- The synthesis of pyrroles and oxazoles based on gold α-imino carbene complexes
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Cationic gold complexes of α-oximimino carbenes have been identified to react with weak nucleophiles including enol ethers and nitriles. These findings allowed us to develop the highly efficient synthesis of pyrroles and oxazoles.
- Loy, Nicole S. Y.,Choi, Subin,Kim, Sunggak,Park, Cheol-Min
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supporting information
p. 7336 - 7339
(2016/06/14)
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- Proton pump inhibitors
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A proton pump inhibitor containing a compound represented by the formula (I) wherein X and Y are the same or different and each is a bond or a spacer having 1 to 20 carbon atoms in the main chain, R 1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R 2 , R 3 and R 4 are the same or different and each is a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted thienyl group, an optionally substituted benzo[b]thienyl group, an optionally substituted furyl group, an optionally substituted pyridyl group, an optionally substituted pyrazolyl group, an optionally substituted pyrimidinyl group, an acyl group, a halogen atom, a cyano group or a nitro group, R 5 and R 6 are the same or different and each is a hydrogen atom or an optionally substituted hydrocarbon group, which has a superior proton pump action and shows an antiulcer activity and the like after conversion to a proton pump inhibitor in the body, or a salt thereof. or a prodrug thereof is provided.
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Paragraph 0270
(2015/11/16)
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- Regioselective synthesis of functionalized pyrroles via gold(I)-catalyzed [3+2] cycloaddition of stabilized vinyl diazo derivatives and nitriles
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The reaction of nitriles with alkenyldiazo compounds in the presence of gold catalysts provides functionalized pyrrole derivatives in moderate to high yields. This formal [3+2] cyclization reaction takes place with complete regioselectivity. The observed regiochemical outcome suggests the attack of the nitrile to the terminal position of the alkenylgold carbenoid (vinylogous reactivity). A broad range of nitriles (including those bearing functional groups) is compatible with this cyclization reaction. Copyright
- Lonzi, Giacomo,Lopez, Luis A.
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supporting information
p. 1948 - 1954
(2013/08/23)
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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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- Novel synthesis of [13C4,15N]1H-pyrrole-2, 3,5-tricarboxylic acid: An important biomarker for melatonin metabolism
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1H-pyrrole-2,3,5-tricarboxylic acid is a breakdown product of melatonin. A labeled version of this compound would serve as a key biomarker for drug candidates which track this substance to monitor their effectiveness (e.g. hyperpigmentation drugs). A Hantzsch synthesis using readily available starting materials was used to generate [13C4,15N]1H- pyrrole-2,3,5-tricarboxylic acid in six steps (12% overall yield). Copyright
- Skaddan, Marc B.
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experimental part
p. 73 - 77
(2010/09/14)
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- Synthesis of 3-Acylpyrroles, 3-(Alkoxycarbonyl)pyrroles, 1,5,6,7-Tetrahydro-4H-indol-4-ones and 3-Benzoylpyridines Based on Staudinger-Aza-Wittig Reactions of 1,3-Dicarbonyl Compounds with 2- and 3-Azido-1,1-dialkoxy- alkanes
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The Staudinger-aza-Wittig reaction of 1,3-dicarbonyl compounds with 2-azido-1,1-diethoxyethane and subsequent cy- clization allowed an efficient synthesis of a variety of pyrroles, 1,5,6,7-tetrahydro-4H-indol-4-ones, and of a pyridine. Georg Thieme Verlag
- Bellur, Esen,Yawer, Mirza A.,Hussain, Ibrar,Riahi, Abdolmajid,Fatunsin, Olumide,Fischer, Christine,Langer, Peter
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experimental part
p. 227 - 242
(2009/06/24)
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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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- PROTON PUMP INHIBITORS
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A proton pump inhibitor containing a compound represented by the formula (I) wherein X and Y are the same or different and each is a bond or a spacer having 1 to 20 carbon atoms in the main chain, R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R2, R3 and R4 are the same or different and each is a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted thienyl group, an optionally substituted benzo[b]thienyl group, an optionally substituted furyl group, an optionally substituted pyridyl group, an optionally substituted pyrazolyl group, an optionally substituted pyrimidinyl group, an acyl group, a halogen atom, a cyano group or a nitro group, R5 and R6 are the same or different and each is a hydrogen atom or an optionally substituted hydrocarbon group, which has a superior proton pump action and shows an antiulcer activity and the like after conversion to a proton pump inhibitor in the body, or a salt thereof. or a prodrug thereof is provided.
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- Acid secretion inhibitor
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The present invention provides a compound having a superior acid secretion inhibitory effect and showing an antiulcer activity and the like. The present invention provides a compound represented by the formula (I) wherein R1 is a nitrogen-containing monocyclic heterocyclic group optionally condensed with a benzene ring or a heterocycle, the nitrogen-containing monocyclic heterocyclic group optionally condensed with a benzene ring or a heterocycle optionally has substituent(s), R2 is an optionally substituted C6-14 aryl group, an optionally substituted thienyl group or an optionally substituted pyridyl group, R3 and R4 are each a hydrogen atom, or one of R3 and R4 is a hydrogen atom and the other is an optionally substituted lower alkyl group, an acyl group, a halogen atom, a cyano group or a nitro group, and R5 is an alkyl group or a salt thereof.
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Page/Page column 23
(2008/06/13)
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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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- PROTON PUMP INHIBITORS
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Proton pump inhibitors which have excellent proton pumping activity and which can be converted in vivo into proton pump inhibitors to exhibit antiulcer effect and so on, containing compounds represented by the general formula (I) or salts thereof or prodrugs of the same: (I) wherein X and Y are each independently a free valency or a spacer whose main chain has 1 to 20 carbon atoms; R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group; R2, R3 and R4 are each independently hydrogen, an optionally substituted hydrocarbon group, optionally substituted thienyl, optionally substituted benzo[b]thienyl, optionally substituted furyl, optionally substituted pyridyl, optionally substituted pyrazolyl, optionally substituted pyrimidinyl, acyl, halogeno, cyano, or nitro; and R5 and R6 are each independently hydrogen or an optionally substituted hydrocarbon group.
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Page/Page column 145-146; 288
(2010/10/20)
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- Efficient synthesis of pyrroles and 4,5,6,7-tetrahydroindoles via palladium-catalyzed oxidation of hydroxy-enamines
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Facile and one-pot synthetic route of poly-substituted pyrroles and 4-oxo-4,5,6,7-tetrahydroindoles is established, which consists of three steps: (1) palladium-catalyzed oxidation of hydroxy-enamines by using tetrakis(triphenylphosphine)palladium and mesityl bromide oxidation system, (2) intramolecular cyclization, and (3) dehydration.
- Aoyagi, Yutaka,Mizusaki, Toshihiko,Shishikura, Masahiro,Komine, Takashi,Yoshinaga, Tokuji,Inaba, Haruko,Ohta, Akihiro,Takeya, Koichi
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p. 8533 - 8538
(2007/10/03)
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- Synthesis of functionalized pyrroles and 6,7-dihydro-1H-indol-4(5H)-ones by reaction of 1,3-dicarbonyl compounds with 2-azido-1,1-diethoxyethane
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The condensation of 1,3-dicarbonyl compounds with 2-azido-1,1- diethoxyethane and subsequent cyclization allowed an efficient synthesis of a variety of pyrroles and 6,7-dihydro-1H-indol-4(5H)-ones.
- Bellur, Esen,Langer, Peter
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p. 2151 - 2154
(2007/10/03)
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- Synthesis of 2-alkylidenepyrrolidines, pyrroles, and indoles by condensation of silyl enol ethers and 1,3-bis-silyl enol ethers with 1-azido-2,2-dimethoxyethane and subsequent reductive cyclization
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The condensation of 1,3-bis-silyl enol ethers with 1-azido-2,2- dimethoxyethane and subsequent reductive cyclization allowed an efficient regio- and diastereoselective synthesis of a variety of 2-alkylidene-4- methoxypyrrolidines. The thermal elimination of methanol resulted in the formation of functionalized pyrroles. Similarly, 2,3,3a,4,5,6-hexahydro-2,3- benzopyrroles were prepared and transformed into 4,5,6,7-tetrahydro-2,3- benzopyrroles. In contrast, treatment of 2-alkylidenepyrrolidines with trifluoroacetic acid resulted in formation of indoles by [4 + 2] cycloaddition and subsequent extrusion of a nitrogen atom.
- Bellur, Esen,Goerls, Helmar,Langer, Peter
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p. 4751 - 4761
(2007/10/03)
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- A Powerful New Strategy for Diversity-Oriented Synthesis of Pyrroles from Donor-Acceptor Cyclopropanes and Nitriles
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(Equation presented) Lewis acid activated donor-acceptor cyclopropanes react with aliphatic, aromatic, and α,β-unsaturated nitriles in a novel cascade [3 + 2] dipolar cycloaddition, dehydration, and tautomerization sequence to afford pyrroles in moderate
- Yu, Ming,Pagenkopf, Brian L.
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p. 5099 - 5101
(2007/10/03)
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- Versatility of Weinreb amides in the Knorr pyrrole synthesis
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N-Methoxy-N-methyl-α-enaminocarboxamides were prepared starting from enamines and Weinreb α-aminoamides. Their reaction with oganometallic compounds and subsequent cyclization constitute a versatile alternative in the Knorr pyrrole synthesis.
- Alberola, Angel,Ortega, Alfonso Gonzalez,Sadaba, M. Luisa,Sanudo, Carmen
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p. 6555 - 6566
(2007/10/03)
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- Facile and efficient synthesis of pyrroles and indoles via palladium-catalyzed oxidation of hydroxy-enamines and -amines
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The palladium-catalyzed oxidation of hydroxy-enamines, which were obtained by the condensation of β-aminoalcohols and carbonyl compounds, proceeded to give the corresponding polysubstituted pyrroles and 4,5,6,7-tetrahydroindoles in good yields. The treatment of o-(2-hydroxyethyl)aniline with the palladium catalyst also gave indole in 78% yield.
- Aoyagi, Yutaka,Mizusaki, Toshihiko,Ohta, Akihiro
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p. 9203 - 9206
(2007/10/03)
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- Unsaturated Sulfoxides in Organic Synthesis: a New General Pyrrole Synthesis
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Pyrroles have been efficiently synthesised by a three-step reaction sequence.Michael addition of keto esters onto phenyl vinyl sulfoxide followed by Pummerer rearrangement gave the cyclic key intermediate 3.Mercury(II) salt induced carbon-sulfur bond clea
- Chan, Wing Hong,Lee, Albert W. M.,Lee, Ka Ming,Lee, Tin Yau
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p. 2355 - 2356
(2007/10/02)
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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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- Reaction of Acyclic Imides with 1-Ethoxycarbonylcyclopropyltriphenylphosphonium Tetrafluoroborate: An Easy Route to 1H-Pyrrole-3-carboxylates
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The reaction of anions of the acyclic imides 1 with the cyclopropylphosphonium salt 2 yields ethyl 1-acyl-Δ2-pyrroline-3-carboxylates 3, substituted in position 2, which can be dehydrogenated to yield the corresponding 1-acylpyrroles 4 and subsequently deacylated to give the pyrroles 5.The scope of the reaction is discussed.
- Flitsch, Wilhelm,Pandl, Klaus,Russkamp, Petra
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p. 529 - 534
(2007/10/02)
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