- Biobased High-Performance Aromatic-Aliphatic Polyesters with Complete Recyclability
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The development of high-performance recyclable polymers represents a circular plastics economy to address the urgent issues of plastic sustainability. Herein, we design a series of biobased seven-membered-ring esters containing aromatic and aliphatic moie
- Cai, Zhongzheng,Fan, Hua-Zhong,Gong, Fu-Long,Tu, Yi-Min,Wang, Xue-Mei,Yang, Xing,Zhu, Jian-Bo
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supporting information
p. 20591 - 20597
(2021/12/09)
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- Synthesis and biological evaluation of novel shikonin-benzo[b]furan derivatives as tubulin polymerization inhibitors targeting the colchicine binding site
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A novel series of shikonin-benzo[b]furan derivatives were designed and synthesized as tubulin polymerization inhibitors, and their biological activities were evaluated. Most compounds revealed the comparable anti-proliferation activities against the cancer cell lines to that of shikonin and simultaneously low cytotoxicity to non-cancer cells. Among them, compound 6c displayed powerful anti-cancer activity with the IC50 value of 0.18 μM against HT29 cells, which was significantly better than that of the reference drugs shikonin and CA-4. What's more, 6c could inhibit tubulin polymerization and compete with [3H] colchicine in binding to tubulin. Further biological studies depicted that 6c can induce cell apoptosis and cell mitochondria depolarize, regulate the expression of apoptosis related proteins in HT29 cells. Besides, 6c actuated the HT29 cell cycle arrest at G2/M phase, and influenced the expression of the cell-cycle related protein. Moreover, 6c displayed potent inhibition on cell migration and tube formation that contributes to the antiangiogenesis. These results prompt us to consider 6c as a potential tubulin polymerization inhibitor and is worthy for further study.
- Kong, Ling-Yi,Leng, Jia-Fu,Lian, Bao-Ping,Shao, Yu-Ying,Xia, Yuan-Zheng,Yin, Yong
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- INHIBITORS OF ALPHA-AMINO-BETA-CARBOXYMUCONIC ACID SEMIALDEHYDE DECARBOXYLASE
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The present disclosure discloses compounds capable of modulating the activity of α- amino-β-carboxymuconic acid semialdehyde decarboxylase (ACMSD), which are useful for the prevention and/or the treatment of diseases and disorders associated with defects in NAD+ biosynthesis, e.g., metabolic disorders, neurodegenerative diseases, chronic inflammatory diseases, kidney diseases, and diseases associated with ageing. The present application also discloses pharmaceutical compositions comprising said compounds and the use of such compounds as a medicament.
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Paragraph 0547; 0558
(2018/04/27)
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- Purple acid phosphatase inhibitors as leads for osteoporosis chemotherapeutics
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Purple acid phosphatases (PAPs) are metalloenzymes that catalyse the hydrolysis of phosphate esters under acidic conditions. Their active site contains a Fe(III)Fe(II) metal centre in mammals and a Fe(III)Zn(II) or Fe(III)Mn(II) metal centre in plants. In humans, elevated PAP levels in serum strongly correlate with the progression of osteoporosis and metabolic bone malignancies, which make PAP a target suitable for the development of chemotherapeutics to combat bone ailments. Due to difficulties in obtaining the human enzyme, the corresponding enzymes from red kidney bean and pig have been used previously to develop specific PAP inhibitors. Here, existing lead compounds were further elaborated to create a series of inhibitors with Ki values as low as ～30 μM. The inhibition constants of these compounds were of comparable magnitude for pig and red kidney bean PAPs, indicating that relevant binding interactions are conserved. The crystal structure of red kidney bean PAP in complex with the most potent inhibitor in this series, compound 4f, was solved to 2.40 ? resolution. This inhibitor coordinates directly to the binuclear metal centre in the active site as expected based on its competitive mode of inhibition. Docking simulations predict that this compound binds to human PAP in a similar mode. This study presents the first example of a PAP structure in complex with an inhibitor that is of relevance to the development of anti-osteoporotic chemotherapeutics.
- Hussein, Waleed M.,Feder, Daniel,Schenk, Gerhard,Guddat, Luke W.,McGeary, Ross P.
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p. 462 - 479
(2018/08/21)
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- HEMIAMINAL-TAG FOR PROTEIN LABELING AND PURIFICATION
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The invention pertains to the synthesis, isolation, and characterization of hemiaminal for selective labeling of peptides, proteins, antibodies, and organic fragments with -C(=0) CH2NH2 and derivatives with -CH2NH2 group over -C(=0) CHRNH2 group (where R≠H). The invention also pertains to the method of single-site immobilization of proteins through N-terminus Gly on solid phase. The invention includes late-stage tagging of N-terminus Gly with an affinity tag, 19F NMR probe, and a fluorophore and a method for metal-free protein purification and isolation of analytically pure proteins.
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Page/Page column 15
(2018/06/30)
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- In situ Bronsted-Lowry acid catalyzed syntheses, characterization, single crystal XRD, electronic spectral-, DPPH radical scavenging-, and DNA protection studies of aryl-3,3′-bis(indolyl)methanes
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A series of novel aryl-3,3′-bis(indolyl)methanes (BIMs) were synthesized using indole and formylphenoxyaliphatic acid(s) in water in the absence of any catalyst. The formylphenoxyaliphatic acid behaves as an in situ Bronsted-Lowry acid catalyst in water. UV-Visible and fluorescence spectra of the compounds were recorded in selected solvents. The gas phase geometry optimization of the compounds were achieved using DFT calculations at B3LYP/3-21G(*) level of theory. The electronic properties, such as HOMO-LUMO energies were calculated using the above method based on the optimized structure. Compounds have better DPPH radical scavenging activity and reduction of oxidative damage of DNA.
- Suresh Kumar,Antony Muthu Prabhu,Seethalaksmi,Bhuvanesh,Kumaresan
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supporting information
p. 249 - 256
(2014/01/23)
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- Biotransformation of new racemic (R,S)-5-benzylhydantoin derivatives by D-hydantoinases from adzuki bean
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In the present work the scope of D-hydantoinase enzyme application was increased towards new racemic (R,S)-5-benzylhydantoin derivatives. Five new substrates for the D-hydantoinase (R,S)-5-(3′-carboxybenzyl)hydantoin, (R,S)-5-(4′-carboxybenzyl)hydantoin, (R,S)-5-(2′-carbomethoxybenzyl) hydantoin, (R,S)-5-(3′-carbomethoxybenzyl)hydantoin and (R,S)-5-(4′(4-ethoxycarboxy)propoxybenzyl)hydantoin were synthesised and converted using a two-step hydantoinase process into their corresponding D-phenylalanine derivatives. In this study two D-hydantoinases from Vigna angularis (adzuki bean) obtained from commercial sources were used: pure, isolated directly from Vigna angularis (V.a.D-HYD) 494 U/g and immobilised, recombinant, cloned and expressed in Escherichia coli (rD-HYD) 53.1 U/g. The results obtained showed that the examined enzymes catalysed hydrolysis of all new substrates into their corresponding N-carbamoyl-D-phenylalanine derivatives. High enantiomeric purities of the resulting D-phenylalanine derivatives were also determined. However, very low conversion yields of (R,S)-5-(3′- carboxybenzyl)hydantoin and (R,S)-5-(2′-carbomethoxybenzyl)hydantoin to corresponding N-carbamoyl-D amino acid were observed. Three D-phenylalanine derivatives: 4-carboxy-D-phenylalanine, 3-carbomethoxy-D-phenylalanine and 4-carbopropoxy-D-phenylalanine were obtained and isolated from the reaction mixtures using ion-exchange chromatography.
- Latacz, Gniewomir,Kie?-Kononowicz, Katarzyna
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p. 117 - 124
(2014/04/17)
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- Small molecule mimetics of an interferon-α receptor interacting domain
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Small molecules that mimic IFN-α epitopes that interact with the cell surface receptor, IFNAR, would be useful therapeutics One such 8-amino acid region in IFN-α2, designated IRRP-1, was used to derive 11 chemical compounds that belong to 5 distinct chemotypes, containing the molecular features represented by the key residues Leu30, Arg33, and Asp35 in IRRP-1 Three of these compounds exhibited potential mimicry to IRRP-1 and, in cell based assays, as predicted, effectively inhibited IFNAR activation by IFN-α Of these, compound 3 did not display cell toxicity and reduced IFN-α- inducible STAT1 phosphorylation and STAT-DNA binding Based on physicochemical properties' analyses, our data suggest that moieties with acidic pKa on the small molecule may be a necessary element for mimicking the carboxyl group of Asp35 in IRRP-1 Our data confirm the relevance of this strategy of molecular mimicry of ligand-receptor interaction domains of protein partners for small molecule drug discovery
- Bello, Angelica M.,Wei, Lianhu,Majchrzak-Kita, Beata,Salum, Noruê,Purohit, Meena K.,Fish, Eleanor N.,Kotra, Lakshmi P.
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p. 978 - 985
(2014/02/14)
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- An efficient one pot syntheses of aryl-3,3′-bis(indolyl)methanes and studies on their spectral characteristics, DPPH radical scavenging-, antimicrobial-, cytotoxicity-, and antituberculosis activity
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An efficient one-pot syntheses of aryl-3,3′-bis(indolyl)methanes (BIMs) from indole/2-methylindole and formylphenoxyaliphatic acid(s) is described. Esterification of carboxylic acid and aromatic electrophilic substitution reactions are achieved simultaneous in the presence of potash alum as a catalyst. This catalyst could be recovered and reused without substantial loss in its catalytic activity and the methodology could be applied on a range of closely related substrates. The solvation characteristics in ground and excited states of the compounds by monitoring the absorbance and fluorescence band maxima have been studied. The fluorescence studies in protic and aprotic solvents were rationalized on the basis of solute-solvent interaction and substituents effect on these photophysical processes analyzed. The compounds prepared showed efficient antimicrobial effect against human pathogens, cytotoxicity against A431 cell line, and DPPH radical scavenging effect. Single crystal XRD studies have been carried out for a few compounds synthesized in this work.
- Suresh Kumar,Kumaresan,Antony Muthu Prabhu,Bhuvanesh,Seethalakshmi
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p. 254 - 263
(2013/02/23)
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- Potash alum [KAL(SO4)2.12H2O] catalysed esterification of formylphenoxyaliphatic acids
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A convenient and clean procedure for esterification is reported. Direct condensation of formylphenoxyaliphatic acids with low to high boiling alcohols catalysed by potash alum gave moderate to good yields. This catalyst could be recovered and reused without substantial loss in its catalytic activity and the methodology could be used for a range of closely related substrates.
- Shunmugadhas, Ganesan,Kumar, Suresh,Kumaresan, Sudalaiandi
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p. 857 - 863,7
(2020/09/09)
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- Synthesis and metal ion complexation of acyclic Schiff base podands with lipophilic amide and ester end groups
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A series of acyclic Schiff base podands 14-19 with lipophilic amide and ester end groups were synthesized in good yield and in a simple way. Their transition metal ions complexation was studied using conductometric method in acetonitrile (AN) at 25 °C. Schiff base podands 14-16 showed a continuous decrease in the molar conductances in their complexation with Hg2+, Pb2+, Cu2+, Zn2+ and Cd2+ which begins to level off at a mole ratio of 1:1 crown-to-metal indicating the formation of a stable 1:1 complexes. The order of the stability constants of the metal ions studied with the Schiff base podands 14, 15 and 16 is: Hg 2+ > Pb2+ > Cu2+ > Zn2+ > Cd2+ > Ag+. Metal ion complexation by acyclic diamide or diester podands involves presumably the oxygen atoms of the carbonyl groups in addition to the nitrogen atoms of the imino groups.
- Mizyed, Shehadeh,Ashram, Muhammad
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scheme or table
p. 135 - 142
(2012/03/27)
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- SUBSTITUTED TRICYCLIC PYRIDINE OR PYRIMIDINE VANILLOID RECEPTOR LIGANDS
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The present invention relates to substituted tricyclic compounds, which can be used as vanilloid receptor ligands. In particular, compounds described herein are useful for treating or preventing diseases, conditions and/or disorders modulated by vanilloid receptor-1 (VRl). Also provided herein are pharmaceutical compositions and methods for treating or preventing diseases, conditions and/or disorders modulated by VRl.
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Page/Page column 27
(2009/07/25)
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- Microwave induced thermal gradients in solventless reaction systems
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Development of thermal heterogeneity under microwave irradiation for solventless solid-liquid phase-transfer catalytic (PTC) reactions has been studied by means of a thermovision camera and fiber-optics thermometer.
- Bogdal, Dariusz,Bednarz, Szczepan,Lukasiewicz, Marcin
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p. 9440 - 9445
(2007/10/03)
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- TARGET-ORIENTED CHEMOTHERAPY FOR TREATING TUMORS OF THE SEXUAL ORGANS
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The invention relates to dialkyltriazene-supporting estrogens and antiestrogens that are suited for use as chemotherapeutic drugs for treating carcinomas of the sexual organs of humans and animals.
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Page/Page column 29
(2010/02/09)
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- Synthesis of calix[4]crowns containing soft donor atoms and a study of their metal-cation binding properties: Highly selective receptors for Cu2+
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Two new calix[4]arenethiacrown derivatives 1 and 2 in the cone conformation were synthesized by two different pathways in good yield. Their complexation properties toward alkali, alkaline earth and transition metal cations were studied in acetonitrile at 298.15 K using a conductometric titration technique. The selectivity for Cu2+ over other cations with these novel ligands was excellent.
- Ashram, Muhammad
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p. 1662 - 1668
(2007/10/03)
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- P(MeNCH2CH2)3N: An efficient catalyst for the synthesis of substituted ethyl benzofuran-2-carboxylates
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A superior method for the synthesis of substituted ethyl benzofuran-2-carboxylates in 80-99% yields from substituted 2-formylphenoxy ethylcarboxylates using 0.4 equiv of commercially available P(MeNCH2CH2)3N at 70 °C for 3 hours is described.
- D'Sa, Bosco A.,Kisanga, Philip,Verkade, John G.
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p. 670 - 672
(2007/10/03)
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- Synthesis and properties of new 2-alkyl-1,4-benzoxazepine derivatives. Part III. Synthesis and cyclization of 2-(2-carboxyphenoxy)alkanamides
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A series of novel 2-(2-carboxyphenoxy)aIkanamides 4a-f have been obtained as result of condensation of salicylaldehydes with 2-halo esters, amination of prepared esters 1a-f with methylamine followed by oxidation of amides 3a-f with sodium chlorite. The intramolecular cyclization of amides 4a-f to 1,4-benzoxazepin-3,5-dione system has been investigated.
- Kwiecien
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p. 2254 - 2260
(2007/10/03)
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- 6-aryl pyrazolo?3,4-D! pyrimidin-4-ones and compositions and method of use thereof
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6-Aryl pyrazolo?3,4-d!pyrimidin-4-one derivatives, pharmaceutical compositions containing them and methods for effecting c-GMP-phosphodiesterase inhibition and for treating heart failure and/or hypertension.
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- Synthesis and biochemical evaluation of (carbamoylalkenyl)phenyloxy carboxylic acid derivatives as non-steroidal 5α-reductase inhibitors
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Several (carbamoylalkenyl)- and (carbamoylalkenyl)phenyloxy carboxylic acids and some of their ethyl esters were synthesized and evaluated in vitro as inhibitors of steroid 5α-reductase. Inhibitors of this enzyme may be useful in treating dihydrotestosterone-related diseases such as prostate cancer and benign prostatic hyperplasia. Using an enzyme preparation obtained from human prostate carcinoma tissue, the inhibition values ranged from 0 to 57% at the given dose of 100 μM. In the series of free acids, surprisingly, the compounds showed only modest inhibitory potency (0-26%). By contrast, the ethyl esters displayed inhibition values up to 57%. Sttructure-activity relationships are discussed.
- Kattner,Gohring,Hartmann
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p. 239 - 245
(2007/10/02)
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- A Membrane Protein Model: Polypeptides with Four α-Helix Bundle Structure on 5,10,15,20-Tetrakisporphyrin
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A novel template for the polypeptide-porphyrin hybrid, 5,10,15,20-tetrakisporphyrin (2) was synthesized in 17percent yield.Four protected carboxyl groups are installed in 2 at the ortho-phenyl groups as the anchoring points, to which the N-termini of the polypeptides can be linked after the hydrolysis.Thus, 2 is a new analog of the porphyrin template tetrakisporphyrin.The atropisomerization of 2 was much more rapid than that of tetrakisporphyrin: At 353 K, 2 reached their equilibrium within 15 min.Such atropisomeric flexibility of 2 allows the self-organization of the α-helical peptide segments which are connected to 2.After the hydrolyses of the ethyl ester groups of 2, four α-helical 21-peptides, H-(-Gln-Leu-Leu-Gln-Ala-Leu-Ala-)3-NHCH2CH2OH were combined through the amide bonds to yield a new polypeptide-porphyrin hybrid (12).The polypeptide moieties of 12 showed typical α-helix profiles on circular dichroism measurements in methanol-water (3/1, v/v) and in Tris*HCl buffer solution.Thus, the four α-helix polypeptides are considered to fold into a bundle structure on the porphyrin template through the hydrophobic interaction.The circular dichroism spectrum of 12 in methanol showed an induced Cotton effect at the porphyrin region, and the CD band was symmetrically split.The hybrid (12) was also successfully incorporated into the egg yolk lecithin membrane almost quantitatively.When the molar ratio of egg yolk lecithin/12 was 500/1, the α-helix structure of the peptide segments in 12 was completely retained in the vesicles.
- Arai, Toru,Kobata, Keisuke,Mihara, Hisakazu,Fujimoto, Tsutomu,Nishino, Norikazu
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p. 1989 - 1998
(2007/10/02)
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- Photocyclization Reactions. Part 2. Synthesis of Dihydrobenzofuranols Using Photocyclization of Ethyl 2-Formylphenoxyacetates and Ethyl 2-Acetylphenoxyacetates
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Photocyclization reactions were carried out on ethyl 2-formylphenoxyacetates 1a-e and ethyl 2-acetylphenoxyacetates 2a-e in acetonitrile.Irradiation of 1a-e gave dihydrobenzofuranols 3 in 20-46percent yields.Similarly, irradiation of 2a-e afforded dihydrobenzofuranols 6 and their derivatives 7, 8 in 40-86percent yields.Substitution effects on photocyclization and reaction pathways are discussed.
- Horaguchi, Takaaki,Tsukada, Chikara,Hasegawa, Eietsu,Shimizu, Takahachi,Suzuki, Tsuneo,Tanemura, Kiyoshi
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p. 1273 - 1280
(2007/10/02)
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- SYNTHESIS OF TETRAPHENYLPORPHINES WITH ACTIVE GROUPS IN THE PHENYL RINGS. 5. TETRA(CARBOXYMETHYLENOXYPHENYL)PORPHINES AND THEIR ETHYL ESTERS.
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Tetra(carboxymethylenoxyphenyl)porphines which are soluble in bases are prepared by hydrolysis of the ethyl esters of tetra(carboxymethylenoxyphenyl)porphines.The starting ethyl esters of the tetra(carboxymethylenoxyphenyl)porphines were synthesized by alkylation of tetra(oxyphenyl)porphines with ethylchloroacetate, as well as by condensation of pyrrole with ethyl esters of formylphenoxyacetic acids.
- Syrbu, S. A.,Semeikin, A. S.,Berezin, B. D.,Koifman, O. I.
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p. 1149 - 1153
(2007/10/02)
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- Use of Phosphorus Pentoxide. Preparation of Half-esters through Selective Esterification
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Methyl 2-,3-,4-carboxyphenylacetate and methyl 2-,3-,4-carboxyphenoxyacetate have been prepared through selective esterification of the aliphatic carboxylic acid function of the corresponding dicarboxylic acids using a mixture of phosphorus pentoxide (1 part), anhydrous copper sulphate (5 parts) and anhydrous sodium sulphate (5 parts).All the isomeric half-esters have been prepared through partial hydrolysis of the corresponding dimethylesters.
- Banerjee, Amalendu,Adak, Mohini Mohan,Das, Sankar,Banerjee, Santa,Sengupta, Saumitra
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- Aromatic Carbonyl Compounds from 2-Aryloxycarboxylic Acid Esters
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Reactions of 2-(4-methoxyphenoxy)propanoic acid methylester, aryloxyacetic acids and their derivatives with di-tert-butylperoxide at 150 deg C result in the formation of 4-methoxyacetophenone and benzaldehydes.This transformation is explained by a 1,2 O->C aryl-migration, induced by a capto-dativ substituted radical and followed by a β-fragmentation of an alkoxyradical.The success of this radical rearrangement depends heavily on the nature of the capto-substituent and on the reaction temperature.Both parameters are subjects of this investigation. - Keywords: Capto- dativ substituted radical; 1,2 O->C Arylmigration; Neophyllike radical rearrangement; SH2-Reaction
- Woergoetter, Erich,Hohenlohe-Oehringen, Kraft
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p. 995 - 1004
(2007/10/02)
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