- Facile synthesis of 6-hydroxyindole-3-acetic acid: On the structure of the aromatic subunit of nephilatoxin-1~6
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A facile synthesis of 6-hydroxyindole-3-acetic acid 1a, which is the proposed aromatic subunit of NPTX-1~6, is described. Radical cyclization of isonitrile 2 successfully afforded 9 in high yield. The aromatic subunit of NPTX-1~6 was confirmed as 4-hydroxyindole-3-acetic acid 12 by comparison of the 1H-NMR spectra with those of authentic 4- and 6-hydroxyindole-3-acetic acids.
- Shinada, Tetsuro,Miyachi, Miki,Itagaki, Yasuhiro,Naoki, Hideo,Yoshihara, Kazuo,Nakajima, Terumi
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- Iodinated Choline Transport-Targeted Tracers
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We present a novel series of radioiodinated tracers and potential theranostics for diseases accompanied by pathological function of proteins involved in choline transport. Unlike choline analogues labeled with 11C or 18F that are currently used in the clinic, the iodinated compounds described herein are applicable in positron emission tomography, single-photon emission computed tomography, and potentially in therapy, depending on the iodine isotope selection. Moreover, favorable half-lives of iodine isotopes result in much less challenging synthesis by isotope exchange reaction. Six of the described compounds were nanomolar ligands, and the best compound possessed an affinity 100-fold greater than that of choline. Biodistribution data of 125I-labeled ligands in human prostate carcinoma bearing (PC-3) mice revealed two compounds with a biodistribution profile superior to that of [18F]fluorocholine.
- ?vec, Pavel,Novy, Zbyněk,Ku?ka, Jan,Pet?ík, Milo?,Sedlá?ek, Ond?ej,Kucha?, Martin,Li?ková, Barbora,Medvedíková, Martina,Kolouchová, Kristyna,Groborz, Ond?ej,Loukotová, Lenka,Konefa?, Rafa? ?.,Hajdúch, Marián,Hruby, Martin
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supporting information
p. 15960 - 15978
(2020/12/23)
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- Oxidative Approach Enables Efficient Access to Cyclic Azobenzenes
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Azobenzenes are versatile photoswitches that have found widespread use in a variety of fields, ranging from photopharmacology to the material sciences. In addition to regular azobenzenes, the cyclic diazocines have recently emerged. Although diazocines have fascinating conformational and photophysical properties, their use has been limited by their synthetic accessibility. Herein, we present a general, high-yielding protocol that relies on the oxidative cyclization of dianilines. In combination with a modular substrate synthesis, it allows for rapid access to diversely functionalized diazocines on gram scales. Our work systematically explores substituent effects on the photoisomerization and thermal relaxation of diazocines. It will enable their incorporation into a wide variety of functional molecules, unlocking the full potential of these emerging photoswitches. The method can be applied to the synthesis of a new cyclic azobenzene with a nine-membered central ring and distinct properties.
- Maier, Martin S.,Hüll, Katharina,Reynders, Martin,Matsuura, Bryan S.,Leippe, Philipp,Ko, Tongil,Sch?ffer, Lukas,Trauner, Dirk
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supporting information
p. 17295 - 17304
(2019/11/03)
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- Design and synthesis of alkoxyindolyl-3-acetic acid analogs as peroxisome proliferator-activated receptor-γ/δ agonists
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A series of carbazole or phenoxazine containing alkoxyindole-3-acetic acid analogs were prepared as PPARγ/δ agonists and their transactivation activities for PPAR receptor subtypes (α, γ and δ) were investigated. Structure-activity relationship studies disclosed the effect of the lipophilic tail, attaching position of the alkoxy group and N-benzyl substitution at indole. Compound 1b was the most potent for PPARδ and 3b for PPARγ. Molecular modeling suggested two different binding modes of our alkoxyindole-3-acetic acid analogs providing the insight into their PPAR activity.
- Gim, Hyo Jin,Li, Hua,Lee, Eun,Ryu, Jae-Ha,Jeon, Raok
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supporting information
p. 513 - 517
(2013/02/25)
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- Synthetic study on tetrapetalones: Stereoselective cyclization of N-acyliminium ion to construct substituted 1-benzazepines
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The synthesis of the tetracyclic core of complex antibiotic tetrapetalones has been achieved In three steps starting from the simple Intermediate γ-hydroxy amide, which can be accessed through a high-yielding six-step sequence. The successful synthesis relies on a novel strategy based on the N-acyliminium ion cyclizatlon.
- Cheng, Li,Xlnyu, L.I. And,Ran, Hong
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supporting information; experimental part
p. 4036 - 4039
(2009/12/09)
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- Synthesis of photoaffinity probe based on the leaf-opening factor from genus Albizzia
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The circadian rhythmic leaf-movements in legumes, called nyctinasty, are regulated by a pair of leaf-closing and -opening factors. Recent fluorescence studies revealed that cis-p-coumaroylagmatine (1), the leaf-opening factor from genus Albizzia, specific
- Okada, Masahiro,Matsubara, Akira,Ueda, Minoru
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p. 3794 - 3796
(2008/12/20)
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- Synthesis of macrocyclic molecular rods as potential electronic devices
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The design and synthesis of the macrocycles 1 and 2 as model compounds for the investigation of negative differential conductance phenomena in molecular junctions are reported. The macrocycles 1 and 2 comprise a molecular rod subunit consisting of three ethynyl-linked phenyl rings. While the rotational freedom along the rod axis of both terminal phenyl rings is limited by the macrocyclic frame, the central phenyl ring is revolving. The rod substructure is terminally functionalized with acetyl-protected thiol groups to enable its immobilization between gold contacts. The central phenyl ring is functionalized with one and two nitro groups for 1 and 2, respectively. The nitro groups are of particular importance as i) both macrocycles are model compounds to investigate a hypothetical intramolecular interaction of the nitro group with the opposite macrocyclic subunits and ii) the nitro group(s) result in limited thermal stability of the compounds due to the intramolecular rearrangement to macrocycles comprising isatogen subunits. These highly functionalized macrocycles have been assembled by acetylene scaffolding strategies in combination with functional group transformation chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Blaszczyk, Alfred,Chadim, Martin,Von Haenisch, Carsten,Mayor, Marcel
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p. 3809 - 3825
(2007/10/03)
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- FLUORINATED TRICYCLIC NEUROLEPTICS WITH PROLONGED ACTION: DERIVATIVES AND ANALOGUES OF 2-(4-(7-FLUORO-2-ISOPROPYL-10,11-DIHYDRODIBENZOTHIEPIN-11-YL)PIPERAZINE-1-YL)ETHANOL
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The preparation of 4-fluoro-2-nitrobenzonitrile (V), an intermediate in the synthesis of the title compound I, from 4-fluoro-2-nitroaniline via 5-fluoro-2-iodonitrobenzene (VII) was elaborated.Syntheses of 1,1,1,3,3,3-hexadeutero-2-propyl (XX) and 1,3,4-trideutero (XXVIII) analogues of compound I from hexadeuteroacetone, and pentadeuterobromobenzene, respectively, were carried out.Compound I was esterified with acetic anhydride, decanoic acid and 3,4,5-trimethoxybenzoyl chloride to give the esters II-IV.Acylation of compound XXX with acetyl chloride, 4-fluorophenoxyacetyl chloride and (4-fluorophenylthio)acetyl chloride and the following reduction of the amides with lithium aluminium hydride gave compounds XXXII, XXXIX, and XL.Substitution reactions of 11-chloro-7-fluoro-2-isopropyl-10,11-dihydrodibenzothiepin with the corresponding N-monosubstituted piperazines resulted in compounds XXXIII-XXXV, XXXVII, XXXVIII, XLI and XLII.Alkylation of XXX with 2-(2-chloroethyl)-1,3-dioxolane afforded compound XXXVI.Pharmacological testing of the new compounds, derivatives and analogues of the neuroleptic agent isofloxythepin (I), for discoordinating and cataleptic activities, showed especially for compounds II, XXXIV and XXXVI very intensive and long-lasting effects.The decanoate III has properties of a depot neuroleptic agent.
- Protiva, Miroslav,Jilek, Jiri,Rajsner, Miroslav,Sindelar, Karel,Bartl, Vaclav,et al.
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p. 1811 - 1833
(2007/10/02)
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- Kinetics and Mechanism of Iodination of Phenol and Substituted Phenols by Iodine Monochloride in Aqueous Acetic Acid
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In the title reactions the order with respect to ICl is unity and with respect to the substrate it is fractional in the concentration range studied.The effect of varying is negligible at lower acid (HClO) concentrations but at higher (> 0.01 M) there is unit dependence on .From the double reciprocal plot of 1/k1 versus 1/ the decomposition constants have been evaluated.Using these a linear ρ+ - ?+ plot is obtained indicating C-iodination.A mechanism consistent with the results obtained has been postulated.
- Prasada Rao, M. D.,Padmanabha, J.
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p. 133 - 135
(2007/10/02)
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