2199-49-7Relevant academic research and scientific papers
Propentdyopents and Related Compounds. Part 2. The Z E Photoisomerisation of Pyrromethenone Systems
Bonnett, Raymond,Hamzetash, Dariush,Valles, Maria Asuncion
, p. 1383 - 1388 (1987)
The Z E photoisomerisation of four α-unsubstituted pyrromethenones which are potential precursors of alkanol-propentdyopent adducts is studied using a direct n.m.r. spectroscopic approach in CD3OD-CDCl3.Chemical-shift assignments are made with the help of n.O.e. and decoupling experiments.For the polyalkylpyrromethenones the photostationary state contains ca. 25percent of the E isomer: a system with a β-ethoxycarbonyl group leads to 43percent E isomer at photoequilibrium.The E isomers can be manipulated in solution without appreciable change, but thermodynamic equilibration to the Z isomer (ca. 99percent) occurs on dry silica.A similar photoisomerisation of (4Z,15Z)-bilirubin IIIα in ND3-CD3OD leads to a photoequilibrated mixture containing 16percent of (4E,15Z)-bilirubin IIIα.
Proton pump inhibitors
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Paragraph 0219, (2015/11/16)
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.
Synthesis and biological evaluation of 3-substituted-indolin-2-one derivatives containing chloropyrrole moieties
Jin, Yun-Zhou,Fu, Da-Xu,Ma, Nan,Li, Zhan-Cheng,Liu, Quan-Hai,Xiao, Lin,Zhang, Rong-Hua
experimental part, p. 9368 - 9385 (2012/01/05)
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.
Efficient synthesis of an A-B-C-tricycle fragment for a structural model of tolyporphin
Hu, Bing C.,Zhou, Wei Y.,Liu, Zu L.,Cai, Chao J.,Xu, Shi C.
experimental part, p. 89 - 100 (2010/11/18)
An efficient stereocontrolled synthesis of an A-B-C-tricycle fragment 7 for a structural model of tolyporphin 3 is described. All the rings were prepared from readily available starting materials. One of the two key steps is a selective ring-opening reaction of the lactone cycle in bicyclolactam-lactone 17 to cyanopyrrolidone 18, which introduces the chirality into synthetic compounds. The other key step is the combination of A ring with B-C-bicycle via a two-time Eschenmoser sulfide contraction. A-B-C-tricycle fragment 7 allows a new approach toward tolypophin compounds and other uroporphinoids.
PROTON PUMP INHIBITORS
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, (2008/06/13)
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.
Methods for treating diseases and disorders related to unregulated angiogenesis and/or vasculogenesis
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, (2008/06/13)
The present invention relates to methods for treating diseases and disorders related to unregulated angiogenesis and/or vasculogenesis. More specifically, this invention relates to methods for treating diseases and disorders, such as rheumatoid arthritis,
4-aryl substituted indolinones
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, (2008/06/13)
The present invention relates to 4-arylindolinones, as well as pharmaceutical compositions thereof, capable of modulating protein kinase signal transduction in order to regulate, modulate and/or inhibit abnormal cell proliferation. The present invention also relates to methods for treating protein kinase related disorders.
5-ARALKYSUFONYL-3-(PYRROL-2-YLMETHYLIDENE)-2-INDOLINONE DERIVATIVES AS KINASE INHIBITORS
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, (2008/06/13)
The present invention relates to certain 5-aralkylsulfonyl-3-(pyrrol-2-yl-methylidene)-2-indolinone derivatives that inhibit kinases, in particular met kinase. Pharmaceutical compositions comprising these compounds, methods of treating diseases mediated by kinases utilizing pharmaceutical compositions comprising these compounds, and methods of preparing them are also disclosed.
The total synthesis of chlorophyll a
Woodward, Robert Burns,Ayer, William A.,Beaton, John M.,Bickelhaupt, Friedrich,Bonnett, Raymond,Buchschacher, Paul,Closs, Gerhard L.,Dutler, Hans,Hannah, John,Hauck, Fred P.,Ito, Sho,Langemann, Albert,Le Goff, Eugene,Leimgruber, Willy,Lwowski, Walter,Sauer, Juergen,Valenta, Zdenek,Volz, Heinrich
, p. 7599 - 7659 (2007/10/02)
The total synthesis of chlorophyll a starting from Knorr's pyrrole (1) is described with full experimental detail. Forty six stages are involved to reach the target molecule, chlorin e6 trimethyl ester (46), from which the preparation of chlorophyll a has already been described. The four pyrroles which are required for rings A, B, C and D are elaborated largely by known reactions, although with considerable improvements. These pyrroles are manipulated to give two dipyrrin derivatives: a left-hand component (26, comprising rings A and D) and a right-hand component (the thioaldehyde 31, comprising rings B and C). These are brought together in a carefully controlled, stepwise, condensation to give a single porphyrin product (35) in 50% yield. This synthesis of an unsymmetrically-substituted porphyrin bearing an electron-withdrawing substituent and a meso-substituent is seen as a very considerable advance, both in conceptual and practical terms, over earlier approaches. During the course of the closure of the macrocycle, intermediates which exemplify a new group of dihydroporphyrins, the phlorins (e.g. 34), are recognised. Eleven steps remain. The porphyrin (35) is shown to undergo dehydrogenation (again via a phlorin intermediate) on brief treatment with acetic acid in air to give the meso-crylic acid derivative (36), which in acetic acid under nitrogen at 110° slowly reaches equilibrium with the purpurin (37). The introduction of the reactive vinyl group at C-3 has been delayed until this point in the synthesis. Photo-oxygenation of the product, the vinylpurpurin (38), cleaves the cyclopenteno-ring giving the methoxalylpurpurin (39). A reverse Claisen reaction now generates the methoxylactone, rac-isopurpurin 5 methyl ester (40), the first substance in this synthetic series which can be compared with a sample (albeit optically active) derived from natural chlorophyll a. rac-Isopurpurin 5 methyl ester (40) is hydrolysed to the lactol, chlorin 5 (41), which is resolved (diastereoisomeric salts with quinine). The less soluble salt gives synthetic act-chlorin 5, identical with a sample of natural provenance. Diazomethane treatment of the free acid (42) yields purpurin 5 dimethyl ester (43), again identical with the naturally-derived compound. Treatment with hydrogen cyanide in triethylamine leads to the cyanolactone (44), reductive cleavage and methylation of which give the chlorin e6 nitrile (45). Methanolysis of this furnishes synthetic crystalline chlorin e6 trimethyl ester (46), identical (mp, mixed mp, electronic spectrum, infra red spectrum) with a naturally-derived sample, so completing the total synthesis.
