Pub Date : 2020-09-27DOI: 10.25135/ACG.OC.84.20.09.1792
H. Şenol, Kübra Çokuludağ, Asude Sena Aktaş, Sezen Atasoy, Aydan Dağ, G. Topçu
In this study, 12 new oleanane and ursane derivative triterpene compounds, having fatty acids in the form of esters with carbon numbers of 12, 13, 18, 19, 24 and 25, were synthesized starting from natural products oleanolic and ursolic acids. Initially, 3-methylerythrodiol (3β-methoxyolean-12-en-28-ol) and 3-methyluvaol (3β-methoxyurs12-en-28-ol) were synthesized from oleanolic acid and ursolic acid, respectively. For this purpose, secondary OH group at C-3 of oleanolic and ursolic acids were protected as methyl ether and, then, their carboxylic acid moieties were reduced by aluminum hydride. New fatty acid derivatives 5a-f and 8a-f were synthesized through the reaction of 3-methylerythrodiol/3-methyluvaol and corresponding fatty acid halides. In vitro cytotoxic activities of the all synthesized compounds were investigated on 3T3 fibroblast cells and PC3 prostate cancer cell lines. While all the compounds showed at least 70% inhibition on PC3 prostate cancer cells at a concentration of 25 μM, they had average of 50% inhibition on 3T3 fibroblast human healthy cells at the same concentration. Compounds 5c and 8c demonstrated the least toxic effect on 3T3 fibroblast human healthy cells and the highest toxic effect on PC3 prostate cancer cells at a concentration of 12.5 μM. Moreover, compounds 8c and 8e had the least toxic effect on 3T3 fibroblast human healthy cells and the highest toxic effect on PC3 prostate cancer cells at the same concentration.
{"title":"Synthesis of new fatty acid derivatives of oleanane and ursane triterpenoids and investigation of their in vitro cytotoxic effects on 3T3 fibroblast and PC3 prostate cancer cell linesLines","authors":"H. Şenol, Kübra Çokuludağ, Asude Sena Aktaş, Sezen Atasoy, Aydan Dağ, G. Topçu","doi":"10.25135/ACG.OC.84.20.09.1792","DOIUrl":"https://doi.org/10.25135/ACG.OC.84.20.09.1792","url":null,"abstract":"In this study, 12 new oleanane and ursane derivative triterpene compounds, having fatty acids in the form of esters with carbon numbers of 12, 13, 18, 19, 24 and 25, were synthesized starting from natural products oleanolic and ursolic acids. Initially, 3-methylerythrodiol (3β-methoxyolean-12-en-28-ol) and 3-methyluvaol (3β-methoxyurs12-en-28-ol) were synthesized from oleanolic acid and ursolic acid, respectively. For this purpose, secondary OH group at C-3 of oleanolic and ursolic acids were protected as methyl ether and, then, their carboxylic acid moieties were reduced by aluminum hydride. New fatty acid derivatives 5a-f and 8a-f were synthesized through the reaction of 3-methylerythrodiol/3-methyluvaol and corresponding fatty acid halides. In vitro cytotoxic activities of the all synthesized compounds were investigated on 3T3 fibroblast cells and PC3 prostate cancer cell lines. While all the compounds showed at least 70% inhibition on PC3 prostate cancer cells at a concentration of 25 μM, they had average of 50% inhibition on 3T3 fibroblast human healthy cells at the same concentration. Compounds 5c and 8c demonstrated the least toxic effect on 3T3 fibroblast human healthy cells and the highest toxic effect on PC3 prostate cancer cells at a concentration of 12.5 μM. Moreover, compounds 8c and 8e had the least toxic effect on 3T3 fibroblast human healthy cells and the highest toxic effect on PC3 prostate cancer cells at the same concentration.","PeriodicalId":19553,"journal":{"name":"Organic Communications","volume":"1 1","pages":""},"PeriodicalIF":1.7,"publicationDate":"2020-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41699705","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 : 2020-07-01DOI: 10.25135/ACG.OC.86.20.09.1802
Ceyda Köse, Esra Uysal, B. Yazici, Z. Tuğay, Serap İpek Dingiş Birgül, Hamdullah Yanık, E. Tavukçuoğlu, Sevgi Gulyuz, A. Akdemir, G. Esendagli, Ö. Yılmaz, Onur Alptürk
Tumor cells benefit from some certain signals, which are referred to as “immune checkpoints”, to escape immune-mediated destruction. With that in mind, it is believed that the blockade of these points, such as programmed cell death Ligand-1 (PD-L1) and programmed cell death 1 (PD-1), can restore an adaptative immune response against tumoral cells. In this study, we have designed and synthesized some novel peptidomimetics with a 2-aminobenzathiazole scaffold, which targets the PD-1/PDL-1 pathway. In the viability assay, it was found that these compounds decreased the proliferation of peripheral blood mononuclear cells in the concentration of 10 uM. Overall, our results indicate that these novel compounds are potential checkpoint inhibitors for cancer immunotherapy.
{"title":"Design and synthesis of novel peptidomimetics for cancer immunotherapy","authors":"Ceyda Köse, Esra Uysal, B. Yazici, Z. Tuğay, Serap İpek Dingiş Birgül, Hamdullah Yanık, E. Tavukçuoğlu, Sevgi Gulyuz, A. Akdemir, G. Esendagli, Ö. Yılmaz, Onur Alptürk","doi":"10.25135/ACG.OC.86.20.09.1802","DOIUrl":"https://doi.org/10.25135/ACG.OC.86.20.09.1802","url":null,"abstract":"Tumor cells benefit from some certain signals, which are referred to as “immune checkpoints”, to escape immune-mediated destruction. With that in mind, it is believed that the blockade of these points, such as programmed cell death Ligand-1 (PD-L1) and programmed cell death 1 (PD-1), can restore an adaptative immune response against tumoral cells. In this study, we have designed and synthesized some novel peptidomimetics with a 2-aminobenzathiazole scaffold, which targets the PD-1/PDL-1 pathway. In the viability assay, it was found that these compounds decreased the proliferation of peripheral blood mononuclear cells in the concentration of 10 uM. Overall, our results indicate that these novel compounds are potential checkpoint inhibitors for cancer immunotherapy.","PeriodicalId":19553,"journal":{"name":"Organic Communications","volume":" ","pages":""},"PeriodicalIF":1.7,"publicationDate":"2020-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42094230","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 : 2020-03-28DOI: 10.25135/acg.oc.71.02.01.1521
A. Shinde, N. Deshmukh, S. Zangade
A series of bis-1, 3-benzoxazines (3a-f) were synthesized from reduced product of propane-1, 3-diamine Schiff bases in the presence of formalin under conventional heating and microwave irradiation. The structures of newly synthesized diamines and bis-1, 3-benzoxazines were established on the basis of spectroscopic data. Further, all the synthesized compounds were screened for antimicrobial activity. Some of the compounds showed very good activity compared to standard drugs against all pathogenic bacteria and fungi.
{"title":"Microwave-assisted synthesis of some new bis-1,3-benzoxazines and their antimicrobial activity","authors":"A. Shinde, N. Deshmukh, S. Zangade","doi":"10.25135/acg.oc.71.02.01.1521","DOIUrl":"https://doi.org/10.25135/acg.oc.71.02.01.1521","url":null,"abstract":"A series of bis-1, 3-benzoxazines (3a-f) were synthesized from reduced product of propane-1, 3-diamine Schiff bases in the presence of formalin under conventional heating and microwave irradiation. The structures of newly synthesized diamines and bis-1, 3-benzoxazines were established on the basis of spectroscopic data. Further, all the synthesized compounds were screened for antimicrobial activity. Some of the compounds showed very good activity compared to standard drugs against all pathogenic bacteria and fungi.","PeriodicalId":19553,"journal":{"name":"Organic Communications","volume":" ","pages":""},"PeriodicalIF":1.7,"publicationDate":"2020-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45099703","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 : 2019-09-03DOI: 10.25135/acg.oc.65.19.07.1330
M. Koçer, Z. O. Erdogan, Mehmet Oguz, S. Kucukkolbasi, M. Yılmaz
{"title":"A Calix[4]arene-tren mdified electrode for determination of Lead ions in aqueous solution","authors":"M. Koçer, Z. O. Erdogan, Mehmet Oguz, S. Kucukkolbasi, M. Yılmaz","doi":"10.25135/acg.oc.65.19.07.1330","DOIUrl":"https://doi.org/10.25135/acg.oc.65.19.07.1330","url":null,"abstract":"","PeriodicalId":19553,"journal":{"name":"Organic Communications","volume":" ","pages":""},"PeriodicalIF":1.7,"publicationDate":"2019-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45144650","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 : 2019-09-01DOI: 10.25135/acg.oc.66.19.07.1352
O. Kazakova, L. Rubanik, I. Smirnova, O. Savinova, A. Petrova, N. Poleschuk, E. Khusnutdinova, E. Boreko, Yu. M. Kapustina
Modified synthesis of 3β-nicotinoyloxy-olean-12(13)-en-28-oic acid and 3-deoxy-3a-homo-3a-aza28-hydroxy-olean-12(13)-ene from natural occurring oleanolic acid is suggested. These compounds and two others of ursane and lupane type triterpenoids (3-oximino-urs-12-en-28-oic acid and 3-deoxy-3a-homo-3a-aza28-hydroxy-lup-12(13)-ene) were screened in vitro against Chlamydia trachomatis strain F-3271/Belarus/2015. Oleanane triterpenoids became the leading compounds with chemotherapeutic index > 8 and were chosen for further research.
{"title":"Synthesis and in vitro activity of oleanane type derivatives against Chlamydia trachomatis","authors":"O. Kazakova, L. Rubanik, I. Smirnova, O. Savinova, A. Petrova, N. Poleschuk, E. Khusnutdinova, E. Boreko, Yu. M. Kapustina","doi":"10.25135/acg.oc.66.19.07.1352","DOIUrl":"https://doi.org/10.25135/acg.oc.66.19.07.1352","url":null,"abstract":"Modified synthesis of 3β-nicotinoyloxy-olean-12(13)-en-28-oic acid and 3-deoxy-3a-homo-3a-aza28-hydroxy-olean-12(13)-ene from natural occurring oleanolic acid is suggested. These compounds and two others of ursane and lupane type triterpenoids (3-oximino-urs-12-en-28-oic acid and 3-deoxy-3a-homo-3a-aza28-hydroxy-lup-12(13)-ene) were screened in vitro against Chlamydia trachomatis strain F-3271/Belarus/2015. Oleanane triterpenoids became the leading compounds with chemotherapeutic index > 8 and were chosen for further research.","PeriodicalId":19553,"journal":{"name":"Organic Communications","volume":" ","pages":""},"PeriodicalIF":1.7,"publicationDate":"2019-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44107704","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 : 2019-09-01DOI: 10.25135/acg.oc.60.19.07.1358
M. Balci
Dear Editor Secen, In 1869, Vladimir Vasilyevich Markovnikov, a Russian organic chemist from the University of Kazan formulated in his doctoral thesis the famous rule which is named after his name. According to this rule: When an unsymmetrically substituted unsaturated hydrocarbon reacts with hydrogen halides, the halide adds to the least hydrogenated carbon, that is to the one which experience more influence from the other neighbouring carbons. In other words: when an unsymmetrical alkene reacts with a hydrogen halide, the hydrogen adds to the carbon that has the greater number of hydrogen substituents, and the halogen to the carbon having the fewer number of hydrogen substituents” Markovnikov’s rule predicted the regioselectivity of electrophilic addition reactions of alkenes. This rule was an important milestone in the development of the structural theory in organic chemistry. The chemical basis for Markovnikov's Rule is the formation of the most stable carbocation during the addition process. In 1933 Karasch described the addition of hydrogen bromide in the presence of peroxides to unsymmetrically substituted alkenes and the formation of a product called as Anti-Markovnikov product. Hyroboration reaction also forms the Anti-Markovnikov products. In all these reactions the electrophiles (H, Br , and BH3) attack the carbon atom with the greater number of hydrogen substituents forming the most stable intermediate. However, the students are getting ignored. They assume that the anti-Markovnikov addition results in the formation of the least stable intermediate. Therefore, I assume, that this formulation of Anti-Markovnikov addition for radiacal addition and hydroboration should be changed. Lomonosov Moscow State University and Kazan Federal Universities jointly organized a conference Markovnikov Congress on Organic Chemistry dedicated to the 150 anniversary of the discovery by the Russian chemist Vladimir Vasilyevich Markovnikov in 1869 this year. This congress was attended by 117 well selected invited speakers from around the world, as well as more than 400 scientists. As Markovnikov was the founder of the Moscow University School of Chemistry and graduated from Kazan Chemical School, the conference started on 21th June in Moscow as Pre-symposium and the main part was held on 24-28, 2019 in Kazan. The quality of this congress was very high. The participants had also the opportunity to visit Markovnikov’s laboratory and the historical sites of Moscow and Kazan. Thanks to the organizers... Metin Balcı Emeritus Professor Middle East Technical University Ankara/Turkey E-Mail: mbalci@metu.edu.tr ORCID Metin Balcı: 0000-0003-4443-9245 Received July 31, 2019; Published online August 23, 2019
{"title":"On the 150th anniversary of Markovnikov Rule","authors":"M. Balci","doi":"10.25135/acg.oc.60.19.07.1358","DOIUrl":"https://doi.org/10.25135/acg.oc.60.19.07.1358","url":null,"abstract":"Dear Editor Secen, In 1869, Vladimir Vasilyevich Markovnikov, a Russian organic chemist from the University of Kazan formulated in his doctoral thesis the famous rule which is named after his name. According to this rule: When an unsymmetrically substituted unsaturated hydrocarbon reacts with hydrogen halides, the halide adds to the least hydrogenated carbon, that is to the one which experience more influence from the other neighbouring carbons. In other words: when an unsymmetrical alkene reacts with a hydrogen halide, the hydrogen adds to the carbon that has the greater number of hydrogen substituents, and the halogen to the carbon having the fewer number of hydrogen substituents” Markovnikov’s rule predicted the regioselectivity of electrophilic addition reactions of alkenes. This rule was an important milestone in the development of the structural theory in organic chemistry. The chemical basis for Markovnikov's Rule is the formation of the most stable carbocation during the addition process. In 1933 Karasch described the addition of hydrogen bromide in the presence of peroxides to unsymmetrically substituted alkenes and the formation of a product called as Anti-Markovnikov product. Hyroboration reaction also forms the Anti-Markovnikov products. In all these reactions the electrophiles (H, Br , and BH3) attack the carbon atom with the greater number of hydrogen substituents forming the most stable intermediate. However, the students are getting ignored. They assume that the anti-Markovnikov addition results in the formation of the least stable intermediate. Therefore, I assume, that this formulation of Anti-Markovnikov addition for radiacal addition and hydroboration should be changed. Lomonosov Moscow State University and Kazan Federal Universities jointly organized a conference Markovnikov Congress on Organic Chemistry dedicated to the 150 anniversary of the discovery by the Russian chemist Vladimir Vasilyevich Markovnikov in 1869 this year. This congress was attended by 117 well selected invited speakers from around the world, as well as more than 400 scientists. As Markovnikov was the founder of the Moscow University School of Chemistry and graduated from Kazan Chemical School, the conference started on 21th June in Moscow as Pre-symposium and the main part was held on 24-28, 2019 in Kazan. The quality of this congress was very high. The participants had also the opportunity to visit Markovnikov’s laboratory and the historical sites of Moscow and Kazan. Thanks to the organizers... Metin Balcı Emeritus Professor Middle East Technical University Ankara/Turkey E-Mail: mbalci@metu.edu.tr ORCID Metin Balcı: 0000-0003-4443-9245 Received July 31, 2019; Published online August 23, 2019","PeriodicalId":19553,"journal":{"name":"Organic Communications","volume":" ","pages":""},"PeriodicalIF":1.7,"publicationDate":"2019-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48266627","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 : 2019-09-01DOI: 10.25135/acg.oc.62.19.07.1323
F. N. A. A. Rashid, Mohd Fazli t Mohamma, Zurina i Shaamer, Hardeli Hamzah
{"title":"An unprecedented synthesis of some novel 3,4-fused pyrazolidinone-γ-lactam bicyclic moieties from 2,3-dioxo-4-carboxy-5-(subtituted)pyrrolidines","authors":"F. N. A. A. Rashid, Mohd Fazli t Mohamma, Zurina i Shaamer, Hardeli Hamzah","doi":"10.25135/acg.oc.62.19.07.1323","DOIUrl":"https://doi.org/10.25135/acg.oc.62.19.07.1323","url":null,"abstract":"","PeriodicalId":19553,"journal":{"name":"Organic Communications","volume":" ","pages":""},"PeriodicalIF":1.7,"publicationDate":"2019-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44103117","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 : 2019-09-01DOI: 10.25135/acg.oc.64.19.06.1309
B. Özgeriş, F. Tümer
We aimed the synthesis of carboxamide 8 and 10, however, beside the main product, one more species was detected in the reaction solution. The characterization of this side product showed that it was the other isomer of the main product. To establish reaction conditions for the synthesis of carboxamide derivatives, we have set up several experiments by changing the Fe stoichiometry. When a molar equivalent Fe was used, only two reaction products 8 and 10 were obtained. The increase in Fe stoichiometry caused the formation of side product 9 and 11 even formation of reduced alcohol products (12-15) by Minisci reaction.
{"title":"A study of Minisci reaction by changing Fe2+ equivalency: Preparation of arylpyridinyl methanol","authors":"B. Özgeriş, F. Tümer","doi":"10.25135/acg.oc.64.19.06.1309","DOIUrl":"https://doi.org/10.25135/acg.oc.64.19.06.1309","url":null,"abstract":"We aimed the synthesis of carboxamide 8 and 10, however, beside the main product, one more species was detected in the reaction solution. The characterization of this side product showed that it was the other isomer of the main product. To establish reaction conditions for the synthesis of carboxamide derivatives, we have set up several experiments by changing the Fe stoichiometry. When a molar equivalent Fe was used, only two reaction products 8 and 10 were obtained. The increase in Fe stoichiometry caused the formation of side product 9 and 11 even formation of reduced alcohol products (12-15) by Minisci reaction.","PeriodicalId":19553,"journal":{"name":"Organic Communications","volume":" ","pages":""},"PeriodicalIF":1.7,"publicationDate":"2019-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46762342","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 : 2019-06-23DOI: 10.25135/ACG.OC.57.19.04.1242
V. Nguyen, .kim-chi Huynh, Thanh-Danh Nguyen, Kim Hoang
{"title":"xidation of hesperidin into diosmin using ionic liquids","authors":"V. Nguyen, .kim-chi Huynh, Thanh-Danh Nguyen, Kim Hoang","doi":"10.25135/ACG.OC.57.19.04.1242","DOIUrl":"https://doi.org/10.25135/ACG.OC.57.19.04.1242","url":null,"abstract":"","PeriodicalId":19553,"journal":{"name":"Organic Communications","volume":" ","pages":""},"PeriodicalIF":1.7,"publicationDate":"2019-06-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47693498","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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