Pub Date : 2023-11-01DOI: 10.1177/17475198231218387
M. Farhan, M. Al-Jumaili, E. A. Bakr
New bis-heterocyclic compounds were synthesized by reacting two moles of isoniazid, cyanoguanidine and 2-aminophenol with one mole of a bis-chalcone. The bis-chalcone was prepared from the reaction between acetophenone and terephthalaldehyde using sodium hydroxide. All the prepared compounds were purified and their structures confirmed by spectroscopic methods, such as Fourier transform infrared, 1H NMR and 13C NMR. Their effect against three types of bacteria (negative and positive) for gram stain Escherichia coli, Klebsiella pneumoniae and Staphylococcus aureus was studied and discussed. The results obtained were compared with those of gentamicin, chloramphenicol and amikacin. Our new compounds showed clear inhibition of the different bacteria types with some of them exceeding the effects of the drugs possibly due to the bis-heterocyclic structures of our compounds. The effects of our compounds on the growth of certain types of fungi, Trichophyton and Aspergillus, were studied, showing inhibition of the growth of these fungi at high concentrations.
{"title":"New bis-heterocyclic structures: Synthesis, characterization and biological activity","authors":"M. Farhan, M. Al-Jumaili, E. A. Bakr","doi":"10.1177/17475198231218387","DOIUrl":"https://doi.org/10.1177/17475198231218387","url":null,"abstract":"New bis-heterocyclic compounds were synthesized by reacting two moles of isoniazid, cyanoguanidine and 2-aminophenol with one mole of a bis-chalcone. The bis-chalcone was prepared from the reaction between acetophenone and terephthalaldehyde using sodium hydroxide. All the prepared compounds were purified and their structures confirmed by spectroscopic methods, such as Fourier transform infrared, 1H NMR and 13C NMR. Their effect against three types of bacteria (negative and positive) for gram stain Escherichia coli, Klebsiella pneumoniae and Staphylococcus aureus was studied and discussed. The results obtained were compared with those of gentamicin, chloramphenicol and amikacin. Our new compounds showed clear inhibition of the different bacteria types with some of them exceeding the effects of the drugs possibly due to the bis-heterocyclic structures of our compounds. The effects of our compounds on the growth of certain types of fungi, Trichophyton and Aspergillus, were studied, showing inhibition of the growth of these fungi at high concentrations.","PeriodicalId":15323,"journal":{"name":"Journal of Chemical Research","volume":"100 1","pages":""},"PeriodicalIF":1.4,"publicationDate":"2023-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139300247","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-11-01DOI: 10.1177/17475198231221434
Hayat MR Mehdi, H. A. Abdulhassan, Baqer A. Almayyahi, B. A. Saleh, Natalie L Hewitt, Gamal A. El‐Hiti
The whitefly Bemisia tabaci is a destructive insect pest that infects many plants. Finding solutions to reduce the damage associated with whiteflies and their widespread use is of great interest. Therefore, the current research aims to synthesize four polyesters containing a curcumin ring system and investigate their effects against B. tabaci. The synthesized polyesters killed whitefly eggs and their nymphs. Polyester containing a methoxy group (P3) showed the best performance (80.3%) toward the mortality of insect eggs among all the tested polymers. Polyester containing a 4-hydroxybenzaldehyde moiety (P2) showed the lowest mortality efficiency (50.9%) against whitefly eggs after 72 h of treatment. The effect of polyester concentration on the mortality of insect nymphs varied during the treatment period. The mortality rate of nymphs after P3 treatment was the highest (78.0%), whereas that after P2 treatment was the lowest (46.9%). The polyester type, concentration, and treatment duration significantly affected the insect nymph mortality rate. Polyester containing a methoxy group for 72 h resulted in the highest mortality rate (90.0%) against whitefly nymphs.
{"title":"Evaluation of the effect of polyesters containing a curcumin ring system on Bemisia tabaci","authors":"Hayat MR Mehdi, H. A. Abdulhassan, Baqer A. Almayyahi, B. A. Saleh, Natalie L Hewitt, Gamal A. El‐Hiti","doi":"10.1177/17475198231221434","DOIUrl":"https://doi.org/10.1177/17475198231221434","url":null,"abstract":"The whitefly Bemisia tabaci is a destructive insect pest that infects many plants. Finding solutions to reduce the damage associated with whiteflies and their widespread use is of great interest. Therefore, the current research aims to synthesize four polyesters containing a curcumin ring system and investigate their effects against B. tabaci. The synthesized polyesters killed whitefly eggs and their nymphs. Polyester containing a methoxy group (P3) showed the best performance (80.3%) toward the mortality of insect eggs among all the tested polymers. Polyester containing a 4-hydroxybenzaldehyde moiety (P2) showed the lowest mortality efficiency (50.9%) against whitefly eggs after 72 h of treatment. The effect of polyester concentration on the mortality of insect nymphs varied during the treatment period. The mortality rate of nymphs after P3 treatment was the highest (78.0%), whereas that after P2 treatment was the lowest (46.9%). The polyester type, concentration, and treatment duration significantly affected the insect nymph mortality rate. Polyester containing a methoxy group for 72 h resulted in the highest mortality rate (90.0%) against whitefly nymphs.","PeriodicalId":15323,"journal":{"name":"Journal of Chemical Research","volume":"20 1","pages":""},"PeriodicalIF":1.4,"publicationDate":"2023-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139302878","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-11-01DOI: 10.1177/17475198231168948
Fatma Aytan Kılıçarslan, I. Erden
As a result of the increasing in the world population, the development of technology to meet increasing energy needs and to find other energy resources is one of the biggest tests for society. Triphenylamine and its derivatives attract the attention of researchers due to their many applications such as in solar cells, electronics, and medicine. The nitro group, an electron-accepting chromophore, is a good candidate for D–π–A sensitizers for dye-sensitized solar cells. In this study, the power conversion efficiency of an anchor nitro group in dye-sensitized solar cells and the synthesis of new compounds containing a donor triphenylamine unit, functionalized with a nitro group as an anchor group and possessing a π-conjugated structure are investigated. The structures of the compounds are determined by FTIR, UV-Vis spectrometry, NMR, and MS. Considering the photovoltaic performance of the produced dye-sensitized solar cell devices, the anchor group, and its acceptor effect, it is observed that the efficiency increases, in the order, F2 < F1. The highest power conversion efficiency value of 0.45% was obtained with the F1-based dye-sensitized solar cell under amplitude modulation irradiation (100 mW cm−2). From the obtained results, it can be seen that an increase in the number of electron-donor groups located close to the anchor group increases the power conversion efficiency.
随着世界人口的不断增长，开发技术以满足日益增长的能源需求并寻找其他能源资源是社会面临的最大考验之一。三苯胺及其衍生物因其在太阳能电池、电子学和医学等领域的广泛应用而备受研究人员的关注。硝基是一种接受电子的发色团，是染料敏化太阳能电池 D-π-A 感光剂的良好候选材料。本研究考察了染料敏化太阳能电池中锚定硝基的功率转换效率，并合成了含有供体三苯胺单元、以硝基作为锚定基团并具有π-共轭结构的新化合物。化合物的结构是通过傅立叶变换红外光谱、紫外可见光谱、核磁共振和质谱测定的。考虑到所制备的染料敏化太阳能电池器件的光伏性能、锚基团及其受体效应，可以观察到效率按照 F2 < F1 的顺序增加。在调幅辐照（100 mW cm-2）条件下，基于 F1 的染料敏化太阳能电池的功率转换效率最高，达到 0.45%。从所得结果可以看出，靠近锚基团的电子-供体基团数量的增加会提高功率转换效率。
{"title":"Investigation of the effect of a nitro group as an anchor group in dye-sensitized solar cells","authors":"Fatma Aytan Kılıçarslan, I. Erden","doi":"10.1177/17475198231168948","DOIUrl":"https://doi.org/10.1177/17475198231168948","url":null,"abstract":"As a result of the increasing in the world population, the development of technology to meet increasing energy needs and to find other energy resources is one of the biggest tests for society. Triphenylamine and its derivatives attract the attention of researchers due to their many applications such as in solar cells, electronics, and medicine. The nitro group, an electron-accepting chromophore, is a good candidate for D–π–A sensitizers for dye-sensitized solar cells. In this study, the power conversion efficiency of an anchor nitro group in dye-sensitized solar cells and the synthesis of new compounds containing a donor triphenylamine unit, functionalized with a nitro group as an anchor group and possessing a π-conjugated structure are investigated. The structures of the compounds are determined by FTIR, UV-Vis spectrometry, NMR, and MS. Considering the photovoltaic performance of the produced dye-sensitized solar cell devices, the anchor group, and its acceptor effect, it is observed that the efficiency increases, in the order, F2 < F1. The highest power conversion efficiency value of 0.45% was obtained with the F1-based dye-sensitized solar cell under amplitude modulation irradiation (100 mW cm−2). From the obtained results, it can be seen that an increase in the number of electron-donor groups located close to the anchor group increases the power conversion efficiency.","PeriodicalId":15323,"journal":{"name":"Journal of Chemical Research","volume":"1 1","pages":""},"PeriodicalIF":1.4,"publicationDate":"2023-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139303076","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-11-01DOI: 10.1177/17475198231216422
Ianina Graur, Tatiana Bespalova, Vasilii Graur, V. Tsapkov, O. Garbuz, E. Melnic, Pavlina Bourosh, A. Gulea
2-[1-Oxo-1-(piperidin-1-yl)propan-2-ylidene]- N-(prop-2-en-1-yl)hydrazinecarbothioamide (HL) and its six coordination compounds [Cu(L)X] (X = Cl− (1), NO3− (2)), [Cu(A)(L)NO3](A = 1,10-Phen (3), 2,2′-Bpy (4)), [Ni(HL)2](NO3)2 (5), and [Fe(L)2]Cl (6) are synthesized and characterized by elemental analysis, Fourier-transform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR), and single-crystal X-ray crystallography. Uncoordinated thiosemicarbazone HL shows higher antioxidant activity against 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS+•) cation radicals compared with most of the other complexes. Complex 5 is the most active and its activity exceeds that of HL and is close to that of trolox, which is used in medicine as an antioxidant. The introduction of N-heteroaromatic bases (1,10-phenanthroline and 2,2′-bipyridine) into the inner sphere of the complex [Cu(L)NO3] did not lead to an increase in antioxidant activity.
{"title":"A new thiosemicarbazone and its 3d metal complexes: Synthetic, structural, and antioxidant studies","authors":"Ianina Graur, Tatiana Bespalova, Vasilii Graur, V. Tsapkov, O. Garbuz, E. Melnic, Pavlina Bourosh, A. Gulea","doi":"10.1177/17475198231216422","DOIUrl":"https://doi.org/10.1177/17475198231216422","url":null,"abstract":"2-[1-Oxo-1-(piperidin-1-yl)propan-2-ylidene]- N-(prop-2-en-1-yl)hydrazinecarbothioamide (HL) and its six coordination compounds [Cu(L)X] (X = Cl− (1), NO3− (2)), [Cu(A)(L)NO3](A = 1,10-Phen (3), 2,2′-Bpy (4)), [Ni(HL)2](NO3)2 (5), and [Fe(L)2]Cl (6) are synthesized and characterized by elemental analysis, Fourier-transform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR), and single-crystal X-ray crystallography. Uncoordinated thiosemicarbazone HL shows higher antioxidant activity against 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS+•) cation radicals compared with most of the other complexes. Complex 5 is the most active and its activity exceeds that of HL and is close to that of trolox, which is used in medicine as an antioxidant. The introduction of N-heteroaromatic bases (1,10-phenanthroline and 2,2′-bipyridine) into the inner sphere of the complex [Cu(L)NO3] did not lead to an increase in antioxidant activity.","PeriodicalId":15323,"journal":{"name":"Journal of Chemical Research","volume":"90 1","pages":""},"PeriodicalIF":1.4,"publicationDate":"2023-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139303913","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-11-01DOI: 10.1177/17475198231212143
Nguyen Van Phuoc, Hao Le Quoc, Thi Tuu Tran, Lam Van Tan, B. Hoang
Activated carbon is produced from Burmese grapes using NaOH as the activator under microwave irradiation. Through scanning electron microscopy, Fourier-transform infrared spectroscopy, X-ray diffraction analysis, and Brunauer–Emmett–Teller analysis methods, the activated carbon material is found to have a rough and uneven surface with the formation of pores, an amorphous structure, and possesses hydroxy, C–H, carbonyl, alkene, and ether functional groups. The surface area (478.5 m2 g−1) and pore size (about 3.4 nm) are calculated from the adsorption N2 equation. The adsorption mechanism of activated carbon is evaluated and follows a pseudo-first-order kinetic model (large single adsorption) and the Langmuir isotherm model (physical interaction). The factors affecting ciprofloxacin adsorption using activated carbon derived from Burmese grapes are also evaluated and optimized by the response surface method model based on influencing factors including the contact time, the solution pH, the antibiotic concentration, and the material dosage. The optimal parameters are as follows: pH = 6.26, concentration = 58.9 mg L−1, content = 0.15 g L−1, time = 54 min. Under optimal conditions, the adsorption capacity predicted from the model is 191.33 mg g−1 with an efficiency of 41.35%.
{"title":"Optimization of ciprofloxacin removal by response surface methodology using activated carbon from Burmese grape obtained from Vietnam","authors":"Nguyen Van Phuoc, Hao Le Quoc, Thi Tuu Tran, Lam Van Tan, B. Hoang","doi":"10.1177/17475198231212143","DOIUrl":"https://doi.org/10.1177/17475198231212143","url":null,"abstract":"Activated carbon is produced from Burmese grapes using NaOH as the activator under microwave irradiation. Through scanning electron microscopy, Fourier-transform infrared spectroscopy, X-ray diffraction analysis, and Brunauer–Emmett–Teller analysis methods, the activated carbon material is found to have a rough and uneven surface with the formation of pores, an amorphous structure, and possesses hydroxy, C–H, carbonyl, alkene, and ether functional groups. The surface area (478.5 m2 g−1) and pore size (about 3.4 nm) are calculated from the adsorption N2 equation. The adsorption mechanism of activated carbon is evaluated and follows a pseudo-first-order kinetic model (large single adsorption) and the Langmuir isotherm model (physical interaction). The factors affecting ciprofloxacin adsorption using activated carbon derived from Burmese grapes are also evaluated and optimized by the response surface method model based on influencing factors including the contact time, the solution pH, the antibiotic concentration, and the material dosage. The optimal parameters are as follows: pH = 6.26, concentration = 58.9 mg L−1, content = 0.15 g L−1, time = 54 min. Under optimal conditions, the adsorption capacity predicted from the model is 191.33 mg g−1 with an efficiency of 41.35%.","PeriodicalId":15323,"journal":{"name":"Journal of Chemical Research","volume":"139 1","pages":""},"PeriodicalIF":1.4,"publicationDate":"2023-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139292080","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-11-01DOI: 10.1177/17475198231221458
Walaa H Ali, Mohammed A Bahili, B. A. Saleh, Gamal A. El‐Hiti
Polyether is a synthetic polymer that has low toxicity and, therefore, it is used in many applications. It can be used as a detergent, emulsifier, drug excipient, pesticide emulsifier, antiseptic, and papermaking additive agent. This study outlines the synthesis, characterization, and fluorescence evaluation of polyethers derived from curcumin analogs. Condensation polymerization of curcumin analogs and dibromoalkanes produces the corresponding polyethers. The Fourier-transform infrared and proton nuclear magnetic resonance spectroscopy confirmed the structures of the newly synthesized polyethers. The thermal stability and solubility of the synthesized polyethers of various solvents were investigated. They showed high stability at high temperatures as thermoplastics. The synthesized polyethers have fluorescent properties in solutions, and the absorption and intensity were dependent on the type of functional groups present in the polymers. The fluorination intensity of polyethers was found to be dependent on the presence of electron-donating groups, the pH of the solution, and the type of solvent used. One of the synthesized polyethers exhibited strong emissive properties at one or two specific wavelengths.
{"title":"Synthesis, characterization, and fluorescence properties of new polyethers derived from curcumin analogs","authors":"Walaa H Ali, Mohammed A Bahili, B. A. Saleh, Gamal A. El‐Hiti","doi":"10.1177/17475198231221458","DOIUrl":"https://doi.org/10.1177/17475198231221458","url":null,"abstract":"Polyether is a synthetic polymer that has low toxicity and, therefore, it is used in many applications. It can be used as a detergent, emulsifier, drug excipient, pesticide emulsifier, antiseptic, and papermaking additive agent. This study outlines the synthesis, characterization, and fluorescence evaluation of polyethers derived from curcumin analogs. Condensation polymerization of curcumin analogs and dibromoalkanes produces the corresponding polyethers. The Fourier-transform infrared and proton nuclear magnetic resonance spectroscopy confirmed the structures of the newly synthesized polyethers. The thermal stability and solubility of the synthesized polyethers of various solvents were investigated. They showed high stability at high temperatures as thermoplastics. The synthesized polyethers have fluorescent properties in solutions, and the absorption and intensity were dependent on the type of functional groups present in the polymers. The fluorination intensity of polyethers was found to be dependent on the presence of electron-donating groups, the pH of the solution, and the type of solvent used. One of the synthesized polyethers exhibited strong emissive properties at one or two specific wavelengths.","PeriodicalId":15323,"journal":{"name":"Journal of Chemical Research","volume":"43 1","pages":""},"PeriodicalIF":1.4,"publicationDate":"2023-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139305768","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-11-01DOI: 10.1177/17475198231203972
Er-Nu Liu, Pei-Pei Huang, Jia-Hao Gao, Jia-Xin Wang, Ting-Ting Wu, Bo Liu, Sheng-Rui Zhang, Jiu-Fu Lu
A new zinc(II) metal organic framework has been obtained from the solvothermal assembly of 1,3,5-benzene tricarboxylate and 1,3-bis(imidazole)propane with zinc nitrate in DMAc–H 2 O (DMAc is N,N-dimethylacetamide), namely {[Zn 2 (μ 2 -OH)(1,3-BIP)(BTC)]·DMAc·2H 2 O} n (SNUT-6). The product is characterized by single-crystal and powder X-ray diffraction, infrared spectroscopy, thermogravimetric analysis, and elemental analysis. The single-crystal X-ray diffraction reveals that SNUT-6 exhibits a 3D→3D two-fold interpenetrating framework. Furthermore, SNUT-6 demonstrates a highly efficient turn-off fluorescent detection ability for aniline in methanol and shows high sensitivity with a K sv value of 4.771 × 10 4 M −1 . It also shows excellent photocatalytic degradation performance for a three-dye molecular model: rhodamine b, methyl orange, and methyl blue.
{"title":"A two-fold interpenetrated Zn(II) organic framework based on mixed ligands: Synthesis, crystal structure, and properties","authors":"Er-Nu Liu, Pei-Pei Huang, Jia-Hao Gao, Jia-Xin Wang, Ting-Ting Wu, Bo Liu, Sheng-Rui Zhang, Jiu-Fu Lu","doi":"10.1177/17475198231203972","DOIUrl":"https://doi.org/10.1177/17475198231203972","url":null,"abstract":"A new zinc(II) metal organic framework has been obtained from the solvothermal assembly of 1,3,5-benzene tricarboxylate and 1,3-bis(imidazole)propane with zinc nitrate in DMAc–H 2 O (DMAc is N,N-dimethylacetamide), namely {[Zn 2 (μ 2 -OH)(1,3-BIP)(BTC)]·DMAc·2H 2 O} n (SNUT-6). The product is characterized by single-crystal and powder X-ray diffraction, infrared spectroscopy, thermogravimetric analysis, and elemental analysis. The single-crystal X-ray diffraction reveals that SNUT-6 exhibits a 3D→3D two-fold interpenetrating framework. Furthermore, SNUT-6 demonstrates a highly efficient turn-off fluorescent detection ability for aniline in methanol and shows high sensitivity with a K sv value of 4.771 × 10 4 M −1 . It also shows excellent photocatalytic degradation performance for a three-dye molecular model: rhodamine b, methyl orange, and methyl blue.","PeriodicalId":15323,"journal":{"name":"Journal of Chemical Research","volume":"2019 8","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135614277","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-11-01DOI: 10.1177/17475198231212673
M. Plater, William TA Harrison
p-Phenylenediamine reacts with Sanger’s reagent in hot ethanol to give the expected mono- and di-substitution products, but in ethanol at room temperature, it gave exclusively 2-nitro-5-fluorophenyl- p-phenylenediamine, where a hydrogen atom is displaced by attack at an activated, unsubstituted position. The reactions of p-phenylenediamine and aniline with Sanger’s reagent were compared in the cheap, ‘green’ solvent ethanol.
{"title":"Expected and unexpected products from reacting Sanger’s reagent with p-phenylenediamine","authors":"M. Plater, William TA Harrison","doi":"10.1177/17475198231212673","DOIUrl":"https://doi.org/10.1177/17475198231212673","url":null,"abstract":"p-Phenylenediamine reacts with Sanger’s reagent in hot ethanol to give the expected mono- and di-substitution products, but in ethanol at room temperature, it gave exclusively 2-nitro-5-fluorophenyl- p-phenylenediamine, where a hydrogen atom is displaced by attack at an activated, unsubstituted position. The reactions of p-phenylenediamine and aniline with Sanger’s reagent were compared in the cheap, ‘green’ solvent ethanol.","PeriodicalId":15323,"journal":{"name":"Journal of Chemical Research","volume":"63 1","pages":""},"PeriodicalIF":1.4,"publicationDate":"2023-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139300821","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-11-01DOI: 10.1177/17475198231219451
Duc Quan Tran, Ngoc-Hung Truong, Thi Hoang Anh Nguyen, T. T. Trinh, Thi Cham Ba, Thi Thuy Linh Nguyen, Van Tu Ngo, T. I. Cam, Minh Quan Pham, V. Luu
In a five-step procedure, 18 new esters (20a–i and 21a–i) of ataluren and its analogs with dihydroartemisinin and zerumbone were synthesized from methyl 3-cyanobenzoate. The screening for their cytotoxic activity against two cancer cell lines, HepG2 and MCF-7, showed that most esters exhibit activity against the tested cell lines, with IC50 values in the range of 1.61–36.52 µM. Among the tested compounds, ester 21f containing 4-methoxy in structure R did not show cytotoxic activity. The interactions of these new derivatives with the epidermal growth factor receptor protein were also investigated by molecular docking studies. The obtained binding conformation revealed several notable results, demonstrating similarities between molecular modeling theory and experiment. These results contributed to interpreting the in vitro cytotoxicity of esters and proposed the basis for predicting the mechanism of their cytotoxic action.
{"title":"Dihydroartemisinin and zerumbone esters of ataluren and its analogs as anticancer agents and EGFR inhibitors","authors":"Duc Quan Tran, Ngoc-Hung Truong, Thi Hoang Anh Nguyen, T. T. Trinh, Thi Cham Ba, Thi Thuy Linh Nguyen, Van Tu Ngo, T. I. Cam, Minh Quan Pham, V. Luu","doi":"10.1177/17475198231219451","DOIUrl":"https://doi.org/10.1177/17475198231219451","url":null,"abstract":"In a five-step procedure, 18 new esters (20a–i and 21a–i) of ataluren and its analogs with dihydroartemisinin and zerumbone were synthesized from methyl 3-cyanobenzoate. The screening for their cytotoxic activity against two cancer cell lines, HepG2 and MCF-7, showed that most esters exhibit activity against the tested cell lines, with IC50 values in the range of 1.61–36.52 µM. Among the tested compounds, ester 21f containing 4-methoxy in structure R did not show cytotoxic activity. The interactions of these new derivatives with the epidermal growth factor receptor protein were also investigated by molecular docking studies. The obtained binding conformation revealed several notable results, demonstrating similarities between molecular modeling theory and experiment. These results contributed to interpreting the in vitro cytotoxicity of esters and proposed the basis for predicting the mechanism of their cytotoxic action.","PeriodicalId":15323,"journal":{"name":"Journal of Chemical Research","volume":"51 1","pages":""},"PeriodicalIF":1.4,"publicationDate":"2023-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139302362","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-09-01DOI: 10.1177/17475198231199428
Duc Quan Tran, Ngoc Hung Truong, Thi Hoang Anh Nguyen, Thi Thuy Trinh, Thi Cham Ba, Thi Thuy Linh Nguyen, Xuan Ha Nguyen, Manh Cuong Nguyen, Van Chinh Luu
Sixteen conjugates of dihydroartemisinin and zerumbone with 2-mercapto-1,3,4-oxadiazoles were synthesized and structurally elucidated by 1D NMR, 2D NMR, and HRMS spectra. The cytotoxic screening results showed that all the conjugates of dihydroartemisinin with 2-mercapto-1,3,4-oxadiazoles (19a-h) exhibited cytotoxic activity against two human cancer cell lines, HepG2 and LU-1, with the IC 50 values ranging from 2.22 to 40.69 µM. Among dihydroartemisinin conjugates, conjugate 19b displayed the strongest activity against both HepG2 and LU-1 cell lines, with the IC 50 values of 3.49 and 2.22 μM, respectively. The zerumbone conjugates (20a-h) expressed their cytotoxic activity stronger than that of 19a-h series, with IC 50 values ranging from 1.54 to 2.00 µM. In addition, all 16 compounds exhibited an impressively inhibitory effect against EGFR tyrosine kinase with binding affinities ranging from −8.61 to −10.2 kcal/mol, higher than that of the erlotinib drug (−7.50 kcal/mol), a co-crystallized inhibitor of EGFR receptor. Both conjugates (19a and 20a) containing the 2-hydroxyphenyl-2mercapto-1,3,4-oxadiazole moiety had the best binding energies (−10.2 and −9.494 kcal/mol, respectively) on the EGFR tyrosine kinase. Furthermore, the potential interactions and binding patterns between the compounds and the relevant amino acid residues revealed the most significant contribution to amplifying their efficacy against this protein, according to docking studies, which identified both hydrogen bonds and hydrophobic contacts at the active site of the EGFR protein.
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