole
Di Santo,Massa,Costi,Simonetti,Retico,Apuzzo,Troccoli
, p. 229 - 236 (2007/10/02)
Various bipyrryl analogues of bifonazole were synthesized starting from aryl-3-pyrryl-1-imidazolylmethanes. The introduction of a second pyrryl portion was performed by linking an acrylate moiety at 1-position of the pyrrole ring and then by treatment with TosMIC. The bipyrryl esters were hydrolyzed and decarboxylated to afford the required imidazoles. All new imidazole derivatives were tested against Candida albicans and Candida spp using as standard controls miconazole, bifonazole and ketoconazole.
General Methods for Synthesizing 2,4-Diacylpyrroles and their Precursors Containing One or Two Masked Acyl Groups
Cadamuro, Silvano,Degani, Iacopo,Dughera, Stefano,Fochi, Rita,Gatti, Antonella,Piscopo, Laura
, p. 273 - 284 (2007/10/02)
A thorough study of the synthesis of 2,4-diacylpyrroles by direct acylation of pyrrole and 2- and 3-acylpyrroles is reported.Among these, Friedel-Crafts acylation of 3-acylpyrroles is the most general and advantageous method because it utilises easily accessible starting materials.In addition it is always regiospecific and readily provides 2,4-diacylpyrroles containing identical or different acyl groups in very high yields (81-100percent) under mild conditions, Alternative procedures concern the synthesis of precursors of 2,4-diacylpyrroles containing one or two acyl groups masked by a 1,3-benzodithiolyl or 1,3-benzoxathiolyl group and subsequent hydrolysis with HgO-35percent aq.HBF4-Me2SO.Overall yields are always good (52-60percent).Indirect acylation constitutes a secure complement to direct acylation when it is necessary to operate in the presence of protected acyl groups.
Pyrrole chemistry. XXVIII. Substitution reactions of 1-(phenylsulfonyl)pyrrole and some derivatives
Anderson, Hugh J.,Loader, Charles E.,Xu, Ru Xun,Le, Nghia,Gogan, Niall J.,et al.
, p. 896 - 902 (2007/10/02)
The preparative value of the 1-(phenylsulfonyl) N-blocking and directing group for the synthesis of 3-acylpyrroles has been further evaluated.Acetylation and benzoylation are strongly regiospecific and give good yields.However, the regiospecificity is not general and other substitution reactions give mixtures of 2- and 3-substitution or even mostly 2-substitution.Friedel and Crafts tert-butylation gives 3-tert-butyl-1-(phenylsulfonyl)pyrrole and provides a useful route to tert-butylpyrrole, but ethylation and isopropylation give mixtures.Acylations of 2- and 3-alkyl-1-(phenylsulfonyl)pyrroles show little evidence of useful regiospecificity.
Synthesis of Alkylpyrroles by the Sodium Borohydride Reduction of Acylpyrroles
Greenhouse, Robert,Ramirez, Coral,Muchowski, Joseph M.
, p. 2961 - 2965 (2007/10/02)
N-Unsubstituted alkylpyrroles are obtained by the reduction of the corresponding acylpyrroles with sodium borohydride in boiling 2-propanol.This reaction was demonstrated to proceed via the pyrrolylalkylcarbinol and was extended to the synthesis of a branched chain alkylpyrrole 25 from the tertiary alcohol 24.
Regioselective Synthesis of Acylpyrroles
Kakushima, Masatoshi,Hamel, Pierre,Frenette, Richard,Rokach, Joshua
, p. 3214 - 3219 (2007/10/02)
The regioselective synthesis of several pyrrole derivatives is described.AlCl3-catalyzed acylation reactions of 1-(phenylsulfonyl)pyrrole (1) give 3-acyl derivatives, whereas the corresponding BF3*OEt2-catalyzed reactions give 2-acyl derivatives predominantly.Mild alkaline hydrolysis gives the corresponding acyl-1H-pyrroles in excellent yields.AlCl3-catalyzed reactions of 1 with 1,1-dichloromethyl methyl ether and oxalyl chloride give 1-(phenylsulfonyl)-2-formylpyrrole (6) and 1-(phenylsulfonyl)-2-(chlorocarbonyl)pyrrole (7), respectively. 3-Pyrrolylacetic acid (10) was prepared by thallium(III) nitrate promoted rearrangement of 1-(phenylsulfonyl)-3-acetylpyrrole (2a).Trifluoroacetic anhydride catalyzed cyclization of 4-butyric acid (14) gives 1-(phenylsulfonyl)-7-oxo-4,5,6,7-tetrahydroindole (17).Attempts to cyclize 14 at the 4-position have been unsuccessful.
