Pub Date : 2023-12-13DOI: 10.25135/acg.oc.160.2308.2876
Nitin A. Sasane, B. Popatkar, G. Meshram
{"title":"An efficient synthesis of quinoxaline derivatives using HCTU as catalyst in DMF","authors":"Nitin A. Sasane, B. Popatkar, G. Meshram","doi":"10.25135/acg.oc.160.2308.2876","DOIUrl":"https://doi.org/10.25135/acg.oc.160.2308.2876","url":null,"abstract":"","PeriodicalId":19553,"journal":{"name":"Organic Communications","volume":"67 8","pages":""},"PeriodicalIF":1.7,"publicationDate":"2023-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139004252","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}
Pub Date : 2023-11-30DOI: 10.25135/acg.oc.159.2310.2920
Muamer Dizdar, M. Maksimović, Anela Topčagić, M. Avdic, Danijela Vidic
: Phenolic aldehydes and their derivatives found in nature are well-known for their potential biological activity. In this study, four 1-substituted 1,2,3,4-tetrahydroisoquinolines (THIQs) derived from phenolic aldehydes were synthesized by phosphate buffer mediated Pictet-Spengler reaction. All derivatives were chemically and structurally characterized by elemental CHN analysis and spectroscopic methods (IR, HR-ESI-MS, 1 H-and 13 C-NMR). 1-Substituted THIQs derived from 3,4-dihydroxybenzaldehyde and 4-hydroxy-3-methoxybenzaldehyde were described for the first time. In order to cover the diversity of the mechanistic approach, but also to establish the relationship between structure and activity, antioxidant activity was examined by five different in vitro methods, namely: neutralization and reduction of stable free radicals 2,2-diphenyl-1-picrylhydrazyl and radical cation derived from [(2,2´-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)], ferric reducing antioxidant power, oxygen radical absorbance capacity, and ability to chelate Fe(II) ions. In vitro inhibition of acetylcholinesterase (AChE) was examined by the Ellman's colorimetric method, while computer-simulated docking was used to reveal the preferred binding site and major interaction between AChE and THIQs. Antibacterial testing was examined using the agar well method and results were presented in the form of zones of inhibition (mm).
{"title":"Synthesis and bioactivity of 1-substituted tetrahydroisoquinolines derived from phenolic aldehydes","authors":"Muamer Dizdar, M. Maksimović, Anela Topčagić, M. Avdic, Danijela Vidic","doi":"10.25135/acg.oc.159.2310.2920","DOIUrl":"https://doi.org/10.25135/acg.oc.159.2310.2920","url":null,"abstract":": Phenolic aldehydes and their derivatives found in nature are well-known for their potential biological activity. In this study, four 1-substituted 1,2,3,4-tetrahydroisoquinolines (THIQs) derived from phenolic aldehydes were synthesized by phosphate buffer mediated Pictet-Spengler reaction. All derivatives were chemically and structurally characterized by elemental CHN analysis and spectroscopic methods (IR, HR-ESI-MS, 1 H-and 13 C-NMR). 1-Substituted THIQs derived from 3,4-dihydroxybenzaldehyde and 4-hydroxy-3-methoxybenzaldehyde were described for the first time. In order to cover the diversity of the mechanistic approach, but also to establish the relationship between structure and activity, antioxidant activity was examined by five different in vitro methods, namely: neutralization and reduction of stable free radicals 2,2-diphenyl-1-picrylhydrazyl and radical cation derived from [(2,2´-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)], ferric reducing antioxidant power, oxygen radical absorbance capacity, and ability to chelate Fe(II) ions. In vitro inhibition of acetylcholinesterase (AChE) was examined by the Ellman's colorimetric method, while computer-simulated docking was used to reveal the preferred binding site and major interaction between AChE and THIQs. Antibacterial testing was examined using the agar well method and results were presented in the form of zones of inhibition (mm).","PeriodicalId":19553,"journal":{"name":"Organic Communications","volume":"20 3","pages":""},"PeriodicalIF":1.7,"publicationDate":"2023-11-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139206312","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}
Pub Date : 2023-10-29DOI: 10.25135/acg.oc.158.2309.2893
Ali Dişli, Doğukan Doyduk, Özge Çağlar Teknikel, Hatice Öğütcü
{"title":"Synthesis and antimicrobial activities of unsymmetrical thioditetrazoles and their precursor thiotetrazoles","authors":"Ali Dişli, Doğukan Doyduk, Özge Çağlar Teknikel, Hatice Öğütcü","doi":"10.25135/acg.oc.158.2309.2893","DOIUrl":"https://doi.org/10.25135/acg.oc.158.2309.2893","url":null,"abstract":"","PeriodicalId":19553,"journal":{"name":"Organic Communications","volume":"22 12","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136157805","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}
Pub Date : 2023-09-29DOI: 10.25135/acg.oc.148.2303.28001
Cenk A Andac
{"title":"Erratum to “Facile microwave synthesis of a novel phenothiazine derivative and its cytotoxic activity” [Org. Commun. 13:4 (2020) 175-183]","authors":"Cenk A Andac","doi":"10.25135/acg.oc.148.2303.28001","DOIUrl":"https://doi.org/10.25135/acg.oc.148.2303.28001","url":null,"abstract":"","PeriodicalId":19553,"journal":{"name":"Organic Communications","volume":"3 1","pages":""},"PeriodicalIF":1.7,"publicationDate":"2023-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139334096","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}
Pub Date : 2023-09-29DOI: 10.25135/acg.oc.158.2308.2887
Özgür Yılmaz
: Peptides have low oral bioavailability, low plasma stability, and short circulation time; therefore, they are used in targeted strategies in cancer. In this study, according to in silico analysis, novel small peptide sequences, which are consist of three amino acid residues, with high binding capacity against the human FOLR1 surface molecule were obtained. Modeling studies were carried out to determine peptide sequences. RhB-K*FFF, RhB-K*WFE, and RhB-K*YDY peptides have been synthesized by using the Solid Phase Peptide Synthesis (SPPS) method, purified by Reverse Phase High-Performance Liquid Chromatography (RP-HPLC) and characterized by Liquid Chromatography-High Resolution Mass Spectrometry (LC-HRMS/MS) and proton nuclear magnetic resonance ( 1 H-NMR). The purity of RhB-K*FFF, RhB-K*WFE, and RhB-K*YDY peptide are 96%, 95%, and 92%, respectively. Also, cell viability test was performed for the peptides. In our further study, the peptide with highest binding affinity will be conjugated with chemotherapeutic agent in order to improve its anti-cancer activity.
{"title":"Molecular modeling, synthesis and characterization of FOLR1 specific peptides for tumor targeting activity","authors":"Özgür Yılmaz","doi":"10.25135/acg.oc.158.2308.2887","DOIUrl":"https://doi.org/10.25135/acg.oc.158.2308.2887","url":null,"abstract":": Peptides have low oral bioavailability, low plasma stability, and short circulation time; therefore, they are used in targeted strategies in cancer. In this study, according to in silico analysis, novel small peptide sequences, which are consist of three amino acid residues, with high binding capacity against the human FOLR1 surface molecule were obtained. Modeling studies were carried out to determine peptide sequences. RhB-K*FFF, RhB-K*WFE, and RhB-K*YDY peptides have been synthesized by using the Solid Phase Peptide Synthesis (SPPS) method, purified by Reverse Phase High-Performance Liquid Chromatography (RP-HPLC) and characterized by Liquid Chromatography-High Resolution Mass Spectrometry (LC-HRMS/MS) and proton nuclear magnetic resonance ( 1 H-NMR). The purity of RhB-K*FFF, RhB-K*WFE, and RhB-K*YDY peptide are 96%, 95%, and 92%, respectively. Also, cell viability test was performed for the peptides. In our further study, the peptide with highest binding affinity will be conjugated with chemotherapeutic agent in order to improve its anti-cancer activity.","PeriodicalId":19553,"journal":{"name":"Organic Communications","volume":"17 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135199734","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}
Pub Date : 2023-09-29DOI: 10.25135/acg.oc2307.2838
Erkan Ertürk, Ömer Dİlek
: Enantioselective reduction of a new 1-oxotetrahydrocarbazole compound (ethyl 2-(1-oxo-9-tosyl-2,3,4,9-tetrahydro-1 H -carbazol-2-yl)acetate) through asymmetric transfer hydrogenation by using the commercially available Noyori–Ikariya ruthenium catalyst and HCO 2 H/Et 3 N or HCO 2 H/DABCO as the hydrogen source have been investigated. High enantiomeric excesses (up to 96% ee ) and moderate to good yields (24–72%) for corresponding alcohol and lactone compounds have been achieved. Structures of all compounds have been characterized by spectroscopic techniques.
{"title":"Asymmetric transfer hydrogenation of a new N-tosyltetrahydrocarbazole-1-one ester with the Noyori-Ikariya catalyst","authors":"Erkan Ertürk, Ömer Dİlek","doi":"10.25135/acg.oc2307.2838","DOIUrl":"https://doi.org/10.25135/acg.oc2307.2838","url":null,"abstract":": Enantioselective reduction of a new 1-oxotetrahydrocarbazole compound (ethyl 2-(1-oxo-9-tosyl-2,3,4,9-tetrahydro-1 H -carbazol-2-yl)acetate) through asymmetric transfer hydrogenation by using the commercially available Noyori–Ikariya ruthenium catalyst and HCO 2 H/Et 3 N or HCO 2 H/DABCO as the hydrogen source have been investigated. High enantiomeric excesses (up to 96% ee ) and moderate to good yields (24–72%) for corresponding alcohol and lactone compounds have been achieved. Structures of all compounds have been characterized by spectroscopic techniques.","PeriodicalId":19553,"journal":{"name":"Organic Communications","volume":"61 2 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135132000","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}
Pub Date : 2023-09-29DOI: 10.25135/acg.oc.155.2307.2833
Koppula Shiva Kumar, Abhilasha Dubba
: The synthesis and structural determination of several new fused [1,2,3]triazolo-[4',5':3,4]pyrrolo-[1,2-a ]indole derivatives ( 4a-4p ) utilising 1 HNMR, 13 CNMR, and mass spectrum analysis were discussed. The in vitro antibacterial activity of the compounds ( 4a-4p ) against three gramme positive bacterial strains such as B.subtilis , S.aureus , and S.epidermidis revealed that the compounds 4h , 4j , and 4k demonstrated greater activity than the remaining compounds. Compounds 4d , 4i , and 4l had comparable activity to the standard. The antioxidant activity screening findings show that compounds 4c , 4d , and 4j have higher activity than conventional Trolox. Compounds 4b , 4h , 4k , and 4l have high activity, whereas the remaining compounds have moderate to low activity.
{"title":"Synthesis and biological evaluation of [1,2,3]triazolo[4',5':3,4]pyrrolo[1,2-a] indoles: one-pot reaction under microwave irradiation","authors":"Koppula Shiva Kumar, Abhilasha Dubba","doi":"10.25135/acg.oc.155.2307.2833","DOIUrl":"https://doi.org/10.25135/acg.oc.155.2307.2833","url":null,"abstract":": The synthesis and structural determination of several new fused [1,2,3]triazolo-[4',5':3,4]pyrrolo-[1,2-a ]indole derivatives ( 4a-4p ) utilising 1 HNMR, 13 CNMR, and mass spectrum analysis were discussed. The in vitro antibacterial activity of the compounds ( 4a-4p ) against three gramme positive bacterial strains such as B.subtilis , S.aureus , and S.epidermidis revealed that the compounds 4h , 4j , and 4k demonstrated greater activity than the remaining compounds. Compounds 4d , 4i , and 4l had comparable activity to the standard. The antioxidant activity screening findings show that compounds 4c , 4d , and 4j have higher activity than conventional Trolox. Compounds 4b , 4h , 4k , and 4l have high activity, whereas the remaining compounds have moderate to low activity.","PeriodicalId":19553,"journal":{"name":"Organic Communications","volume":"1 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135131579","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}
Pub Date : 2023-08-15DOI: 10.25135/acg.oc.154.2306.2820
B. Kuzu, C. Hepokur, Ö. Algül
: In the present study, new oxalamide-based compounds were designed from thalidomide and synthesized easily and with high yields (from 69% up to 93%) by a two-step method. The antiproliferative effects of synthesized 6a-d and 7a-d compounds on (ER+) MCF-7 and (ER-) MDA-MB-231 breast cancer cell line and human fibroblast WI-38 healthy cell line were investigated by the MTT method. The results showed that compound 7d was the most potent candidate against both MCF-7 and MDA-MB-231 cell lines with IC 50 = 4.72 µM and 6.37 µM, respectively. To investigate whether antiproliferative effect of the compounds on breast cancer cell lines is dependent on COXs, expressions of COX-1/2 on the MCF-7 cell line were investigated by the Western-Blot technique. Among synthesized compounds, compound 7d increased the expression of both COX-1 and COX-2. The inhibition potential of compounds on COX-1/2 enzymes was investigated by molecular docking compared to inhibitor co-ligand celecoxib in crystal structures of COX-1 (PDB ID: 3KK6) and COX-2 (PDB ID: 3LN1). Docking results indeed showed that compound 7d had a higher binding affinity for both COX-1 and COX-2 active sites. Consequently, the novel oxalamide-based compounds presented here may be important candidate molecules for the development of new COX-dependent antiproliferative agents.
{"title":"Novel oxalamide derivatives for COXs expression and breast cancer: design, synthesis, biological evaluation, and docking studies","authors":"B. Kuzu, C. Hepokur, Ö. Algül","doi":"10.25135/acg.oc.154.2306.2820","DOIUrl":"https://doi.org/10.25135/acg.oc.154.2306.2820","url":null,"abstract":": In the present study, new oxalamide-based compounds were designed from thalidomide and synthesized easily and with high yields (from 69% up to 93%) by a two-step method. The antiproliferative effects of synthesized 6a-d and 7a-d compounds on (ER+) MCF-7 and (ER-) MDA-MB-231 breast cancer cell line and human fibroblast WI-38 healthy cell line were investigated by the MTT method. The results showed that compound 7d was the most potent candidate against both MCF-7 and MDA-MB-231 cell lines with IC 50 = 4.72 µM and 6.37 µM, respectively. To investigate whether antiproliferative effect of the compounds on breast cancer cell lines is dependent on COXs, expressions of COX-1/2 on the MCF-7 cell line were investigated by the Western-Blot technique. Among synthesized compounds, compound 7d increased the expression of both COX-1 and COX-2. The inhibition potential of compounds on COX-1/2 enzymes was investigated by molecular docking compared to inhibitor co-ligand celecoxib in crystal structures of COX-1 (PDB ID: 3KK6) and COX-2 (PDB ID: 3LN1). Docking results indeed showed that compound 7d had a higher binding affinity for both COX-1 and COX-2 active sites. Consequently, the novel oxalamide-based compounds presented here may be important candidate molecules for the development of new COX-dependent antiproliferative agents.","PeriodicalId":19553,"journal":{"name":"Organic Communications","volume":" ","pages":""},"PeriodicalIF":1.7,"publicationDate":"2023-08-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49016106","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}
京公网安备 11010802042870号
京ICP备2023020795号-1
扫码关注我们
求助内容：
应助结果提醒方式：