- Preparation method of acetamide compound
-
The invention discloses a preparation method of an acetamide compound, the preparation method comprises the following steps: reacting tetracarbonyl dichloride rhodium, 1, 3-bis (diphenylphosphine) propane, tungsten carbonyl, sodium phosphate, sodium iodide, water, a nitro compound and dimethyl carbonate at 120 DEG C for 24 hours, and after the reaction is completed, performing post-treatment to obtain the acetamide compound. According to the preparation method, dimethyl carbonate serves as a C1 source and also serves as a green solvent, operation is easy, reaction starting raw materials are low in price and easy to obtain, the tolerance range of substrate functional groups is wide, and reaction efficiency is high. Various acetamide compounds can be synthesized according to actual needs, so that the practicability of the method is widened while the operation is convenient.
- -
-
Paragraph 0035-0047
(2021/05/19)
-
- A novel construction of acetamides from rhodium-catalyzed aminocarbonylation of DMC with nitro compounds
-
Dimethyl carbonate (DMC), an environment-friendly compound prepared from CO2, shows diverse reactivities. In this communication, an efficient procedure using DMC as both a C1 building block and solvent in the aminocarbonylation reaction with nitro compounds has been developed. W(CO)6acts both a CO source and a reductant here.
- Bao, Zhi-Peng,Miao, Ren-Guan,Qi, Xinxin,Wu, Xiao-Feng
-
supporting information
p. 1955 - 1958
(2021/03/02)
-
- Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications
-
Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.
- Zhao, Lixing,Hu, Chenyang,Cong, Xuefeng,Deng, Gongda,Liu, Liu Leo,Luo, Meiming,Zeng, Xiaoming
-
supporting information
p. 1618 - 1629
(2021/01/25)
-
- Sulfuryl Fluoride Mediated Synthesis of Amides and Amidines from Ketoximes via Beckmann Rearrangement
-
A metal-free and redox-neutral method for Beckmann rearrangement employing inexpensive and readily available SO2F2 gas is described. The reported transformation proceeds at ambient temperature and is compatible with a wide range of sterically and electronically diverse aromatic, heteroaromatic, aliphatic and lignin-like oximes providing amides in good to excellent yields. The reaction proceeds through the formation of an imidoyl fluoride intermediate that can also be used for the synthesis of amidines.
- Gurjar, Jitendra,Fokin, Valery V.
-
supporting information
p. 10402 - 10405
(2020/07/25)
-
- Preparation and Antibacterial Activity of Some New 4-(2-Heterylidenehydrazinyl)-7-chloroquinoline Derivatives
-
N-(4-Substituted phenyl)acetamides, which were prepared from acetic anhydride and p-substituted anilines, were utilized as precursors for reactions to Vilsmeier-Haack reagent to form 6-substituted-2-chloroquinoline-3-carbaldehydes 3a-c. Meanwhile, a similar reagent was applied to 1-[1-(4-substituted phenyl)ethylidene]-2-phenylhydrazines as substrates, which were synthesized from phenylhydrazine hydrochloride and p-substituted acetophenones, and 1,3-diarylpyrazole-4-carbaldehydes 3d-f were observed as a result. Reactions between the aldehydes 3a-f and 7-chloro-4-hydrazinylquinoline 2, obtained from reaction of 4,7-dichloroquinoline 1 and hydrazine hydrate, formed six new hydrazone compounds, namely, 4-{2-[(6-substituted-2-chloroquinolin-3-yl)methylidene]hydrazinyl}-7-chloroquinolines 4a-c and 4-(2-{[3-(4-substituted phenyl)-1-phenyl-1H-pyrazol-4-yl]methylene}hydrazinyl)-7-chloroquinolines 4d-f. The chemical structures of all synthesized compounds were elucidated by the analysis of IR, 1H, 13C-NMR, and HRMS spectral data. Additionally, all of the synthesized hydrazones were evaluated in terms of cytotoxic activity against four strains of bacteria and four strains of fungus at several concentrations of substrates. As a result, three of them, 4a-c, possess the good ability as growth inhibitor of Bacillus subtilis and Aspergillus Niger at the concentration of 25 μg/mL and 50 μg/mL, respectively, while compound 4e only shows a cytotoxic activity against Aspergillus Niger at the concentration of 25 μg/mL.
- Le, Trong Duc,Pham, Ngoc Nam,Nguyen, Tien Cong
-
-
- Synthesis and mesomorphic properties of 2,4-bis(4′-n-pentyloxybenzoyloxy)- benzylidine-4″- n-alkoxyaniline
-
The synthesis and mesomorphic properties of a new series of 2,4-bis(4′-npentyloxybenzoyloxy)- benzylidine-4″ -n-alkoxyaniline (DC5An) are reported. The molecular structure of compounds was confirmed by FTIR, 1H-NMR, 13C-NMR, mass spectroscopy and elemental analysis. The mesomorphic properties were studied by differential scanning calorimetry (DSC) and polarizing optical microscopy (POM) measurements. All compounds of the series exhibit nematic (N) and smectic C (SmC) phases. The first four homologues (DC5A1-DC5A4) display a N mesophase, whereas the highest homologues (DC5A5-DC5A10) exhibit an enantiotropic dimorphism N and SmC phases. The mesomorphic properties of the present series are compared and discussed with other structurally related series.
- Hamad, Wali M.,Azeez, Hashim J.,Al-Dujaili, Ammar H.
-
-
- Preparation and crystallization method of phenacetin
-
The invention discloses a preparation and crystallization method of phenacetin, and belongs to the field of chemical industry. According to the preparation and crystallization method, p-phenetidine is reacted with an acid in water so as to obtain a p-phenetidine salt; the p-phenetidine salt is reacted with an anhydride in a buffer solution system; after reaction, a mixed solution of water and an organic solvent is added into an obtained reaction solution, and phenacetin crystals are obtained via stirring. Product yield is high; two-step reaction total yield is higher than 92%; the obtained products are crystalline solids; stability is high; purity is high, and is higher than 99%; reaction time is short; reaction conditions are mild; product separation operation is simple; direct filtering separation can be carried out after reaction; and batch production period is shortened greatly.
- -
-
Paragraph 0039
(2016/11/24)
-
- Highly efficient dehydrogenative cross-coupling of aldehydes with amines and alcohols
-
A common protocol for the synthesis of amides, esters and α-ketoesters via cross dehydrogenative coupling of aldehydes and amines/alcohols has been developed. The method is applicable to a wide variety of alcohols and amines as well as aliphatic and aromatic aldehydes. Also, the use of acetaldehyde for acetylation and ethyl glyoxalate to access 2-oxo-amino esters is presented for the first time.
- Deshidi, Ramesh,Rizvi, Masood Ahmad,Shah, Bhahwal Ali
-
p. 90521 - 90524
(2015/11/11)
-
- A metal-free approach for transamidation of amides with amines in aqueous media
-
An efficient, environmentally benign and a mild protocol for transamidation of amides with a variety of amines in the presence of K2S2O8 using stoichiometric quantity in aqueous conditions has been established. This method works under conventional thermal conditions and in microwave irradiation as well. A series of amides have been prepared using this reaction and this is a greener protocol for transamidation, which offers a diverse kind of substrate scope with exclusive product formation (yields 90-98%).
- Srinivas, Mahesuni,Hudwekar, Abhinandan D.,Venkateswarlu, Vunnam,Reddy, G. Lakshma,Kumar, K. A. Aravinda,Vishwakarma, Ram A.,Sawant, Sanghapal D.
-
supporting information
p. 4775 - 4779
(2015/07/20)
-
- Synthesis of secondary amides from N-Substituted amidines by tandem oxidative rearrangement and isocyanate elimination
-
In this work an efficient tandem process transforming N-substituted amidines into secondary amides has been described. The process involves N-acylurea formation by reaction of the substrate with bis(acyloxy)(phenyl)-λ3-iodane followed by isocyanate elimination. The periodinane reagents are obtained from the commercially available phenyl-iodine(III) diacetate [PhI(OAc)2, (PIDA)] by ligand exchange with carboxylic acids. The N-substituted amidine substrates are easily synthesized from readily available nitriles. The method is applicable for secondary amide synthesis, based on both aliphatic and (hetero)aromatic amines, including challenging amides consisting of sterically hindered acids and amines. Moreover, the protocol allows one to combine steric bulk with electron deficiency in the target amides (aniline based). Such compounds are difficult to synthesize efficiently based on classical condensation reactions involving carboxylic acids and amines. Overall, the synthetic protocol transforms a nitrile into a secondary amide in both aliphatic and (hetero)aromatic systems.
- Debnath, Pradip,Baeten, Mattijs,Lefvre, Nicolas,Van Daele, Stijn,Maes, Bert U. W.
-
supporting information
p. 197 - 209
(2015/03/03)
-
- H2O2-mediated oxidative formation of amides from aromatic amines and 1,3-diketones as acylation agents via C-C bond cleavage at room temperature in water under metal-free conditions
-
1,3-Diketones, as novel acylation agents, reacted with aromatic amines promoted by commercially available H2O2 (30% aq.) as the sole oxidant at room temperature under metal-free conditions in water, leading to a novel and rapid amide bond formation strategy. The reported method is high-yielding, simple and mild, and is the first example of the use of 1,3-diketones as acylation agents via C-C bond cleavage.
- Sun, Xi,Wang, Min,Li, Pinhua,Zhang, Xiuli,Wang, Lei
-
supporting information
p. 3289 - 3294
(2013/12/04)
-
- A facile and efficient method for the selective deacylation of N-arylacetamides and 2-chloro-Narylacetamides catalyzed by SOCl2
-
Thionyl chloride efficiently and selectively promoted the deacylation of N-arylacetamides and 2-chloro-N-arylacetamides, under anhydrous conditions, without effecting the ester group, aminosulfonyl group, or benzyloxyamide group. This method, which has been successfully applied to a variety of substrates including different N-arylacetamides and 2-chloro-N-arylacetamides, has the attractive advantages of inexpensive reagents, satisfactory selectivity, excellent yields, short reaction time, and convenient workup. This new method can probably be used to selectively deacylate between aromatic amides and alkyl amides. Springer Science+Business Media B.V. 2011.
- Wang, Gong-Bao,Wang, Lin-Fa,Li, Chao-Zhang,Sun, Jing,Zhou, Guang-Ming,Yang, Da-Cheng
-
experimental part
p. 77 - 89
(2012/05/20)
-
- Studies of calamitic liquid crystalline compounds involving ester-azo central linkages with a biphenyl moiety
-
Two mesogenic homologous series involving ester-azo central linkages with a biphenyl moiety have been synthesized, such as 4'-[(4-n-alkoxyphenyl)diazenyl] biphenyl-4-ol (series I) and 4'-[(4-n-alkoxyphenyl) diazenyl]-4-butoxy phenyl biphenyl-4-carboxylate (series II). Azobiphenyl of series I having a free hydroxyl group with strong hydrogen bonding exhibits a high-temperature enantiotropic smectic phase. Whereas in series II, compounds containing C 1-C8 carbon atoms exhibit only a monotropic smectic phase and compounds with C10, C12, C14, and C 16 atoms show an enantiotropic smectic phase. These compounds were characterized by elemental analysis, FT-IR, 1H-NMR, and mass spectral studies. The phase transition and mesogenicity of these substances were studied by polarizing optical microscopic and differential scanning calorimetric techniques. Their thermal stabilities and other characteristics are discussed. Copyright Taylor &Francis Group, LLC.
- Thaker,Dhimmar,Patel,Solanki,Patel,Chothani,Kanojiya
-
experimental part
p. 172 - 191
(2012/07/27)
-
- Direct acetoxylation and etherification of anilides using phenyliodine bis(trifluoroacetate)
-
Treatment of various anilides with 1.5 equiv. of phenyliodine bis(trifluoroacetate) (PIFA) and 1.0 equiv. of BF3·OEt 2 in AcOH at room temperature afforded the corresponding para-acetoxylated products with high regioselectivity. In addition, this reaction could be expanded to the etherification of anilides. In the presence of 2.0 equiv. of PIFA and 2.0 equiv. of BF3·OEt2, the reaction of anilides with alcohols provided the corresponding para-etherified products in good yields. The Royal Society of Chemistry 2011.
- Liu, Huan,Wang, Xuemin,Gu, Yonghong
-
experimental part
p. 1614 - 1620
(2011/04/22)
-
- Palladium-catalyzed C-H aminations of anilides with N - fluorobenzenesulfonimide
-
The first amide-directed, palladium-catalyzed, intermolecular, highly selective C-H aminations with the non-nitrene-based nitrogen source N-fluorobenzenesulfonimide have been developed. This methodology might provide a new pathway for directed metal-catalyzed aromatic C-H amination.
- Sun, Kai,Li, Yan,Xiong, Tao,Zhang, Jingping,Zhang, Qian
-
supporting information; experimental part
p. 1694 - 1697
(2011/04/17)
-
- Role of terminal heterocyclic ring on mesomorphic properties of homologous series
-
Two new homologous series of compounds with a heterocyclic ring having sulfur and oxygen as a hetero atom derived from p-hydroxy acetophenone and alkoxy aniline containing cinnamate-azomethine as central linkages have been synthesized. viz. 4(furalacryloxy) α-methyl benzylidine-4′-alkoxy aniline and 4(thianylacryloxy) α-methyl benzylidine-4′-alkoxy aniline. The compound of both the series have been characterized by elemental analysis, FT-IR, 1H-NMR, and mass spectrometry method. Their liquid crystalline properties have been investigated by optical polarizing microscopy and differential scanning calorimetry (DSC) studies. All the derivatives are mesomorphic in nature showing the nemetic phase. The mesomorphic properties of the present two series are compared with other structurally related series to evaluate the effect of thiophene and furan on mesomorphism. Copyright Taylor & Francis Group, LLC.
- Thaker,Patel,Solanki,Dhimmer,Dave
-
experimental part
p. 63 - 80
(2010/09/05)
-
- INDOLE COMPOUNDS AS AN INHIBITOR OF CELLULAR NECROSIS
-
The present invention relates to new indole compounds, pharmaceutically acceptable salts or isomers thereof which are useful for the prevention or treatment of cellular necrosis and necrosis-associated diseases. The present invention also relates to a method and a composition for the prevention or treatment of cellular necrosis and necrosis-associated diseases, comprising said indole compounds as an active ingredient.
- -
-
Page/Page column 18
(2010/08/22)
-
- INDOLE AND INDAZOLE DERIVATIVES HAVING A CELL-, TISSUE- AND ORGAN-PRESERVING EFFECT
-
The present invention relates to a composition for preserving cells, tissues and organs, comprising as an active ingredient indole and indazole compounds of formula (1), or a pharmaceutically acceptable salt or isomer thereof, which are effective for preventing injury of organs, isolated cell systems or tissues caused by cold storage, transplant operation or post-transplantation reperfusion; a preservation method; and a preparation method of the composition.
- -
-
Page/Page column 20
(2010/12/18)
-
- HPLC analysis of a syrup containing nimesulide and its hydrolytic degradation product
-
The present paper deals with the evaluation of nimesulide, 2-phenoxy-4-nitroaniline, the main hydrolytic degradation product of nimesulide, of methylparaben and propylparaben, and eventually of 4-hydroxybenzoic acid by HPLC with UV detection at 254 nm in syrup as a pharmaceutical formulation. HPLC analysis was employed on the reversed phase C18 with methanol and 0. 01 M dibasic ammonium phosphate (ρr = 60: 40, pH 4. 0). Validation was performed using standards and a pharmaceutical preparation containing the compounds described above.
- Mokry, Milan,Klimes, Jir,Pechova, Jana
-
body text
p. 405 - 408
(2011/10/09)
-
- INDOLE COMPOUNDS AS AN INHIBITOR OF CELLULAR NECROSIS
-
The present invention relates to new indole compounds, pharmaceutically acceptable salts or isomers thereof which are useful for the prevention or treatment of cellular necrosis and necrosis-associated diseases. The present invention also relates to a method and a composition for the prevention or treatment of cellular necrosis and necrosis-associated diseases, comprising said indole compounds as an active ingredient.
- -
-
Page/Page column 59
(2009/04/25)
-
- GLUCOKINASE ACTIVATORS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AS AN ACTIVE INGREDIENT
-
The present invention relates to new compounds of formula (1) exhibiting excellent activity for glucokinase, and pharmaceutical compositions comprising the same as an active ingredient.
- -
-
Page/Page column 71-72
(2009/07/25)
-
- New, efficient, selective, and one-pot method for acylation of amines
-
Hydrazine hydrate with acetic and propionic acids was an efficient reagent for acylation of primary and secondary amines at reflux temperatures. The reported one-pot method is high-yielding, simple, mild, and inexpensive. Copyright Taylor & Francis Group, LLC.
- Basanagouda, Mahantesha,Kulkarni, Manohar V.,Kalkhambkar, Raj G.,Kulkarni, Geeta M.
-
p. 2929 - 2940
(2008/12/22)
-
- SDS/Ac2O/H2O: Surfactant-mediated cleavage of imines with acetic anhydride to carbonyls and acetanilides in water
-
Surfactant (SDS)-mediated cleavage of imines was achieved with acetic anhydride to the corresponding carbonyls (aldehydes and ketones) and acetanilides in water at 25-30°C with very good to excellent yields, thus contributing significantly to the green chemistry concept. Copyright Taylor & Francis Group, LLC.
- Sharma, Saikat Das,Gogoi, Pranjal,Boruah, Monalisa,Konwar, Dilip
-
p. 2473 - 2481
(2008/02/10)
-
- Large scale Biginelli reaction via water-based biphasic media: A green chemistry strategy
-
An important stage in process development is kilo scale preparation of the target compound. For this reason, a procedure involving water-based biphasic reaction media has been developed for conducting some exothermic reactions on a large scale. This protocol is illustrated by the energy-efficient and rapid preparation of dihydropyrimidinones by a solvent-free, green chemistry procedure applied to the Biginelli reaction using p-toluenesulfonic acid as catalyst. 2005 Elsevier Ltd.
- Bose, Ajay K.,Manhas, Maghar S.,Pednekar, Suhas,Ganguly, Subhendu N.,Dang, Hoang,He, William,Mandadi, Arun
-
p. 1901 - 1903
(2007/10/03)
-
- Method for the synthesis of amides and related products from esters or ester-like compounds
-
A versatile, eco-friendly, and efficient method for the convenient conversion of esters and ester-like compounds into amides, peptides, carbamates, ureas, oxamides, oxamates, hydrazides, oxazolidinones, pyrazolones, oxazolidinediones, barbituric acids, and other molecules containing one or more OCN moieties in the presence of a diol or polyol is disclosed.
- -
-
Page/Page column 10
(2008/06/13)
-
- Solid supported microwave-assisted Beckmann rearrangement of ketoximes in dry media
-
An AlCl3-ZnCl2 mixture supported on silica gel is found to be a new efficient medium for the Beckmann rearrangement in solvent-free conditions under microwave irradiation. The yields are good to excellent.
- Matloubi Moghaddam, Firouz,Rad, Abbas Ali Rastegar,Zali-Boinee, Hassan
-
p. 2071 - 2075
(2007/10/03)
-
- A novel one pot reductive acetylation of nitroarenes
-
Nitroarenes are reductively acetylated in one pot to the corres, ponding N-arylacetamides and N-(acetyloxy)-N-arylacetamides with Zn and Ac2O in presence of acidic Al2O3 in dichloromethane at room temperature.
- Baruah
-
p. 300 - 303
(2007/10/03)
-
- Batch microwave reactor
-
An apparatus for performing batchwise chemical reactions using microwave energy (10-11-12) includes a vessel (15) within a microwave cavity (13). The vessel has a sealed cover (16), located outside cavity (13), which mounts a cold-finger type heat exchanger (24) for immersion in the vessel's contents (23). Cover (16) also mounts a pressure measuring device (17) and a temperature sensing device (20) for monitoring the vessel's contents during a chemical reaction. A pressure operable safety valve (18) and a sampling facility (19) are also mounted on the cover (16). The vessel also contains a magnetically operated stirrer (22). The reactor apparatus is constructed to withstand high pressures and temperatures that may be developed within the vessel (15). Various uses of the cold-finger (24) to facilitate the conduct or completion of a chemical reaction are described.
- -
-
-
- NMR spectroscopic studies on the metabolism and futile deacetylation of phenacetin in the rat
-
1. 1H-NMR spectroscopy of urine was used to determine the % deacetylation and re-acetylation of 2H-labelled (in the acetyl) phenacetin metabolites in the rat. 2. Male Sprague-Dawley rats were each dosed with either phenacetin or phenacetin-C2H3, at 50 mg kg-1. The total urinary recoveries for phenacetin and phenacetin-C2H3, were 47·6±16·7 and 50·1±16·2% respectively (not significantly different, p > 0·05). Paracetamol sulphate and glucuronide are the major urinary metabolites of both protio and deuteriophenacetin. 2. The futile deacetylation given by the urinary recovery of protio-acetyl metabolites of phenacetin-C2H3, was 29·6±0·9% for paracetamol sulphate and 36·6±3·1% for paracetamol glucuronide. These observations demonstrate a high level of futile deacetylation in the paracetamol conjugates formed by metabolism of phenacetin-C2H3, and this may indicate a high metabolic flux through the nephrotoxic intermediate 4-aminophenol. 4. The level of futile deacetylation for phenacetin was significantly higher than that found previously in studies of labelled paracetamol in rat or man, and may be important in understanding the higher nephrotoxicity of phenacetin as compared with paracetamol.
- Nicholls,Lindon,Caddick,Farrant,Wilson,Nicholson
-
p. 1175 - 1186
(2007/10/03)
-
- Retention behavior of compounds with active hydrogen atoms and their acetylated derivatives in reversed-phase HPLC
-
In view of poor interlaboratory reproducibility of retention indices I in reversed-phase high-performance liquid chromatography, not the indices themselves but their differences for reactants and products of interaction with various reagents can be used to identify compounds with active hydrogen atoms. For acetylated derivatives of phenols and aromatic amines, the quantity ?I = I(ArXH) -I(ArXCOCH3), where X = O or NH. has statistically significant distinguishable values of 126 ± 15 and 70 ± 20, respectively. The additivity of the parameters ?I is first revealed for the polyfunctional compounds of these classes that are incapable of intramolecular hydrogen bonding. Abnormal ?I values and deviations from the additivity rule are observed only for substances with intramolecular hydrogen bonding. This finding can be used to confirm the presence of relevant structural units in molecules.
- Zenkevich,Kosman
-
p. 1173 - 1176
(2007/10/03)
-
- Diethoxymethyl: A useful nitrogen-protecting group for lactams and amides
-
Treatment of the lactams 3a-e and the amide 3f with triethyl orthoformate leads to the N-diethoxymethyl substituted derivatives 4a-f. Additionally, the indolinones 3a and 3b can react at the lactam α-position to give the reaction products 2 and 5, respectively. The diethoxymethyl group can be easily removed by subsequent treatment with trifluoroacetic acid and NaOH.
- Gmeiner,Bollinger
-
p. 168 - 170
(2007/10/02)
-
- Polymer Supported Acetylaminophenoxide Anion: Convenient Method for O-Alkylation
-
Alkylation of acetylaminophenoxide supported on Amberlyst A-26 gives O-alkylated products in high yields and purity.In addition to ease and simplicity of the method and regeneration of polymeric by-product, the polymeric reagent seems to increase the nucleophilicity of the anions.
- Salunkhe, D. G.,Jagdale, M. H.,Shinde, S. S.,Salunkhe, M. M.
-
-
- Comparative Structure-Activity Relationships of Antifolate Triazines Inhibiting Murine Tumor Cells Sensitive and Resistant to Methotrexate
-
The inhibitory effect of 108 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(substituted-phenyl)-s-triazines on murine L5178Y tumor cells, resistant and sensitive to methotrexate (MTX), has been studied.From the pI50 values, quantitative structure-activity relationships have been formulated which show that the lipophilic triazines are much more inhibitory against resistant cells than methotrexate or hydrophilic triazines.The results are compared with the behavior of other antifolate drugs that have been used in chemotherapy, as well as with eight antitumor drugs that are notantifolates.The acquired resistance of these cells toward hydrophilic antifolates may be attributed to the combined effect of an impaired active-transport system, a change in the conformation of dihydrofolate reductase in the resistant cells, and an amplified production of dihydrofolate reductase in the resistant cells.
- Selassie, Cynthia Dias,Hansch, Corwin,Khwaja, Tasneem A.,Dias, Cecilia B.,Pentecost, Stephanie
-
p. 347 - 357
(2007/10/02)
-
- Photolysis and Thermolysis of Phenyl Azide in Acetic Acid. Trapping of 1-Azacyclohepta-1,2,4,6-tetraene and Nucleophilic Aromatic Substitution
-
Photolysis and thermolysis of phenyl azide in acetic acid yielded 1H-azepin-2(3H)-one (4), 2-methylbenzoxazole (15), 2- and 4- acetamidophenyl acetates (16) and (12), 2- and 4- acetamidophenols (14) and (13), acetanilide, and azobenzene.Addition of ethanol to the system caused a linear decrease in the yield of (4) and a more remarkable decrease in total yield for the para-products than that for the ortho-products to give 2- and 4- acetamidophenyl ethyl ethers (9) and (8).Photolysis of the azide in ethanol in the presence of phenol afforded 2-phenoxy-3H-azepine (5) and aniline, but no 2- and 4-phenetidines.The yield of compounds (4) and (12)-(16) was independent of the presence of penta-1,3-diene(0.01 M), and somewhat decreased by an addition of bromobenzene.The rate of decomposition of azide in acetic acid was not accelerated as compared with that in 1,4-dioxan, and the activation parameters varied little in the two solvents.The results suggest that 1-azacyclohepta-1,2,4,6-tetraene (1) formed via singlet phenylnitrene or via singlet excited phenyl azide is trapped by acetic acid or phenol to give (4) or (5), and that a resonance-stabilized ion (3) neighbouring acetate anion is formed by an attack of the singlet nitrene on acetic acid to give aromatic nucleophilic substitution.
- Takeuchi, Hiroshi,Koyama, Kikuhiko
-
p. 1269 - 1274
(2007/10/02)
-
- Photolysis and Thermolysis of Phenyl Azide in Acetic Acid
-
The photolysis and thermolysis of phenyl azide in acetic acid gave 2,3-dihydro-1H-azepin-2-one via 1-azacyclohepta-1,2,4,6-tetraene, and ring-disubstituted products via a resonance-stabilized ion formed by attack of singlet phenylnitrene on acetic acid.
- Takeuchi, Hiroshi,Koyama, Kikuhiko
-
p. 202 - 204
(2007/10/02)
-
- Solid, frozen stabilized hair dye
-
A cosmetic composition which at ambient temperature comprises a solution in a water or hydroalcoholic solvent of at least one cosmetic component which in said solution at ambient temperature is not stable, can be preserved, stabilized and packaged by freezing said composition and storing it at a temperature below its freezing point.
- -
-
-
