- Bioreductively-activated prodrugs for targeting hypoxic tissue: Elimination of aspirin from 2-nitroimidazole derivatives
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2-Nitroimidazoles were synthesised substituted with aspirin or salicylic acid, as leaving groups linked through the (imidazole-5-yl)methyl position. Activation of aqueous solutions by CO2- (a model one-electron reductant) resulted in release of aspirin or salicylate, probably via the 2- hydroxyaminoimidazole. The analogous 2-nitroimidazole with bromide as leaving group eliminated bromide in 1 ms via radical-anion.
- Everett,Naylor,Patel,Stratford,Wardman
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Read Online
- Two Keggin polyoxometalate-based hybrid compounds with different helix: Syntheses, structure and catalytic activities
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By adjusting pH value, two new Keggin polyoxometalate-based hybrid compounds with different helical structure, [Ag6(btp)(pyttz)6·(HSiMo12O40)2]·4H2O (1) and [Ag2(pyttz)4·(H2SiMo12O40)2]·(TMA)2·4H2O (2), (pyttz?=?3-(pyrid-4-yl)-5-(1?H-1,2,4–3-yl)-1,2,4-triazolyl, btp?=?5,5′-di(pyridin-4-yl)-1?H,1′H-3,3′-bi(1,2,4-triazole), TMA?=?tetramethylammonium), were successfully isolated by hydrothermal reaction and structurally characterized. Structural analysis shows the nature of the inorganic meso-helical channel in compound 1 and 2D homological helical layer in compound 2. It is also interesting that a new organic ligand btp is formed in situ by the coupling of N-Heterocycle in 1. In addition, the catalytic activities of 1 and 2 as solid-acid catalyst are explored, and the results indicate that 1 and 2 are a kind of highly-efficient and promising solid catalysts. Additionally, the proposed generation mechanism of btp in situ is also discussed.
- Zhu, Peipei,Sheng, Ning,Liu, Guodong,Sha, Jingquan,Yang, Xiya
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- Catalytic method for synthesis of aspirin by a green, efficient and recyclable solid acid catalyst (Preyssler's anion) at room temperature
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Synthesis of aspirin at room temperature via O-acetylation of salicylic acid in the presence of Preyssler type heteropolyacids has been investigated in order to contribute toward clean technology, which is the most important need of the society. All of the catalysts are recyclable and reusable.
- Bamoharram, Fatemeh F.,Heravi, Majid M.,Roshani, Mina,Gharib, Ali,Jahangir, Manouchehr
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- Raman spectrum online monitoring in aspirin synthesis process
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In this work, the Raman spectra were obtained directly in the synthesis process of aspirin as prediction set. The concentration sample according to the amount of material changes before and after reaction and it's extracted Raman information made up training set and a quantitative analysis model of the salicylic acid-acetic anhydride-aspirin mixed system was established by applying partial least squares (PLS). The values of correlation coefficient squared between measured and regression (R2), root mean square error of prediction set (RMSEP), mean deviation (MD) indicate that the influence of the prediction precision by the baseline drift can be effectively reduced in the method of spectrum pretreatment via mormalize + savitzky-go1ay smoothing first derivative. After the prediction set was used in this analysis mode, the mass per cent between salicylic acid and aspirin of online monitoring was 4.59 %, while the off-line Raman analysis and high performance liquid chromatography analysis results were 5.66 and 2.75 %. The relative deviations were -1.07 and 1.84 %. This method provides effective data support for synthesis of aspirin Raman spectroscopy online monitoring.
- Su, Hui,Sun, Kuo,Yao, Zhixiang,Huang, Peixian,Liu, Liu
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- Solvent free synthesis of acetyl salicylic acid over nano-crystalline sulfated zirconia solid acid catalyst
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Acetyl salicylic acid, commonly known as Aspirin or Ecotrin, has been synthesized by an eco-friendly route using solid acid catalysts namely nano-crystalline sulfated zirconia, sulfated titania, zeolite H-beta, H-Y, H-ZSM-5 and acid treated K-10 clay. Among all the solid acid catalysts studied, nano-crystalline sulfated zirconia showed highest catalytic activity and was found to be efficient in minimal amount to obtain excellent yield (95 wt%) of acetyl salicylic acid crystals. Thermally regenerated catalyst showed similar yield as obtained with the fresh catalyst.
- Tyagi, Beena,Mishra, Manish Kumar,Jasra, Raksh Vir
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- Evaluation and establishment of a cleaning protocol for the production of vanisal sodium and aspirin using a continuous oscillatory baffled reactor
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The robustness and adaptability of a continuous oscillatory baffled reactor (COBR) in organic syntheses of vanisal sodium and aspirin were tested whilst meeting the stringent regulatory standards. In one week-long continuous operation, vanisal sodium was produced to a purity level of 99.94%, aspirin to a level of 99.57%. The loss of product during the cleaning process amounted to 0.001% and 0.005% for vanisal sodium and aspirin, respectively. The data of the continuous syntheses show that the operation of the COBR is robust and consistent throughout the week-long period. The cleaning stage that was used after each production campaign exhibited a first-order kinetics and was effective and efficient.
- Ricardo, Caldeira,Xiongwei, Ni
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- Construction and catalytic activities of polyoxometalate-based compound containing helical chains
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A polyoxometalate-based, inorganic–organic hybrid compound containing a helical structure along the a axis, [Ag(pyttz)2][H2PW12O40]·2H2O (p-pyttz?=?3-(pyrid-4-yl)-5-(1H-1,2,4-triazol-3-yl)-1,2,4-triazolyl), has been isolated and structurally characterized. Single-crystal X-ray diffraction analysis reveals that the new compound possesses two helical channels constructed by the left- and right-handed helical chains, respectively, which are fused together through sharing POMs dimer fabricating a 3-D framework with {44·53·63} {44·53·63} topolopy. The new compound displays good acid-catalytic activity toward the synthesis of Aspirin and good oxidation-catalytic activity to the decomposition of Rhodamine B dye; the catalytic reaction kinetics are discussed.
- Sha, Jing-Quan,Yang, Xi-Ya,Sun, Long-Jiang,Li, Shu-Xian,Sheng, Ning,Li, Ji-Shen
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- On the polymorphism of aspirin: Crystalline aspirin as intergrowths of two "polymorphic" domains
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Aspirin: No end to the headaches? The two known crystalline arrangements of aspirin are so closely related that aspirin crystals form intergrowth structures containing domains of form I and domains of form II. The ratio and distribution of the domains is variable among aspirin samples, raising questions for the definition of the term polymorph in this case. (Figure Presented).
- Bond, Andrew D.,Boese, Roland,Desiraju, Gautam R.
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- Synthesis and antioxidant activities of berberine 9-: O -benzoic acid derivatives
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Although berberine (BBR) shows antioxidant activity, its activity is limited. We synthesized 9-O-benzoic acid berberine derivatives, and their antioxidant activities were screened via ABTS, DPPH, HOSC and FRAP assays. The para-position was modified with halogen elements on the benzoic acid ring, which led to an enhanced antioxidant activity and the substituent on the ortho-position was found to be better than the meta-position. Compounds 8p, 8c, 8d, 8i, 8j, 8l, and especially 8p showed significantly higher antioxidant activities, which could be attributed to the electronic donating groups. All the berberine derivatives possessed proper lipophilicities. In conclusion, compound 8p is a promising antioxidant candidate with remarkable elevated antioxidant activity and moderate lipophilicity.
- Liu, Yanfei,Long, Shuo,Zhang, Shanshan,Tan, Yifu,Wang, Ting,Wu, Yuwei,Jiang, Ting,Liu, Xiaoqin,Peng, Dongming,Liu, Zhenbao
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p. 17611 - 17621
(2021/05/29)
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- BiCl3-Facilitated removal of methoxymethyl-ether/ester derivatives and DFT study of -O-C-O- bond cleavage
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A simple method for the cleavage of methoxymethyl (MOM)-ether and ester derivatives using bismuth trichloride (BiCl3) is described. The alkyl, alkenyl, alkynyl, benzyl and anthracene MOM ether derivatives, as well as MOM esters of both aliphatic and aromatic carboxylic acids, were deprotected in good yields. To better understand the molecular roles of BiCl3and water for MOM cleavage, two possible binding pathways were investigated using the density functional theory (DFT) method. The theoretical results indicate the differential initial binding site preferences of phenolic and alcoholic MOM substrates to the Bi atom and suggest that water plays a key role in facilitating the cleavage of the MOM group.
- Pacherille, Angela,Tuga, Beza,Hallooman, Dhanashree,Dos Reis, Isaac,Vermette, Mélodie,Issack, Bilkiss B.,Rhyman, Lydia,Ramasami, Ponnadurai,Sunasee, Rajesh
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supporting information
p. 7109 - 7116
(2021/05/03)
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- Identification of Novel Resorcinol Amide Derivatives as Potent and Specific Pyruvate Dehydrogenase Kinase (PDHK) Inhibitors
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Pyruvate dehydrogenase kinases (PDHKs) promote abnormal respiration in cancer cells. Studies with novel resorcinol amide derivatives based on VER-246608 (6) led to the identification of 19n and 19t containing five-membered heteroaromatic rings as unique structural features. These substances possess single-digit nanomolar activities against PDHKs. 19t exhibits higher potencies against PDHK1/2/4 than does 6 and inhibits only PDHKs among 366 kinases. Moreover, 19g, 19l, and 19s were found to be isotype-selective PDHK inhibitors. Molecular dynamics simulations provide a better understanding of how the heteroaromatic rings affect the activities of 19n and 19t on PDHK1/2/3/4. Moreover, 19n possesses a much higher antiproliferative activity against cancer cells than does 6. We demonstrated that the results of PDH assays better correlate with cellular activities than do those of PDHK kinase assays. Furthermore, 19n induces apoptosis of cancer cells via mitochondrial dysfunction, suppresses tumorigenesis, and displays a synergistic effect on satraplatin suppression of cancer cell proliferation.
- Cho, Hanna,Cho, Kyungseon,Kim, Mi-Jin,Kim, Nam Doo,Lee, In-Kyu,Park, Sungmi,Shin, Injae,Sim, Taebo,Yoo, Eun Kyung,Yoon, Hojong
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- Synthesizing method of acetylsalicylic acid
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The invention relates to a synthesizing method of acetylsalicylic acid. The synthesizing method comprises the following steps: a rare-earth modified solid superacid catalyst is provided, the solid superacid catalyst comprises a composite carrier, sulfate radicals bonded to the composite carrier, and rare earth ions doped with the composite carrier, wherein the composite carrier is formed by silicon dioxide and aluminum oxide which are composited; and salicylic acid and acetic anhydride react under the effect of the rare-earth modified solid superacid catalyst, and then the acetylsalicylic acidis obtained. According to the synthesizing method of the acetylsalicylic acid, rare-earth modified solid superacid serves as the catalyst, the salicylic acid and the acetic anhydride serve as the rawmaterials of an acetylation reaction to prepare the acetylsalicylic acid, in the process of the acetylation reaction, the product yield is high, corrosion of the catalyst to equipment is small, pollution to the environment is small, the recyclable rate of the catalyst is high, the product aftertreatment process is simplified, and energy consumption is low.
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Paragraph 0059; 0064; 0065
(2019/03/08)
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- Preparation method of acetylsalicylic acid
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The invention discloses a preparation method of acetylsalicylic acid. The preparation method comprises the following steps: mixing salicylic acid, acetic anhydride and SO4/ZrO2@GO, carrying out areaction at 60-70 DEG C for 4-10 hours, then sending the product into a rectifying tower to rectify and recover unreacted acetic anhydride, then adding water for crystallization, and recrystallizing an acetylsalicylic acid crude product with a mixed solvent of ethanol and water to obtain acetylsalicylic acid. The method provided by the invention is simple, low in cost, small in equipment damage and free of environmental pollution; by optimizing the conditions such as catalyst, reaction temperature, and reaction time, the amount of catalyst used is small, and the yield of the product can be greatly improved.
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Paragraph 0027; 0028; 0029; 0030
(2018/09/13)
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- Werner transition-metal complex (WTMC)-mediated mild and efficient chemo-selective acylation of phenols and anilines under solvent-free condition
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Werner-type transition-metal complexes (WTMC) such as [Co(NH3)5Cl]Cl2, Cu[(NH3)4]SO4, Mn(acac)3, Ni[(NH3)6]Cl2, Ni[(en)3]S2O3, and Hg[Co(SCN)4] efficiently promote the chemoselective acetylation of phenols and anilines under solvent-free condition. The results of this study clearly shows that the optimal condition for the acetylation of anilines/phenols (1 mmol) (2a–r) with acetic anhydride (1.2 mmol) in the presence of WTMC (1 mmol) and two drops of H3PO4 on heating for 10 min under solvent-free condition gives the corresponding acetanilides/phenyl acetate (3a–r) in good to excellent yield. Furthermore, the method is simple, efficient, chemoselective, and eco-friendly under solvent-free condition for the acetylation of anilines and phenols promoted by WTMC by using acetic anhydrate as the acetylating agent. The simple preparation of the catalyst, easy procedure of the acetylation reaction, and simple work-up indicate the importance of WTMC for such reactions.
- Sarief, Abdulla,Haque, SK Manirul,Feroze, Syed Mudabbir,Arifuddin, Mohammed
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p. 1104 - 1109
(2018/09/27)
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- Novel method for preparing acetylsalicylic acid
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The invention discloses a novel method for preparing acetylsalicylic acid. The method comprises the following steps: adding reaction materials into a continuous flow tubular reactor for reaction, discharging a product, and carrying out cooling, extraction, concentration and purification. The temperature of a reaction part of the reactor is set at 150-250 DEG C, the residence time is 3-20min, the temperature of a cooling part is set at 0-80 DEG C, the residence time is 3-20min, the pressure of a feed pump is set to be 1.5-2.5MPa, and the feed speed is 20-200ml/min. The continuous flow reactor is adopted by the method provided by the invention, so that the method is more efficient and safe, can effectively strengthen the reaction process, shorten the reaction time and improve the reaction efficiency.
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Paragraph 0033; 0034; 0035; 0037; 0039
(2018/07/06)
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- Amide type phytoalexin compound and preparation method thereof and whitening cosmetic composition containing it
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The present invention relates to a phytoalexin compound having an amide structure represented by chemical formula 1, a production method thereof, and a whitening cosmetic composition containing the same. In the chemical formula 1, R_1 and R_2 are hydrogen, R_1 is hydroxy, and R_2 is hydrogen, or R_1 and R_2 are hydroxy.COPYRIGHT KIPO 2019
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Paragraph 0076-0079
(2019/02/16)
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- New method of catalyzed synthesis of aspirin
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The invention discloses a new method of catalyzed synthesis of aspirin and belongs to the technical field of organic synthetic chemistry. By taking tyrosine as a catalyst , the new method of catalyzedsynthesis of the aspirin synthesizes aspirin under ultrasonic condition through an esterification reaction of acetic anhydride and salicylic acid. Experimental results show that the yield of productproduced from reaction is 93.43% under the condition that the ultrasonic power is 500 W, mole ratio of acetic anhydride to salicylic acid is 2:1, time of ultrasonic reaction is 20 min, temperature ofreaction is 60 DEG C, and the catalyst accounts for 8% of the mass of salicylic acid, indicating that the product has high purity, the invention avoids defects that a conventional preparation method is easy to produce side reactions, and the product is poor in color and is not conducive to purification, stronger corrosion of concentrated sulfuric acid as the catalyst on the equipment, and seriousenvironmental pollution caused by a mass of produced waste acid and has a pretty good practical value.
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Paragraph 0031-0097
(2018/11/22)
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- Synthesis and molecular docking based exploration of salicylic acid derivatives
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In present study, four salicylic acid derivatives viz., 2-acetoxybenzoic acid (2a), 2-(1H-indol-2-yl)benzoic acid (3a), 5-chloro-2-acetoxybenzoic acid (2b) and 5-chloro-2-(1H-indol-2-yl)benzoic acid (3b) were synthesized and studied for molecular docking on 3JUS and 3UPI protein selected from pdb. The studies show that all of the four synthesized compounds were found to be docked. Compound 3a and 3b showed the best ligand pose energy -10.8163 kcal/mol and -11.1354 kcal/mol with docking run: elapsed time 9 s and 12 s, respectively in respect of 3JUS Further, compounds 3a and 3b showed the best ligand pose energy -9.17851 and -9.54722 kcal/mol with docking run: elapsed time 10 and 14 s, respectively in case of 3UPI. Hence, studies showed that 5-chloro-2-(1H-indol-2-yl)benzoic acid (3b) emerged as potent compound which might show diverse nature of biological and therapeutic activity.
- Singh, Navneet,Garg, Geetika
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p. 2377 - 2382
(2018/10/05)
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- Acetylsalicylic acid synthesis method
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The invention discloses an acetylsalicylic acid synthesis method. The acetylsalicylic acid synthesis method comprises following steps: after salicylic acid, acetic acid, concentrated sulfuric acid andSO4/TiO2@GO are mixed, a mixture is subjected to a reaction for 4-10 h at 60-70 DEG C and then is sent into a distillation tower for distillation recovery of unreacted acetic acid, water is addedfor crystallization, a crude acetylsalicylic acid product is recrystallized by an ethanol and water mixed solvent, and acetylsalicylic acid is obtained. The method is simple and low in cost, the esterification reaction of salicylic acid and acetic acid can be catalyzed with lower catalyst dosage by optimizing a catalyst, reaction temperature, reaction time and other conditions, and product yieldcan be greatly increased.
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Paragraph 0027; 0028; 0029; 0030
(2018/09/13)
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- Preparation of acetylsalicylic acid
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A preparing process of acetylsalicylic acid comprises: placing 6-8 parts of dry salicylic acid and 10-12ml of acetyl anhydride in a 100ml conical flask, and after full shaking, dropwise adding 10 drops of concentrated sulfuric acid; conducting heating on a water bath, and immediately dissolving the salicylic acid; if the salicylic acid is not fully dissolved, needing to replenish the concentrated sulfuric acid and the acetyl anhydride; keeping a temperature in the conical flask at 70-75DEG C and carrying out reaction for 20 minutes; after slight cooling, pouring the solution into 100ml of cold water while continuously stirring the solution; cooling and separating out crystals; carrying out suction filtration so as to obtain a crude product, and carrying out washing twice so as to wash off acetic acid produced by reaction and the sulfuric acid in the reaction, wherein 10ml of water is used for each washing; and carrying out re-crystallization, to be specific, using about 15ml of 95% ethanol and water (7ml: 8ml), additionally arranging a condensing pipe, carrying out heating and reflowing for 1-2 hours, filtering while the solution is hot, cooling, carrying out suction filtration, drying and weighing.
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Paragraph 0008; 0009; 0010
(2017/05/19)
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- Diphenylurea derivatives for combating methicillin- and vancomycin-resistant Staphylococcus aureus
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A new class of diphenylurea was identified as a novel antibacterial scaffold with an antibacterial spectrum that includes highly resistant staphylococcal isolates, namely methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA & VRSA). Starting with a lead compound 3 that carries an aminoguanidine functionality from one side and a n-butyl moiety on the other ring, several analogues were prepared. Considering the pharmacokinetic parameters as a key factor in structural optimization, the structure-activity-relationships (SARs) at the lipophilic side chain were rigorously examined leading to the discovery of the cycloheptyloxyl analogue 21n as a potential drug-candidate. This compound has several notable advantages over vancomycin and linezolid including rapid killing kinetics against MRSA and the ability to target and reduce the burden of MRSA harboring inside immune cells (macrophages). Furthermore, the potent anti-MRSA activity of 21n was confirmed in?vivo using a Caenorhabditis elegans animal model. The present study provides a foundation for further development of diphenylurea compounds as potential therapeutic agents to address the burgeoning challenge of bacterial resistance to antibiotics.
- Eissa, Ibrahim H.,Mohammad, Haroon,Qassem, Omar A.,Younis, Waleed,Abdelghany, Tamer M.,Elshafeey, Ahmed,Abd Rabo Moustafa, Mahmoud M.,Seleem, Mohamed N.,Mayhoub, Abdelrahman S.
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supporting information
p. 73 - 85
(2017/03/02)
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- Tunable microwave-assisted method for the solvent-free and catalyst-free peracetylation of natural products
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Background: The peracetylation is a simple chemical modification that can be used to enhance the bioavailability of hydrophilic products and to obtain safe and stable pro-drugs. Results: A totally green, solvent-free and catalyst-free microwave (MW)-assisted method for peracetylation of natural products such as oleuropein, alpha-hederin, quercetin and rutin is presented. By simply tuning the MW heating program, polyols with chemical diverse -OH groups or thermolabile functionalities can be peracetylated to improve the biological activity without degradation of the natural starting molecules. An evaluation of the process greenness was performed. Conclusion: The method is potentially universally applicable for green acetylation of hydrophilic biological molecules, potentially easily scalable for industrial applications, including pharmaceutical, cosmetic and food industry.
- Oliverio, Manuela,Costanzo, Paola,Nardi, Monica,Calandruccio, Carla,Salerno, Raffaele,Procopio, Antonio
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supporting information
p. 2222 - 2233
(2016/11/17)
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- Highly efficient and recyclable acetylation of phenols and alcohols by nickel zirconium phosphate under solvent-free conditions
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Nickel zirconium phosphate nanoparticles have been used as an efficient catalyst for the acetylation of a wide range of alcohols and phenols with acetic anhydride in good to excellent yields under solvent-free conditions. The steric and electronic properties of the different substrates had a significant influence on the reaction conditions required to achieve the acetylation. The catalyst used in the current study was characterized by inductively coupled plasma optical emission spectroscopy, X-ray diffraction, N2 adsorption-desorption, scanning electron microscopy, and transmission electron microscopy. This nanocatalyst could also be recovered and reused at least six times without any discernible decrease in its catalytic activity.
- Hajipour, Abdol Reza,Karimi, Hirbod,Kohi, Afshin
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- Synthesis and evaluation of the 2-aminothiazoles as anti-tubercular agents
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The 2-aminothiazole series has anti-bacterial activity against the important global pathogen Mycobacterium tuberculosis. We explored the nature of the activity by designing and synthesizing a large number of analogs and testing these for activity against M. tuberculosis, as well as eukaryotic cells. We determined that the C-2 position of the thiazole can accommodate a range of lipophilic substitutions, while both the C-4 position and the thiazole core are sensitive to change. The series has good activity against M. tuberculosis growth with sub-micromolar minimum inhibitory concentrations being achieved. A representative analog was selective for mycobacterial species over other bacteria and was rapidly bactericidal against replicating M. tuberculosis. The mode of action does not appear to involve iron chelation. We conclude that this series has potential for further development as novel antitubercular agents.
- Kesicki, Edward A.,Bailey, Mai A.,Ovechkina, Yulia,Early, Julie V.,Alling, Torey,Bowman, Julie,Zuniga, Edison S.,Dalai, Suryakanta,Kumar, Naresh,Masquelin, Thierry,Hipskind, Philip A.,Odingo, Joshua O.,Parish, Tanya
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- METHOD TO PREPARE PHENOLICS FROM BIOMASS
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The present invention is directed to a method for preparing a final phenolic product from biomass comprising the steps of providing a furanic compound obtainable from biomass; reacting the furanic compound with a dienophile to obtain a phenolic compound; reacting the phenolic compound further to obtain the final phenolic product.
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Page/Page column 43
(2016/08/10)
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- A rigid organic ligand-induced POMCP with a helical self-penetrating structure as a redox and acid catalyst
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By the utilization of rigid organic ligands, a new POMCP with inorganic helical configuration features was isolated and structurally characterized, in which inorganic double chains are constructed from POMs and single Ag ions, and the contribution of the rigid ligand to the helical structure of POMCPs is firstly reported and discussed. In particular, the new POMCP displays good acid-catalytic activity toward the synthesis of aspirin and photocatalytic selectivity for the degradation of organic dyes, as well as excellent photocatalytic activity toward the degradation of MB. Finally, the catalytic reaction kinetics are also discussed.
- Sha, Jing-Quan,Zhu, Pei-Pei,Yang, Xi-Ya,Sheng, Ning,Li, Ji-Shen,Sun, Long-Jiang,Yan, Hong
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p. 7049 - 7055
(2016/10/03)
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- Synthesis and biological evaluation of salicylic acid conjugated isoxazoline analogues on immune cell proliferation and angiogenesis
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Mitogenicity is the ability of the natural or synthetic compounds to induce cell division or proliferation. A series of salicylic acid derivatives containing isoxazoline moiety (8a-j) were synthesized and their immunopharmacological activities targeting lymphocyte proliferation and angiogenesis were evaluated. The compounds 8a-j mitogenicity were investigated on immunological cells that include human peripheral blood lymphocytes and murine splenocytes in-vitro. The results implicate that among the series of 8a-j, compound 8e showed a potent proliferative response on both human and murine lymphocytes. The proliferative index of the compound 8e was comparable to the reference mitogen Con A and mitogenecity is due to increased secretion IL-2. In-vivo CAM and rat corneal angiogenesis assays were performed to assess the compound's effect on endothelial cell migration and proliferation which inferred that 8e also induces the proliferation of endothelial cells. The study reports the synthetic immunostimulatory and pro-angiogenic activity of novel mitogen 8e which could be translated into new drug in future.
- Puttaswamy, Naveen,Pavan Kumar,Al-Ghorbani, Mohammed,Vigneshwaran,Prabhakar,Khanum, Shaukath Ara
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p. 153 - 161
(2016/05/02)
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- Acetylation of alcohols and phenols under solvent-free conditions using iron zirconium phosphate
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Iron zirconium phosphate (ZPFe) nanoparticles were found to function as an efficient catalyst for the acetylation of a wide range of alcohols and phenols using acetic anhydride, generating good to excellent yields under solvent-free conditions. The steric and electronic properties of various substrates had a significant influence on the reaction conditions required to achieve the acetylation. The catalyst used in the current study was characterized by inductively coupled plasma-optical emission spectrometry, X-ray diffraction, N2 adsorption-desorption, scanning electron microscopy, and transmission electron microscopy. These analyses revealed that the interlayer distance in the catalyst increased from 7.5 to 9.3 ? when Fe3+ was intercalated between the layers, whereas the crystallinity of the material was reduced. This nanocatalyst could also be recovered and reused at least six times without any discernible decrease in its catalytic activity. This new method for the acetylation of alcohols and phenols has several important advantages, including mild and environmentally friendly reaction conditions, as well as good to excellent yields and a facile work-up.
- Hajipour, Abdol R.,Karimi, Hirbod,Masti, Amir
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p. 595 - 602
(2015/09/28)
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- PRODRUG FOR RELEASE OF CISPLATIN AND CYCLOOXYGENASE INHIBITOR
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Pt(IV) prodrugs include one or more conjugated cyclooxygenase inhibitor. Reduction of Pt(IV) to Pt(II) can result cisplatin and a cyclooxygenase inhibitor. For proof of concept, a Pt(IV) prodrug that can produce cisplatin and aspirin, Platin-A, was synthesized. Platin-A exhibited excellent anticancer and anti-inflammatory properties, which were better than the combination of free formulation of cisplatin and aspirin.
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Paragraph 00104
(2015/06/25)
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- Synthesis and in vitro anticancer activity of novel 2-((3-thioureido) carbonyl)phenyl acetate derivatives
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Novel simplified Aspirin derivatives were developed, characterized by using IR, 1H NMR, 13C NMR and elementalanalysis techniques and evaluated for anticancer activity in human cell lines. The results revealed that most of the compounds exhibited inhibitory effects of growth of cancer cell lines in vitro against T-acute lymphoblastic leukemia cell lines Molt-4, chronic myclogenous leukemia cell lines K-562, acute myelocytic leukemia cells lines HL-60, human breast cancer cell lines MCF-7, human hepatic carcinoma cell lines HepG-2 and human lung cancer cell lines A-549. It was observed that some of these compounds exhibited significant anticancer activity particularly 5i which had stronger antileukemia activity with IC50 values ranging from 11.12 to 19.25 μmol·L-1 against 3 leukemia cells than control fluorouracil, so some of the compounds may constitute a novel class of anticancer medicines, which deserves further study.
- Xiong, Lin,Gao, Ya-Qin,Niu, Chu-E.,Wang, Hong-Bo,Li, Wei-Hong
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p. 132 - 137
(2014/03/21)
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- Acetylation of alcohols and phenols by zinc zirconium phosphate as an efficient heterogeneous catalyst under solvent-free conditions
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An efficient method for the acetylation of a wide range of alcohols as well as phenols with acetic anhydride in good to excellent yields under solvent-free conditions, using zinc zirconium phosphate as the catalyst was investigated. The catalyst was characterized by XRD, inductivity coupled plasma-optical emission spectroscopy, and scanning electron microscope. Products are easily isolated and the protocol is mild and green, compared to the existing methods. Graphical abstract: [Figure not available: see fulltext.]
- Hajipour, Abdol Reza,Karimi, Hirbod,Karimzadeh, Morteza
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p. 1461 - 1472
(2014/09/30)
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- Acetylation of alcohols and phenols under solvent-free conditions using copper zirconium phosphate
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Copper zirconium phosphate nanoparticles have been used as an efficient catalyst for the acetylation of a wide range of alcohols and phenols with acetic anhydride in good to excellent yields under solvent-free conditions. The steric and electronic properties of the different substrates had a significant influence on the reaction conditions required to achieve the acetylation. The catalyst used in the current study was characterized by inductively-coupled plasma optical emission spectroscopy, energy dispersive spectroscopy, X-ray diffraction, N2 adsorption-desorption, scanning electron microscopy, and transmission electron microscopy. These analyses revealed that the interlayer distance in the catalyst increased from 7.5 to 8.0 ? when Cu2+ was intercalated between the layers, whereas the crystallinity of the material was reduced. This nanocatalyst could also be recovered and reused at least six times without any discernible decrease in its catalytic activity. This new method for the acetylation of alcohols and phenols has several key advantages, including mild and environmentally friendly reaction conditions, as well as good to excellent yields and a facile work-up.
- Hajipour, Abdol R.,Karimi, Hirbod
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p. 1982 - 1989
(2015/09/28)
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- Silica-supported boric acid catalyzed synthesis of dihydropyrimidin-2-ones, bis(indolyl)methanes, esters and amides
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Silica-supported boric acid (H3BO3-SiO2) has been established as a green, efficient and recyclable catalyst for the synthesis of dihydropyrimidin-2-ones, bis(indolyl)methanes, and acetylation of alcohols, phenols, amines and thiols under solvent free conditions. The main features of the present method include clean reaction, mild conditions, low loading of environment friendly catalyst and easy workup procedure. The catalyst can be recycled at least five times without any significant loss in activity.
- Kumar, Vishal,Singh, Chitra,Sharma, Upendra,Verma, Praveen K.,Singh, Bikram,Kumar, Neeraj
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- Solvent-free per-O-acetylation of carbohydrates
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A facile, solvent-free acetylation method promoted by commercial 4? molecular sieves is described here for the synthesis of per-Oacetylated carbohydrates, which are important intermediates in carbohydrate chemistry. Several examples of carbohydrate and noncarbohydrate substrates are provided.
- Cai, Li,Rufty, Chris,Liquois, Megan
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p. 4367 - 4369
(2014/08/05)
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- Donor specificity and regioselectivity in Lipolase mediated acylations of methyl α-d-glucopyranoside by vinyl esters of phenolic acids and their analogues
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Methyl α-d-glucopyranoside as a model acceptor was acylated by several phenolic and non-phenolic vinyl esters using immobilised Lipolase. Donor specificity and regioselectivity of reaction were investigated. Conversion and rate of acylation by structurally varied donors indicates that the synthetic reactivity of Lipolase corresponds to the hydrolytic activity of feruloyl esterase type A. Lipolase exhibited remarkable regioselectivity for primary position of methyl α-d-glucopyranoside. The acylation occurred exclusively at 6-O primary position when vinyl esters of phenolic acids (hydroxybenzoates, hydroxyphenylalkanoates and hydroxycinnamates) served as acyl donors (5-77%). In addition to the major 6-O-acyl products (52-79%), 2,6-di-O-acylated derivatives were isolated from reaction mixtures (2-13%) when non-phenolic donors were used (vinyl esters of fully methoxylated derivatives of phenolic acids, along with vinyl benzoates, cinnamates or some heterocyclic analogues).
- Mastihubova, Maria,Mastihuba, Vladimir
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supporting information
p. 5389 - 5392
(2013/09/23)
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- Synthesis and chemical and biological comparison of nitroxyl- and nitric oxide-releasing diazeniumdiolate-based aspirin derivatives
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Structural modifications of nonsteroidal anti-inflammatory drugs (NSAIDs) have successfully reduced the side effect of gastrointestinal ulceration without affecting anti-inflammatory activity, but they may increase the risk of myocardial infarction with chronic use. The fact that nitroxyl (HNO) reduces platelet aggregation, preconditions against myocardial infarction, and enhances contractility led us to synthesize a diazeniumdiolate-based HNO-releasing aspirin and to compare it to an NO-releasing analogue. Here, the decomposition mechanisms are described for these compounds. In addition to protection against stomach ulceration, these prodrugs exhibited significantly enhanced cytotoxcity compared to either aspirin or the parent diazeniumdiolate toward nonsmall cell lung carcinoma cells (A549), but they were not appreciably toxic toward endothelial cells (HUVECs). The HNO-NSAID prodrug inhibited cylcooxgenase-2 and glyceraldehyde 3-phosphate dehydrogenase activity and triggered significant sarcomere shortening on murine ventricular myocytes compared to control. Together, these anti-inflammatory, antineoplasic, and contractile properties suggest the potential of HNO-NSAIDs in the treatment of inflammation, cancer, or heart failure.
- Basudhar, Debashree,Bharadwaj, Gaurav,Cheng, Robert Y.,Jain, Sarthak,Shi, Sa,Heinecke, Julie L.,Holland, Ryan J.,Ridnour, Lisa A.,Caceres, Viviane M.,Spadari-Bratfisch, Regina C.,Paolocci, Nazareno,Velázquez-Martínez, Carlos A.,Wink, David A.,Miranda, Katrina M.
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supporting information
p. 7804 - 7820
(2013/11/06)
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- Glycation Cross-link Breakers to Increase Resistance to Enzymatic Degradation
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The present invention relates to a method to treat a grafts, implant, scaffold, and constructs, including allografts, xenografts, autografts, and prosthetics comprising collagen, with an inhibitor of collagen cross-links and/or advanced glycation endproducts (AGE), in order to alleviate the mechanical weakness induced by the cross-links The invention also provides for kits for use in the operating theater during autograft, allograft or xenograft procedures, or for preparing allograft, xenografts or prosthetics that have not been already treated prior to packaging. The kit comprises a first agent or agents that inhibit collagen cross-links and/or advanced glycation endproducts, instructions for use, optionally a wash or rinse agent, and a device for containing the graft and first agent.
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- Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy
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Thioredoxin reductase (TrxR) is critical for cellular redox regulation and is involved in tumor proliferation, apoptosis and metastasis. Its C-terminal redox-active center contains a cysteine (Cys497) and a unique selenocysteine (Sec498), which are exposed to solvent and easily accessible. Thus, it is becoming an important target for anticancer drugs. Selective inhibition of TrxR by 1,2-(bis-1,2-benzisoselenazol-3(2H)-one)ethane (4a) prevents proliferation of several cancer cell lines both in vivo and in vitro. Using the structure of 4a as a starting point, a series of novel bis-1,2-benzisoselenazol-3(2H)-ones was designed, prepared and tested to explore the structure-activity relationships (SARs) for this class of inhibitor and to improve their potency. Notably, 1,2-(5,5′-dimethoxybis(1,2-benzisoselenazol-3(2H)-one))ethane (12) was found to be more potent than 4a in both in vitro and in vivo evaluation. Its binding sites were confirmed by biotin-conjugated iodoacetamide assay and a SAR model was generated to guide further structural modification.
- He, Jie,Li, Dongdong,Xiong, Kun,Ge, Yongjie,Jin, Hongwei,Zhang, Guozhou,Hong, Mengshi,Tian, Yongliang,Yin, Jin,Zeng, Huihui
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supporting information; scheme or table
p. 3816 - 3827
(2012/08/27)
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- REACTIVE DISTILLATION PROCESS FOR PREPARATION OF ACETAMINOPHEN
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The present invention relates to continuous processes for the preparation of primary and secondary N-acetylated aromatic amines of formula I or O-acetylated product of o-hydroxy benzoic acid of Formula II using acetic acid as an acetylating agent. wherein R1 has a definition of hydrogen atom, C1-C4 alkyl group or C1-C4 alkoxy group.
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Page/Page column 6
(2012/03/27)
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- Kinetics of proton transfer between ortho substituted benzoic acids and the carbinol base of crystal violet in toluene. Ortho effect on the reactivity of benzoic acids in apolar aprotic solvents
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Apolar aprotic solvents are particularly advantageous for investigating the intrinsic ortho effect free from complications of specific solvent effects. A kinetic study for toluene-phase proton transfers between ortho F, Cl, Br, I, OMe, OEt, OPh, OAc, Me, NO2, COMe, COPh, OH, NH2, and H benzoic acids and crystal violet carbinol base has shown the forward rate constant (log k+1) is the most appropriate reactivity parameter in toluene. log k+1 (toluene) as compared to other reported reactivity parameters in benzene, toluene, or chlorobenzene has been found more sensitive to the ortho substituent effect. The regression results of the correlation of log k+1 (toluene) of the acids (except OH and NH2 substituted ones) according to seven ortho effect models are all very significant, and the best result is given by Fujita-Nishiokas model. The overall analysis reveals that a substituents ortho effect pattern is a 58:24:18 ratio of its ordinary electrical, proximity electrical, and steric effects and that the proximity electrical effect is the major component to account for the peculiarity of the substituents ortho effect. The results further favor the transmission of this effect mainly through the molecular cavity. The effect may, however, be outweighed by the steric component for bulky enough substituents, e.g., Me. The enhanced strength exhibited by salicylic acid in toluene has been quantitatively described using Pytela-Lisas δHB i parameter. The abnormally high log k+1 observed for anthranilic acid in toluene has been ascribed to a very extensive homoconjugation in its acid-acid anion complex induced by the acids three hydrogen bond donors.
- Sen Gupta, Susanta K.,Mishra, Sangeeta
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experimental part
p. 4616 - 4623
(2011/06/26)
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- Flow processing of microwave-assisted (heterogeneous) organic reactions
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A commercially available continuous-flow reactor was adapted to run three organic reactions, e.g. two heterogeneous and one homogeneous mixture under microwave heating. The setup was operated either as a batch-loop reactor for running a biocatalyzed esterification of (R,S)-1-phenylethanol with vinyl acetate and the esterification of (S)-pyroglutamic acid with n-decanol (i.e., Laurydone process) or in a single pass for the aspirin synthesis as a homogeneous mixture. The tubular reactor has been characterized to perform a series of three equally sized, continuously operated stirred tank reactors on average. Although the (operational) costs of the microwave-heated tubular reactor are higher than conventionally heated processes in fine chemical operations, it was demonstrated that the experimental data can be used for process design. Plugging remains an important obstacle to be dealt with. However, benefits with respect to safety and scalability are expected to enable a fair compensation for the costs when implementing this novel technique.
- Hulshof, Lumbertus A.,Dressen, Mark H. C. L.,Van De Kruijs, Bastiaan H. P.,Meuldijk, Jan,Vekemans, Jef A. J. M.
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experimental part
p. 351 - 361
(2011/03/21)
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- Integrating computation and visualization to enhance learning IR spectroscopy in the general chemistry laboratory: Computer-assisted learning of IR spectroscopy
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An exercise to compute and visualize the IR spectra of small organic molecules was incorporated into a general chemistry laboratory module on the synthesis of aspirin. The effectiveness of the computation- visualization component was measured by pre- and postquizzes, a survey, and correct interpretation of experimental IR spectra. The assessment results showed that the students' conceptual understanding of IR spectroscopy was enhanced and that their ability to interpret IR spectra improved. Students learned the basics of the Scigress Explorer software package, gained invaluable introductory skills in molecular modeling and computational chemistry, and enjoyed the experience. Taylor & Francis Group, LLC.
- Furlan, Ping Y.,Bell-Loncella, Elisabeth T.
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experimental part
p. 618 - 625
(2011/10/19)
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- Practical and chemoselective reduction of acyl chloride to alcohol by borohydride in aqueous dichloromethane
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A simple methodology for the reduction of acid chlorides to their corresponding alcohols has been developed. Various carboxylic acids were converted to alcohols in excellent yields using NaBH4-K2CO3 in a mixed solvent system of dichloromethane and water (1:1) in the presence of a phase-transfer catalyst at low temperature. The importance of the work is its simplicity, selectivity, excellent yield, and very short reaction time. This new reduction condition has proved to be an excellent chemoselective method for a range of acid chlorides in the presence of various functional groups.
- Rajan, Ramya,Badgujar, Sachin,Kaur, Kamaljit,Malpani, Yashwardhan,Kanjilal, Pranab R.
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experimental part
p. 2897 - 2907
(2010/11/18)
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- Trimethylsilyl chloride promoted selective desulfurization of thiocarbonyls to carbonyls with hydrogen peroxide
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In the presence of hydrogen peroxide and trimethylsilyl chloride, thiocarbonyls desulfurize to the corresponding carbonyls. The safe, operationally simple, general reaction gives excellent yields in short reaction times with no side reactions and excellent regioselectivity, which makes this process an attractive, environmentally benign alternative for the desulfurization of thiocarbonyls
- Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Tajik, Maryam
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experimental part
p. 4282 - 4286
(2011/02/25)
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- GREEN CATALYTIC PROCESS FOR THE SYNTHESIS OF ACETYL SALICYLIC ACID
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The present invention provides a green catalytic process for the synthesis of acetyl salicylic acid using solid acid catalysts at atmospheric pressure. The invention involve the solid acid catalyst such as sulfated transition metal oxides namely nano-crystalline sulfated zirconia, sulfated titania; modified zeolites namely zeolite H-beta, H—Y, H-ZSM-5 and K-10 montmorillonite clay in a solvent free environment using salicylic acid and acetic anhydride with yield about 95% and high selectivity (100%). The solid acid catalysts can be recovered, regenerated and reused.
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Page/Page column 5-6
(2009/04/24)
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- Amide-containing diketoacids as HIV-1 integrase inhibitors: Synthesis, structure-activity relationship analysis, and biological activity
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HIV-1 integrase, which catalyzes the integration of the viral genome into the cellular chromosome, is an essential enzyme for retroviral replication, and represents an attractive and validated target in the development of therapeutics against AIDS. In this paper, 17 amide-containing novel diketoacids were designed and synthesized, and their ability to inhibit HIV-1 integrase was tested. The structure-activity relationships were also analyzed.
- Li, Hongcai,Wang, Chao,Sanchez, Tino,Tan, Yanmei,Jiang, Chunying,Neamati, Nouri,Zhao, Guisen
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experimental part
p. 2913 - 2919
(2009/09/06)
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- PROCESS FOR THE MODIFICATION OF THE SOLID STATE OF A COMPOUND AND CO-AMORPHOUS COMPOSITIONS PRODUCED WITH SAME
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The invention provides a process for preparing non-crystalline organic compositions and non-crystalline, co-amorphous blends of organic compounds.
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Page/Page column 20-23
(2009/05/28)
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- ANTI-AMNESIC COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM
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The present invention relates to the use of at least one compound of formula (I) as follows: or of at least one pharmaceutically acceptable salt thereof for the preparation of a drug for the prevention or treatment of memory disorders.
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- Lithium chloride-assisted selective hydrolysis of methyl esters under microwave irradiation
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A rapid and mild method for the selective hydrolysis of methyl ester in lithium chloride-N,N-dimethylformamide (LiCl-DMF) system under microwave irradiation has been developed. The effects of substituent, metal salt, and solvent on the reactivity and selectivity of the hydrolysis reaction have been investigated. Microwave irradiation significantly improves the reaction yield within a short time in an LiCl-DMF system. Moreover, the chiral-carbon of methyl esters retained its configuration during the reaction. Finally, the catalytic mechanism of hydrolysis by LiCl salt has also been proposed.
- Wu, Xiao-Ai,Ying, Ping,Liu, Jun-Yang,Shen, Heng-Shui,Chen, Yue,He, Ling
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experimental part
p. 3459 - 3470
(2009/12/03)
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- H2O2/SOCl2: a useful reagent system for the conversion of thiocarbonyls to carbonyl compounds
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The H2O2/SOCl2 reagent system has been used as a new and efficient reagent for deprotection of thiocarbonyls to carbonyl compounds. The salient features of this protocol are short reaction times, good chemoselectivity, clean reaction profiles, and simple work-up that preclude the use of toxic solvents.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Farrokhi, Azita
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supporting information; experimental part
p. 7658 - 7661
(2009/12/04)
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- FORM AB OF ACETYL SALICYCLIC ACID
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The invention relates to a new form of acetyl salicylic acid designated as Form AB as well as processes for the preparation and formulation comprising it.
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Page/Page column 10-11
(2008/06/13)
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- Erbium(III) chloride: A very active acylation catalyst
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Erbium(iii) chloride is a powerful catalyst for the acylation of alcohols and phenols. The reaction works well for a large variety of simple and functionalized substrates by using different kinds of acidic anhydrides (Ac 2O, (EtCO)2O, (PriCO)2O, (Bu tCO)2O, and (CF3CO)2), without isomerization of chiral centres. Moreover, the catalyst can be easily recycled and reused without significant loss of activity. CSIRO 2007.
- Dalpozzo, Renato,De Nino, Antonio,Maiuolo, Loredana,Oliverio, Manuela,Procopio, Antonio,Russo, Beatrice,Tocci, Amedeo
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