74163-48-7Relevant academic research and scientific papers
Synthesis and unusual crystal structure of syn-6,15-dicyano-2,11-dithia[3.3]metacyclophane
Bodwell, Graham J.,Bridson, John N.,Houghton, Tom J.,Yarlagadda, Bala
, p. 7475 - 7478 (1997)
syn-6,15-Dicyano-2,11-dithia[3.3]metacyclophane 4 is the first of its kind to crystallize with both bridges in the pseudo-boat conformation. A number of other unusual features are also apparent in the crystal structure, none of which are predicted by AM1
COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USE THEREOF AS INHIBITORS OF RAN GTPASE
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Paragraph 00107, (2019/04/09)
Compounds of general formula IA, IB and IC outlined below, including pharmaceutically acceptable salts, solvates and hydrates thereof. Such compounds and pharmaceutical compositions comprising them may be used in medical conditions involving Ran GTPase.
AMIDE-LINKED EP4 AGONIST-BISPHOSPHONATE COMPOUNDS AND USES THEREOF
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Paragraph 00158-00159, (2017/01/31)
The present invention relates to EP4 agonist-bisphosphonate conjugates or related compounds and uses thereof. Said conjugates or related compounds may be used to provide delivery of an EP4 agonist or related compound to a desired site of action, such as a bone. Bisphosphonate moieties, linked to the EP4 agonists via amide linkers, have been implicated in the inhibition of bone resorption and bone targeting.
Structure-guided design of selective inhibitors of neuronal nitric oxide synthase
Huang, He,Li, Huiying,Martásek, Pavel,Roman, Linda J.,Poulos, Thomas L.,Silverman, Richard B.
, p. 3024 - 3032 (2013/06/04)
Nitric oxide synthases (NOSs) comprise three closely related isoforms that catalyze the oxidation of l-arginine to l-citrulline and the important second messenger nitric oxide (NO). Pharmacological selective inhibition of neuronal NOS (nNOS) has the potential to be therapeutically beneficial in various neurodegenerative diseases. Here, we present a structure-guided, selective nNOS inhibitor design based on the crystal structure of lead compound 1 in nNOS. The best inhibitor, 7, exhibited low nanomolar inhibitory potency and good isoform selectivities (nNOS over eNOS and iNOS are 472-fold and 239-fold, respectively). Consistent with the good selectivity, 7 binds to nNOS and eNOS with different binding modes. The distinctly different binding modes of 7, driven by the critical residue Asp597 in nNOS, offers compelling insight to explain its isozyme selectivity, which should guide future drug design programs.
Synthesis and in vitro properties of trimethylamine- and phosphonate-substituted carboranylporphyrins for application in BNCT
Easson, Michael W.,Fronczek, Frank R.,Jensen, Timothy J.,Vicente, M. Graca H.
, p. 3191 - 3208 (2008/09/20)
A series of carboranylporphyrins containing either amine or phosphonic acid functionalities and two to six closo-carborane clusters have been synthesized via a [2 + 2] condensation of a dimethylamino- or diethylphosphonate-substituted dipyrromethane with
Rigid dendritic donor-acceptor ensembles: Control over energy and electron transduction
Guldi, Dirk M.,Swartz, Angela,Luo, Chuping,Gomez, Rafael,Segura, Jose L.,Martin, Nazario
, p. 10875 - 10886 (2007/10/03)
Several generations of phenylenevinylene dendrons, covalently attached to a C60 core, have been developed as synthetic model systems with hierarchical, fine-tuned architectures. End-capping of these dendritic spacers with dibutylaniline or dode
Synthesis of photo- and electroactive stilbenoid dendrimers carrying dibutylamino peripheral groups
Segura, Jose L.,Gomez, Rafael,Martin, Nazario,Guldi, Dirk M.
, p. 2645 - 2647 (2007/10/03)
(Equation presented) A novel convergent synthetic route for the preparation of functionalized and fluorescent stilbenoid dendrons built on the 1,3,5-benzene core and endowed with a periphery of dibutylamino groups has been developed. Long alkyl chains hav
Reversible dioxygen binding and aromatic hydroxylation in O2-reactions with substituted xylyl dinuclear copper(I) complexes: Syntheses and low-temperature kinetic/thermodynamic and spectroscopic investigations of a copper monooxygenase model system
Karlin, Kenneth D.,Nasir, M. Sarwar,Cohen, Brett I.,Cruse, Richard W.,Kaderli, Susan,Zuberbühler, Andreas D.
, p. 1324 - 1336 (2007/10/02)
The binding and subsequent reactivity of dioxygen (O2) upon binding to copper ion centers is of fundamental interest in chemical and biological processes. We provide here a detailed account of the reaction of O2 with dicopper(I) complexes, involving O2-reversible binding, followed by the stoichiometric aromatic hydroxylation of the ligand. Thus, tricoordinated dicopper(I) complexes [Cu2(R-XYL)]2+ (R = H, MeO, t-Bu, F, CN, NO2; 1a-f) possess dinucleating meta-substituted xylylene ligands with two chelating tridentate bis[2-(2-pyridyl)ethyl]amine (PY2) moieties and a 5-R substituent. Upon reaction with O2, dioxygen adducts [Cu2(R-XYL)(O2)]2+ (2a,c-f) form reversibly, and these subsequently yield 2-xylylene-hydroxylated products [Cu2(R-XYL-O-)(OH)]2+ (3a-f), which are phenoxo- and hydroxo-bridged copper(II) complexes. The products 3 have been characterized via the X-ray structure of the parent complex 3a, and by their UV-visible, infrared, and room-temperature magnetic properties. Incorporation of the O-atom from dioxygen into the phenolic products has been proven by isotopic labeling experiments, except in the case of 3f, where workup results in an exchange reaction causing loss of the oxygen label. In reactions of O2 with 1 in dichloromethane at room temperature, 10-25% yields of unhydroxylated complexes [Cu2(R-XYL)(OH)]3+ (5) are obtained. A stopped-flow kinetics study of O2 reactions of 1 in CH2Cl2 demonstrates that [Cu2(R-XYL)(O2)]2+ (2a,c-f) complexes form reversibly, proceeding via the reaction 1 + O2 ? 2 (K1 = k1/k-1); this is followed by the irreversible reaction 2 → 3 (k2). Analysis of temperature-dependent data which is accompanied by spectrophotometric monitoring yields both kinetic and thermodynamic parameters for R = H, t-Bu, F, and NO2. Dioxygen binding to 1 occurs in a single observable step with low activation enthalpies (6-29 kJ mol-1) and large, negative activation entropies (-66 to -167 J K-1 mol-1). The remote R-substituent has a significant effect on the dioxygen-binding process and this is explained in terms of its multistep nature. Strong binding (K1) occurs at low temperature (e.g. -80 °C), and thermodynamic parameters indicate a large enthalpic contribution (ΔH° = -52 to -74 kJ mol-1), but room-temperature stabilities of the dioxygen adducts are precluded by very large unfavorable entropies (ΔS° = -156 to -250 J K-1 mol-1). Electron-releasing R-substituents cause a small but significant enhancement of k2, the hydroxylation step, consistent with a mechanism involving electrophilic attack of the Cu2O2 intermediate 2 upon the xylyl aromatic ring. The influence of substituent upon the various rates of reaction allows for stabilization (～minutes), allowing the bench-top observation of 2d,e,f using UV-visible spectroscopy at -80 °C. "Vacuum-cycling" experiments can be carried out on 1f/2f, i.e., the repetitive oxygenation of 1f at -80 °C, followed by removal of O2 from 2f by application of a vacuum. Dicopper(I) complexes I have been characterized by 1H and 13C NMR spectroscopy, along with analogs in which an ethyl group has been placed in the 5-position of the pyridyl ring donor groups, i.e., [CuI2(R-XYL-(5-Et-PY))]2+ (1g, R = H; 1h, R = NO2). Variable-temperature 1H NMR spectroscopic studies provide clues as to why [Cu2(MeO-XYL)]2+ (1b) does not oxygenate (i.e., bind O2 and/or hydroxylate) at low temperature, the conclusion being that significant interactions of the coordinately unsaturated copper(I) ion(s) with the chelated methoxybenzene group result in conformations unsuitable for O2-reactivity. The biological implications of the biomimetic chemistry described here are discussed, as a system effecting oxidative C-H functionalization using O2 under mild conditions and as a monooxygenase model system for tyrosinase (phenol o-monooxygenase), with its dinuclear active site.
