- Anti-GM1/GD1a complex antibodies in GBS sera specifically recognize the hybrid dimer GM1-GD1a
-
It is now emerging the new concept that the antibodies from some patients with Guillain-Barre syndrome (GBS) recognize an antigenic epitope formed by two different gangliosides, a ganglioside complex (GSC). We prepared the dimeric GM1-GD1a hybrid ganglioside derivative that contains two structurally different oligosaccharide chains to mimic the GSC. We use this compound to analyze sera from GBS patients by high-performance thin-layer chromatography immunostaining and enzyme-linked immunosorbent assay. We also synthesized the dimeric GM1-GM1 and GD1a-GD1a compounds that were used in control experiments together with natural gangliosides. The hybrid dimeric GM1-GD1a was specifically recognized by human sera from GBS patients that developed anti-oligosaccharide antibodies specific for grouped complex oligosaccharides, confirming the information that GBS patients developed antibodies against a GSC. High-resolution 1H-13C heteronuclear single-quantum coherence-nuclear overhauser effect spectroscopy nuclear magnetic resonance experiments showed an interaction between the IV Gal-H1 of GM1 and the IV Gal-H2 of GD1a suggesting that the two oligosaccharide chains of the dimeric ganglioside form a single epitope recognized by a single-antibody domain. The availability of a method capable to prepare several hybrid gangliosides, and the availability of simple analytical approaches, opens new perspectives for the understanding and the therapy of several neuropathies. The Author 2011. Published by Oxford University Press. All rights reserved.
- Mauri, Laura,Casellato, Riccardo,Ciampa, Maria G.,Uekusa, Yoshinori,Kato, Koichi,Kaida, Ken-Ichi,Motoyama, Mayumi,Kusunoki, Susumu,Sonnino, Sandro
-
-
Read Online
- Self-assembly, binding, and dynamic properties of heterodimeric porphyrin macrocycles
-
A series of heterodimeric tetralactam macrocycles have been self-assembled using two kinetically labile zinc porphyrin-pyridine interactions. The stability constants have been determined by UV-vis titrations in CHCl3. The stability constants depend on the degree of preorganization of the linker units connecting the interacting groups. The ability of the self-assembled macrocycles to bind a terephthalamide guest was also investigated. One of the macrocycles was used for the construction of a [2]rotaxane. The dynamic properties of this system provide insight into the exchange mechanisms that operate in complex noncovalent assemblies.
- Ballester, Pablo,Costa, Antoni,Deya, Pere M.,Frontera, Antonio,Gomila, Rosa M.,Oliva, Ana I.,Sanders, Jeremy K. M.,Hunter, Christopher A.
-
-
Read Online
- Nucleating effect and crystal morphology controlling based on binary phase behavior between organic nucleating agent and poly(l-lactic acid)
-
A new kind of nucleating agent for poly(l-lactic acid) (PLLA), N,N'-bis(benzoyl) hexanedioic acid dihydrazide (BHAD), was synthesized. Differential scanning calorimetry (DSC), polarization optical microscopy (POM), wide-angle X-ray diffraction (WAXD) and rheometer were used to study the crystallization behavior and crystal morphology of PLLA nucleated by BHAD. In order to ensure the same thermal history of the samples characterized by DSC, POM and XRD, these samples were all thermally treated by DSC. In nonisothermal crystallization, BHAD showed excellent nucleating ability to PLLA. However, it was different from the traditional heterogeneous nucleation mechanism. POM observation showed that morphologies of PLLA crystals varied with the concentration of BHAD and can be classified into three types. Through the systematic investigation of DSC, POM and rheological analysis, it was clearly demonstrated that BHAD had solubility in PLLA matrix, depending on its concentration and processing temperature. Consequently, a highly schematic binary phase diagram of the PLLA/BHAD system was presented, accompanied with a reasonable mechanism of how the PLLA crystal morphologies controlled by BHAD.
- Fan, Yinqing,Zhu, Jun,Yan, Shifeng,Chen, Xuesi,Yin, Jingbo
-
-
Read Online
- Synthesis of Functional Fluorescent BODIPY-based Dyes through Electrophilic Aromatic Substitution: Straightforward Approach towards Customized Fluorescent Probes
-
Fluorescent materials are widely used in biological and material applications as probes for imaging or sensing; however, their customization is usually complicated without the support of an organic chemistry laboratory. Here, we present a straightforward method for the customization of BODIPY cores, which are among the most commonly used fluorescent probes. The method is based on the formation of a new C?C bond through Friedel–Crafts electrophilic aromatic substitution carried out at room temperature. The method presented can be used to obtain completely customized fluorescent materials in one or two steps from commercially available compounds. Examples of the preparation of fluorescent materials for cell staining and functionalization of silica colloids are also presented.
- Mirri, Giorgio,Schoenmakers, Dani?l C.,Kouwer, Paul H. J.,Verani?, Peter,Mu?evi?, Igor,?tefane, Bogdan
-
-
Read Online
- New β-phospholactam as a carbapenem transition state analog: Synthesis of a broad-spectrum inhibitor of metallo-β-lactamases
-
In an effort to test whether a transition state analog is an inhibitor of the metallo-β-lactamases, a phospholactam analog of carbapenem has been synthesized and characterized. The phospholactam 1 proved to be a weak, time-dependent inhibitor of IMP-1 (70%), CcrA (70%), L1 (70%), NDM-1 (53%), and Bla2 (94%) at an inhibitor concentration of 100 μM. The phospholactam 1 activated ImiS and BcII at the same concentration. Docking studies were used to explain binding and to offer suggestions for modifications to the phospholactam scaffold to improve binding affinities.
- Yang, Ke-Wu,Feng, Lei,Yang, Shao-Kang,Aitha, Mahesh,Lacuran, Alecander E.,Oelschlaeger, Peter,Crowder, Michael W.
-
-
Read Online
- Synthesis and opioid receptor binding affinities of 2-substituted and 3-aminomorphinans: Ligands for μ, κ, and δ opioid receptors
-
The phenolic group of the potent μ and κ opioid morphinan agonist/antagonists cyclorphan and butorphan was replaced by phenylamino and benzylamino groups including compounds with parasubstituents in the benzene ring. These compounds are highly potent μ and κ ligands, e.g., p-methoxyphenylaminocyclorphan showing a Ki of 0.026 nMat the μ receptor and a Ki of 0.03 nM at the κ receptor. Phenyl carbamates and phenylureas were synthesized and investigated. Selective o-formylation of butorphan and levorphanol was achieved. This reaction opened the way to a large set of 2-substituted 3-hydroxymorphinans, including 2-hydroxymethyl-, 2-aminomethyl-, and N-substituted 2-aminomethyl-3- hydroxymorphinans. Bivalent ligands bridged in the 2-position were also synthesized and connected with secondary and tertiary aminomethyl groups, amide bonds, and hydroxymethylene groups, respectively. Although most of the 2-substituted morphinans showed considerably lower affinities compared to their parent compounds, the bivalent ligand approach led to significantly higher affinities compared to the univalent 2-substituted morphinans. 2009 American Chemical Society.
- Decker, Michael,Si, Yu-Gui,Knapp, Brian I.,Bidlack, Jean M.,Neumeyer, John L.
-
-
Read Online
- Synthetic phosphorylation of p38α recapitulates protein kinase activity
-
Through a "tag-and-modify" protein chemical modification strategy, we site-selectively phosphorylated the activation loop of protein kinase p38α. Phosphorylation at natural (180) and unnatural (172) sites created two pure phospho-forms. p38α bearing only a single phosphocysteine (pCys) as a mimic of pThr at 180 was sufficient to switch the kinase to an active state, capable of processing natural protein substrate ATF2; 172 site phosphorylation did not. In this way, we chemically recapitulated triggering of a relevant segment of the MAPK-signaling pathway in vitro. This allowed detailed kinetic analysis of global and stoichiometric phosphorylation events catalyzed by p38α and revealed that site 180 is a sufficient activator alone and engenders dominant mono-phosphorylation activity. Moreover, a survey of kinase inhibition using inhibitors with different (Type I/II) modes (including therapeutically relevant) revealed unambiguously that Type II inhibitors inhibit phosphorylated p38α and allowed discovery of a predictive kinetic analysis based on cooperativity to distinguish Type I vs II.
- Chooi, K. Phin,Galan, Sebastien R. G.,Raj, Ritu,McCullagh, James,Mohammed, Shabaz,Jones, Lyn H.,Davis, Benjamin G.
-
-
Read Online
- Synthesis, characterization and biological analysis of transition metal complexes with macro cyclic ligands derived from adipic acid, ethylenediamine with diethyloxalate and diethylmalonate
-
Macro-cyclic ligands from adipic acid, ethylenediamine with diethyloxalate and diethylmalonate and their respective metal complexes of Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) with macro cyclic ligands (LO) and (LM) L [N,N′-bis(2-aminoethyl)hexanediamide] were synthesized successfully. These metal complexes were characterized by Fourier transform infrared, ultraviolet visible spectrometry, proton nuclear magnetic resonance spectroscopy, and mass Spectrometry, CHNS and thermogravimetric analysis. The elemental analysis confirms the structures for Mn(II), Co(II) and Ni(II) complexes similar to octahedral geometry, Cu(II) complexes as a square planar geometry and Zn(II) complexes in the tetrahedral geometry. The molar conductivities of all the metal complexes were taken in 10?3?M DMSO, and values of all the metal complexes showed their electrolytic nature which indicates the presence of chloride ions. Thermal analysis supports as the metal complexes are thermally stable. The result of antimicrobial activity against various microorganisms confirms that the metal complexes are potent bactericides and fungicides than the ligand. Metal complexes of LO with Cu(II) and Zn(II) were found to be highly active against S. typhimurium than the complexes of LM. Graphical abstract: [Figure not available: see fulltext.].
- Nishat, Nahid,Bhat, Shahnawaz Ahmad,Kareem, Abdul,Dhyani, Swati,Mohammad, Abdulrahman,Mirza, Azar Ullah
-
-
Read Online
- Preliminary studies of a novel cyclopentadienyl tricarbonyl technetium-99m fatty acid derivative for myocardical imaging
-
This study reports the synthesis and evaluation studies of 6′-cyclopentadienyl tricarbonyl technetium-99m 6′-oxo-11- (hexanamide)undecanoic acid (1). 1 was prepared with 26.5 ± 4.3% of radiochemical yield and more than 98% of radiochemical purity. Tissue distribution in mice showed that high radioactivity accumulated in the heart with moderate clearance. However, unfortunately, similar to those of other technetium-labeled fatty acid analogs, the biodistribution studies of 1 in mice showed poor heart-to-blood ratios, which suggested that 1 cannot be used as myocardial imaging agent, and it may provide a theoretical basis or a lab experience for corresponding fatty acid tracers studies. Tc-99m-labeled fatty acid is very important for the evaluation of myocardial metabolism. 1 was radiolabeled by a double ligand transfer reaction between ferrocene and 99mTc. Amidated 99mTc-labeling fatty acid is beneficial to prolonging retention in myocardium. Copyright
- Zhang, Hong,Zeng, Huahui,Zhang, Huabei,Wu, Xiangxiang,Chao, Fangfang,Yu, Gang,Zhang, Liqing,Jiang, Han,Liu, Hongbiao,Hou, Haifeng,Zhan, Hongwei,Tian, Mei
-
-
Read Online
- Chemoenzymatic Synthesis of Thiazolyl Peptide Natural Products Featuring an Enzyme-Catalyzed Formal [4 + 2] Cycloaddition
-
Thiocillins from Bacillus cereus ATCC 14579 are members of the well-known thiazolyl peptide class of natural product antibiotics, the biosynthesis of which has recently been shown to proceed via post-translational modification of ribosomally encoded precursor peptides. It has long been hypothesized that the final step of thiazolyl peptide biosynthesis involves a formal [4 + 2] cycloaddition between two dehydroalanines, a unique transformation that had eluded enzymatic characterization. Here we demonstrate that TclM, a single enzyme from the thiocillin biosynthetic pathway, catalyzes this transformation. To facilitate characterization of this new class of enzyme, we have developed a combined chemical and biological route to the complex peptide substrate, relying on chemical synthesis of a modified C-terminal fragment and coupling to a 38-residue leader peptide by means of native chemical ligation (NCL). This strategy, combined with active enzyme, provides a new chemoenzymatic route to this promising class of antibiotics.
- Wever, Walter J.,Bogart, Jonathan W.,Baccile, Joshua A.,Chan, Andrew N.,Schroeder, Frank C.,Bowers, Albert A.
-
-
Read Online
- Synthesis and biological evaluation of fatty acids conjugates bearing cyclopentadienyl-donors incorporated [99mTc/Re(CO)3] + for myocardical imaging
-
Four 99mTc-labeled fatty acid analogs, 1b, 2b, 3b, 4b were synthesized by a double ligand transfer reaction and theirs potential were investigated. The radiochemical yield of the radiotracers was from 11.7% to 30.3% (no decay corrected). Those compounds were found to be chemically stable when incubated in SD rat serum for 3 h at 37 C. The biodistribution studies in mice showed that high radioactivity accumulated of Tc-99m complexes were observed, followed by moderate clearance from the heart. The maximum heart/blood ratio was 5.7 at 15 min postinjection of 1b. Metabolite analysis showed 1b was not metabolized by β-oxidation in the heart. These results suggest that 1b may be a promising radiotracer for evaluation of myocardial viability.
- Zeng, Huahui,Zhang, Huabei
-
-
Read Online
- Chemical generation and modification of peptides containing multiple dehydroalanines
-
Chemical formation of dehydroalanine has been widely used for the post-translational modification of proteins and peptides, however methods to incorporate multiple dehydroalanine residues into a single peptide have not been defined. We report the use of methyl 2,5-dibromovalerate which can be used to cleanly carry out this transformation.
- Morrison, Philip M.,Foley, Patrick J.,Warriner, Stuart L.,Webb, Michael E.
-
-
Read Online
- Synthesis of α,ω-Diketodiesters from Betulin
-
A new synthesis of 3-oxo-28-hydroxylup-20(29)-ene from the available natural triterpenoid betulin was developed. α,ω-Diketodiesters were prepared for the first time by different methods from 3-oxo-28-hydroxylup-20(29)-ene and a series of natural dicarboxylic acids. Steglich reaction conditions gave the highest yields. One of the synthesized α,ω-diketodiesters was moderately active in vitro against A-549 lung carcinoma.
- Ishmuratov, G. Yu.,Sayakhov, R. R.,Talipov, R. F.,Vydrina, V. A.,Yakovleva, M. P.,Zileeva, Z. R.
-
p. 706 - 711
(2021/07/31)
-
- Gemfibrozil derivatives as activators of soluble guanylyl cyclase – A structure-activity study
-
Previous studies demonstrated that anti-hyperlipidemic drug gemfibrozil acts as NO- and heme-independent activator of NO receptor soluble guanylyl cyclase. A series of new gemfibrozil derivatives were synthesized and evaluated for sGC activation. The structure-activity relationship study identified the positions in gemfibrozil's scaffold that are detrimental for sGC activation and those that are amendable for optimizing modifications. Compared with gemfibrozil, compounds 7c and 15b were more potent activators of cGMP-forming activity of purified sGC and exhibited enhanced relaxation of preconstricted mouse thoracic aorta rings. These studies established the overall framework needed for futher improvement of sGC activators based on gemfibrozil scaffold.
- Baker, Hannah,Ferreira, Liam D.,Gayler, Kevin M.,Kane, Robert R.,Karunananthan, Johann W.,Kostyo, Jessica H.,Martin, Emil,Mattke, Jordan,Nguyen, Harold,Plunk, Michael A.,Quintana, Jeremy M.,Sharina, Iraida,Shuda, Mina,Stinchcomb, Alexandra L.
-
-
- Aziridine-2-carboxylic acid derivatives and its open-ring isomers as a novel PDIA1 inhibitors
-
[Figure not available: see fulltext.] Acyl derivatives of aziridine-2-carboxylic acid have been synthesized and tested as PDIA1 inhibitors. Calculations of charge value and distribution in aziridine ring system and some alkylating agents were performed. For the first time was found that acyl derivatives of aziridine-2-carboxylic acid are weak to moderately active PDIA1 inhibitors.
- Leite, Irena,Andrianov, Victor,Zelencova-Gopejenko, Diana,Loza, Einars,Kazhoka-Lapsa, Iveta,Domracheva, Ilona,Stoyak, Marta,Chlopicki, Stefan,Kalvins, Ivars
-
p. 1086 - 1106
(2022/01/12)
-
- Trityl-containing alcohols—an efficient chirality transmission process from inductor to the stereodynamic propeller and their solid-state structural diversity
-
The cascade process of a dynamic chirality transmission from the permanent chirality center to the stereodynamic triphenylmethyl group has been studied for series of optically active trityl derivatives. The structural analysis, carried out with the use of complementary methods, enabled us to determine the mechanism of chirality transfer. The process of chirality transmission involves a set of weak but complementary electrostatic interactions. The induction of helicity in a trityl propeller is revealed by rising non-zero cotton effects in the area of trityl UV-absorption. The presence of an additional stereogenic center in close proximity to the trityl-containing stereogenic center significantly affects the sign and, to a lesser extent, magnitude of the respective cotton effects. Despite the bulkiness of the trityl, in the crystalline phase, the molecules under study strictly fill the space. In the crystal, molecules form aggregates stabilized by OH???O hydrogen bonds. However, the presence of two trityl groups precludes formation of OH???O hydrogen bonding. Additionally, the trityl group seems to be responsible for the formation of the solid solutions by e.g., racemates of trans- and cis-2-tritylcyclohexanol. Therefore, the trityl group acts as a supramolecular protective group, which in turn can be used in the crystal engineering.
- Górczyńska, Sylwia,Brzdonkiewicz, Aleksandra,Jelecki, Maciej,Czapik, Agnieszka,Stasiak, Bartosz,Kwit, Marcin
-
supporting information
(2020/02/18)
-
- Cobalt(II)-Catalyzed Stereoselective Olefin Isomerization: Facile Access to Acyclic Trisubstituted Alkenes
-
Stereoselective synthesis of trisubstituted alkenes is a long-standing challenge in organic chemistry, due to the small energy differences between E and Z isomers of trisubstituted alkenes (compared with 1,2-disubstituted alkenes). Transition metal-catalyzed isomerization of 1,1-disubstituted alkenes can serve as an alternative approach to trisubstituted alkenes, but it remains underdeveloped owing to issues relating to reaction efficiency and stereoselectivity. Here we show that a novel cobalt catalyst can overcome these challenges to provide an efficient and stereoselective access to a broad range of trisubstituted alkenes. This protocol is compatible with both mono- and dienes and exhibits a good functional group tolerance and scalability. Moreover, it has proven to be a useful tool to construct organic luminophores and a deuterated trisubstituted alkene. A preliminary study of the mechanism suggests that a cobalt-hydride pathway is involved in the reaction. The high stereoselectivity of the reaction is attributed to both a π-πstacking effect and the steric hindrance between substrate and catalyst.
- Zhang, Sheng,Bedi, Deepika,Cheng, Lu,Unruh, Daniel K.,Li, Guigen,Findlater, Michael
-
supporting information
p. 8910 - 8917
(2020/12/23)
-
- Double Addition of Alkynyllithium Reagents to Amides/Lactams: A Direct and Flexible Synthesis of 3-Amino-1,4-diynes Bearing an Aza-Quaternary Carbon Center
-
An efficient and mild protocol for the direct and flexible synthesis of 3-amino-1,4-diynes bearing an aza-quaternary carbon from tertiary amides and lactams has been established. The one-pot method consists of in situ activation of amides with trifluoromethanesulfonic anhydride, followed by double addition of alkynyllithium reagents at a concentration of 0.5 mol·L-1 in dichloromethane. This constitutes an extension of the method of direct reductive bisalkylation of amides that allows both employing alkynyllithium reagents as the first-addition nucleophiles and incorporating an alkynyl group as the first-introduced group.
- Chen, Hang,Huang, Ying-Hong,Ye, Jian-Liang,Huang, Pei-Qiang
-
p. 9270 - 9281
(2019/08/12)
-
- Small-Molecule Activators of Glucose-6-phosphate Dehydrogenase (G6PD) Bridging the Dimer Interface
-
We recently identified AG1, a small-molecule activator that functions by promoting oligomerization of glucose-6-phosphate dehydrogenase (G6PD) to the catalytically competent forms. Biochemical experiments indicate that the activation of G6PD by the original hit molecule (AG1) is noncovalent and that one C2-symmetric region of the G6PD homodimer is important for ligand function. Consequently, the disulfide in AG1 is not required for activation of G6PD, and a number of analogues were prepared without this reactive moiety. Our study supports a mechanism of action whereby AG1 bridges the dimer interface at the structural nicotinamide adenine dinucleotide phosphate (NADP+) binding sites of two interacting G6PD monomers. Small molecules that promote G6PD oligomerization have the potential to provide a first-in-class treatment for G6PD deficiency. This general strategy could be applied to other enzyme deficiencies in which control of oligomerization can enhance enzymatic activity and/or stability.
- Raub, Andrew G.,Hwang, Sunhee,Horikoshi, Naoki,Cunningham, Anna D.,Rahighi, Simin,Wakatsuki, Soichi,Mochly-Rosen, Daria
-
supporting information
p. 1321 - 1324
(2019/07/04)
-
- Structural basis of the inhibition of GH1 β-glucosidases by multivalent pyrrolidine iminosugars
-
The synthesis of multivalent pyrrolidine iminosugars via CuAAC click reaction between different pyrrolidine-azide derivatives and tri- or hexavalent alkynyl scaffolds is reported. The new multimeric compounds, together with the monomeric reference, were evaluated as inhibitors against two homologous GH1 β-glucosidases (BglA and BglB from Paenibacillus polymyxa). The multivalent inhibitors containing an aromatic moiety in the linker between the pyrrolidine and the scaffold inhibited the octameric BglA (μM range) but did not show affinity against the monomeric BglB, despite the similarity between the active site of both enzymes. A modest multivalent effect (rp/n = 12) was detected for the hexavalent inhibitor 12. Structural analysis of the complexes between the monomeric and the trimeric iminosugar inhibitors (4 and 10) and BglA showed the insertion of the inhibitors at the active site of BglA, confirming a competitive mode of inhibition as indicated by enzyme kinetics. Additionally, structural comparison of the BglA/4 complex with the reported BglB/2F-glucose complex illustrates the key determinants responsible for the inhibitory effect and explains the reasons of the inhibition of BglA and the no inhibition of BglB. Potential inhibition of other β-glucosidases with therapeutic relevance is discussed under the light of these observations.
- Martínez-Bailén, Macarena,Jiménez-Ortega, Elena,Carmona, Ana T.,Robina, Inmaculada,Sanz-Aparicio, Julia,Talens-Perales, David,Polaina, Julio,Matassini, Camilla,Cardona, Francesca,Moreno-Vargas, Antonio J.
-
supporting information
(2019/06/21)
-
- Synthetic method for bisamide group-linked disulfonate gemini surfactant
-
The invention discloses a synthetic method for a bisamide group-linked disulfonate gemini surfactant. The method comprises the following steps: performing an acylation reaction; forming an amide; performing a substitution reaction: adding 200 ml of an ethanol solution into a 250 ml three-necked flask equipped with an air condenser pipe on a water bath with constant-temperature magnetic stirring, taking a clean beaker for dissolving the adipamide obtained in the step 2 by using distilled water, adding the dissolved adipamide into the three-necked flask, adding sodium hydroxide to adjust the pHvalue to 7-8, slowly adding halogenated dodecane dropwise by using a dropping funnel, keeping the temperature at 75 DEG C, performing continuous stirring, after the stirring is completed, so as to complete the reaction, and after the reaction is completed, obtaining a reaction liquid; and performing concentration, and performing crystallization to obtain the pale yellow powdered bisbenzene sulfonic acid gemini surfactant. The method provided by the invention realizes synthesis of the amide-type sulfonate gemini surfactant, the operation is simple and convenient in the whole synthetic process and is convenient to implement, and the method facilitates promotion and application.
- -
-
Page/Page column 4-6
(2019/10/01)
-
- Synthesis method, derivative and battery system of anthraquinone derivative containing carboxyl group
-
The invention provides a synthesis method, a derivative and a battery system of an anthraquinone derivative containing a carboxyl group. The synthesis method of the anthraquinone derivative containingthe carboxyl group includes the following steps that S1, dibasic acid containing a terminal carboxyl group and sulfoxide chloride are mixed, toluene is added as a reaction solvent, a catalyst is added, and heated to a set temperature reaction; S2, after the reaction is completed, the solvent and the sulfoxide chloride are removed, the toluene is added for distillation, and a reactant is obtained;S3, the reactant is mixed with amino-anthraquinone, the toluene is added as the reaction solvent, and heating is conducted to a reflux reaction; and S4, after the reaction is completed, the solvent is removed, solids are filtered and removed, the pH value of a filtrate is adjusted to a predetermined value, the solids are separated out, filtered, washed and dried, and the anthraquinone derivativecontaining the carboxyl group is obtained. According to the synthesis method of the anthraquinone derivative containing the carboxyl group, simpleness is achieved, operation is easy, the cost is low,and the synthesis method can be applied to the battery system to solve the problem of electrochemical energy storage.
- -
-
Paragraph 0057; 0093-0095
(2019/12/25)
-
- Symmetric dimeric adamantanes for exploring the structure of two viroporins: Influenza virus M2 and hepatitis C virus p7
-
Background: Adamantane-based compounds have been identified to interfere with the ion-channel activity of viroporins and thereby inhibit viral infection. To better understand the difference in the inhibition mechanism of viroporins, we synthesized symmetric dimeric adamantane analogs of various alkyl-spacer lengths. Methods: Symmetric dimeric adamantane derivatives were synthesized where two amantadine or rimantadine molecules were linked by various alkyl-spacers. The inhibitory activity of the compounds was studied on two viroporins: the influenza virus M2 protein, expressed in Xenopus oocytes, using the two-electrode voltage-clamp technique, and the hepatitis C virus (HCV) p7 channels for five different genotypes (1a, 1b, 2a, 3a, and 4a) expressed in HEK293 cells using whole-cell patch-clamp recording techniques. Results: Upon testing on M2 protein, dimeric compounds showed significantly lower inhibitory activity relative to the monomeric amantadine. The lack of channel blockage of the dimeric amantadine and rimantadine analogs against M2 wild type and M2-S31N mutant was consistent with previously proposed drug-binding mechanisms and further confirmed that the pore-binding model is the pharmacologically relevant drug-binding model. On the other hand, these dimers showed similar potency to their respective monomeric analogs when tested on p7 protein in HCV genotypes 1a, 1b, and 4a while being 700-fold and 150-fold more potent than amantadine in genotypes 2a and 3a, respectively. An amino group appears to be important for inhibiting the ion-channel activity of p7 protein in genotype 2a, while its importance was minimal in all other genotypes. Conclusion: Symmetric dimeric adamantanes can be considered a prospective class of p7 inhibitors that are able to address the differences in adamantane sensitivity among the various genotypes of HCV.
- Mandour, Yasmine M.,Breitinger, Ulrike,Ma, Chunlong,Wang, Jun,Boeckler, Frank M.,Breitinger, Hans-Georg,Zlotos, Darius P.
-
p. 1019 - 1031
(2018/05/22)
-
- Synthesis and characterization of ferrocenyl esters: Their anti-oxidant activity and DNA-binding ability
-
In continuation to our work on biologically active material, some new ferrocenyl esters were prepared by condensation of 4-ferrocenyl phenol (ROH) with ferrocenyl dicarboxylic acid chlorides (DCC) at low temperature. The synthesized compounds (E1-E9) were characterized by analyzing their physical properties, FT-IR, 1H-NMR, UV-visible spectroscopic and cyclic voltammetric studies. The DPPH free radical scavenging assay was performed to explore their potential as antioxidant which showed that the E1 had maximum scavenging ability (77.11%) whereas E3 showed minimum (52%) compared with the standard. Cyclic voltammetric studies indicated that these compounds were electroactive in potential window of 2.0-0.0V. Binding mode found in these esters was an electrostatic interaction which is considered as strongest amongst all. Therefore, these compounds are considered to have DNA-binding capability and are potential DNA binders.
- Bukhari, Syeda Anam,Gul, Asghari,Akhter, Zareen,Bashir, Amna
-
p. 375 - 382
(2018/06/06)
-
- Method for simultaneously preparing 5-chlorovaleryl chloride and adipoyl chloride by using one-pot method
-
The invention discloses a method for simultaneously preparing 5-chlorovaleryl chloride and adipoyl chloride by utilizing a one-pot method. The method comprises the following steps: 1,4-dichlorobutaneis taken as a raw material, in the presence of a phase transfer catalyst, an aqueous solution of sodium cyanide is gradually added dropwise into a reaction kettle, and therefore a 1,4-dichlorobutane solution of 5-chlorovaIeronitrile and adiponitrile is obtained; the obtained organic phase and aqueous phase are separated, hydrolysis is performed, and therefore a 1,4-dichlorobutane solution of 5-chlorovaleric acid and adipic acid is obtained; water is added into the obtained ammonium chloride solid until the solid is completely dissolved, and an aqueous phase is separated; thionyl chloride is added into the obtained 1,4-dichlorobutane solution of 5-chlorovaleric acid and adipic acid for an acylating chlorination reaction, and therefore a 1,4-dichlorobutane solution of 5-chlorovaleryl chloride and adipoyl chloride is obtained; and the obtained 1,4-dichlorobutane solution of 5-chlorovaleryl chloride and adipoyl chloride is put into a vacuum rectification tower for vacuum rectification, andtherefore the adipoyl chloride product with the distillate temperature of 105 DEG C-107 DEG C is obtained through distillation. The method provided by the invention adopts the 1,4-dichlorobutane as the raw material and adopts the ''one-pot method'' to simultaneously produce the two intermediate products 5-chlorovaleryl chloride and adipoyl chloride, and the method has a high yield, large single-pot production capacity, a small solvent circulation amount, low energy consumption, and less ''three wastes'' (waste gas, waste water and solid waste).
- -
-
Paragraph 0017; 0018; 0019; 0020; 0021; 0022; 0023-0028
(2018/07/30)
-
- Novel bivalent securinine mimetics as topoisomerase I inhibitors
-
A series of novel bivalent securinine mimetics incorporating different linkers between C-15 and C-15′ were synthesized and their topoisomerase I (Topo I) inhibitory activities evaluated. It was thus revealed that mimetic R2 incorporating a rigid m-substituted benzene linker exhibits Topo I inhibitory activity three times that of parent securinine. Comprehensive structure-activity relationship analyses in combination with docking studies were used to rationalize the potent activity of these bivalent mimetics. Mechanistic studies served to confirm the deductions arising from docking studies that the active bivalent mimetics not only inhibited complexation between Topo I and DNA but also stabilized the Topo I-DNA complex itself.
- Hou, Wen,Lin, Hui,Wang, Zhen-Ya,Banwell, Martin G.,Zeng, Ting,Sun, Ping-Hua,Lin, Jing,Chen, Wei-Min
-
p. 320 - 328
(2017/03/08)
-
- Structure-based virtual screening and optimization of modulators targeting Hsp90-Cdc37 interaction
-
Identification of novel Hsp90 inhibitors to disrupt Hsp90-Cdc37 protein-protein interaction (PPI) could be an alternative strategy to achieve Hsp90 inhibition. In this paper, a series of small molecules targeting Hsp90-Cdc37 complex are addressed and characterized. The molecules' key characters are determined by utilizing a structure-based virtual screening workflow, derivatives synthesis, and biological evaluation. Structural optimization and structure–activity relationship (SAR) analysis were then carried out on the virtual hit of VS-8 with potent activity, which resulted in the discovery of compound 10 as a more potent regulator of Hsp90-Cdc37 interaction with a promising inhibitory effect (IC50?=?27?μM), a moderate binding capacity (KD?=?40?μM) and a preferable antiproliferative activity against several cancer lines including MCF-7, SKBR3 and A549?cell lines (IC50?=?26?μM, 15?μM and 38?μM respectively). All the data suggest that compound 10 exhibits moderate inhibitory effect on Hsp90-Cdc37 and could be regard as a first evidence of a non-natural compound targeting Hsp90-Cdc37 PPI.
- Wang, Lei,Li, Li,Zhou, Zi-Han,Jiang, Zheng-Yu,You, Qi-Dong,Xu, Xiao-Li
-
-
- Thermotropic liquid crystalline polyesters derived from 2-chloro hydroquinone
-
Abstract: Synthesis of thermotropic liquid crystalline polyesters derived from bis[4-hydroxy benzoyloxy]-2-chloro-1,4-benzene (BHBOCB) and aliphatic dicarboxylic acid chlorides by interfacial polycondensation methodology is presented. Synthesised polyesters consist of bis[4-hydroxy benzoyloxy]-2-chloro-1,4-benzene as a mesogen and aliphatic diacid chloride as flexible spacer. The length of oligomethylene units in the polymer was varied from the trimethylene to the dodecamethylene groups. Synthesized polyesters were characterized by differential scanning calorimetry and optical microscopy. The transition temperatures and thermodynamic properties were studied for all these polymers. These polyesters exhibited thermotropic liquid crystalline behavior and showed nematic texture except decamethylene spacer. Decamethylene spacer based polyester showed marble texture of smectic C. Mesophase stability of these polyesters was higher than 123 °C (except first heating cycle of PE-1). Graphical Abstract:: SYNOPSIS The present study deals with the synthesis of thermotropic liquid crystalline polyesters derived from bis[4-hydroxy benzoyloxy]-2-chloro-1,4-benzene (BHBOCB) and aliphatic dicarboxylic acid chlorides by interfacial polycondensation methodology. [Figure not available: see fulltext.].
- Manurkar, Nagesh,More, Sayaji,Mulani, Khudbudin,Ganjave, Nitin,Chavan, Nayaku
-
p. 1461 - 1468
(2017/09/27)
-
- A mechanochemical approach to access the proline-proline diketopiperazine framework
-
Ball milling was exploited to prepare a substituted proline building block by mechanochemical nucleophilic substitution. Subsequently, the mechanocoupling of hindered proline amino acid derivatives was developed to provide proline-proline dipeptides under solvent-free conditions. A deprotection-cyclization sequence yielded the corresponding diketopiperazines that were obtained with a high stereoselectivity which could be explained by DFT calculations. Using this method, an enantiopure disubstituted Pro-Pro diketopiperazine was synthesized in 4 steps, making 5 new bonds using a ball mill.
- Pétry, Nicolas,Benakki, Hafid,Clot, Eric,Retailleau, Pascal,Guenoun, Farhate,Asserar, Fatima,Sekkat, Chakib,Métro, Thomas-Xavier,Martinez, Jean,Lamaty, Frédéric
-
supporting information
p. 2169 - 2178
(2017/11/16)
-
- Biomimetic Design Results in a Potent Allosteric Inhibitor of Dihydrodipicolinate Synthase from Campylobacter jejuni
-
Dihydrodipicolinate synthase (DHDPS), an enzyme required for bacterial peptidoglycan biosynthesis, catalyzes the condensation of pyruvate and β-aspartate semialdehyde (ASA) to form a cyclic product which dehydrates to form dihydrodipicolinate. DHDPS has, for several years, been considered a putative target for novel antibiotics. We have designed the first potent inhibitor of this enzyme by mimicking its natural allosteric regulation by lysine, and obtained a crystal structure of the protein-inhibitor complex at 2.2 ? resolution. This novel inhibitor, which we named 'bislysine', resembles two lysine molecules linked by an ethylene bridge between the α-carbon atoms. Bislysine is a mixed partial inhibitor with respect to the first substrate, pyruvate, and a noncompetitive partial inhibitor with respect to ASA, and binds to all forms of the enzyme with a Ki near 200 nM, more than 300 times more tightly than lysine. Hill plots show that the inhibition is cooperative, indicating that the allosteric sites are not independent despite being located on opposite sides of the protein tetramer, separated by approximately 50 ?. A mutant enzyme resistant to lysine inhibition, Y110F, is strongly inhibited by this novel inhibitor, suggesting this may be a promising strategy for antibiotic development.
- Skovpen, Yulia V.,Conly, Cuylar J. T.,Sanders, David A. R.,Palmer, David R. J.
-
supporting information
p. 2014 - 2020
(2016/03/01)
-
- COMPOUND AND MANUFACTURING METHOD THEREFOR, MAGNETIC FLUID COMPOSITION AND MANUFACTURING METHOD THEREFOR AND MAGNETIC FLUID SEAL
-
PROBLEM TO BE SOLVED: To provide a novel compound capable of using as a dispersion to a magnetic fluid composition and a manufacturing method therefor, a magnetic fluid composition using the compound and a manufacturing method therefore and a magnetic fluid seal containing the magnetic fluid composition. SOLUTION: There is provided a compound represented by the general formula (1) or a salt thereof. (1), where R1 and R2 are each independently a bivalent organic group which has 2 to 16 carbon atoms and may have a hetero atom, X1 is an alkylene group having 2 to 6 carbon atoms and n is an integer of 1 to 10. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
- -
-
Paragraph 0079
(2016/10/09)
-
- Preparation of Protein Conjugates via Homobifunctional Diselenoester Cross-Linker
-
Adipic acid diselenoester was developed as an efficient cross-linker for covalent protein conjugation with a variety of small molecular haptens, including mono- and disaccharides, peptide, fluorescence dye, and nicotine. Compared to the counterparts of N-hydroxysuccinimide (NHS) and p-nitrophenyl (PNP) linkers, the diselenoester linker demonstrates improved balance between reactivity and stability and coupling of haptens to proteins under mild conditions with high incorporation efficiency.
- Yin, Xu-Guang,Gao, Xiao-Fei,Du, Jing-Jing,Zhang, Xiao-Kang,Chen, Xiang-Zhao,Wang, Jian,Xin, Ling-Ming,Lei, Ze,Liu, Zheng,Guo, Jun
-
supporting information
p. 5796 - 5799
(2016/11/29)
-
- Ostopanic acid analogues and its preparation method and use
-
The invention relates to ostopanic acid, ostopanic acid analogues and their preparation method and use. The preparation method provided by the invention is characterized in that based on a characteristic that the reaction of a Weinreb amide and a Grignard reagent can selectively stay in a ketone stage so that the overreaction is avoided, two side chains of the ostopanic acid analogue can be constructed and thus a series of the ostopanic acid analogues can be synthesized fast. The preparation method provided by the invention adopts easily acquired raw materials, allows mild reaction conditions and has simple processes. The ostopanic acid and the ostopanic acid analogues obtained by the preparation method have obvious antitumor effects.
- -
-
Paragraph 0054; 0055
(2017/03/25)
-
- COMPOUNDS, COMPOSITIONS AND METHODS OF AGELASTATIN ALKALOIDS
-
The present invention, among other things, provides compounds, compositions and methods for treatment of cancer. In some embodiments, the present invention provides methods for treating blood cancer using agelastatin alkaloids.
- -
-
Paragraph 0251
(2015/03/28)
-
- Substrate scope in the copper-mediated construction of bis-oxindoles via a double C-H/Ar-H coupling process
-
Abstract The synthesis of bis-oxindoles via the copper(II)-mediated double cyclisation of linear bis-anilides is described. Cu(OAc)2·H2O was identified as an efficient and inexpensive catalyst for this process. In contrast to previous methods, which rely on the synthesis of the central core from existing oxindole building blocks, this new approach focusses on concurrent formation of both oxindole rings from a simple linear precursor, allowing the formation of bis-oxindoles containing a diverse range of cyclic and acyclic linkers using a single synthetic method.
- Drouhin, Pauline,Hurst, Timothy E.,Whitwood, Adrian C.,Taylor, Richard J.K.
-
supporting information
p. 7124 - 7136
(2015/03/30)
-
- Synthesis and binding profile of haloperidol-based bivalent ligands targeting dopamine D2-like receptors
-
Homodimers of dopamine D2-like receptors are suggested to be of particular importance in the pathophysiology of schizophrenia and, thus, serve as promising targets for the discovery of atypical antipsychotics. This study describes the development of a series of novel bivalent molecules with a pharmacophore derived from the dopamine receptor antagonist haloperidol. These dimers were investigated in comparison to their monomeric analogues for their D2long, D2short, D3, and D4 receptor binding and the ability to bridge two neighboring receptor protomers. Radioligand binding studies provided diagnostic insights when Hill slopes close to two for the bivalent ligand 13 incorporating 22 spacer atoms and a comparative analysis with monovalent control ligands indicated a bivalent binding mode with a simultaneous occupancy of two neighboring binding sites.
- Salama, Ismail,L?ber, Stefan,Hübner, Harald,Gmeiner, Peter
-
supporting information
p. 3753 - 3756
(2014/09/16)
-
- Synthesis, thermal, and photocrosslinking studies of thermotropic liquid crystalline poly(benzylidene-ether)esters containing α,β-unsaturated ketone moiety in the main chain
-
A series of poly(benzylidene-ether)esters containing a photoreactive benzylidene chromophore in the main chain were synthesized from 2,6-bis(4-hydroxy-3-methoxybenzylidene)cyclohexanone (BHMBCH) with various aliphatic and aromatic diacid chlorides by an interfacial polycondensation technique. The intrinsic viscosity of the synthesized homo and copolymers determined by Ubbelohde viscometer was found to be 0.12 to 0.17 dL/g. The molecular structure of the monomer and polymers was confirmed by FT-IR, 1H NMR, and 13C NMR spectral analyses. These polymers were studied for their thermal stability and photochemical properties. Thermal properties were evaluated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). It was found that the polymers were stable up to 280 °C and start degrading thereafter. Increase in acid methylene spacer length decreased the thermal stability. The self-extinguishing property of the synthesized polymers was studied by calculating the limiting oxygen index (LOI) value using a Van Krevelen's equation. The influence of the length of methylene spacer on phase transition was investigated using DSC and odd-even effect has been observed. Hot-stage optical polarizing microscopic (HOPM) study showed that most of the polymers exhibited birefringence and opalescence properties. The photolysis of liquid crystalline poly(benzylidene-ether)esters revealed that α,β-unsaturated ketone moiety in the main chain dimerises through 2π + 2π cycloaddition reaction to form a cyclobutane derivative and leads to crosslinking.
- Muthusamy, Athianna,Balaji, Krishnasamy,Murugavel, Salem Chandrasekaran
-
p. 1707 - 1715
(2013/04/24)
-
- Synthesis and anticancer activity of all known (-)-agelastatin alkaloids
-
The full details of our enantioselective total syntheses of (-)-agelastatins A-F (1-6), the evolution of a new methodology for synthesis of substituted azaheterocycles, and the first side-by-side evaluation of all known (-)-agelastatin alkaloids against nine human cancer cell lines are described. Our concise synthesis of these alkaloids exploits the intrinsic chemistry of plausible biosynthetic precursors and capitalizes on a late-stage synthesis of the C-ring. The critical copper-mediated cross-coupling reaction was expanded to include guanidine-based systems, offering a versatile preparation of substituted imidazoles. The direct comparison of the anticancer activity of all naturally occurring (-)-agelastatins in addition to eight advanced synthetic intermediates enabled a systematic analysis of the structure-activity relationship within the natural series. Significantly, (-)-agelastatin A (1) is highly potent against six blood cancer cell lines (20-190 nM) without affecting normal red blood cells (>333 μM). (-)-Agelastatin A (1) and (-)-agelastatin D (4), the two most potent members of this family, induce dose-dependent apoptosis and arrest cells in the G2/M-phase of the cell cycle; however, using confocal microscopy, we have determined that neither alkaloid affects tubulin dynamics within cells.
- Han, Sunkyu,Siegel, Dustin S.,Morrison, Karen C.,Hergenrother, Paul J.,Movassaghi, Mohammad
-
p. 11970 - 11984
(2014/01/06)
-
- Conversion of cysteine into dehydroalanine enables access to synthetic histones bearing diverse post-translational modifications
-
Six for the price of one: From a single precursor, dehydroalanine, six distinct post-translational modifications can be site-selectively installed on histone proteins (see figure), including the first site-selective phosphorylation and glycosylation of histones. Direct observation of histone deacetylase activity on a full-length modified histone as well as its interactions with both chromatin reader and writer/eraser proteins are reported.
- Chalker, Justin M.,Lercher, Lukas,Rose, Nathan R.,Schofield, Christopher J.,Davis, Benjamin G.
-
supporting information; experimental part
p. 1835 - 1839
(2012/04/04)
-
- Rhodium(II)-catalyzed cyclization of bis(N-tosylhydrazone)s: An efficient approach towards polycyclic aromatic compounds
-
Ahead of the PAC: Polycyclic aromatic compounds (PACs) can be easily accessed by the combination of Suzuki-Miyaura cross-coupling and a [Rh 2(OAc)4]-catalyzed carbene reaction using easily available bis(N-tosylhydrazone)s as intermediates (see scheme; Ts=4-toluenesulfonyl). Copyright
- Xia, Ying,Liu, Zhenxing,Xiao, Qing,Qu, Peiyuan,Ge, Rui,Zhang, Yan,Wang, Jianbo
-
supporting information; experimental part
p. 5714 - 5717
(2012/07/28)
-
- Homobivalent ligands of the atypical antipsychotic clozapine: Design, synthesis, and pharmacological evaluation
-
To date all typical and atypical antipsychotics target the dopamine D 2 receptor. Clozapine represents the best-characterized atypical antipsychotic, although it displays only moderate (submicromolar) affinity for the dopamine D2 receptor. Herein, we present the design, synthesis, and pharmacological evaluation of three series of homobivalent ligands of clozapine, differing in the length and nature of the spacer and the point of attachment to the pharmacophore. Attachment of the spacer at the N4′ position of clozapine yielded a series of homobivalent ligands that displayed spacer-length-dependent gains in affinity and activity for the dopamine D 2 receptor. The 16 and 18 atom spacer bivalent ligands were the highlight compounds, displaying marked low nanomolar receptor binding affinity (1.41 and 1.35 nM, respectively) and functional activity (23 and 44 nM), which correspond to significant gains in affinity (75- and 79-fold) and activity (9- and 5-fold) relative to the original pharmacophore, clozapine. As such these ligands represent useful tools with which to investigate dopamine receptor dimerization and the atypical nature of clozapine.
- McRobb, Fiona M.,Crosby, Ian T.,Yuriev, Elizabeth,Lane, J. Robert,Capuano, Ben
-
supporting information; experimental part
p. 1622 - 1634
(2012/04/17)
-
- N-Heterocyclic dicarboxylic acids: Broad-spectrum inhibitors of metallo-β-lactamases with co-antibacterial effect against antibiotic-resistant bacteria
-
In an effort to identify novel, broad-spectrum inhibitors against the metallo-β-lactamases (MβLs), several N-heterocyclic derivatives were tested as inhibitors of MβLs CcrA, ImiS, and L1, which are representative enzymes from the distinct MβL subclasses. Three N-heterocyclic dicarboxylic acid derivatives were competitive inhibitors of CcrA and L1, exhibiting K i values ≤2 μM, while only 2,4-thiazolidinedicarboxylic acid (1b) was a competitive inhibitor of ImiS. Two 2-mercapto-1,3,4-thiadiazole derivatives were noncompetitive inhibitors of CcrA and ImiS, exhibiting K i values 7 μM; however, these same compounds did not inhibit L1. Two 2-mercapto-1,3,4-triazole derivatives were shown not to inhibit any of the tested MβLs. The N-heterocyclic derivatives were tested for antibacterial activity by examining the MIC values for existing antibiotics in the presence/absence of these derivatives. Consistent with the steady-state inhibition data, the inclusion of three N-heterocyclic dicarboxylic acid derivatives resulted in lower MIC values when using Escherichia coli BL21(DE3) cells containing the CcrA or L1 plasmids or Klebsiella pneumoniae (ATCC 700603), while 1b was the only dicarboxylic acid derivative to lower the MIC value of E. coli cells containing the ImiS plasmid. Inclusion of the 2-mercapto-1,3,4- thiadiazole derivatives resulted in lower MIC values for E. coli cells containing ImiS or L1 plasmids; however, these derivatives did not alter the MIC values for K. pneumoniae or E. coli cells containing the L1 plasmid. None of the N-heterocyclic derivatives affected the MIC of two methicillin resistant Staphylococcus aureus (MRSA) strains. Taken together, these studies demonstrate that N-heterocyclic dicarboxylic acids 1a-c and pyridylmercaptothiadiazoles 2a,b are good scaffolds for future broad-spectrum inhibitors of the MβLs.
- Feng, Lei,Yang, Ke-Wu,Zhou, Li-Sheng,Xiao, Jian-Min,Yang, Xia,Zhai, Le,Zhang, Yi-Lin,Crowder, Michael W.
-
scheme or table
p. 5185 - 5189
(2012/09/07)
-
- Anion recognition by N,N′-diarylalkanediamides
-
The preparation of N,N′-diarylalkanediamides from the respective aliphatic dicarboxylic acids and 4-nitroaniline via microwave-prompted reactions is presented. The most positive effect of microwave irradiation was observed for N,N′-bis(4-nitrophenyl)butanediamide. Anion binding studies on the obtained diamides were carried out in DMSO and acetonitrile using UV-vis and 1H NMR spectroscopy. A mechanism for selective fluoride recognition by N,N′-bis(4-nitrophenyl)butanediamide in DMSO is proposed.
- Wagner-Wysiecka, Ewa,Lukasik, Natalia
-
supporting information
p. 6029 - 6034,6
(2020/08/20)
-
- PRODUCT CONTAINING DIAMIDES, METHOD FOR MAKING SAME AND USES THEREOF
-
The product comprises at least two diamide compounds selected from the diamide compounds of following formulae (Ia), (Ib), and (Ic): [in-line-formulae]R2R3NOC-Aa-CONR4R5??(Ia)[/in-line-formulae] [in-line-formulae]R2R3NOC-Ab-CONR4R5??(Ib)[/in-line-formulae] [in-line-formulae]R2R3NOC-Ac-CONR4R5??(Ic)[/in-line-formulae] wherein: R2, R3, R4, and R5, either identical or different, are groups selected from saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, optionally substituted, hydrocarbon groups comprising an average number of carbon atoms ranging from 1 to 36, R2 and R3 on the one hand and R4 and R5 on the other hand may optionally form together a ring, optionally substituted and/or optionally comprising a heteroatom, andAa, Ab, and Ac are linear divalent alkyl groups, each comprising a different number of carbon atoms.
- -
-
Page/Page column 7
(2012/02/06)
-
- Structure-mechanochemical activity relationships for cyclobutane mechanophores
-
Ultrasound activation of mechanophores embedded in polymer backbones has been extensively studied of late as a method for realizing chemical reactions using force. To date, however, there have been few attempts at systematically investigating the effects of mechanophore structure upon rates of activation by an acoustic field. Herein, we develop a method for comparing the relative reactivities of various cyclobutane mechanophores. Through the synthesis and ultrasonic irradiation of a molecular weight series of poly(methyl acrylate) polymers in which each macromolecule has a single chain-centered mechanophore, we find measurable and statistically significant shifts in molecular weight thresholds for mechanochemical activation that depend on the structure of the mechanophore. We also show that calculations based on the constrained geometries simulate external force method reliably predict the trends in mechanophore reactivity. These straightforward calculations and the experimental methods described herein may be useful in guiding the design and the development of new mechanophores for targeted applications.
- Kryger, Matthew J.,Munaretto, Alexander M.,Moore, Jeffrey S.
-
supporting information; experimental part
p. 18992 - 18998
(2012/02/05)
-
- Synthesis of α,ω-bis(pyrazol-3-yl)alkanes: I. 1,4-bis(1-methyl- and 1-benzyl-5-chloro-1H-pyrazol-3-yl)-butanes from 1,1,10,10-Tetrachlorodeca- 1,9-diene-3,8-dione and 1,1-dimethyl- or benzylhydrazine
-
First representatives of bis-2-chloro- and 2,2-dichlorovinyl ketones, 1,10-dichlorodeca-1,9-diene-3,8-dione and 1,1,10,10-tetrachlorodeca-1,9-diene-3, 8-dione, were synthesized by reaction of hexanedioyl dichloride with acetylene and 1,1-dichloroethene, respectively, in the presence of AlCl3. 1,1,10,10-Tetrachlorodeca-1,9-diene-3,8-dione reacted with benzylhydrazine and 1,1-dimethylhydrazine to give 1,4-bis(1-benzyl-5-chloro-1H-pyrazol-3-yl)butane and 1,4-bis(5-chloro-1-methyl-1H-pyrazol-3-yl)butane, respectively.
- Rudyakova,Samul'Tsev,Bozhenkov,Levkovskaya
-
experimental part
p. 1870 - 1873
(2012/03/22)
-
- PROCESS FOR PRODUCING CARBOXYLIC ACID CHLORIDE
-
This invention relates to a method for producing a carboxylic acid chloride, which efficiently decomposes a Vilsmeier reagent type compound in a carboxylic acid chloride lacking a thermal stability or a carboxylic acid chloride hardly distilled in practice due to a high boiling point with a simple operation and has no adverse effect on a subsequent step, and more particularly to a method for producing a carboxylic acid chloride, characterized by comprising reacting a carboxylic acid with a chlorinating agent in the presence of a catalyst, removing the excessive chlorinating agent from a reaction system after the reaction, and then further adding 1.0 to 3.0 equivalents of the starting carboxylic acid based on the catalyst to the reaction system to decompose a Vilsmeier reagent type compound remaining in the reaction system.
- -
-
Page/Page column 5
(2009/12/23)
-
- Studies on synthesis and plant growth retardant activity of cyclic bis-quaternary salts of ammonia from phthalic acid using conventional and microwave methods
-
Phthalic acid 1 has been converted to bis (oxiran-2-ylmethyl) phthalatc 2 followed by ring opening to di-tcrliary amines viz: bis (3-[dicthylamino)-2- hydroxypropyl] phthalate 3 and bis [2-hydroxy-3-[pipcridin-l-yl) propyl] phthalate 4. Conversion is carried through conventional as well as non-conventional methods (microwave irradiation on solid support). Di-tertiary amines 3 and 4 have been qualcmizcd to give cyclic bis-quaternary ammonium salts 3a-c and 4a, b which in turn are tested for their efficacy as plant growth regulators on rice (Oryza sativa). All the tested compounds are found to be good plant growth retardants. Compound 4c is found to be the best plant growth retardant among the six newly synthesized compounds.
- Bangar, Jyoti,Sharma
-
experimental part
p. 1299 - 1306
(2010/02/27)
-
- A new class of star-shaped cholesteric liquid crystal containing a 1,3,5-trihydroxybenzene unit as a core
-
A new class of star-shaped cholesteric liquid crystals were designed and synthesized, which used 1,3,5-trihydroxybenzene unit as a core and ω-cholesteric alkyl diacid monoester as mesogenic arm. Their chemical structures were confirmed by element analyses, FT-IR, and 1H NMR. The mesomorphic properties and thermal stability were investigated by differential scanning calorimetry, thermogravimetric analysis, polarizing optical microscopy, and X-ray diffraction measurements. The experimental results demonstrated that the mesogenic arm structures strongly affected the phase behavior. 4a did not show any liquid crystallinity, while 4b, 4c and 4d revealed reversible cholesteric phase transition. As the intermedius alkyl chain of the star-shaped compounds lengthened (from n = 2 to n = 8), their melting points decreased but mesomorphic temperature ranges increased. Focal conic texture, one of cholesteric phase can be observed in the liquid crystalline state.
- Yao, Dan-Shu,Zhang, Bao-Yan,Zhang, Wei-Wei,Tian, Mei
-
-
- Catalytic, asymmetric transannular aldolizations: Total synthesis of (+)-hirsutene
-
We report an asymmetric, catalytic transannular aldolization that provides polycyclic products useful for natural product synthesis. We found that a proline-derivative catalyzes the transannular aldol reaction of 1,4-cyclooctanediones to the corresponding cyclic β-hydroxy ketones in good yields and with high enantioselectivities. The utility of our reaction has been demonstrated in a total synthesis of (+)-hirustene. Copyright
- Chandler, Carley L.,List, Benjamin
-
p. 6737 - 6739
(2008/12/22)
-