- π-Bridge Substitution in DASAs: The Subtle Equilibrium between Photochemical Improvements and Thermal Control**
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Donor–acceptor Stenhouse adducts (DASAs) are playing an outstanding role as innovative and versatile photoswitches. Until now, all the efforts have been spent on modifying the donor and acceptor moieties to modulate the absorption energy and improve the c
- Martínez-López, David,Santamaría-Aranda, Eduardo,Marazzi, Marco,García-Iriepa, Cristina,Sampedro, Diego
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- An expedient route to 3-methoxy-2-furaldehyde
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An expedient route to 3-methoxy-2-furaldehyde is presented. Georg Thieme Verlag Stuttgart. New York.
- Ronn, Magnus,Lim, Ngiap-Kie,Hogan, Philip,Zhang, Wu-Yan,Zhu, Zhijian,Dunwoody, Nicholas
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Read Online
- AMIDE COMPOUND OR SALT THEREOF, AGRICULTURAL AND HORTICULTURAL MICROBICIDE COMPRISING THE COMPOUND AND THE SALT, AND METHOD FOR USING THE AGRICULTURAL AND HORTICULTURAL MICROBICIDE
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An amide compound represented by the general formula [I]: or a salt thereof, an agricultural and horticultural microbicide comprising the compound or the salt as an active ingredient, and a method for using the agricultural and horticultural microbicide.
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Paragraph 0193-0194
(2021/01/26)
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- Synthetic and Mechanistic Investigation of an Oxime Ether Electrocyclization Approach to Heteroaromatic Boronic Acid Derivatives
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A range of functionalized heteroaromatic boronic acid derivatives are readily accessed by a diboration/6π-electrocyclization sequence. This study revealed the surprising observation that there is a direct relationship between oxime ether stereochemistry and reactivity towards electrocyclization. Specifically, E-oxime ethers are found to be significantly more reactive than their Z-counterparts (stereochemistry relative to azatriene scaffold). In contrast, the configuration at the azatriene alkene terminus has little impact on reaction rates. Computational analysis offers a rationale for this observation; a Nlone pair→C=C π* orbital interaction lowers the energy of the transition state in the electrocyclization of E-oxime ethers. Finally, unreactive Z-oxime ethers can be converted to the corresponding heterocyclic products by a photolytically promoted E→Z isomerization and electrocyclization sequence.
- Mora-Radó, Helena,Sotorríos, Lia,Ball-Jones, Matthew P.,Bialy, Laurent,Czechtizky, Werngard,Méndez, María,Gómez-Bengoa, Enrique,Harrity, Joseph P. A.
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supporting information
p. 9530 - 9534
(2018/07/14)
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- Preparation of amino-substituted indenes and 1,4-dihydronaphthalenes using a one-pot multireaction approach: Total synthesis of oxybenzo[c]phenanthridine alkaloids
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Allylic trichloroacetimidates bearing a 2-vinyl or 2-allylaryl group have been designed as substrates for a one-pot, two-step multi-bond-forming process leading to the general preparation of aminoindenes and amino-substituted 1,4-dihydronaphthalenes. The synthetic utility of the privileged structures formed from this one-pot process was demonstrated with the total synthesis of four oxybenzo[c]phenanthridine alkaloids, oxychelerythrine, oxysanguinarine, oxynitidine, and oxyavicine. An intramolecular biaryl Heck coupling reaction, catalyzed using the Hermann-Beller palladacycle was used to effect the key step during the synthesis of the natural products.
- Calder, Ewen D. D.,McGonagle, Fiona I.,Harkiss, Alexander H.,McGonagle, Grant A.,Sutherland, Andrew
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p. 7633 - 7648
(2014/09/17)
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- Practical nonazide synthesis of a D-amino acid oxidase inhibitor via a sequential erlenmeyer-ploechl reaction and ligand-free copper(I) amination protocol
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A synthetic route to fused heterocycle 5 (R1 = Et) was developed that avoids the use of troublesome azido functionality. In this approach, 3-bromofuran aldehyde 7 was synthesized from 3-bromofuran 6 using highly regioselective formylation conditions. The crude solution of 7 was treated with hippuric acid under Erlenmeyer-Ploechl conditions to give enamide product 16, which was isolated by crystallization. Intramolecular amination/cyclization to the fused pyrrole was achieved under ligand-free Cu(I) catalysis in toluene, followed by diamine workup to remove the benzoyl protecting group and residual copper. The final product 5 (R1 = Et) was crystallized directly from the reaction mixture, providing up to 60% overall yield over five chemical steps and two isolations.
- Zhao, Hang,Koenig, Stefan G.,Dankwardt, John W.,Singh, Surendra P.
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p. 198 - 204
(2014/05/20)
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- Directed metalation and regioselective functionalization of 3-bromofuran and related heterocycles with NaHMDS
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A mild and regioselective functionalization protocol for 3-bromofuran and analogs has been developed. Selective metalation and functionalization of C2 can be achieved as a result of the directing effect of the adjacent electron-withdrawing bromo group. In addition, the C5 position can also be selectively functionalized by blocking the C2 position via silylation or by simply controlling the reaction temperature. These functionalized compounds bearing a C3 bromo substituent may be further elaborated by utilizing a Suzuki-Miyaura cross-coupling procedure.
- Zhao, Hang,Dankwardt, John W.,Koenig, Stefan G.,Singh, Surendra P.
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experimental part
p. 166 - 169
(2012/01/30)
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- Synthesis and SAR studies of novel heteroaryl fused tetracyclic indole-diamide compounds: Potent allosteric inhibitors of the hepatitis C virus NS5B polymerase
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Presented here are initial structure-activity relationship (SAR) studies on a series of novel heteroaryl fused tetracyclic indole-based inhibitors of the hepatitis C viral polymerase, NS5B. The introduction of alternative heterocyclic moieties into the indolo-fused inhibitor class significantly expands the reported SAR and resulted in the identification of pyridino analogs, typified by compounds 44 and 45 that displayed excellent potency against the NS5B polymerase of both HCV 1a and HCV 1b genotypes.
- Ding, Min,He, Feng,Hudyma, Thomas W.,Zheng, Xiaofan,Poss, Michael A.,Kadow, John F.,Beno, Brett R.,Rigat, Karen L.,Wang, Ying-Kai,Fridell, Robert A.,Lemm, Julie A.,Qiu, Dike,Liu, Mengping,Voss, Stacey,Pelosi, Lenore A.,Roberts, Susan B.,Gao, Min,Knipe, Jay,Gentles, Robert G.
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scheme or table
p. 2866 - 2871
(2012/05/20)
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- 5-[3-(4-Benzyloxyphenylthio)-fur-2-yl]-imidazolidin-2, 4-dione and analogues as inhibitors of macrophage elastase
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5-[3-(4-benzyloxyphenylthio)-fur-2-yl]-imidazolidin-2,4-dione and analogues useful as inhibitors of macrophage elastase are disclosed.
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Page/Page column 2
(2008/06/13)
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- Discovery of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]furo[2,3-c]pyridine-5- carboxamide, an agonist of the α7 nicotinic acetylcholine receptor, for the potential treatment of cognitive deficits in schizophrenia: Synthesis and structure-activity relationship
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N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide (14, PHA-543,613), a novel agonist of the α7 neuronal nicotinic acetylcholine receptor (α7 nAChR), has been identified as a potential treatment of cognitive deficits in schizophrenia. Compound 14 is a potent and selective a7 nAChR agonist with an excellent in vitro profile. The compound is characterized by rapid brain penetration and high oral bioavailability in rat and demonstrates in vivo efficacy in auditory sensory gating and, in an in vivo model to assess cognitive performance, novel object recognition.
- Wishka, Donn G.,Walker, Daniel P.,Yates, Karen M.,Reitz, Steven C.,Jia, Shaojuan,Myers, Jason K.,Olson, Kirk L.,Jacobsen, E. Jon,Wolfe, Mark L.,Groppi, Vincent E.,Hanchar, Alexander J.,Thornburgh, Bruce A.,Cortes-Burgos, Luz A.,Wong, Erik H. F.,Staton, Brian A.,Raub, Thomas J.,Higdon, Nicole R.,Wall, Theron M.,Hurst, Raymond S.,Walters, Rodney R.,Hoffmann, William E.,Hajos, Mihaly,Franklin, Stanley,Carey, Galen,Gold, Lisa H.,Cook, Karen K.,Sands, Steven B.,Zhao, Sabrina X.,Soglia, John R.,Kalgutkar, Amit S.,Arneric, Stephen P.,Rogers, Bruce N.
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p. 4425 - 4436
(2007/10/03)
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- INDANE DERIVATES AS MUSCARINIC RECEPTOR AGONISTS
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The present invention relates to compounds of Formula I: I which are agonists of the M-1 muscarinic receptor.
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- A versatile aminobenzannulation method based on the deprotonation of 2-(1-alkynyl)-benzaldimines and similar 2-aza-2,4-heptadienyl-6-ynes: A multistep rearrangement cascade
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Two ring closures, a ring opening, and two intermolecular proton shifts are the crucial steps in a cascade reaction that is triggered by the simple deprotonation of alkynylimines and leads ultimately to aminobenzannulation products (see scheme). The reactions proceed in good to very good yield and with excellent chemoselectivity.
- Sagar, Pramod,Froehlich, Roland,Wuerthwein, Ernst-Ulrich
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p. 5694 - 5697
(2007/10/03)
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- Quinuclidines-substituted-multi-cyclic-heteroaryls for the treatment of disease
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The invention provides compounds of Formula I: 1where in W is 2These compounds may be in the form of pharmaceutical salts or compositions, racemic mixtures, or pure enantiomers thereof. The compounds of Formula I are useful to treat diseases or conditions in which α7 is known to be involved.
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- Substituted 7-aza[2.2.1]bicycloheptanes for the treatment of disease
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The invention provides compounds of Formula I: which may be in the form of pharmaceutical acceptable salts or compositions, are useful in treating diseases or conditions in which α7 nicotinic acetylcholine receptors (nAChRs) are known to be involved.
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- Azabicyclic-substituted fused-heteroaryl compounds for the treatment of disease
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The invention provides compounds of Formula I: wherein Azabicyclo is These compounds may be in the form of pharmaceutical salts or compositions, racemic mixtures, or pure enantiomers thereof. The compounds of Formula I are useful in pharmaceuticals in which α7 is known to be involved.
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- Endothelin receptor antagonists
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PCT No. PCT/US96/12583 Sec. 371 Date Nov. 25, 1996 Sec. 102(e) Date Nov. 25, 1996 PCT Filed Aug. 2, 1996 PCT Pub. No. WO97/04769 PCT Pub. Date Feb. 13, 1997This invention relates to derivatives of furan and thiophene, their composition, process of making
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- Endothelin receptor antagonists
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Novel furans and thiophenes, pharmaceutical compositions containing these compounds and their use as endothelin receptor antagonist are described.
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- Phenethylthiazolylthiourea (PETT) compounds as a new class of HIV-1 reverse transcriptase inhibitors. 2. Synthesis and further structure-activity relationship studies of PETT analogs
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Phenylethylthiazolylthiourea (PETT) derivatives have been identified as a new series of nonnucleoside inhibitors of HIV-1 RT. Structure-activity relationship studies of this class of compounds resulted in the identification of N-[2-(2-pyridyl)ethyl]-N'-[2-(5-bromopyridyl)]-thiourea hydrochloride (trovirdine; LY300046.HCl) as a highly potent anti-HIV-1 agent. Trovirdine is currently in phase one clinical trials for potential use in the treatment of AIDS. Extension of these structure-activity relationship studies to identify additional compounds in this series with improved properties is ongoing. A part of this work is described here. Replacement of the two aromatic moleties of the PETT compounds by various substituted or unsubstituted heteroaromatic rings was investigated. In addition, the effects of multiple substitution in the phenyl ring were also studied. The antiviral activities were determined on wild-type and constructed mutants of HIV-1 RT and on wild-type HIV-1 and mutant viruses derived thereof, Ile100 and Cys181, in cell culture assays. Some selected compounds were determined on double- mutant viruses, HIV-1 (Ile100/Asn103) and HIV-1 (Ile100/Cys181). A number of highly potent analogs were synthesized. These compounds displayed IC50's against wild-type RT between 0.6 and 5 nM. In cell culture, these agents inhibited wild-type HIV-1 with ED50's between I and 5 nM in MT-4 cells. In addition, these derivatives inhibited mutant HIV-1 RT (Ile 100) with IC50's between 20 and 50 nM and mutant HIV-1 RT (Cys 181) with IC50's between 4 and 10 nM, and in cell culture they inhibited mutant HIV-1 (Ile100) with ED50's between 9 and 100 nM and mutant HIV-1 (Cys181) with ED50's between 3 and 20 nM.
- Cantrell, Amanda S.,Engelhardt, Per,H?gberg, Marita,Jaskunas, S. Richard,Johansson, Nils Gunnar,Jordan, Christopher L.,Kangasmets?, Jussi,Kinnick, Michael D.,Lind, Peter,Morin Jr., John M.,Muesing,Noreén, Rolf,?berg, Bo,Pranc, Paul,Sahlberg, Christer,Ternansky, Robert J.,Vasileff, Robert T.,Vrang, Lotta,West, Sarah J.,Zhang, Hong
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p. 4261 - 4274
(2007/10/03)
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- Preparation of optically active 2-(or 3)(p-tolylsulfinyl)-3(or 2)furyl- or thienylcarboxaldehydes
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The preparation of the four enantiomerically pure title compounds is described by reaction of (I)-(-)-Ss-menthyl-p-toluenesulfinate on furan or thiophene precursors.
- Girodier,Maignan,Rouessac
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p. 2045 - 2052
(2007/10/03)
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- ONE-STEP SYNTHESIS OF 2-AMINO-3-FURANCARBOXYLIC ACID DERIVATIVES FROM 2-FURANCARBALDEHYDE
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Reaction of derivatives of 2-furancarbaldehyde or 2-acetylfuran with malononitrile, methyl cyanoacetate or cyanoacetamide in the presence of secondary amines afforded derivatives of 2-amino-3-furancarboxylic acid in 45 - 88percent yields.
- Safar, Peter,Cepec, Pavel,Povazanec, Frantisek,Korenova, Anna,Pronayova, Nada
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p. 2481 - 2492
(2007/10/02)
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- Certain pyridyl, thienyl or furyl propenoic acids or esters having anti-inflammatory anti-allergic properties
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Compounds of formula (I): STR1 in which R1 is hydrogen or C1-6 alkyl; R2 is hydrogen or a group --CO2 R3 where R3 is hydrogen or C1-6 alkyl; n is an integer of from 2 to 12; X represents a double or triple bond, and each of A and B represents hydrogen when X is a double bond, or both A and B are absent when X is a triple bond; and STR2 represents an aromatic heterocyclic ring, are disclosed as inhibitors of 5-lipoxygenase.
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- Hypoglycemic 5-substituted oxazolidine-2,4-diones
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Hypoglycemic 5-furyl and 5-thienyl derivatives of oxazolidine-2,4-dione and the pharmaceutically-acceptable salts thereof; certain 3-acylated derivatives thereof; and intermediates useful in the preparation of said compounds.
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