4102-53-8Relevant academic research and scientific papers
Immobilization of volatile and corrosive iodine monochloride (ICl) and I2 reagents in a stable metal-organic framework
He, Jun,Duan, Jingjing,Shi, Huatian,Huang, Jian,Huang, Jiahong,Yu, Lin,Zeller, Matthias,Hunter, Allen D.,Xu, Zhengtao
, p. 6837 - 6843 (2014)
The major discovery here is a robust and water-stable metal-organic framework (MOF) material capable of reversible binding of the volatile and reactive molecules of ICl and I2. The immobilization of I2 and ICl, as well as their controllable release thus achieved, is to facilitate the wide-ranging applications of these volatile species as catalysts and reagents in chemical and industrial processes. The framework material TMBP·CuI (hereafter TCuI) can be conveniently prepared in quantitative yields by heating CuI and the organic linker TMBP (3,3′,5,5′- tetramethyl-4,4′-bipyrazol) in acetonitrile. The microporous three-dimensional net of TCuI features CuI chains that contribute to efficient and reversible binding of ICl and I2 molecules, to result in the stoichiometrically well-defined adducts of TCuI·ICl and TCuI·I2, respectively. Moreover, the confinement of a volatile compound like ICl within the MOF medium provides unique opportunities to enhance its reactivity and selectivity as a chemical reagent, as is exemplified by the iodination reactions examined herein. With this exemplary study, we intend to stimulate interest in further exploring MOFs and other porous media (e.g., porous polymers) for entrapping ICl and other volatile reagents (e.g., Br2, SCl2, S2Cl2, and SOCl 2) and for potentially novel reactivity associated with the porous medium.
Active ester functionalized azobenzenes as versatile building blocks
Schultzke, Sven,Staubitz, Anne,Walther, Melanie
supporting information, (2021/07/12)
Azobenzenes are important molecular switches that can still be difficult to functionalize selectively. A high yielding Pd-catalyzed cross-coupling method under mild conditions for the introduction of NHS esters to azobenzenes and diazocines has been established. Yields were consistently high with very few exceptions. The NHS functionalized azobenzenes react with primary amines quantitatively. These amines are ubiquitous in biological systems and in material science.
Imidazolinium-based Multiblock Amphiphile as Transmembrane Anion Transporter
Mori, Miki,Sato, Kohei,Ekimoto, Toru,Okumura, Shinichi,Ikeguchi, Mitsunori,Tabata, Kazuhito V.,Noji, Hiroyuki,Kinbara, Kazushi
, p. 147 - 157 (2020/12/11)
Transmembrane anion transport is an important biological process in maintaining cellular functions. Thus, synthetic anion transporters are widely developed for their biological applications. Imidazolinium was introduced as anion recognition site to a multiblock amphiphilic structure that consists of octa(ethylene glycol) and aromatic units. Ion transport assay using halide-sensitive lucigenin and pH-sensitive 8-hydroxypyrene-1,3,6-trisulfonate (HPTS) revealed that imidazolinium-based multiblock amphiphile (IMA) transports anions and showed high selectivity for nitrate, which plays crucial roles in many biological events. Temperature-dependent ion transport assay using 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) indicated that IMA works as a mobile carrier. 1H NMR titration experiments indicated that the C2 proton of the imidazolinium ring recognizes anions via a (C?H)+???X? hydrogen bond. Furthermore, all-atom molecular dynamics simulations revealed a dynamic feature of IMA within the membranes during ion transportation.
Molecular Hybridization-Inspired Optimization of Diarylbenzopyrimidines as HIV-1 Nonnucleoside Reverse Transcriptase Inhibitors with Improved Activity against K103N and E138K Mutants and Pharmacokinetic Profiles
Han, Sheng,Sang, Yali,Wu, Yan,Tao, Yuan,Pannecouque, Christophe,De Clercq, Erik,Zhuang, Chunlin,Chen, Fen-Er
, (2019/11/11)
Molecular hybridization is a powerful strategy in drug discovery. A series of novel diarylbenzopyrimidine (DABP) analogues were developed by the hybridization of FDA-approved drugs etravirine (ETR) and efavirenz (EFV) as potential HIV-1 nonnucleoside reverse transcriptase inhibitors (NNRTIs). Substituent modifications resulted in the identification of new DABPs with the combination of the strengths of the two drugs, especially compound 12d, which showed promising activity toward the EFV-resistant K103N mutant. 12d also had a favorable pharmacokinetic (PK) profile with liver microsome clearances of 14.4 μL/min/mg (human) and 33.2 μL/min/mg (rat) and an oral bioavailability of 15.5% in rat. However, its activity against the E138K mutant was still unsatisfactory; E138K is the most prevalent NNRTI resistance-associated mutant in ETR treatment. Further optimizations resulted in a highly potent compound (12z) with no substituents on the phenyl ring and a 2-methyl-6-nitro substitution pattern on the 4-cyanovinyl-2,6-disubstitued phenyl motif. The antiviral activity of this compound was much higher than those of ETR and EFV against the WT, E138K, and K103N variants (EC50 = 3.4, 4.3, and 3.6 nM, respectively), and the cytotoxicity was decreased while the selectivity index (SI) was increased. In particular, this compound exhibited acceptable intrinsic liver microsome stability (human, 34.5 μL/min/mg; rat, 33.2 μL/min/mg) and maintained the good PK profile of its parent compound EFV and showed an oral bioavailability of 16.5% in rat. Molecular docking and structure-activity relationship (SAR) analysis provided further insights into the binding of the DABPs with HIV-1 reverse transcriptase and provided a deeper understanding of the key structural features responsible for their interactions.
AN IMPROVED ONE POT, ONE STEP PROCESS FOR THE HALOGENATION OF AROMATICS USING SOLID ACID CATALYSTS
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Page/Page column 0047; 0048, (2019/04/18)
The present invention disclosed an improved one pot, one step process for halogenation of compound of formula (II) to afford corresponding halogenated compound of formula (I) having improved yield and increased selectivity under very mild conditions.
Photosensitive chiral self-assembling materials: Significant effects of small lateral substituents
Cigl, Martin,Bubnov, Alexej,Ka?par, Miroslav,Hampl, Franti?ek,Hamplová, Věra,Pacherová, Oliva,Svoboda, Ji?í
supporting information, p. 5326 - 5333 (2016/07/06)
Novel azobenzene-based photosensitive mesogens with lactate chiral units were synthesized. In order to modify the rate of the thermal Z-E isomerization of these compounds, small lateral substituents were introduced into their core in the proximity of the azo group. The influence of lateral substitution on the kinetics of the Z-E isomerization, mesomorphic behaviour, and UV-Vis absorption spectra was studied. It was found that the position of the substituents in the azobenzene core significantly affects the rate of their thermal isomerization. The stability of Z-isomers of several studied compounds is comparable to that of compounds with complex molecular structures designed for optical data storage. Although lateral substitution influences the breadth/length ratio of the core, liquid-crystalline properties of the studied materials have been preserved.
NOVEL RECYCLABLE IODINATING AGENT AND ITS APPLICATIONS
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Page/Page column 11; 15, (2016/11/07)
The present invention provides a novel recyclable catalysts of formula A, [Formula A should be inserted here] wherein X is selected from the group consisting of [Formula should be inserted here] The present invention also provides a novel recyclable iodinating agent of formula I, II or III and a process for the synthesis thereof. [ Formula I, II & III should be inserted here] Further, the present invention provides a process of halogenation of amines and heterocyclic compounds by employing recyclable catalyst of formula (I).
Di- and trinuclear iron/titanium and iron/zirconium complexes with heterocyclic ligands as catalysts for ethylene polymerization
G?rl, Christian,Betthausen, Eva,Alt, Helmut G.
, p. 37 - 51 (2016/08/23)
The properties of polyolefin resins depend very much on their molecular weights, the amount of side chain branchings and molecular weight distributions. One way to obtain such tailored products in only one reaction step consists in the application of dissymmetric multi nuclear catalysts with different active sites. Since every active site is producing its own polymer, a “molecular blending” is the result. In order to reach this goal, a variety of mono, di- and trinuclear complexes of iron, titanium and zirconium, containing 2,6-bis(aryliminoethyl)pyridine and phenoxyimine building blocks have been synthesized and characterized. The reaction of iodo functionalized 2,6-bis(arylimino-ethyl)pyridine derivatives with alkyne functionalized phenoxyimine compounds via Sonogashira cross-coupling reactions results in ligand precursors that can provide coordination sites for two different metals. Trinuclear complexes with the combinations Ti/Fe and Zr/Fe, each molecule containing two iron atoms in two 2,6-bis(aryliminoethyl)pyridine units, gave the best ethylene polymerization results. Due to fast ligand exchange reactions, dinuclear iron/titanium complexes could not be isolated from reactions of mono(phenoxyimine) titanium complexes and the coupled bis(chelate) ligand precursor. Since the metal centers show their best performances at different polymerization temperatures, the compositions (and, therefore, the molecular weight distributions) of the desired polyethylenes may be adjusted by a simple change of the reaction temperature.
Electrophilic aryl-halogenation using N-halosuccinimides under ball-milling
Bose, Anima,Mal, Prasenjit
, p. 2154 - 2156 (2015/03/18)
We report here a methodology of chemo- and regio-selective aryl bromination and iodination using respective N-halosuccinimides at room temperature in the absence of any solvents, catalyst/additives under ball-milling condition. However, for chlorination ceric ammonium nitrate was used as additive. The coupled product succinimide, produced from the reactions, was recycled via regeneration of NBS. This methodology works with the electron-donor substituted or unsubstituted arenes.
Recyclable ionic liquid iodinating reagent for solvent free, regioselective iodination of activated aromatic and heteroaromatic amines
Deshmukh, Amarsinh,Gore, Babasaheb,Thulasiram, Hirekodathakallu V.,Swamy, Vincent P.
, p. 88311 - 88315 (2015/11/09)
This article describes a simple, efficient method for iodination of activated aromatic and heteroaromatic amines using recyclable 1-butyl-3-methylpyridinium dichloroiodate (BMPDCI) as an ionic liquid iodinating reagent, in the absence of any solvent. The main advantages are a simple efficient procedure, good yields and no need for any base/toxic heavy metals, or oxidizing agents. The ionic liquid was recovered and recycled in five subsequent reactions, without much loss of activity. This method was applied for the synthesis of the antiprotozoal drug iodoquinol and the antifungal drug clioquinol.
