- Synthesis and photovoltaic properties of a new thiophene-cyclopentadiene- based conjugated polymer
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A new low-band gap polymer containing thiophene and cyclopentadiene, poly(5,2,2'-dioctyldithiophenylcyclopentadiene) (PDTCP), has been synthesized via the FeCl3 oxidative polymerization. PDTCP showed a broad absorption band and a low energy band gap of 1.82 eV. The photoluminescence (PL) of PDTCP is completely quenched upon addition of PCBM indicative of efficient charge transfer. Bulk heterojunction organic photovoltaic cells (OPVs) fabricated from PDTCP as an electron donor showed an open-circuit voltage (VOC) of 0.50 V, a short-circuit current (JSC) of 1.24 mA/cm2, and the power conversion efficiency of up to 0.20% under AM 1.5 (100 mW/cm2). Copyright
- Lim, Eunhee,Lee, Sungkoo,Lee, Kyeong K.
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Read Online
- Synthesis and photophysical properties of a new BODIPY-based siloxane dye
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A fluorescent dye comprising four BODIPY derivatives conjugated to a cyclotetrasiloxane core was synthesized by consecutive hydrosilylation and esterification reactions. Photophysical properties of the dye in various organic solvents were investigated. It was shown that due to a fourfold extinction coefficient increase and a moderate quantum yield decrease the brightness of the tetra-BODIPY dye in low-polarity solvents, calculated per molecule, increased 3 times when compared to mono-BODIPY. By contrast, in polar solvents there was a dramatic drop in brightness apparently associated with intramolecular interactions of the low-polar BODIPY chromophores.
- Pakhomov, Alexey A.,Kononevich, Yuriy N.,Stukalova, Maria V.,Svidchenko, Evgeniya A.,Surin, Nikolay M.,Cherkaev, Georgy V.,Shchegolikhina, Olga I.,Martynov, Vladimir I.,Muzafarov, Aziz M.
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Read Online
- Synthesis of optically active hydroxyesters using biocatalysts
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Optically active hydroxyesters were prepared using the fungus Aspergillus niger and the yeast Sacharomyces cerevisiae. Substrate is converted highly specifically into optically active isomers with 95% purity. The R-hydroxyester was isolated by asymmetric reduction. (R,R)-Tartaric acid of 60% optical purity was used as an inductor.
- Shakirzyanova,Abdukakharov,Abduvakhabov
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Read Online
- New compounds for a good old class: Synthesis of two Β-lactam bearing cephalosporins and their evaluation with a multidisciplinary approach
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Antimicrobial resistance is spreading massively in the world and is becoming one of the main health threats of the 21st century. One of the possible strategies to overcome this problem is to modify the known classes of antibiotics in a rational way, with the aim of tuning their efficacy. In this paper, we present the synthesis and the evaluation of the biological activity of a series of two β-lactam bearing cephalosporin derivatives, in which an additional isolated azetidinone ring, bearing different substituents, is joined to the classical cephalosporanic nucleus by a chain of variable length. A computational approach has been also applied in order to predict the molecular interactions between some representative derivatives and selected penicillin-binding proteins, the natural targets of β-lactam antibiotics. All these derivatives are active against Gram-positive bacteria, with MIC100 comparable or even better than that of the reference antibiotic ceftriaxone, and show no or very low cytotoxic activity on different cell lines. Overall, these molecules appear to be able to exert their activity in particular against microorganisms belonging to some of the species more involved in the development of multidrug resistance.
- Vigliotta, Giovanni,Giordano, Deborah,Verdino, Anna,Caputo, Ivana,Martucciello, Stefania,Soriente, Annunziata,Marabotti, Anna,De Rosa, Margherita
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- Two-Dimensional Barriers for Probing Conformational Shifts in Macrocycles
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We describe the development and use of composite two-dimensional barriers in macrocyclic backbones. These tunable constructs derive their mode of action from heterocyclic rearrangements. The Boulton-Katritzky reaction has been identified as a particularly versatile means to effect a composite barrier, allowing the examination of the influence of heterocycle translocation on conformation. Kinetic studies using 1H NMR have revealed that the in-plane atom movement is fast in 17, 18, 19-membered rings but slows down in 16-membered rings. The analysis by NMR and MD simulation experiments is consistent with the maintenance of rare cis-amide motifs during conformational interconversion. Taken together, our investigation demonstrates that heterocyclic rearrangement reactions can be used to control macrocyclic backbones and provides fundamental insights that may be applicable to the development of a wide range of other conformational control elements.
- Kobori, Shinya,Huh, Sungjoon,Appavoo, Solomon D.,Yudin, Andrei K.
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supporting information
p. 5166 - 5171
(2021/05/04)
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- Neutrophil-Selective Fluorescent Probe Development through Metabolism-Oriented Live-Cell Distinction
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Human neutrophils are the most abundant leukocytes and have been considered as the first line of defence in the innate immune system. Selective imaging of live neutrophils will facilitate the in situ study of neutrophils in infection or inflammation events as well as clinical diagnosis. However, small-molecule-based probes for the discrimination of live neutrophils among different granulocytes in human blood have yet to be reported. Herein, we report the first fluorescent probe NeutropG for the specific distinction and imaging of active neutrophils. The selective staining mechanism of NeutropG is elucidated as metabolism-oriented live-cell distinction (MOLD) through lipid droplet biogenesis with the help of ACSL and DGAT. Finally, NeutropG is applied to accurately quantify neutrophil levels in fresh blood samples by showing a high correlation with the current clinical method.
- Gao, Min,Lee, Sun Hyeok,Park, Sang Hyuk,Ciaramicoli, Larissa Miasiro,Kwon, Haw-Young,Cho, Heewon,Jeong, Joseph,Chang, Young-Tae
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supporting information
p. 23743 - 23749
(2021/10/14)
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- AROMATIC RING DERIVATIVE AS IMMUNOREGULATION AND PREPARATION METHOD AND APPLICATION OF AROMATIC RING DERIVATIVE
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Relating to a compound represented by formula (I) and a pharmaceutically acceptable salt of the compound, and an application of the compound as an S1P1 agonist.
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Paragraph 0110-0112
(2021/10/15)
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- Live-Cell Protein Modification by Boronate-Assisted Hydroxamic Acid Catalysis
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Selective methods for introducing protein post-translational modifications (PTMs) within living cells have proven valuable for interrogating their biological function. In contrast to enzymatic methods, abiotic catalysis should offer access to diverse and new-to-nature PTMs. Herein, we report the boronate-assisted hydroxamic acid (BAHA) catalyst system, which comprises a protein ligand, a hydroxamic acid Lewis base, and a diol moiety. In concert with a boronic acid-bearing acyl donor, our catalyst leverages a local molarity effect to promote acyl transfer to a target lysine residue. Our catalyst system employs micromolar reagent concentrations and affords minimal off-target protein reactivity. Critically, BAHA is resistant to glutathione, a metabolite which has hampered many efforts toward abiotic chemistry within living cells. To showcase this methodology, we installed a variety of acyl groups inE. colidihydrofolate reductase expressed within human cells. Our results further establish the well-known boronic acid-diol complexation as abona fidebio-orthogonal reaction with applications in chemical biology and in-cell catalysis.
- Adamson, Christopher,Kajino, Hidetoshi,Kanai, Motomu,Kawashima, Shigehiro A.,Yamatsugu, Kenzo
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supporting information
p. 14976 - 14980
(2021/09/29)
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- Inverse Electron-Demand Diels-Alder Bioconjugation Reactions Using 7-Oxanorbornenes as Dienophiles
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Oligonucleotides, peptides, and peptide nucleic acids incorporating 7-oxanorbornene as a dienophile were reacted with tetrazines linked to either a peptide, d-biotin, BODIPY, or N-acetyl-d-galactosamine. The inverse electron-demand Diels-Alder (IEDDA) cycloaddition, which was performed overnight at 37 °C, in all cases furnished the target conjugate in good yields. IEDDA reactions with 7-oxanorbornenes produce a lower number of stereoisomers than that of IEDDA cycloadditions with other dienophiles.
- Agramunt, Jordi,Ginesi, Rebecca,Grandas, Anna,Pedroso, Enrique
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p. 6593 - 6604
(2020/07/14)
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- Cobalt(III)-Catalyzed C?H Amidation of Dehydroalanine for the Site-Selective Structural Diversification of Thiostrepton
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Thiostrepton is a potent antibiotic against a broad range of Gram-positive bacteria, but its medical applications have been limited by its poor aqueous solubility. In this work, the first C(sp2)?H amidation of dehydroalanine (Dha) residues was applied to the site selective modification of thiostrepton to prepare a variety of derivatives. Unlike all prior methods for the modification of thiostrepton, the alkene framework of the Dha residue is preserved and with complete selectivity for the Z-stereoisomer. Additionally, an aldehyde group was introduced by C?H amidation, enabling oxime ligation for the installation of an even greater range of functionality. The thiostrepton derivatives generally maintain antimicrobial activity, and importantly, eight of the derivatives displayed improved aqueous solubility (up to 28-fold), thereby addressing a key shortcoming of this antibiotic. The exceptional functional group compatibility and site selectivity of CoIII-catalyzed C(sp2)?H Dha amidation suggests that this approach could be generalized to other natural products and biopolymers containing Dha residues.
- Scamp, Ryan J.,deRamon, Edward,Paulson, Eric K.,Miller, Scott J.,Ellman, Jonathan A.
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supporting information
p. 890 - 895
(2019/12/11)
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- Highly Efficient Multigram Synthesis of Dibenzoazacyclooctyne (DBCO) without Chromatography
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The synthesis of 4-[11,12-didehydrodibenzo[b,f]azocin-5(6H)-yl]-4-oxobutanoic acid, also known as dibenzoazacyclooctyne (DBCO) or aza-dibenzocyclooctyne (ADIBO), was optimized for large-scale preparations of at least 10 g with an overall yield of 42%.
- McNelles, Stuart A.,Pantaleo, Julia L.,Adronov, Alex
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p. 2740 - 2745
(2019/11/21)
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- Electrochemical [4+2] Annulation-Rearrangement-Aromatization of Styrenes: Synthesis of Naphthalene Derivatives
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We report the first electrochemical strategy to synthesize functionalized naphthalene derivatives through [4+2] annulation—rearrangement–aromatization from styrenes under mild conditions. The electrolysis does not require metals, oxidants and high valence substrates, indicating the atom and step-economy ideals. The dehydrodimer produced through [4+2] cycloaddition of 4-methoxy α-methyl styrene is isolated and proved to be the key intermediate for the following oxydehydrogenation to form carbon cation, which undergoes rearrangement–aromatization to afford the final products. This reaction represents a powerful access to construct multi-substituted naphthalene blocks in a single step.
- Ma, Yueyue,Lv, Jufeng,Liu, Chengyu,Yao, Xiantong,Yan, Guoming,Yu, Wei,Ye, Jinxing
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supporting information
p. 6756 - 6760
(2019/04/17)
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- Cyclohexyl-Fused, Spirobiindane-Derived, Phosphine-Catalyzed Synthesis of Tricyclic ?3-Lactams and Kinetic Resolution of ?3-Substituted Allenoates
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A C2-symmetric chiral phosphine catalyst, NUSIOC-Phos, which can be easily derived from cyclohexyl-fused spirobiindane, was introduced. A highly enantioselective domino process involving pyrrolidine-2,3-diones and γ-substituted allenoates catalyzed by NUSIOC-Phos has been disclosed. Diastereospecific tricyclic γ-lactams containing five contiguous stereogenic centers were obtained in high yields and with nearly perfect enantioselectivities. A kinetic resolution process of racemic γ-substituted allenoates was developed for the generation of optically enriched chiral allenoates.
- Wu, Mingyue,Han, Zhaobin,Li, Kaizhi,Wu, Ji'En,Ding, Kuiling,Lu, Yixin
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supporting information
p. 16362 - 16373
(2019/10/16)
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- Preparation of (S)-N-(1-amino-1-oxybutane-2-yl)-4-hydroxybutanamide
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Levetiracetam is a novel antiepileptic drug with unique anti-epileptic mechanisms, good pharmacokinetic characteristics, and high and safe clinical effects. The present application aims to establish apreparation method of impurity (S)-N-(1-amino-1-oxybutane-2-yl)-4-hydroxybutanamide which may be generated during the synthesis process of the Levetiracetam to ensure the Levetiracetam final productrelated substance is qualified, so that efficient industrial production is realized.
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Paragraph 0009
(2019/04/26)
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- Method for overcoming drug resistance of EGFR mutation and cancerous stemness of human non-small cell lung carcinoma
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EGFR mutation (T790M) and cancerous stemness have shown drug resistances in human non-small-cell lung cancer (NSCLC), thus development of novel drugs in overcoming drug resistances in the NSCLC therapy is highly desired. SP101 is a novel gefitinib derivative, which can bind the ATP-binding pocket of EGFR to inhibit its EGFR kinase activity. SP101 can reduce the drug resistances of EGFR mutation (T790M) and cancerous stemness in NSCLC. SP101 induced cancer cell death and apoptosis in the gefitinib-resistant EGFR mutation (T790M) H1975 cells. SP101 inhibited phosphorylated EGFR and its downstream Survivin proteins but conversely induced Caspase 3 activation for apoptosis induction. Moreover, SP101 could decrease Oct4 protein level and reduce Survivin proteins but conversely elicited active Caspase 3 in the xenograft human H1975 lung tumors in nude mice.
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Page/Page column 5; 6
(2018/06/08)
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- Intermediate for standard auspicious Luo river (1R, 2S) - 2 - (2,3-difluorophenyl) method for the preparation of cyclopropylamines (by machine translation)
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The invention discloses a method for preparing ticagrelor midbody (1R,2S)-2-(2,3-difluorophenyl) cyclopropylamine, belonging to the technical fields of organic synthesis route design and preparation of raw material medicines and midbodies. The method comprises the following steps: performing alcoholysis on succinic anhydride, thereby obtaining mono-methyl succinate, performing acylating chlorination reaction on mono-methyl succinate, thereby obtaining a compound methyl 4-chloro-4-oxobutyrate, performing Fridel-Crafts reaction on methyl 4-chloro-4-oxobutyrate and o-difluorobenzene, thereby obtaining a compound methyl 4-ketone-4-(3,4-difluorophenyl) butyrate (IV), and further performing asymmetric reduction reaction, cyclization reaction and Hoffman degradation on the compound IV, thereby obtaining the compound (1R,2S)-2-(2,3-difluorophenyl) cyclopropylamine. Initial raw materials used in the method are low in cost and easy to obtain, the reaction condition is gentle, the operation is safe, simple and convenient, the environment pollution is small, and the key ticagrelor midbody prepared by using the method is simple and convenient in after treatment, and is beneficial to on-scale production.
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Paragraph 0037; 0062; 0064
(2017/03/23)
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- COMPOUND FOR PROMOTING APOPTOSIS OF CANCER CELLS AND A PHARMACEUTICAL COMPOSITION CONTAINING THE SAME AND USES THEREOF
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The present invention provides a compound of Formula (I) and a salt thereof, wherein, m is an integer of 2 to 7, and R is independently at least one selected from the group consisting of hydrogen and C1-C20 alkyl. The compound promotes apoptosis in cancer cell and inhibits its growth. The present invention also provides a pharmaceutical composition which comprises the compound of Formula (I), a salt thereof and a pharmaceutically acceptable carrier. The present invention further provides a method for production of the pharmaceutical composition used for treating cancer.
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Paragraph 0047; 0048
(2016/04/20)
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- Optimization of gefitinib analogues with potent anticancer activity
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The interactions of gefitinib (Iressa) in EGFR are hydrogen bonding and van der Waals forces through quinazoline and aniline rings. However the morpholino group of gefitinib is poorly ordered due to its weak electron density. A series of novel piperazino analogues of gefitinib where morpholino group substituted with various piperazino groups were designed and synthesized. Most of them indicated significant anti-cancer activities against human cancer cell lines. In particular, compounds 52-54 showed excellent potency against cancer cells. Convergent synthetic approach has been developed for the synthesis of gefitinib intermediate which can lead to gefitinib as well as numerous analogues.
- Yin, Kai-Hao,Hsieh, Yi-Han,Sulake, Rohidas S.,Wang, Su-Pei,Chao, Jui-I.,Chen, Chinpiao
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supporting information
p. 5247 - 5250
(2015/01/08)
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- Design and synthesis of tri-substituted chiral pyrrolidin-2-one derivatives as CCR4 antagonists
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A series of tri-substituted chiral pyrrolidin-2-one derivatives have been designed and synthesized as CC chemokine receptor 4 (CCR4) antagonists. The structure of CCR4 was built by homology modeling. Asymmetric synthesis was applied to synthesize the R,R configuration chiral pyrrolidin-2-one scaffold. The stereoisomeric configurations of the compounds were identified by 2D 1H-1H COSY spectroscopy and 1D NOESY spectroscopy. This method was more economical and convenient than traditional X-ray single crystal diffraction. In addition, the interactions between these compounds and the N-terminal extracellular tail of CCR4 were studied using capillary zone electrophoresis. The CCR4 chemotaxis inhibition effect was tested in CCR4-transfected HEK293 cells. Several compounds showed potent activities as CCR4 antagonists. Among these compounds, 1c is the most active one. Its apparent binding constant of CZE experiment result is (1.569±0.11)×10 5 L·mol-1, and its percentage inhibition of the HEK293/CCR4 cells migration with the concentration of 1 μmol·L -1 in DMSO is 59%. And compound 1f has slightly higher affinity to N-terminal of CCR4 according to its apparent binding constant than 1b because of the introduced ester linkage. Further studies on the mechanism of these compounds are in progress. The structure of CCR4 based on bovine rhodopsin was built through homology modeling. And six tri-substituted chiral pyrrolidin-2-one derivatives have been designed and synthesized as CCR4 antagonists. Several of these compounds show high inhibitory effect in cell assays and higher affinity for the N-terminal of CCR4. Among the compounds, 1c exhibited excellent activity. Copyright
- Sun, Wei,Tian, Linjie,Qi, Hui,Jiang, Dan,Wang, Ying,Li, Song,Xiao, Junhai,Yang, Xiaohong
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p. 1144 - 1152
(2013/10/21)
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- Insights into soluble guanylyl cyclase activation derived from improved heme-mimetics
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Recently, the structure of BAY 58-2667 bound to the Nostoc sp. H-NOX domain was published. On the basis of this structural information, we designed BAY 58-2667 derivatives and tested their effects on soluble guanylyl cyclase (sGC) activity. Derivative 20 activated sGC 4.8-fold more than BAY 58-2667. Co-crystallization of 20 with the Ns H-NOX domain revealed that the increased conformational distortion at the C-terminal region of αF helix containing 110-114 residues contributes to the higher activation triggered by 20.
- Von Wantoch Rekowski, Margarete,Kumar, Vijay,Zhou, Zongmin,Moschner, Johann,Marazioti, Antonia,Bantzi, Marina,Spyroulias, Georgios A.,Van Den Akker, Focco,Giannis, Athanassios,Papapetropoulos, Andreas
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supporting information
p. 8948 - 8952
(2013/12/04)
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- PROTEASOME ACTIVITY MODULATING COMPOUNDS
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The present invention is directed to compounds having the Formula (I), (la) or (Ib), compositions thereof and methods for the treatment of a condition associated with a dysfunction in proteostasis.
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(2013/08/15)
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- NEAR-INFRARED ABSORBING FILM COMPOSITIONS
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A curable liquid formulation containing at least (i) one or more near-infrared absorbing triphenylamine -based dyes, and (ii) one or more casting solvents. The invention is also directed to solid near- infrared absorbing films composed of crosslinked forms of the curable liquid formulation. The invention is also directed to a microelectronic substrate containing a coating of the solid near-infrared absorbing film as well as a method for patterning a photoresist layer coated on a microelectronic substrate in the case where the near-infrared absorbing film is between the microelectronic substrate and a photoresist film.
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(2011/04/13)
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- ESTERAMIDE SOLVENTS/COALESCING AGENTS IN PHYTOSANITARY, CLEANING, DEGREASING, STRIPPING, LUBRICATING, COATING, AND PIGMENT/INK COMPOSITIONS
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Esteramide compounds are useful solvents/coalescing agents for a variety of phytosanitary, cleaning, degreasing, stripping, lubricating, coating and pigment/ink compositions.
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(2011/07/29)
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- Succinylphosphonate esters are competitive inhibitors of MenD that show active-site discrimination between homologous α-ketoglutarate- decarboxylating enzymes
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MenD is a thiamin diphosphate-dependent enzyme catalyzing the first unique step in menaquinone biosynthesis in bacteria. We have synthesized acylphosphonate ester analogues of a-ketoglutarate, a substrate of MenD. These compounds are competitive inhibitors of MenD, with Ki values as low as 700 nM. Observed structure-activity relationships are in notable contrast to those reported previously for succinylphosphonate inhibition of the a-ketoglutarate dehydrogenase complex, despite the apparent homology of these enzymes, and the identical decarboxylation reactions catalyzed. Inhibiting menaquinone biosynthesis is a proposed approach to inhibiting Mycobacterium tuberculosis growth. These inhibitors showed no significant inhibition of M. tuberculosis growth in vitro under aerobic and hypoxic conditions but give new information about the binding characteristics of the MenD active site. Site-directed mutation of Ser391 to alanine had only a minor effect on catalysis, but even the conservative mutation of Arg395 to lysine had a significant effect on the catalytic processing of isochorismate.
- Fang, Maohai,Daniel Toogood,Macova, Andrea,Ho, Karen,Franzblau, Scott G.,McNeil, Michael R.,Sanders, David A.R.,Palmer, David R.J.
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body text
p. 2672 - 2679
(2011/03/19)
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- Phosphine-mediated olefination between aldehydes and allenes: An efficient synthesis of trisubstituted 1,3-dienes with high E-selectivity
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The phosphine-mediated olefination of aldehydes with electron-deficient allenes to afford trisubstituted conjugated dienes in fair to excellent yields with high E-selectivity is described. The reaction represents a new reactivity pattern of allenes with aldehydes and also provides a highly stereoselective synthetic method for preparing conjugated dienes. In the reaction, the phosphine acts as a nucleophilic promoter to generate in situ an active phosphorus ylide which mediates the intermolecular olefination.
- Xu, Silong,Zhou, Lili,Zeng, San,Ma, Renqin,Wang, Zhihong,He, Zhengjie
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supporting information; scheme or table
p. 3498 - 3501
(2009/12/01)
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- On the synthesis of cepacin A
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Efforts directed toward a total synthesis of cepacin A is presented in full detail. The C-7, C-8, and C-9 stereogenic centers in the target molecule were derived from d-arabinose. The configuration of the allene axis was controlled at the bromoallenation step by the C-10 configuration of the precursor. An unexpected yet very interesting phenomenon was observed with the bromoallenation, where the α-isomer of the propargylic alcohol 31 was entirely resistant to the conditions that worked so well for its β-counterpart. The problem was eventually solved by careful tuning of the size of the neighboring groups based on the clue obtained from conformational analysis. The diyne moiety was incorporated into the molecular framework through a coupling of the TMS protected diyne with a proper bromoallene under the Sonogashira conditions with EtOAc as the solvent. Use of other solvents at this step led to complete failure.
- Tang, Chao-Jun,Wu, Yikang
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p. 4887 - 4906
(2008/02/01)
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- Structure-activity relationships of α-ketooxazole inhibitors of fatty acid amide hydrolase
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A systematic study of the structure-activity relationships of 2b (OL-135), a potent inhibitor of fatty acid amide hydrolase (FAAH), is detailed targeting the C2 acyl side chain. A series of aryl replacements or substituents for the terminal phenyl group provided effective inhibitors (e.g., 5c, aryl = 1-napthyl, K, - 2.6 nM), with 5hh (aryl -3-ClPh, Ki = 900 pM) being 5-fold more potent than 2b. Conformationally restricted C2 side chains were examined, and many provided exceptionally potent inhibitors, of which 11j (ethylbiphenyl side chain) was established to be a 750 pM inhibitor. A systematic series of heteroatoms (O, NMe, S), electron-withdrawing groups (SO, SO2), and amides positioned within and hydroxyl substitutions on the linking side chain were investigated, which typically led to a loss in potency. The most tolerant positions provided effective inhibitors (12p, 6-position S, Ki = 3 nM, or 13d, 2-position OH, Ki = 8 nM) comparable in potency to 2b. Proteome-wide screening of selected inhibitors from the systematic series of >100 candidates prepared revealed that they are selective for FAAH over all other mammalian serine proteases.
- Hardouin, Christophe,Kelso, Michael J.,Romero, F. Anthony,Rayl, Thomas J.,Leung, Donmienne,Hwang, Inkyu,Cravatt, Benjamin F.,Boger, Dale L.
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p. 3359 - 3368
(2008/02/13)
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- New esters of vanillin and vanillal with some alkane- and arenecarboxylic acids
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Previously unknown esters were synthesized by the reaction of vanillin and vanillal with carboxylic acid chlorides. Pleiades Publishing, Inc., 2006.
- Dikusar
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p. 1035 - 1037
(2008/02/05)
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- Synthesis of esters of D, L-, D(+)-, and L(-)-camphor oximes: Structure-odor correlation
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Esters of D,L-, D(+)-, and L(-)-camphor oximes were synthesized, and the correlation between their structure and odor was examined.
- Dikusar,Zhukovskaya,Vyglazov
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p. 1982 - 1985
(2008/02/08)
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- SUBSTITUTED CYCLOHEXYL-1,4-DIAMINE DERIVATIVES WITH A CHAIN EXTENSION
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The invention relates to substituted cyclohexyl-1,4-diamine derivatives, to a method for their production, to medicaments containing said compounds and to the use of substituted cyclohexyl-1,4-diamine derivatives for producing medicaments.
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(2008/06/13)
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- Synthesis and biological evaluation of new phenidone analogues as potential dual cyclooxygenase (COX-1 and COX-2) and human lipoxygenase (5-LOX) inhibitors
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A new series of potential human 5-LOX inhibitors structurally related to the 1-phenyl-3-pyrazolidinone (phenidone, 2) has been synthesized and the activity against COX-1, COX-2, and human 5-LOX enzymes has been evaluated. In contrast with literature data, we observed that phenidone resulted to be inactive against human 5-LOX, while retains its activity against cyclooxygenases in a micromolar range. The present results suggest that the substitution of the amino function at the 4-position is detrimental in terms of activity toward COX-1 and COX-2, while the presence of a double bond at the 4,5-position does not alter the biological profile against COX. The absence of activity vs. human 5-LOX strongly suggests a re-consideration of phenidone and its analogs as 5-LOX inhibitors in humans.
- Cusan, Claudia,Spalluto, Giampiero,Prato, Maurizio,Adams, Michael,Bodensieck, Antje,Bauer, Rudolf,Tubaro, Aurelia,Bernardi, Paolo,Da Ros, Tatiana
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- Novel (3,5-di-tert-butyl-2-hydroxy-phenylcarbamoyl)-alkanoic acids as potent antioxidants
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A series of novel phenolic antioxidants of amphiphilic structure has been synthesized. Investigations into the influence of aliphatic spacer length and nature of a hydrophilic anchor on the antioxidant activity allowed elucidating certain structure requirements for the membrane-addressed antioxidant designing.
- Lodyato, Vladimir I.,Yurkova, Irina L.,Sorokin, Viktor L.,Shadyro, Oleg I.,Dolgopalets, Vladimir I.,Kisel, Mikhail A.
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p. 4253 - 4256
(2007/10/03)
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- Synthesis of enantiomerically pure α-amino-β-hydroxy- cyclobutanone derivatives and their transformations into polyfunctional three- and five-membered ring compounds
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Ketenes readily cycloadded to (R)-tert-butyldihydrooxazole 2a-d to yield enantiomerically pure bicyclic cyclobutanones. The cycloadditions proceeded with unusual regiochemistry giving predominantly or exclusively protected α-amino-β-hydroxycyclobutanone derivatives. The adducts could be converted into a variety of interesting enantiopure intermediates equipped with many functional groups: α-amino-β-hydroxy cyclopropane carboxylic acid derivatives, α-amino-β-hydroxy succinic acid derivatives, α-amino-β-hydroxy lactones and lactams derivatives.
- Ghosez, Léon,Yang, Gaoqiang,Cagnon, José Renato,Bideau, Franck Le,Marchand-Brynaert, Jacqueline
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p. 7591 - 7606
(2007/10/03)
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- A combination of Friedel-Crafts and Lawesson reactions to 5-substituted 2,2′-bithiophenes
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γ-Keto esters (2) derivatives of thiophene were obtained from hemisuccinic esters and transformed to the corresponding amides (4). Lawesson's treatment of 2 and 4 gave the corresponding bithiophenes (5) with alkoxy or amino substituents.
- Raposo, M. Manuela M.,Kirsch
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p. 1487 - 1498
(2007/10/03)
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- Cyclic bis-urea compounds as gelators for organic solvents
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The gelation properties of bis-urea compounds derived from optically pure trans-1,2-diaminocyclohexane and 1,2-diaminobenzene, with pendant aliphatic, aromatic, or ester groups, as well as the structure of the resulting gels, have been studied by differential scanning calorimetry, infrared spectroscopy, small-angle X-ray diffraction, and electron microscopy. These compounds have been found to be very potent gelators for organic solvents, such as aliphatic and aromatic hydrocarbons, esters, ketones, and alcohols, at concentrations well below 1 (w/v)%. Gelation by these compounds is completely thermoreversible, with melting temperatures up to 120°C, and many of the gels display thixotropic properties. Even at low concentrations these compounds self-assemble into elongated and very thin fibers, which in turn form a three-dimensional network in the solvent. Infrared studies showed that aggregation is accompanied by the formation of a hydrogen-bonded network between urea moieties, and a single-crystal X-ray structure of one of the compounds showed that in crystals the molecules assemble into one-dimensional chains, which are stabilized by the formation of eight hydrogen bonds between the urea groups and adjacent molecules. The molecular arrangement in gels is most likely very similar to that in the crystal, but the complete elucidation of the molecular arrangement in gels is complicated because aggregation of these compounds is prone to polymorphism. It is concluded that the very efficient aggregation of these molecules and the elongated shape of the fibers most likely arise from the highly anisotropic hydrogen-bonding properties of these molecules, which is due to the presence of two coplanar oriented urea moieties in a single molecule. Since the bis-urea compounds presented in this paper are very easy to synthesize and many structural variations are possible without loss of the gelation ability, they are excellent building blocks for the construction of functional gels.
- Van Esch, Jan,Schoonbeek, Franck,De Loos, Maaike,Kooijman, Huub,Spek, Anthony L.,Kellogg, Richard M.,Feringa, Ben L.
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p. 937 - 950
(2007/10/03)
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- Synthesis and investigation of N4-substituted cytarabine derivatives as prodrugs.
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Esters of Cytarabine-N4-carboxylates 2a-i and succinamates 3a-f were synthesized as prodrugs of cytarabine (Ara-C) with the aim of developing improved derivatives for oral or parentral administration. At pH 2 series 2 showed relative higher stability than 3, while both series of esters revealed matched stability at pH 7. All esters were susceptible to enzymatic hydrolysis by rat plasma and liver homogenate with half lives ranged from 0.14 h to 12 d, and showed improved stability against cytidine deaminase. A parabolic relation was shown between Kobs of enzymatic hydrolysis and Vw. All compounds are more lipophilic than the parent drug, Ara-C.
- Fadl,Hasegawa,Youssef,Farag,Omar,Kawaguchi
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p. 382 - 387
(2007/10/02)
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- A Convenient Synthesis of Dicarboxylic Monoesters using Isopropenyl Esters: Synthesis of Oxaunomycin Derivatives
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Reaction of various types of alcohols with a novel type of acylating agent, the isopropenyl esters 2a-e in the presence of a catalytic amount of conc. sulfuric acid or toluene-p-sulfonic acid followed by selective deprotection of the terminal ester gives the monoesters 5a-i in good yields.
- Kita, Yasuyuki,Maeda, Hiroshi,Takahashi, Fumie,Fukui, Seiji
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p. 410 - 412
(2007/10/02)
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- Convenient Synthesis of Alcohol O-Hemiesters using Isopropenyl Esters as Acylating Reagents: Synthesis of Hydrophilic Oxaunomycin 10-O-Hemiester Derivatives
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Various types of alcohol O-hemiesters 7a-m were synthesized conveniently in good yield by reaction with isopropenyl esters 4a-f in the presence of a catalytic amount of conc.H2SO4 or toluene-p-sulfonic acid followed by selective deprotection of the terminal esters.This method was applied to a preparation of hydrophilic oxaunomycin 10-O-hemiester derivatives 14a,b and 19a-c.
- Kita, Yasuyuki,Maeda, Hiroshi,Takahashi, Fumie,Fukui, Seiji
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p. 2639 - 2650
(2007/10/02)
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- Synthesis and LTD4 antagonist activity of 2-norleukotriene analogues.
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A series of structural analogues of 4(R)-hydroxy-5(S)-cysteinylglycyl-6(Z)-nonadecenoic acid [4R,5S,6Z)-2-nor-LTD1 (10b), SK&F 101132) has been synthesized and pharmacologically characterized. (4R,5S,6Z)-2-nor-LTD1 significantly antagonized LTD4-induced contractile responses on isolated guinea pig trachea. The cis double-bond geometry appears to be critical for antagonist activity, whereas the trans isomer 17 exhibited weak contractile activity. Replacement of the cysteinylglycyl moiety with cysteine afforded 20, which retained significant antagonist activity, while lengthening or shortening the lipid tail by five methylene groups resulted in complete loss of activity. The eicosanoid amide 15, glycinamide 14, and C-1 carbinol 18 analogues all possessed antagonist activity, whereas the diol derivative 19 exhibited increased intrinsic agonist activity.
- Ku,McCarthy,Weichman,Gleason
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p. 1847 - 1853
(2007/10/02)
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- 2-Acyl-3-substituted cyclopentan-1-ones and process for their preparation
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1,3-Dicarbonyl compounds useful as medicines, agricultural chemicals, perfumes, and their intermediates are prepared by reacting a specific α,β-unsaturated carbonyl compound with a specific organic copper lithium compound in the presence of an aprotic inert organic solvent, and then reacting the reaction product with an organic carboxylic acid halide or anhydride. In particular, novel 2-acyl-3-substituted cyclopentan-1-ones and 2-acyl-3-substituted cyclohexan-1-ones having important physiological activities are provided.
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- N-(acyl)-p-amino-N'-(monosubstituted)-benzamide anti-ulcer agents
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The preparation of novel N-(acyl)-p-amino-N'-(monosubstituted) benzamides by modified Schotten-Baumann reaction of the corresponding p-aminobenzamides is described. These compounds are effective anti-ulcer agents.
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