- New spiropyrans and two spirooxazines compounds with one or two thiophene nuclei. Applications to anticopying protection materials
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The strategy of synthesis of new thiophene-substituted spiroheterocyclic photochromic structures, in spiropyran or spirooxazine series is described. The polymerization of thiophene entity give interesting semi-conductor systems. Such molecular materials prevent the reproduction of documents and could be useful in other applications such as fast optical switches.
- Moustrou,Campredon,Samat,Garnier,Robillard,Guglielmetti
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- Annulated heterocycles through a radical-cation cyclization: synthetic and mechanistic studies
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The wide range of chemical transformations possible with furans and thiophenes, especially reactions leading to dearomatization of the nucleus, make them highly versatile synthons for complex molecule construction. As part of a program to exploit this int
- Sperry, Jeffrey B.,Wright, Dennis L.
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- Charge Trapping by Anionic Quinones Electrostatically Bound to a Highly Charged Cationic Quinone-Viologen Polymer or a Cationic Poly(3-viologen-thiophene)
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Charge associated with quinone reduction is trapped at low pH in systems composed of sulfonated anthraquinones electrostatically bound to a polymer derived from a monomer consisting of a quinone unit flanked by two viologen units.Each monomer repeat unit carriers 6 equiv of positive charge which can be charge compensated by monosulfonated anthraquinone to yield a quinone:viologen ratio of nearly 7:2.At low pH, electrostatic binding is persistent, and the amount of trapped charge is 90percent of the theoretical maximum.Some of the electrostatically bound quinone can be replaced with Fe(CN)6(3-) to allow mediated release of trapped charge via the Fe(CN)6(3-/4-) redox couple.I(-) is blocked from entering the polymer and thus does not mediate release of charge.Electrostatic binding of anionic quinones to a thiophene polymer with pendant viologen units has also demonstrated.This polymer system has the unique property of having built-in mediators for both the reduction (charge trapping) and oxidation (charge release) of the electrostatically bound anthraquinone.
- Hable, Christopher T.,Crooks, Richard M.,Valentine, James R.,Giasson, Richard,Wrighton, Mark S.
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- Synthesis of Thiophene-Substituted Spiropyrans and Spirooxazines, Precursors of Photochromic Polymers
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The synthesis of spiropyrans 11 and 12 and spirooxazines 13-17 containing a thiophene moiety is described.Two different synthetic approaches were used.The spectrokinetic properties of these new compounds are reported.
- Moustrou, Corinne,Samat, Andre,Guglielmetti, Robert,Dubest, Roger,Garnier, Francis
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- Ulotaront: A TAAR1 Agonist for the Treatment of Schizophrenia
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Ulotaront (SEP-363856) is a trace-amine associated receptor 1 (TAAR1) agonist with 5-HT1A receptor agonist activity in Phase 3 clinical development, with FDA Breakthrough Therapy Designation, for the treatment of schizophrenia. TAAR1 is a G-protein-coupled receptor (GPCR) that is expressed in cortical, limbic, and midbrain monoaminergic regions. It is activated by endogenous trace amines, and is believed to play an important role in modulating dopaminergic, serotonergic, and glutamatergic circuitry. TAAR1 agonism data are reported herein for ulotaront and its analogues in comparison to endogenous TAAR1 agonists. In addition, a human TAAR1 homology model was built around ulotaront to identify key interactions and attempt to better understand the scaffold-specific TAAR1 agonism structure-activity relationships.
- Heffernan, Michele L. R.,Herman, Lee W.,Brown, Scott,Jones, Philip G.,Shao, Liming,Hewitt, Michael C.,Campbell, John E.,Dedic, Nina,Hopkins, Seth C.,Koblan, Kenneth S.,Xie, Linghong
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supporting information
p. 92 - 98
(2021/12/17)
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- 4-alkyloxyimino derivatives of uridine-5′-triphosphate: Distal modification of potent agonists as a strategy for molecular probes of P2Y 2, P2Y4, and P2Y6 receptors
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Extended N4-(3-arylpropyl)oxy derivatives of uridine-5′-triphosphate were synthesized and potently stimulated phospholipase C stimulation in astrocytoma cells expressing G protein-coupled human (h) P2Y receptors (P2YRs) activated by UTP (P2Y2/4R) or UDP (P2Y6R). The potent P2Y4R-selective N4-(3- phenylpropyl)oxy agonist was phenyl ring-substituted or replaced with terminal heterocyclic or naphthyl rings with retention of P2YR potency. This broad tolerance for steric bulk in a distal region was not observed for dinucleoside tetraphosphate agonists with both nucleobases substituted. The potent N 4-(3-(4-methoxyphenyl)-propyl)oxy analogue 19 (EC50: P2Y2R, 47 nM; P2Y4R, 23 nM) was functionalized for chain extension using click tethering of fluorophores as prosthetic groups. The BODIPY 630/650 conjugate 28 (MRS4162) exhibited EC50 values of 70, 66, and 23 nM at the hP2Y2/4/6Rs, respectively, and specifically labeled cells expressing the P2Y6R. Thus, an extended N4-(3- arylpropyl)oxy group accessed a structurally permissive region on three G q-coupled P2YRs, and potency and selectivity were modulated by distal structural changes. This freedom of substitution was utilized to design of a pan-agonist fluorescent probe of a subset of uracil nucleotide-activated hP2YRs.
- Jayasekara, P. Suresh,Barrett, Matthew O.,Ball, Christopher B.,Brown, Kyle A.,Hammes, Eva,Balasubramanian, Ramachandran,Harden, T. Kendall,Jacobson, Kenneth A.
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p. 3874 - 3883
(2014/05/20)
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- NOVEL PRENYLARENE COMPOUND AND USE THEREOF
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A compound represented by the general formula (C): (wherein R101 represents a substituted or unsubstituted aromatic heterocyclic group, R102, R103, R104 and R105 may be the same or different, and each
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Paragraph 0046
(2013/03/26)
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- Concise synthesis and structure-activity relationship of furospinosulin-1, a hypoxia-selective growth inhibitor from marine sponge
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Structure-activity relationship of furospinosulin-1 (1), a hypoxia-selective growth inhibitor isolated from marine sponge, was investigated. Concise synthetic method of 1 was developed, and some structurally modified analogues were prepared. Biological evaluation of them revealed that the whole chemical structure was important for the hypoxia-selective growth inhibitory activity of 1. Among prepared, the desmethyl analogue 30 showed excellent hypoxia-selective inhibitory activity similar to that of 1 and also exhibited in vivo anti-tumor activity with oral administration.
- Kotoku, Naoyuki,Fujioka, Shinichi,Nakata, Chiaki,Yamada, Masaki,Sumii, Yuji,Kawachi, Takashi,Arai, Masayoshi,Kobayashi, Motomasa
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supporting information; experimental part
p. 6673 - 6678
(2011/09/30)
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- Enantioselective organo-SOMO cascade cycloadditions: A rapid approach to molecular complexity from simple aldehydes and olefins
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A highly selective, radical-mediated (4 + 2) coupling reaction of aldehydes and conjugated olefins has been achieved through asymmetric SOMO-catalysis. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnishes a cation which is vulnerable to nucleophilic addition. A range of aromatic aldehydes are shown to couple with styrenes and dienes to provide cyclic products with high chemical efficiency, regioselectivity, and stereoselectivity.
- Jui, Nathan T.,Lee, Esther C. Y.,MacMillan, David W. C.
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supporting information; experimental part
p. 10015 - 10017
(2010/10/03)
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- A palladium-catalyzed approach to polycyclic sulfur heterocycles
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(Chemical Equation Presented) The synthesis of a variety of polycyclic thiophenes and benzothiophenes is accomplished via a palladium-catalyzed domino ortho-alkylation/direct arylation reaction. An examination of the intramolecular direct arylation of thi
- Martins, Andrew,Lautens, Mark
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scheme or table
p. 8705 - 8710
(2009/04/11)
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- N-substituted 4β-methyl-5-(3-hydroxyphenyl)-7α-amidomorphans are potent, selective κ opioid receptor antagonists
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In a previous study, we identified (-)-N-[(1R,4S,5S,7R)-5-(3-hydroxyphenyl) -4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]non-7-yl]-3-(1-piperidinyl) propanamide (5a, KAA-1) as the first potent and selective κ opioid receptor antagonist from the 5-(3-hydroxyphenyl)morphan class of opioids. In this study we report an improved synthesis of this class of compounds. The new synthetic method was used to prepare analogues 5b-r where the morphan N-substituent and 7α-amido group were varied. Most of the analogues showed sub-nanomolar potency for the κ opioid receptor and were highly selective relative to the μ and δ opioid receptors. (-)-3-(3,4- Dihydroisoquinolin-2(1H)-yl)-N-{(1R,4S,5S,7R)-5-(3-hydroxyphenyl) -4-methyl-2-[2-(2-methylphenyl)ethyl]-2-azabicyclo[3.3.1]non-7-yl}propanamide (5n, MTHQ) is at least as potent and selective as nor-BNI as a κ opioid receptor antagonist in the [35S]GTP-γ-S in vitro functional test.
- Carroll, F. Ivy,Melvin, Matt S.,Nuckols, Michel C.,Mascarella, S. Wayne,Navarro, Hernán A.,Thomas, James B.
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p. 1781 - 1791
(2007/10/03)
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- Design, synthesis and cytotoxicity of 7-deoxy aryl discodermolide analogues
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A series of 7-deoxy discodermolide analogues in which the lactone fragment 'C' was replaced by aryl substituents were designed, synthesized, and evaluated for cytotoxicity.
- Burlingame, Mark A.,Shaw, Simon J.,Sundermann, Kurt F.,Zhang, Dan,Petryka, Joseph,Mendoza, Esteban,Liu, Fenghua,Myles, David C.,LaMarche, Matthew J.,Hirose, Tomoyasu,Freeze, B. Scott,Smith III, Amos B.
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p. 2335 - 2338
(2007/10/03)
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- SYNTHESE ET PROPRIETES DES DEUX FORMES ENANTIOMERES DE POLY(THIOPHENES) CHIRAUX
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Chiral poly(thiophenes) obtained from two enantiomerically pure monomers can stereoselectively recognize anions used as doping agents during voltammetric cycles.
- Lemaire, M.,Delabouglise, D.,Garreau, R.,Roncali, J.
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p. 193 - 198
(2007/10/02)
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- Enantioselective Chiral Poly(thiophenes)
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Chiral poly(thiophenes) have been synthesized by electropolymerisation: they exhibit high specific rotation, stability, and conductivity and can stereoselectively recognize chiral anions used as doping agents during voltammetric cycles.
- Lemaire, Marc,Delabouglise, Didier,Garreau, Robert,Guy, Alain,Roncali, Jean
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p. 658 - 661
(2007/10/02)
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