Antonio Jesús Galera Carrillo, Antonio Franconetti-García, Francisca Cabrera-Escribano
Our research focuses on the synthesis of new tacrine derivatives with an expected similar or higher inhibitory activity of AChE and BuChE than commercial tacrine and hybrids tacrine-chitosan derivatives with tunable biological properties by reaction of the biopolymer with the different tacrine derivatives synthesized. All new compounds have been characterized by NMR techniques both in solution and in solid state.
{"title":"New Tacrine derivatives and Tacrine-Chitosan systems for application against degenerative diseases","authors":"Antonio Jesús Galera Carrillo, Antonio Franconetti-García, Francisca Cabrera-Escribano","doi":"10.3390/ecsoc-23-06499","DOIUrl":"https://doi.org/10.3390/ecsoc-23-06499","url":null,"abstract":"Our research focuses on the synthesis of new tacrine derivatives with an expected similar or higher inhibitory activity of AChE and BuChE than commercial tacrine and hybrids tacrine-chitosan derivatives with tunable biological properties by reaction of the biopolymer with the different tacrine derivatives synthesized. All new compounds have been characterized by NMR techniques both in solution and in solid state.","PeriodicalId":20537,"journal":{"name":"Proceedings of The 23rd International Electronic Conference on Synthetic Organic Chemistry","volume":"121 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77377254","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
S. E. Rayes, I. Ali, Walid Fathalla, Mostafa A A Mahmoud
Methyl 2-(4-oxobenzotriazin-3(4H)-yl) alkanoates4a-c proved to be important intermediates for the preparation of some biologically interesting compounds containing the benzotriazinone ring system. Esters 4a-c were prepared by direct diazotization of methyl anthranilate followed by addition of amino acid esters hydrochloride in a one-pot strategy. An equivocal synthesis of methyl 2-(4oxobenzotriazin-3(4H)-yl) acetate 4a was achieved by alkylation of benzotriazin-4(3H)one with methyl chloroacetate on the basis of chemoselective reaction of heterocyclic amide with electrophiles. A series of N-alkyl-2-(4-oxobenzotriazin-3(4H)-yl) alkanamides7-8(a-h) and methyl 2-(2-(4oxobenzotriazin-3(4H)-yl)alkanamido)alkanoates (dipeptides) 9-10(a-d) were prepared via azide coupling from 4a-b. Esters 4a-b were converted into the corresponding hydrazides followed by condensation with aldehydes; 4-methoxybenzaldehyde, 4-dimethylamino benzaldehyde and arabinose to afford the corresponding hydrazone derivatives11-13. All the synthesized compounds were subjected to the molecular docking using MOE 2008-10 software as agonist for; E. coli Fab-H receptor and Vitamin D receptor for antibacterial and anticancer evaluation, respectively. The most pronounced strong binding affinity towards the target E. coli Fab-H receptor were compounds 7a, 11a, 11b,10a,10cand 12b. On the other hand, the most pronounced strong binding affinity towards the target Vitamin D receptor were compounds 3, 9c, 11a and 10d. The in vitro antibacterial activity of highest binding affinity docked compounds were tested against E. coli, Staphylococcus aureus and Salmonella spp. All the tested compounds gave effective positive results against E. coli with inhibitory zone of about 1.1 cm, while were inactive against Staphylococcus aureus and Salmonella spp. The in vitro cytotoxic activity of the highest binding affinity docked compounds were tested against human liver carcinoma cell line (HepG2) cancer cell lines. Many compounds showed potent cytotoxic activity with low IC50 values, especially for 3(6.525μM) and 11a (10.97 μM), while for standard drug doxorubicin (5.8 μM).
{"title":"Synthesis, Molecular Docking and Biological Evaluation of Some New Benzotriazines","authors":"S. E. Rayes, I. Ali, Walid Fathalla, Mostafa A A Mahmoud","doi":"10.3390/ecsoc-23-06481","DOIUrl":"https://doi.org/10.3390/ecsoc-23-06481","url":null,"abstract":"Methyl 2-(4-oxobenzotriazin-3(4H)-yl) alkanoates4a-c proved to be important intermediates for the preparation of some biologically interesting compounds containing the benzotriazinone ring system. Esters 4a-c were prepared by direct diazotization of methyl anthranilate followed by addition of amino acid esters hydrochloride in a one-pot strategy. An equivocal synthesis of methyl 2-(4oxobenzotriazin-3(4H)-yl) acetate 4a was achieved by alkylation of benzotriazin-4(3H)one with methyl chloroacetate on the basis of chemoselective reaction of heterocyclic amide with electrophiles. A series of N-alkyl-2-(4-oxobenzotriazin-3(4H)-yl) alkanamides7-8(a-h) and methyl 2-(2-(4oxobenzotriazin-3(4H)-yl)alkanamido)alkanoates (dipeptides) 9-10(a-d) were prepared via azide coupling from 4a-b. Esters 4a-b were converted into the corresponding hydrazides followed by condensation with aldehydes; 4-methoxybenzaldehyde, 4-dimethylamino benzaldehyde and arabinose to afford the corresponding hydrazone derivatives11-13. All the synthesized compounds were subjected to the molecular docking using MOE 2008-10 software as agonist for; E. coli Fab-H receptor and Vitamin D receptor for antibacterial and anticancer evaluation, respectively. The most pronounced strong binding affinity towards the target E. coli Fab-H receptor were compounds 7a, 11a, 11b,10a,10cand 12b. On the other hand, the most pronounced strong binding affinity towards the target Vitamin D receptor were compounds 3, 9c, 11a and 10d. The in vitro antibacterial activity of highest binding affinity docked compounds were tested against E. coli, Staphylococcus aureus and Salmonella spp. All the tested compounds gave effective positive results against E. coli with inhibitory zone of about 1.1 cm, while were inactive against Staphylococcus aureus and Salmonella spp. The in vitro cytotoxic activity of the highest binding affinity docked compounds were tested against human liver carcinoma cell line (HepG2) cancer cell lines. Many compounds showed potent cytotoxic activity with low IC50 values, especially for 3(6.525μM) and 11a (10.97 μM), while for standard drug doxorubicin (5.8 μM).","PeriodicalId":20537,"journal":{"name":"Proceedings of The 23rd International Electronic Conference on Synthetic Organic Chemistry","volume":"77 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88557369","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The catalytic application of a novel magnetic periodic mesoporous organosilica functionalized 3-propylamine(Fe3O4@PMO-ICS-PrNH2) in the synthesis of imidazopyrimidine derivatives was investigated. At first, the Fe3O4@PMO-ICS-PrNH2 nanocatalyst was prepared and characterized by N2 adsorption-desorption isotherms techniques, field emission scanning electron microscopy (FESEM), thermogravimetric analysis (TGA), energy-dispersive X-ray (EDX) spectroscopy, Fourier transform infrared (FTIR) spectroscopy and vibrating sample magnetometer (VSM). Then, the catalyst was shown to be a efficient recyclable and highly active catalyst and used in the three-component synthesis of 2-aminobenzaldehyde with aromatic aldehydes various and dimedone/malononitrile under H2O solvent conditions. Also, imidazopyrimidine products were obtained in mild reaction conditions, good to excellent yields and at short reaction times. Moreover, the catalyst was recovered and successfully reused at least five times without considerable reduction in its activity.
{"title":"New magnetic periodic mesoporous organosilica functionalized 3-propyl amine (Fe3O4@PMO-ICS-PrNH2) as highly efficien and recyclable catalysts in one-pot synthesis of imidazopyrimidine derivatives","authors":"Mohammad Dekamine, A. Akbari","doi":"10.3390/ecsoc-23-06513","DOIUrl":"https://doi.org/10.3390/ecsoc-23-06513","url":null,"abstract":"The catalytic application of a novel magnetic periodic mesoporous organosilica functionalized 3-propylamine(Fe3O4@PMO-ICS-PrNH2) in the synthesis of imidazopyrimidine derivatives was investigated. At first, the Fe3O4@PMO-ICS-PrNH2 nanocatalyst was prepared and characterized by N2 adsorption-desorption isotherms techniques, field emission scanning electron microscopy (FESEM), thermogravimetric analysis (TGA), energy-dispersive X-ray (EDX) spectroscopy, Fourier transform infrared (FTIR) spectroscopy and vibrating sample magnetometer (VSM). Then, the catalyst was shown to be a efficient recyclable and highly active catalyst and used in the three-component synthesis of 2-aminobenzaldehyde with aromatic aldehydes various and dimedone/malononitrile under H2O solvent conditions. Also, imidazopyrimidine products were obtained in mild reaction conditions, good to excellent yields and at short reaction times. Moreover, the catalyst was recovered and successfully reused at least five times without considerable reduction in its activity.","PeriodicalId":20537,"journal":{"name":"Proceedings of The 23rd International Electronic Conference on Synthetic Organic Chemistry","volume":"5 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85063591","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
V. Safarifard, M. Rad, Yeganeh Davoudabadi Farahani
{"title":"Efficient Fluorescence detection of Fe3+, Cd2+, and CH2Cl2 based on an azine-Functionalized Zn-Metal-Organic Framework","authors":"V. Safarifard, M. Rad, Yeganeh Davoudabadi Farahani","doi":"10.3390/ecsoc-23-06510","DOIUrl":"https://doi.org/10.3390/ecsoc-23-06510","url":null,"abstract":"","PeriodicalId":20537,"journal":{"name":"Proceedings of The 23rd International Electronic Conference on Synthetic Organic Chemistry","volume":" 34","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91412872","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Julio Corredoira-Vázquez, A. M. García-Deibe, J. Sanmartín-Matalobos, M. Fondo
: The formation of hemiacetals from aldehydes and alcohols is quite well known, as these are usually developed as intermediates in the preparation of acetals from aldehydes or ketones. Nevertheless, as far as we know, the examples of transformation of imines into hemiacetals are very scarce, and this reaction seems to be promoted by coordination to a metal ion. In this work, we describe the partial hydrolysis of a Schiff base, and its subsequent evolution to an hemiacetal donor in the presence of dysprosium(III) in an alcoholic medium. Full characterization of the final product, including single X-ray studies, is reported.
{"title":"Hemiacetal formation from a Schiff base in the presence of dysprosium(III)","authors":"Julio Corredoira-Vázquez, A. M. García-Deibe, J. Sanmartín-Matalobos, M. Fondo","doi":"10.3390/ecsoc-23-06471","DOIUrl":"https://doi.org/10.3390/ecsoc-23-06471","url":null,"abstract":": The formation of hemiacetals from aldehydes and alcohols is quite well known, as these are usually developed as intermediates in the preparation of acetals from aldehydes or ketones. Nevertheless, as far as we know, the examples of transformation of imines into hemiacetals are very scarce, and this reaction seems to be promoted by coordination to a metal ion. In this work, we describe the partial hydrolysis of a Schiff base, and its subsequent evolution to an hemiacetal donor in the presence of dysprosium(III) in an alcoholic medium. Full characterization of the final product, including single X-ray studies, is reported.","PeriodicalId":20537,"journal":{"name":"Proceedings of The 23rd International Electronic Conference on Synthetic Organic Chemistry","volume":"89 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84388822","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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