Synthesis and reversal effect of a novel N-substituted phthalimidesugar on doxorubicin resistant of human breast cancer cells

Thalidomide （α-N-phthalimido-glutarimide, TLD） is a kind of anti-angiogenic and anti-inflammatory drug, and showed effects in the treatment of several disease entities. In this study, the biological effects of a novel N-sugar substituted phthalimide （STA-35） on the regulation of multidrug resistance （MDR） to doxorubicin （ADR） were investigated. The proliferation of cancer cells was detected by a SRB assay. The activity of P-glycoprotein （P-gp） was determined by a Flow cytometry. The expression of P-gp was measured by western blotting. The results showed that STA-35 inhibited the proliferation of human breast cancer cell line MCF-7 and its ADR resistant cell line MCF-7/ADR, and the relative resistance was only 1.19. Meanwhile, STA-35 could sensitize the cytotoxicity of ADR in MCF-7/ADR cells. In addition, we found that STA-35 reduced the activity of P-gp by suppressing the P-gp expression, which was indicated by the increase in the accumulation of rhodamine 123 in MCF-7/ADR cells. These results suggested a promising application of STA-35 as the MDR reversing agent. The underlying mechanism of the effects might be attributed to the inhibition of P-gp.

2,4,6-Trichloro-1,3,5-triazine/dimethylformamide as an efficient reagent for one-pot conversion of alcohols into N-alkylphthalimides

An efficient and mild method for the direct conversion of alcohols into N-alkylphthalimides using 2,4,6-trichloro-1,3,5-triazine and dimethylformamide was described.The reaction was preceded via(alcoxymethylene) dimethylammonium chloride intermediate and produced corresponding N-alkylphthalimides in good-to-excellent yields.

Synthesis and cytotoxic activity of heterocycle-substituted phthalimide derivatives

A series of heterocycle-substituted phthalimide derivatives were synthesized.Structurally diverse derivatives with heterocyclic rings,including furan,imidazo[1,2-a]pyridine,1,3,4-thiadiazine,imidazo[2,1-b][1,3,4]thiadiazine,pyrazole,1,2,4-triazolo[3,4- b][1,3,4]thiadiazine,thiazole and thiazoline,were obtained by the reactions ofα-bromoketone intermediate with various nucleophiles containing oxygen,nitrogen and sulfur atom.Their cytotoxic activity was also evaluated against five human cancer cell lines in vitro.

PHOTO-CIDNP STUDIES OF PHTHALIMIDE DERIVATIVES IN THE PRESENCE OF TRIETHYLAMINE

The photoreactivity of some phthalimides was tested by CIDNP studies on the reactions with triethylamine.

An Unusual Reductive Ring-opening Reaction of Phthalimide with Sodium Hydride in DMF

An unusual reductive ring-opening reaction of phthalimide with sodium hydride in anhydrous DMF was observed for the first time. The presumed mechanism was described in detail.

Ionic liquid [bmim][BF_4] acts as solvent and promoter for synthesis of halo-containing N-arylphthalimides

A new synthetic process of N-arylphthalimide and halo-containing N-arylphthalimides through the reaction between phthalic anhydride and aromatic amines bearing halo groups in [bmim][BF4] was described, ionic liquid [bmim][BF4] acted as the dual role of solvent and promoter.

Fragmentation of Some Substituted Phthalimides on Electron Impact Ionization

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The Synthesis of Arylsulfonylphthalimides and Their Reactions with Several Amines in Acetonitrile

In this study, several N-(p-substituted-arylsulfonyl)phthalimides (1a-e) were synthesized. The synthesized compounds were then examined with respect to their substitution reactions with t-butylamine, diethylamine, cyclohexylamine, and trans-1,2-diaminocyclohexane in acetonitrile. In order to determine the mechanism, substituent effect, activation entropy, and nucleophile effect were used as criteria.

Synthesis, Spectral Characterization and Ligation of <i>N</i>-[2-(Phenylseleno)ethyl]phthalimide

PhSe-Na+ generated in situ by reduction of PhSeSePh, with sodium borohydride on reaction with N-(2-bromoethyl) phthalimide in N2 atmosphere results in the formation of N-[2-(phenylseleno)ethyl]phthalimide (L1). The title compound has been characterized by elemental analysis, FT-IR, 1H and 13C NMR techniques. The crystal structure of L1 has been solved by direct methods and refined by full-matrix least squares. The ligand L1 crystallize in the monoclinic space group. Selenium forms two Se-C linkages, one is due to Se-Calkyl and the other one to Se-Caryl. Further, the ligation reaction of L1 with complex 1 is also explored whose identities are characterized by spectroscopic techniques.

Solvent-Free Synthesis of 5-Alkenyl-2,2-butylidene-1, 3-dioxane-4,6-diones under Ultrasonic Irradiation with o-Phthalimide-N-Sulfonic Acid as Catalyst

5-Alkenyl-2,2-butylidene-1,3-dioxane-4,6-diones were synthesized by the Knoevenagel condensation reaction of aromatic aldehydes with 2,2-butylidene-1,3-dioxane-4,6-dione using o-phthalimide-N-sulfonic acid as catalyst, without solvent under ultrasonic irradiation. The present method has some notable advantages such as mild reaction conditions, short reaction times, less catalyst dosage and high yields with the green aspects by avoiding toxic catalysts and solvents. Further, the catalyst can be reused for five times without any noticeable decrease in the catalytic activity.

Synthesis, Characterization and Antiepileptic Activity of Some New N-Substituted Phthalimide Analogs

The present study was designed to investigate the anticonvulsant effect of series phthalimides possessing an N-aromatic amines moiety substituted at position 2 （2-7）. The compounds synthesized using phthalic anhydride and various amines in reflux synthesizer. The chemical structures of the titled compound were confirmed by physical and spectra analysis. All the synthesized compounds were evaluated in vivo for antiepileptic activity by using standard experimental models. Compounds： 2-（3H-1, 2, 4-Triazole-3-y） isoindoline-1, 3-dione （2）, Ethyl-4（1, 3-dioxoisoindoline-2-yl） benzoate 3 and 2-（4-nitrophenyl） isoindoline-1,3dione （7） were found significantly （P 〈 0.01-0.00001） delayed the onset and antagonized picrotoxin-induced seizures.

双酚A型苯酰亚胺溶解度测定及关联

用平衡法测定了273.15~353.15 K下双酚A型苯酰亚胺在不同溶剂中的溶解度。结果表明,随着温度的升高,苯酰亚胺溶解度增大,通过改进的Apelblat方程,λh方程和Wilson活度系数方程关联该物质的溶解度数据,相关系数分别不低于0.9880,0.9771,0.9394,3种模型均能较好地拟合苯酰亚胺的溶解度数据,对比几种模型的拟合结果,改进的Apelblat方程拟合效果最好,其中ARD≤6.18%,RSMD≤2.39,且R^(2)≥0.9880,为结晶过程的设计提供热力学依据。

松油烯基邻苯二甲酰亚胺衍生物的合成及其除草活性研究

以α-松油烯(1)为起始原料,通过与丁炔二酸二甲酯发生Alder-Rickert反应制备了松油烯基丁烯二酸二甲酯(2),并通过闭环反应合成了松油烯基邻苯二甲酸酐(3),继而与一系列芳胺化合物发生取代反应,合成了13个新型结构的松油烯基邻苯二甲酰亚胺衍生物(4a~4m)。通过红外光谱、质谱、核磁共振氢谱和碳谱等手段对目标化合物的结构进行了表征,相关表征数据表明目标化合物4a~4m成功合成。初步的除草活性测试结果表明:在1.5 kg/hm^(2)施药量下,当采用茎叶处理时,大部分化合物对稗草、马唐、苘麻和反枝苋均具有一定的除草活性,其中化合物4b(R=p-CH_(3))和4c(R=p-OCH_(3))对苘麻的抑制活性最好,抑制率分别为62.2%和64.0%,均达到B级。

Photoinduced generation of alkyl and phthalimide nitrogen radicals from N-hydroxyphthalimide esters for the synthesis of benzophenone-type bioisosteres

N-Hydroxyphthalimide(NHPI)esters have emerged as powerful sources of alkyl radicals generated by single-electron transfer,but homolysis of NHPI ester to produce an alkyl radical and a phthalimide nitrogen radical is still in its infancy.In this study,we developed a light-induced method for generation of alkyl and phthalimide nitrogen radicals from NHPI esters and subsequent reactions of the radicals with[1.1.1]propellane and aryl aldehydes for rapid generation of bicycle[1.1.1]pentane ketones.This method does not require metals or photosensitizers,features a broad substrate scope(90 examples)and excellent functional group tolerance,and can be used for the functionalization of structurally complex natural products and drugs.Mechanistic investigations indicate that the reaction involves photoinduced homolytic cleavage of the Cs_(2)CO_(3)-NHPI ester complex to produce alkyl and phthalimide nitrogen radicals and subsequent hydrogen atom transfer between the phthalimide nitrogen radical and the aldehyde to generate an acyl radical.

染料木素邻苯二甲酰亚胺衍生物合成及其抗乳腺癌活性研究

目的研究染料木素邻苯二甲酰亚胺衍生物的体外抗乳腺癌活性及其作用机制。方法合成染料木素邻苯二甲酰亚胺衍生物,通过MTT法检测其对癌细胞株MCF-7、MBA-MD-231、MBA-MD-435增殖抑制作用;并通过分子对接的方法探讨染料木素邻苯二甲酰亚胺衍生物与雌激素受体α(ERα)的作用方式。结果合成了3个染料木素邻苯二甲酰亚胺衍生物,并对其生物活性及抗乳腺癌机制进行了验证。结论染料木素邻苯二甲酰亚胺衍生物具有较强的抗乳腺癌活性,可能与竞争性抑制ERα等机制有关。

CATALYSIS OF POLYSTYRENE N-HYDROXYL SULFONAMIDE FOR ESTERIFICATION OF BUTANOL WITH ACETIC ANHYDRIDE

Polystyrene N-hydroxyl sulfonamide resin 1 was prepared and used to catalyze the esterification of n-butanol and acetic anhydride. The mechanism of catalytic esterification proved by IR spectra of the resins was found that O-H and N-H of the N-hydroxyl sulfonamide resin reacted with the acetic anhydride respectively to form the active intermediate polystyrene N,O-diacetyl sulfonamate which was cleaved by n-butanol to produce butyl acetate. The catalytic esterification by resin 1 was in good agreement with the kinetic model of 揵i-bi-ping-pong?mechanism.

Synthesis of Novel Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors-1-(3-Phthalimido-2-oxobutyl)-4-Substituted-phenylpiperazines

We have designed and synthesized a series of new phthalimidopiperazines, biological activity test show that the target compounds(Ic, Ie, ii) can inhibit HIV-I RT with IC50 20.0, 43.8, and 63.7 mu M, respectively.

FLOTATION BEHAVIOUR AND MECHANISM OF BASTNAESITE WITH N-HYDROXYL PHTHALICIMIDE

The flotation behaviour and mechanism of bastnaesite with N-hydroxyl phthalicimide were investigated by ξ-potential measurement,infrared spectrum and quantum chemistry calculation.The results show that 3 oxygen atoms from N-hydroxyl phthalicirnide chelate the rare earth ions on the surface of bastnaesite to form double five-chain O=C-N-O- RE(Ⅲ)-O chelate which is chemically adsorbed on the surface of bastnasite,thus making N-hydroxyl phthalicimide an effective collector for bastnaesite.

Synthesis and structure characterization of a novel series of N-alkylphthalimidylaminocarbonylmethoxylcalix[4]arenes

A novel series of N-alkylphthalimidylaminocarbonylmethoxylcalix[4]arenes with the reaction between 4-（N-bromoacetyla- mino）-phthalimide derivatives and calix[4]arene has been synthesized and structurally characterized by IR, IH NMR and MS. From their analysis data, it was found that compounds 7a-Td adopted a cone conformation.

金属/电催化NHPI烷基酯脱羧构筑碳-碳键研究进展

近年来,由于自由基反应在碳-碳键构筑中独特的作用,有机化学家相继开发了各种自由基前体化合物。N-取代丁二酰亚胺(NHPI)还原活性酯作为一种重要的自由基前体化合物,近期受到了有机化学家的广泛关注。本文综述了该领域的最新研究进展,主要介绍在电、金属催化条件下,自由基诱导N-取代丁二酰亚胺酯类化合物参与的碳-碳键构筑。