- Synthesis, α-glucosidase inhibition and molecular docking studies of novel thiazolidine-2,4-dione or rhodanine derivatives
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A series of novel thiazolidine-2,4-dione or rhodanine derivatives (5a-5k, 6a-6k) were synthesized and evaluated for their α-glucosidase inhibitory activity. The majority of compounds exhibited potent inhibitory activity in the range of 5.44 ± 0.13 to 50.45 ± 0.39 μM, when compared to the standard drug acarbose (IC50 = 817.38 ± 6.27 μM). Among the compounds in the series, compounds 5k, 6a, 6b, 6e, 6h and 6k showed potent inhibitory potential with IC50 values of 20.95 ± 0.21, 16.11 ± 0.19, 7.72 ± 0.16, 7.91 ± 0.17, 6.59 ± 0.15 and 5.44 ± 0.13 μM, respectively. Compound 6k (IC50 = 5.44 ± 0.13 μM), containing chloro and rhodanine groups at the 2- and 4-positions of the phenyl ring respectively, was found to be the most active compound that inhibits α-glucosidase activity. Furthermore, molecular docking studies were performed to understand the binding interactions between the molecule and enzyme.
- Wang, Guang-Cheng,Peng, Ya-Ping,Xie, Zhen-Zhen,Wang, Jing,Chen, Ming
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- Application of ultrasound irradiation for the reactions of N-hydroxymethylation
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A convenient and high yield method for the N-hydroxymethylation of substituted phthalimide and benzimidazole under ultrasound irradiation is reported.
- Zhong,Song,Peng,Qian
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- A Cyanine-Bridged Somatostatin Hybrid Probe for Multimodal SSTR2 Imaging in Vitro and in Vivo: Synthesis and Evaluation
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Multimodal imaging probes have attracted the interest of ongoing research, for example, for the surgical removal of tumors. Modular synthesis approaches allow the construction of hybrid probes consisting of a radiotracer, a fluorophore and a targeting unit. We present the synthesis of a new asymmetric bifunctional cyanine dye that can be used as a structural and functional linker for the construction of such hybrid probes. 68Ga-DOTATATE, a well-characterized radiopeptide targeting the overexpressed somatostatin receptor subtype 2 (SSTR2) in neuroendocrine tumors, was labeled with our cyanine dye, thus providing additional information along with the data obtained from the radiotracer. We tested the SSTR2-targeting and imaging properties of the resulting probe 68Ga-DOTA-ICC-TATE in vitro and in a tumor xenograft mouse model. Despite the close proximity between dye and pharmacophore, we observed a high binding affinity towards SSTR2 as well as elevated uptake in SSTR2-overexpressing tumors in the positron emission tomography (PET) scan and histological examination.
- Heing-Becker, Isabelle,Gr?tzinger, Carsten,Beindorff, Nicola,Prasad, Sonal,Erdmann, Sarah,Exner, Samantha,Haag, Rainer,Licha, Kai
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- Bi(OTf)3-Catalysed Access to 2,3-Substituted Isoindolinones and Tricyclic N,O-Acetals by Trapping of Bis-N-Acyliminium Species in a Tandem Process
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New 1,3-bis-N-acyliminium species generated easily with nontoxic Bi(OTf)3catalyst at very low loadings (2 mol-%) were trapped inter- and intramolecularly with various poly-nucleophiles. This mild, efficient, practical and general tandem approach provides an array of substituted isoindolinones and cyclic N,O-acetals.
- Aliyenne, Ahmed,Pin, Frédéric,Nimbarte, Vijaykumar D.,Lawson, Ata Martin,Comesse, Sébastien,Sanselme, Morgane,Tognetti, Vincent,Joubert, Laurent,Da?ch, Adam
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- Synthesis of soft alkyl phenolic ether prodrugs using Mitsunobu chemistry
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The synthesis of soft alkyl phenolic ether prodrugs in excellent yields has been reported by coupling a phenol with a hydroxymethylimide using Mitsunobu chemistry. The imides used in this study include saccharin, phthalimide, succinimide and two other compounds containing acidic imide-like N-H groups, benzotriazole, and imidazole.
- Majumdar, Susruta,Juntunen, Juha,Sivendran, Sashi,Bharti, Neelam,Sloan
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- Cyclic amide derivatives as potential prodrugs. Synthesis and evaluation of N-hydroxymethylphthalimide esters of some non-steroidal anti-inflammatory carboxylic acid drugs
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N-Hydroxymethylphthalimide (HMPhI) esters 5a-d of some nonsteroidal anti-inflammatory drugs were synthesized and evaluated as potential prodrugs with the aim of depressing the gastrotoxicity of the parent drugs by temporarily masking the carboxylic acid function. The ester prodrugs were synthesized through condensation of N-hydroxymethylphthalimide and the mixed carboxylic-carbonic anhydride intermediate or the corresponding acid chloride of the parent acid. Their structures were confirmed by 1H-NMR spectra and the purity has been assessed by TLC and elemental analyses. An HPLC method has been developed for investigation of the hydrolysis kinetics in aqueous buffer solutions and in 80% rabbit plasma. The lipophilicity parameters log P and log k' were determined and showed that the prodrugs were found to be more lipophilic (log P > 2) than the parent drugs. A considerable chemical stability of all compounds (t( 1/4 ) = 4.7-21.9 h) has been observed in non-enzymatic simulated gastric fluid (hydrochloric acid buffer of pH 1.3), while at pH 7.4 only prodrugs 5b-d are sufficiently stable (t( 1/4 ) ~3-5 h). Meanwhile, rapid conversion to the parent drugs 3a-d was observed in 80% rabbit plasma (t( 1/4 ) ~1.0-11.5 min). Potential ulcerogenicity on rat stomach mucosa of the prodrugs and the parent drugs after oral administration for 4 days was studied using a scanning electron microscope. Gross observations and scanning electro-micrographs showed that the prodrugs are significantly less irritating to gastric mucosa than the parent NSAIDs. This result suggests that N-hydroxymethylphthalimide esters may be useful as nonulcerogenic prodrug forms for acidic NSAIDs.
- Omar, Farghaly A.
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- The novel product of cathodic reduction of phthalimide anion
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Cathodic reduction of phthalimide anion in methanol was studied. The novel product, N-hydroxymethyl-3-hydroxyphthalimidine, was found. Full characterization of this new compound was carried out by means of NMR, FT- IR, MS, and X-ray crystallography. The mechanism of electrolytic formation of N-hydroxymethyl-3-hydroxyphthalimidine is proposed.
- Orzeszko, Andrzej,Maurin, Jan K.,Niedzwiecka-Kornas, Anna,Kazimierczuk, Zygmunt
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- Interrupting the Barton?McCombie reaction: Aqueous deoxygenative trifluoromethylation of o-alkyl thiocarbonates
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The site-selective trifluoromethylation of aliphatic systems remains an important challenge. This work describes a light-driven, copper-mediated trifluoromethylation of O-alkyl thiocarbonates. The reaction provides broad functional group tolerance (e.g., alkyne, alkene, phenol, free alcohol, electron-rich and -deficient arenes), thereby offering orthogonality and practicality for trifluoromethylation. A radical organometallic mechanism is proposed.
- Liu, Zhi-Yun,Cook, Silas P.
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supporting information
p. 808 - 813
(2021/02/01)
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- Synthetic method N - hydroxymethyl phthalimide
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The invention discloses a method for synthesizing N - hydroxymethyl phthalimide, wherein phthalimide and solid paraformaldehyde are used as raw materials, water is used as a solvent, and N - hydroxymethyl phthalimide is prepared through reflux reaction. The filtered water produced by the reaction does not need to be treated and can be recycled to the next batch production, and the process itself realizes zero emission. The solid polyformaldehyde is used in the invention, so that the raw materials are transported. The links of storage, use and the like are safe and reliable, VOCS emission is reduced, and the sustainable development direction of clean production is represented. The process realizes the molar conversion rate of up to 98%, and the purity of the product reaches 99% or above.
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Paragraph 0011-0021
(2021/08/25)
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- Design of a "two-in-One" Mutant-Selective Epidermal Growth Factor Receptor Inhibitor That Spans the Orthosteric and Allosteric Sites
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Inhibitors targeting the epidermal growth factor receptor (EGFR) are an effective therapy for patients with non-small cell lung cancer harboring drug-sensitive activating mutations in the EGFR kinase domain. Drug resistance due to treatment-acquired mutations has motivated the development of successive generations of inhibitors that bind in the ATP site. The third-generation agent osimertinib is now a first-line treatment for this disease. Recently, allosteric inhibitors have been developed to overcome drug-resistant mutations that confer a resistance to osimertinib. Here, we present the structure-guided design and synthesis of a mutant-selective lead compound, which consists of a pyridinyl imidazole-fused benzylisoindolinedione scaffold that simultaneously occupies the orthosteric and allosteric sites. The compound potently inhibits enzymatic activity in L858R/T790M/C797S mutant EGFR (4.9 nM), with a significantly lower activity for wild-type EGFR (47 nM). Additionally, this compound achieves modest cetuximab-independent and mutant-selective cellular efficacies on the L858R (1.2 μM) and L858R/T790M (4.4 μM) variants.
- Bauer, Nicolas,Berger, Benedict-Tilman,Berger, Lena M.,Beyett, Tyler S.,Corona, Cesear R.,Eck, Michael J.,Heppner, David E.,Knapp, Stefan,Laufer, Stefan A.,Rana, Jaimin K.,Robers, Matthew B.,Schmoker, Anna M.,Shin, Bo Hee,To, Ciric,Vasta, James D.,Wittlinger, Florian,Günther, Marcel,J?nne, Pasi A.
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- Synthesis method of N-hydroxymethyl-3, 4, 5, 6-tetrahydrophthalimide
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The invention discloses a synthesis method of N-hydroxymethyl-3, 4, 5, 6-tetrahydrophthalimide, which comprises the following steps of adding phthalimide and tetrabutylammonium bromide into water, dropwise adding a formaldehyde aqueous solution after adding, carrying out heat preservation reaction after dropwise adding, drying a solvent after reaction, recrystallizing by using an acetone aqueous solution, putting the recrystallized material into a high-pressure kettle, adding Pd/C, introducing hydrogen, conducting heat preservation and pressure retaining reaction, desiccating the solvent and recrystallizing toluene after the reaction is finished. According to the method, the two-step synthesis yield of the method can reach 80% or above, and the normalized content of a product liquid spectrum can reach 97.6%. The solvent used in the method can be used in a reaction system after being recycled, the reduction catalyst can be used for more than 10 times, and the method is simple in process, easy to operate, high in reaction selectivity, low in product yield, quality and energy consumption and free of phosphorus and nitrogen-containing wastewater, the production field environment is remarkably improved, and industrial clean production is facilitated.
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Paragraph 0010; 0030-0035; 0040-0045
(2021/06/13)
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- Synthesis and antiviral activities of some 2,3-disubstituted quinazoline derivatives
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In the search of new leads towards potent antiviral agents 2,3-disubstituted quinazoline derivatives were synthesized and tested for their antiviral activity. Anthranilic acid (1) on treatment with an aromatic acid chloride in pyridine gives 2-aryl-4-oxo-3H-benzoxazines (2) which in turn reacts with p-amino benzoic acid (PABA) to afford 2-aryl-3-p-carboxylatophenyl-4-oxo-3H-quinazolines (3). The compound 3 further reacts with amido alcohols in the presence of conc. H2SO4 resulting 3-[benzoic acid-(3-phthalimidomethyl/3-ethyl-3H-2-phenyl- 4-oxo-quinazolinyl/1-ethyl-7-hydroxy-4-methyl-2-oxo-quinolinyl)]-2-aryl-3H-quinazoline-4-ones (4). The resulting compounds 4a-f have been evaluated for their in vitro and in vivo antiviral activity against JEV and HSV type-I. The synthesized compounds were characterized through their physical and chemical analysis. The obtained results can be used as the key step for the building of novel chemical entities with interesting antiviral activity compare with the standard drugs.
- Gupta,Singh, Joginder,Kinger, Mayank,Arora, Avnish Kumar,Jaswal, Vivek Sheel
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p. 4379 - 4382
(2015/11/28)
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- Organocatalytic amination of alkyl ethers via n-Bu4NI/t-BuOOH-mediated intermolecular oxidative C(sp3)-N bond formation: Novel synthesis of hemiaminal ethers
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A novel method for constructing the hemiaminal ether framework under metal-free conditions has been developed. It involves direct organocatalytic amination of alkyl ethers through intermolecular oxidative C(sp3)-N bond formation, with t-BuOOH being the oxidant and n-Bu4NI as the catalyst.
- Dian, Longyang,Wang, Sisi,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
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supporting information
p. 11738 - 11741
(2015/05/20)
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- Efficient synthesis of N-protected 1-substituted homotaurines from a xanthate and olefins
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A series of N-protected 1-substituted homotaurines was synthesized efficiently from various olefins with O-ethyl S-2-phthalimidomethylxanthate as a sulfur-aminomethylation reagent via a radical addition and subsequent performic acid oxidation. The current method is a convenient and practical method for the synthesis of 1-substituted homotaurines with high yields and short synthetic route.
- Huang, Zhongyan,Xu, Jiaxi
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p. 1050 - 1056
(2013/02/23)
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- Aminomethylation of Michael acceptors: Complementary radical and polar approaches mediated by dialkylzincs
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Phtalimidomethyl iodide and substituted maleimidomethyl iodide were used as radical precursors in dialkylzinc-mediated radical addition to diethyl fumarate. The reactions led stereoselectively to functionalized pyrrolizidines. The radical mechanism was supported by spin-trapping experiments and rationalized by theoretical calculations. Radical additions, on the one hand, and carbozincation followed by transmetalation with copper(I), on the other, were shown to be complementary methods to achieve the formal aminomethylation of activated unsaturated compounds. Copyright
- Maury, Julien,Mouysset, Dominique,Feray, Laurence,Marque, Sylvain R. A.,Siri, Didier,Bertrand, Michele P.
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supporting information; experimental part
p. 3241 - 3247
(2012/05/20)
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- Synthesis of new cyclic imides derivatives with potential hypolipidemic activity
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Certain new nitrogen-substituted derivatives of cyclic imides phthalimide (a), 1,8-naphthalimide (b), and diphenimide (c), were synthesized aiming to obtain potent hypolipidemic agents. Thus, 2-(N-imido) propanoic acids, 2-(N-phthalimido)-2-methylpropionic acid, and their ethyl esters were synthesized (Target derivative A). Also their corresponding N-substituted-2-(N- imido) propionamides and 2-(N-phthalimido)-2-methylpropionamides were prepared (Target derivative B). In addition, N-phthalimidomethyleneoxy acetate was prepared. Some of the newly prepared compounds were subjected to 3D studies and were found to be superimposed on Clofibrate, which is the first generation of fibrate drugs. The preliminary evaluation of hypolipidemic activity of the newly prepared compounds against triton WR-1339-induced hyperlipidemia in rat showed that several derivatives have demonstrated significant lowering of serum total cholesterol and triglyceride levels at dose of 150 mg/kg/i.p. comparing with Fenofibrate which is one of the second generations of fibrate drugs. Springer Science+Business Media, LLC 2010.
- El-Zahabi, Mohamed A.,Gad, Laila M.,Bamanie, Faida H.,Al-Marzooki, Zohair
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experimental part
p. 75 - 84
(2012/06/01)
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- N-Alkoxymethylation of heterocyclic compounds with diethyl phosphite via cleavage of P-O bond
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N-Alkoxymethylation of heterocyclic compounds with diethyl phosphite via cleavage of P-O bond was investigated and a series of N3-ethoxymethylated heterocyclic compounds were synthesized. A mechanism in which diethyl phosphite acts as an efficient surrogate of ethanol was proposed and supported by several evidences.
- Quan, Zheng-Jun,Ren, Rong-Guo,Jia, Xiao-Dong,Da, Yu-Xia,Zhang, Zhang,Wang, Xi-Cun
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experimental part
p. 2462 - 2467
(2011/04/26)
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- Design, synthesis, and pharmacological evaluation of novel hybrid compounds to treat sickle cell disease symptoms
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A novel series of thalidomide derivatives (4a-f) designed by molecular hybridization were synthesized and evaluated in vitro and in vivo for their potential use in the oral treatment of sickle cell disease symptoms. Compounds 4a-f demonstrated analgesic, anti-inflammatory, and NO-donor properties. Compounds 4c and 4d were considered promising candidate drugs and were further evaluated in transgenic sickle cell mice to determine their capacity to reduce the levels of the proinflammatory cytokine tumor necrosis factor α (TNFα). Unlike hydroxyurea, the compounds reduced the concentrations of TNFα to levels similar to those induced with the control dexamethasone (300 μMol/kg). These compounds are novel lead drug candidates with multiple beneficial actions in the treatment of sickle cell disease symptoms and offer an alternative to hydroxyurea treatment.
- Dos Santos, Jean Leandro,Lanaro, Carolina,Lima, Ldia Moreira,Gambero, Sheley,Franco-Penteado, Carla Fernanda,Alexandre-Moreira, Magna Suzana,Wade, Marlene,Yerigenahally, Shobha,Kutlar, Abdullah,Meiler, Steffen E.,Costa, Fernando Ferreira,Chung, Manchin
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p. 5811 - 5819
(2011/10/09)
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- A novel and efficient route for the preparation of atorvastatin
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A novel and efficient synthetic method of atorvastatin was described. The key step of the synthesis was the construction of the olefin linkage between the chiral side chain and skeleton via a Horner-Wadsworth-Emmons reaction, resulting in the advanced intermediate of atorvastatin under hydrogenation of the olefin over Pd/C. This novel method is more useful for the practical synthesis of atorvastatin than its document reported methods.
- Gao, Jian,Guo, Yang Hui,Wang, Ya Ping,Wang, Xiang Jing,Xiang, Wen Sheng
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scheme or table
p. 1159 - 1162
(2012/01/16)
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- Enviro-economic synthesis of some phthalimide derivatives using microwave irradiation
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An environmentally benign, efficient and facile route is developed for the preparation of phthalimidc derivatives by using LiBr as a catalyst under solvent free condition and microwave exposure. In comparison to conventional synthesis involving tedious workup, excessive use of solvent and extra labour for separation and purification of compounds, the present method indicates operational simplicity, shorter reaction time and higher yields which can prove this procedure as a useful alternative for the synthesis of heterocycles. The potent antimicrobial effects of the synthesized compounds were investigated.
- Ameta, Chetna,Ameta, Rakshit,Tiwari, Urvashi,Punjabi,Ameta, Suresh C.
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experimental part
p. 827 - 833
(2012/04/04)
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- NMR study of the tautomeric behavior of N -(α-Aminoalkyl)tetrazoles
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N-(α-Aminoalkyl)tetrazoles exist in solution as equilibrium mixtures of N1 and N2 tautomers. The position of equilibrium depends significantly on the polarity of the solvent and the substituents in the tetrazole ring. Interconversion between individual tautomers is shown to proceed via tight ion-pair intermediates in which intramolecular recombination is faster than the intermolecular crossover since the latter probably requires solvent separation of ion-pair intermediates.
- Katritzky, Alan R.,El-Gendy, Bahaa El-Dien M.,Draghici, Bogdan,Hall, C. Dennis,Steel, Peter J.
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scheme or table
p. 6468 - 6476
(2010/12/24)
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- Convenient routes to trifluoromethyl-substituted pyridyl-isothiocyanates and isocyanates starting from 2,3-dichloro-5-trifluoromethyl pyridine
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A convenient preparative route for the synthesis of 3-chloro-2- (isothiocyanatoethyl)-5-(trifluoromethyl)pyridine (1) and 3-chloro-2- (isocyanatoethyl)-5-(trifluoromethyl)pyridine (2) has been developed, involving 5 steps starting from 2, 3-dichloro-5-(trifluoromethyl)pyridine (3). All intermediates and final products were obtained in good yields and purity. The structure of one intermediate, 2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl) malonate, was confirmed by X-ray crystallography.
- Fodor, Elena,Maftei, Catalin-Vasile,Mangalagiu, Ionel,Jones, Peter G.,Daniliuc, Constantin-Gabriel,Franz, M. Heiko,Neda, Ion
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scheme or table
p. 559 - 564
(2011/08/22)
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- An efficient and convenient transformation of α-haloketones to α-hydroxyketones using cesium formate
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A new safe and convenient transformation has been developed. In the presence of cesium formate in dry MeOH solution, α-haloketones underwent direct conversion reaction to afford α-hydroxyketone in excellent yields. Furthermore, this methodology can be extended and applied in 2-chloro-N-(1,3-diphenyl-1H-pyrazol-5-yl)acetamide, 2-chloro-N-(2,6-dimethylphen-yl)acetamide, 1-(bromomethylsulfonyl)benzene, and N-(bromomethyl)phthalimide to give the corresponding products in moderate to excellent yields. Crown Copyright
- Wong, Fung Fuh,Chang, Po-Wei,Lin, Hui-Chang,You, Bang-Jau,Huang, Jiann-Jyh,Lin, Shao-Kai
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supporting information; experimental part
p. 3452 - 3455
(2010/01/11)
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- Reaction of γ-dicarboxylic acids amides and imides with trifluoromethanesulfonamide and formaldehyde
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Three-component condensation of trifluoromethanesulfonamide with paraformaldehyde and succinamide depending on the reaction conditions led alongside bis(trifluoromethanesulfonamido)methane to the formation of a substitution product, bis[(trifluoromethylsulfonyl)aminomethyl]succinamide, or to a cyclization product, N-[trifluoromethylsulfonyl)aminomethyl]succinimide. The attempt to obtain the latter by the reaction of the trifluoromethanesulfonamide sodium salt CF3SO2NHNa with N-chloromethylsuccinimide unexpectedly resulted in N,N-bis(succinimidomethyl)-trifluoromethanesulfonamide. Analogously the reaction of CF3SO2NHNa with N-chloromethyl-phthalimide gave N,N-bis(phthalimidomethyl)trifluoromethanesulfonamide. The reaction of CF3SO2NHNa with succinimide and phthalimide in water and alcohol solution resulted in the ring opening and further transformation of the formed monosubstituted N-(trifluoromethylsulfonyl)amides of succinic and phthalic acids.
- Moskalik,Meshcheryakov,Shainyan
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experimental part
p. 1644 - 1650
(2010/04/27)
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- Synthesis and biological evaluation of 3-(phthalimidomethyl)-4-(5- substituted isoxazoline and pyrazoline) substituted benzanilides
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3-Phthalimidomethylbenzoic acids 2 were prepared by treating N-hydroxymethylplithalimide 1 with substituted benzoic acids. The corresponding acid chlorides 3 were condensed with 4-aminoacetophenone in the presence of anhydrous potassium carbonate to give 3-phthalimidomethyl-4-acetyl substituted benzanilides 4. The substituted benzanilide derivatives 4 were condensed with diverse aromatic aldehydes to afford the compounds 5. Compounds 5a 1-d7 on treatment with hydroxylamine hydrochloride in the presence of sodium acetate and with hydrazine dihydrochloride in the presence of sodium acetate afforded the title compounds 6a1-d7 and 7a1-a9, respectively. Compounds 6a1-d 1 and 7a1-a3 were screened for their antibacterial and antifungal activities and 6a1 and 7a1 for anthelmintic and hypoglycemic activities.
- Sahu,Azam, Afzal Md.,Banerjee,Choudhury,Sutradhar,Panda,Misro
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p. 1011 - 1015
(2008/09/19)
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- Solvent-free N-hydroxymethylation using formalin over basic alumina
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A convenient and high yield method for N-hydroxymethylation of amines with formalin over basic alumina under solvent-free conditions with microwave heating is described.
- Gupta, Rajive,Paul, Satya,Nanda, Puja
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p. 573 - 574
(2007/10/03)
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- Synthesis, characterization and biological activity of 1,3,4-substituted 2-azetidinones
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Amido/imido alcohol/2-phenyl-3-hydroxyethylquinazolin-4 (3H) -one 1 on treatment with benzoic acid in the presence of cone. H2SO4 yields m-(aralkylamido/imidoalkyl/2-phenyl-3-ethyl-3H-4-oxoquinazolinyl) benzoic acids 2. The acid chloride of 2 on reaction with hydrazine hydrate affords m-(aralkylamido/imidoalkyl/2-phenyl-3-ethyl-3H-4-oxo-quinazolinyl) benzoic acid hydrazides 4 which on condensation with an aromatic aldehyde in acetic acid gives m-(aralkylamido/imidoalkyl/2-phenyl-3-ethyl-3H-4-oxo- quinazolinyl) benzoic acid hydrazones 5. Compounds 5 undergo cyclization with phenoxy acetic acid in the presence of thionyl chloride in dry benzene to furnish 1-[m-(aralkylamido/imidoalkyl/2-phenyl-3-ethyl-3H-4-oxo-quinazolinyl- benzamido)]-3-phenoxy-4-phenyl-2-azetidinones 6. The antiviral and antifungal activities of 6 have been reported.
- Pandey,Gupta,Upadhyay, Mrinalini,Upadhyay, Mridula,Singh,Tandon, Meenal
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p. 158 - 162
(2007/10/03)
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- Photolysis experiments on phosmet, an organophosphorus insecticide
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The organophosphorus insecticide phosmet is used in plant protection as well as against parasites on animals. Phosmet showed numerous photoinduced reaction pathways, which first were studied in the presence of model environments for animal fur lipids (e.g
- Sinderhauf, Katrin,Schwack, Wolfgang
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p. 5990 - 5995
(2007/10/03)
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- Rapid and convenient microwave-assisted synthesis of aromatic imides and N-hydroxymethylimides
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Extremely simple high-yielding and rapid microwave-assisted synthesis of wide array of aromatic mono and diimides and mono- and bis-N-hydroxymethylimides is reported.
- Kacprzak, Karol
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p. 1499 - 1507
(2007/10/03)
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- Use of improved cyan pigments in electrophotographic toners and developers, powder coatings and inkjet inks
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The present invention relates to the use of a CuPc composition consisting essentially of CuPc, e.g., C.I. Pigment Blue 15:3, and a hydroxymethylphthalimido CuPc, as a colorant in electrophotographic toners and developers, powders and powder coating materials, electret materials, inkjet inks, and color filters, wherein the phthalocyanines have a particle morphology with an average length-to-width ratio of more than 2.5:1.
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- Mechanism of Hydrolysis of O-Imidomethyl Derivatives of Phenols
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Three series of O-imidomethyl derivatives of para-substituted phenolic compounds were synthesized and their rates of hydrolysis were studied.Saccharin, phthalimide, and succinimide served as the imide portions of the derivatives.Their rates of hydrolysis were found to be first order with respect to hydroxide from pH 7.0 to 10 or 11 and dependent on the acidity (leaving group potential) of both the imide and the phenol portions.The more acidic the imide or the phenol, the faster the rate of hydrolysis.However, the rates of hydrolysis were more sensitive to the acidity of the phenol.Trapping experiments with cyanide also suggested that the phenol anion was functioning as the leaving group in what is apparently an SN2 reaction.An amide derivative was found to hydrolyze more slowly than predicted from the analogous series and the pKa of the amide.This result is apparently due partially stereoelectronic constraints in the imide series that cause the CH2-O bond to be oriented more nearly perpendicular to the plane of the C(=O)N group and hence more accessible to nucleophilic attack.
- Getz, John J.,Prankerd, Richard J.,Sloan, Kenneth B.
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p. 4913 - 4918
(2007/10/02)
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- PHOTOCHEMICAL CLEAVAGE OF N-(HYDROPEROXYALKYL)PHTHALIMIDES BY INTRAMOLECULAR ENERGY TRANSFER
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An unusual type of selective photocleavage of N-(hydroperoxyalkyl)phthalimides by intramolecular energy transfer has been described.
- Matsugo, Seiichi,Saito, Isao
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p. 2949 - 2950
(2007/10/02)
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- Photochemical Cyclisation of Phthalimide Mannich Bases
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Ultraviolet irradiation of Mannich bases derived from phthalimide, formaldehyde, and a secondary amine leads to cyclised products containing a new imidazolidine ring.The reaction is much less efficient when the secondary amine has an aromatic group adjacent to the nitrogen atom.Exceptionally, the Mannich base derived from 3-pyrroline does not cyclise but undergoes an internal oxidation-reduction reaction to give a substituted pyrrole.
- Coyle, John D.,Newport, Graham L.
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