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Spectral, optical, and cytotoxicity studies on N-(2-isonicotinoylhydrazine-carbonothioyl)benzamide and its metal complexes N-（2-异烟酸肼基羰基）苯甲酰胺及其金属配合物的光谱、光学和细胞毒性研究
IF 0.3 4区 化学
Heteroatom Chemistry Pub Date : 2018-06-04 DOI: 10.1002/hc.21415
Nasser Mohammed Hosny, Heba M. Mahmoud, Mohamed H. Abdel-Rhman
{"title":"Spectral, optical, and cytotoxicity studies on N-(2-isonicotinoylhydrazine-carbonothioyl)benzamide and its metal complexes","authors":"Nasser Mohammed Hosny,&nbsp;Heba M. Mahmoud,&nbsp;Mohamed H. Abdel-Rhman","doi":"10.1002/hc.21415","DOIUrl":"10.1002/hc.21415","url":null,"abstract":"<p>The ligand <i>N</i>-(2-isonicotinoylhydrazine-carbonothioyl)benzamide (H<sub>3</sub>L) and its metal complexes with Co(II), Ni(II), Cu(II), and Zn(II) acetates have been synthesized. The synthesized compounds have been characterized by elemental analyses, FT-IR, UV-Visible spectra, <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, ESR, MS, effective magnetic moments, molar conductance, and thermal analyses. The free organic ligand exists in the keto form, but in the metal complexes, it forms chelates with the metal ions in the enol form. The measured optical band gap (<i>E</i><sub>g</sub>) values confirmed the presence of direct electronic transition and the semiconductivity of the current compounds. The ligand and its Zn(II) complex were examined as cytotoxic agents against HePG-2 and HCT-116 and showed. H<sub>3</sub>L exhibited strong cytotoxicity, while Zn complex showed moderate activity.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":null,"pages":null},"PeriodicalIF":0.3,"publicationDate":"2018-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21415","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43412728","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 15
A practical one-pot three-component procedure for preparation of 3a,8a-dihydroxyindeno[1,2-d]imidazole derivatives in aqueous ethanol 在乙醇水溶液中制备3a,8a-二羟基茚二酮[1,2-d]咪唑衍生物的一锅三组分工艺
IF 0.3 4区 化学
Heteroatom Chemistry Pub Date : 2018-06-04 DOI: 10.1002/hc.21417
Azar Jamaledini, Mohammad Reza Mohammadizadeh
{"title":"A practical one-pot three-component procedure for preparation of 3a,8a-dihydroxyindeno[1,2-d]imidazole derivatives in aqueous ethanol","authors":"Azar Jamaledini,&nbsp;Mohammad Reza Mohammadizadeh","doi":"10.1002/hc.21417","DOIUrl":"10.1002/hc.21417","url":null,"abstract":"<p>The results of our investigations on the preparation of 3a,8a-dihydroxyindeno[1,2-<i>d</i>]imidazole derivatives via reaction of thiourea, ninhydrin, and alkyl/benzyl chlorides in aqueous ethanol and under convenient conditions is reported. On the other hand, when guanidinium chloride was used instead of thiourea, the reaction mixtures reached with unexpected products; 2,2-dialkoxy-1<i>H</i>-indene-1,3(2<i>H</i>)-diones.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":null,"pages":null},"PeriodicalIF":0.3,"publicationDate":"2018-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21417","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48066329","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
A facile and convenient synthesis of 3-alkylidene-oxindoles bearing tetrahydropyrazine scaffold under catalyst-free conditions 在无催化剂条件下简单方便地合成带有四氢吡嗪支架的3-亚烷基环氧吲哚
IF 0.3 4区 化学
Heteroatom Chemistry Pub Date : 2018-05-30 DOI: 10.1002/hc.21416
Firouz Matloubi Moghaddam, Atiyeh Moafi
{"title":"A facile and convenient synthesis of 3-alkylidene-oxindoles bearing tetrahydropyrazine scaffold under catalyst-free conditions","authors":"Firouz Matloubi Moghaddam,&nbsp;Atiyeh Moafi","doi":"10.1002/hc.21416","DOIUrl":"10.1002/hc.21416","url":null,"abstract":"<p>A facile and efficient synthesis of 2-oxindole derivatives bearing tetrahydropyrazine scaffold has been developed. Using water as solvent without any additional acid or metal catalyst, easy work up and high yield of products are the main advantages of this protocol.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":null,"pages":null},"PeriodicalIF":0.3,"publicationDate":"2018-05-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21416","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46691349","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of new functionalized hydroxy- and aminomethylphosphinates with indan moieties 新型茚丹官能化羟基和氨基甲基膦酸酯的合成
IF 0.3 4区 化学
Heteroatom Chemistry Pub Date : 2018-05-30 DOI: 10.1002/hc.21419
Andrey A. Prishchenko, Mikhail V. Livantsov, Olga P. Novikova, Ludmila I. Livantsova, Valery S. Petrosyan
{"title":"Synthesis of new functionalized hydroxy- and aminomethylphosphinates with indan moieties","authors":"Andrey A. Prishchenko,&nbsp;Mikhail V. Livantsov,&nbsp;Olga P. Novikova,&nbsp;Ludmila I. Livantsova,&nbsp;Valery S. Petrosyan","doi":"10.1002/hc.21419","DOIUrl":"10.1002/hc.21419","url":null,"abstract":"<p>The convenient synthesis of new functionalized organophosphorus acids and their derivatives containing indan moieties was developed. The regioselective radical addition of bis(trimethylsiloxy)phosphine to indene proceeds to give rise to 2-indanylphosphonite as key compound for preparation of above acids with bicyclic substituents. Azobis(isobutyronitrile) (AIBN) in the conditions of its thermolysis was used as effective initiator of the addition reaction. The further treatment of organophosphorus acids trimethylsilyl esters with the methanolic sodium methoxide solution resulted in the water-soluble sodium salts of the corresponding acids.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":null,"pages":null},"PeriodicalIF":0.3,"publicationDate":"2018-05-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21419","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42367605","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 6
A facile and sustainable protocol to the preparation of aryl iodides using stable arenediazonium bis(trifluoromethylsulfonyl)imide salts via the telescopic process 使用稳定的阿二唑双（三氟甲基磺酰基）酰亚胺盐通过伸缩过程制备芳基碘化物的简单和可持续的方案
IF 0.3 4区 化学
Heteroatom Chemistry Pub Date : 2018-05-30 DOI: 10.1002/hc.21418
Nader Ghaffari Khaligh
{"title":"A facile and sustainable protocol to the preparation of aryl iodides using stable arenediazonium bis(trifluoromethylsulfonyl)imide salts via the telescopic process","authors":"Nader Ghaffari Khaligh","doi":"10.1002/hc.21418","DOIUrl":"10.1002/hc.21418","url":null,"abstract":"<p>The preparation of aryl iodides in a telescopic reaction using <i>tert</i>-butyl nitrite as a diazotization reagent and a mixture of bis(trifluoromethane) sulfonamide and glacial acetic acid as a mild acidic agent in ethanol followed by iododediazoniation with tetraethylammonium iodide in water was investigated. The current method has other advantages such as minimized waste by avoiding solvent for the purification of products in diazotization step, simple experimental procedure, and good yield of the sterically hindered aryl amines, metal and strong acid-free waste and environmentally benign conditions. The noteworthy features of this study are the preparation of stable arenediazonium bis(trifluoromethylsulfonyl)imide salts that can be used with no significant loss activity after 1 week and bis(trifluoromethane)sulfonamide was recovered in high yields from reactions.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":null,"pages":null},"PeriodicalIF":0.3,"publicationDate":"2018-05-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21418","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47752963","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 3
Cu(II) complex of phenylthiosemicarbazone: An in situ catalyst for formation of C-N bond between different N-based neucleophiles with arylboronic acids at room temperature 苯基硫代氨基脲Cu(II)配合物:室温下不同n基亲核试剂与芳基硼酸之间形成C-N键的原位催化剂
IF 0.3 4区 化学
Heteroatom Chemistry Pub Date : 2018-05-21 DOI: 10.1002/hc.21414
Nibedita Gogoi, Geetika Borah, Pradip K. Gogoi
{"title":"Cu(II) complex of phenylthiosemicarbazone: An in situ catalyst for formation of C-N bond between different N-based neucleophiles with arylboronic acids at room temperature","authors":"Nibedita Gogoi,&nbsp;Geetika Borah,&nbsp;Pradip K. Gogoi","doi":"10.1002/hc.21414","DOIUrl":"10.1002/hc.21414","url":null,"abstract":"<p>We have reported here a new synthetic protocol for the formation of C-N bond catalyzed by a thiosemicarbazone complex of copper. This in situ complex has been found to be very effective for Chan-Lam C-N cross-coupling reaction of anilines and various imidazoles at room temperature. Pyrazole and 4-bromoindole were also activated for C-N bond formation by using this protocol at room temperature. This catalytic system gave good-to-excellent yield using a mixture of DMF and water as solvent in a 1:1 proportion.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":null,"pages":null},"PeriodicalIF":0.3,"publicationDate":"2018-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21414","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47825256","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 3
Ethyl ester and silyl ester of imidodiphosphate: An alternative route to access phosphorus-nitrogen-phosphorus bonds via Staudinger reaction 氨基二磷酸乙酯和硅基酯:通过Staudinger反应获得磷-氮-磷键的另一种途径
IF 0.3 4区 化学
Heteroatom Chemistry Pub Date : 2018-03-25 DOI: 10.1002/hc.21413
Jia En Low, Joëlle Levalois-Grützmacher
{"title":"Ethyl ester and silyl ester of imidodiphosphate: An alternative route to access phosphorus-nitrogen-phosphorus bonds via Staudinger reaction","authors":"Jia En Low,&nbsp;Joëlle Levalois-Grützmacher","doi":"10.1002/hc.21413","DOIUrl":"10.1002/hc.21413","url":null,"abstract":"<p>We present herein an alternative synthesis route to obtain tetraethyl imidodiphosphate (EtO)<sub>2</sub>P(O)NH(O)P(OEt)<sub>2</sub> (<b>3</b>) and its silylester derivative tetrakis(trimethylsilyl) imidodiphosphate (Me<sub>3</sub>SiO)<sub>2</sub>P(O)NH(O)P(OSiMe<sub>3</sub>)<sub>2</sub> (<b>4</b>) involving a phosphorazidate intermediate (<b>1</b>) and the Staudinger reaction. Compared to previous methods, this synthesis route is simpler, more atom efficient, and energetically inexpensive. Moreover, the final compounds are obtained with larger yield and higher purity.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":null,"pages":null},"PeriodicalIF":0.3,"publicationDate":"2018-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21413","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"51412674","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Preparation of enantiopure 1-isopentyl-3-methyl-3-phospholene 1-oxide via the formation of diastereomeric complexes 通过形成非对映体配合物制备对映纯1-异戊基-3-甲基-3-磷烯- 1-氧化物
IF 0.3 4区 化学
Heteroatom Chemistry Pub Date : 2018-03-03 DOI: 10.1002/hc.21411
Péter Bagi, Kinga Juhász, Mihály Kállay, Dóra Hessz, Miklós Kubinyi, Elemér Fogassy, György Keglevich
{"title":"Preparation of enantiopure 1-isopentyl-3-methyl-3-phospholene 1-oxide via the formation of diastereomeric complexes","authors":"Péter Bagi,&nbsp;Kinga Juhász,&nbsp;Mihály Kállay,&nbsp;Dóra Hessz,&nbsp;Miklós Kubinyi,&nbsp;Elemér Fogassy,&nbsp;György Keglevich","doi":"10.1002/hc.21411","DOIUrl":"10.1002/hc.21411","url":null,"abstract":"<p>The resolution of 1-isopentyl-3-methyl-3-phospholene 1-oxide via the formation of diastereomeric complexes using TADDOL derivatives or the Ca<sup>2+</sup>-salts of tartaric acid derivatives was studied. Both enantiomers of the 1-isopentyl-3-phospholene oxide were prepared in an enantiopure form with (<i>R</i>,<i>R</i>)-spiro-TADDOL, or with the acidic Ca<sup>2+</sup>-salt of <i>O</i>,<i>O</i>′-dibenzoyl-(<i>R</i>,<i>R</i>)-tartaric acid. The absolute configuration of the 1-isopentyl-3-phospholene oxide enantiomer with negative optical rotation was also substantiated by a study involving CD spectroscopy and theoretical calculations.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":null,"pages":null},"PeriodicalIF":0.3,"publicationDate":"2018-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21411","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"51412655","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Characterization of C20 fullerene and its isolated C20-nGen derivatives (n = 1-5) by alternating germanium atom(s) in equatorial position: A DFT survey 在赤道位置交替锗原子表征C20富勒烯及其分离的C20- ngen衍生物(n = 1-5): DFT调查
IF 0.3 4区 化学
Heteroatom Chemistry Pub Date : 2018-02-27 DOI: 10.1002/hc.21410
Mohammad T. Baei, Maryam Koohi, Minoo Shariati
{"title":"Characterization of C20 fullerene and its isolated C20-nGen derivatives (n = 1-5) by alternating germanium atom(s) in equatorial position: A DFT survey","authors":"Mohammad T. Baei,&nbsp;Maryam Koohi,&nbsp;Minoo Shariati","doi":"10.1002/hc.21410","DOIUrl":"10.1002/hc.21410","url":null,"abstract":"<p>DFT calculations are applied to compare and contrast germanium atom(s) substituted <b>C</b><sub><b>20-</b></sub><sub><b>n</b></sub><b>G</b><b>e</b><sub><b>n</b></sub> heterofullerenes with n = 1-5, where the substitution is completely isolated from each other by means of one carbon atom in equatorial position. The structural stabilities, geometry, and electronic properties of <b>C</b><sub><b>20</b></sub> and its heterofullerene derivatives are compared and contrasted at M062X/6-311++G**, B3LYP/AUG-cc-pVTZ, B3LYP/6-311++G**, B3LYP/6-311+G*, and B3PW91/6-311++G** levels of theory. Vibrational frequency analysis shows that all of the heterofullerenes are real minima. Contrary to identical bonds in <b>C</b><sub><b>20</b></sub>, contractions of C=C double bonds are encountered at the expense of longer C―Ge bonds in <b>C</b><sub><b>20-</b></sub><sub><b>n</b></sub><b>G</b><b>e</b><sub><b>n</b></sub>. In contrast to previous reports on silicon doped heterofullerenes, none of the computed heterofullerenes collapses to open cage structures. Successive Ge doping on <b>C</b><sub><b>20</b></sub> induces more positive atomic charge on Ge atoms and more negative charge on C atoms. High charge transfer on the surfaces of our stable heterofullerenes provokes further investigations on their possible application for hydrogen storage. As to band gap, binding energy, heat of atomization per carbon, nucleus-independent chemical shift, aromaticity, and the smallest vibrational frequency <b>C</b><sub><b>19</b></sub><b>Ge</b> immerges with the highest value. The reactivity in terms of ionization potential, nucleophilicity, electrophilicity, hardness, softness, maximum electronic charge, and proton affinity issues predicts <b>C</b><sub><b>19</b></sub><b>Ge</b> as the most stable heterofullerene against electronic excitation.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":null,"pages":null},"PeriodicalIF":0.3,"publicationDate":"2018-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21410","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"51412477","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 10
An easy synthetic protocol for imidazo-1,4-oxazines and evaluation of their toxicities 咪唑-1,4-恶嗪的简易合成方法及其毒性评价
IF 0.3 4区 化学
Heteroatom Chemistry Pub Date : 2018-02-27 DOI: 10.1002/hc.21412
Burak Kuzu, Hasan Genç, Mehmet Taşpinar, Meltem Tan, Nurettin Menges
{"title":"An easy synthetic protocol for imidazo-1,4-oxazines and evaluation of their toxicities","authors":"Burak Kuzu,&nbsp;Hasan Genç,&nbsp;Mehmet Taşpinar,&nbsp;Meltem Tan,&nbsp;Nurettin Menges","doi":"10.1002/hc.21412","DOIUrl":"10.1002/hc.21412","url":null,"abstract":"<p>Imidazo-1,5-alkynyl alcohol derivatives were synthesized, and they were cyclized to imidazo-1,4-oxazines by means of cesium carbonate. Propargyl-allene isomerization was examined, and the reaction mechanism was proposed. Moreover, cytotoxicity of synthesized molecules against LN405 cell lines was investigated by means of structure-activity relationship (SAR). With SAR study, toxicities of some functional groups have been shown. In addition, two lead compounds were tested against DNA damaging.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":null,"pages":null},"PeriodicalIF":0.3,"publicationDate":"2018-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21412","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"51412665","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 9
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