Yasutaka Shimotori, M. Hoshi, N. Ogawa, T. Miyakoshi, T. Kanamoto
{"title":"Synthesis, antibacterial activities, and sustained perfume release properties of optically active5-hydroxy- and 5-acetoxyalkanethioamide analogues","authors":"Yasutaka Shimotori, M. Hoshi, N. Ogawa, T. Miyakoshi, T. Kanamoto","doi":"10.1515/hc-2019-0103","DOIUrl":"https://doi.org/10.1515/hc-2019-0103","url":null,"abstract":"Abstract 5-Acetoxy- and 5-hydroxyalkanethioamide analogues showed high antibacterial activity against Staphylococcus aureus. Antibacterial thioamides were prepared from 5-alkyl-δ-lactones by amidation, thionation, and subsequent deacetylation. Optically active thioamides with 99% diastereomeric excesses were prepared by diastereomeric resolution using Cbz-L-proline as the resolving agent. Antibacterial thioamides were slowly lactonized by a lipase catalyst. Therefore, these thioamides are potential sustained-release perfume compounds having antibacterial properties.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"26 1","pages":"84 - 98"},"PeriodicalIF":2.3,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2019-0103","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42475294","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Safia Rasheed, Mukhtiar Ahmed, M. Faisal, M. Naseer
{"title":"Isatin-3-thiosemicarbazone as Chromogenic Sensor for the Selective Detection of Fluoride Anion","authors":"Safia Rasheed, Mukhtiar Ahmed, M. Faisal, M. Naseer","doi":"10.1515/hc-2020-0104","DOIUrl":"https://doi.org/10.1515/hc-2020-0104","url":null,"abstract":"Abstract In this study, we describe the anion recognition ability of isatin-3-thiosemicarbazone 2, which contains two different anion recognition units i.e. isatin NH and the thiourea moiety. Both have the ability to act as proton donors. Most importantly, a significant colour change of 2 was observed (from light yellow to reddish orange) in organic medium only after the addition of the F– anion. No such colour change could be observed for any other anions including Cl–, Br–, I–, H2PO4−, ${{text{H}}_{2}}text{P}{{text{O}}_{4}}^{-},$ NO2−, $text{N}{{text{O}}_{text{2}}}^{-},$ PF4− $text{P}{{text{F}}_{4}}^{-}$etc. The UV-Vis spectroscopic studies also indicate the potential of this compound for selective detection of fluoride anions. 1H-NMR titrations clearly indicate the formation of the 2.F– anionic complex. The Density-functional theory (DFT) calculations are also performed to get further insights on the formation of 2.F– complex.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"26 1","pages":"123 - 129"},"PeriodicalIF":2.3,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2020-0104","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46031313","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Visible light mediated aerobic oxidative hydroxylation of 2-oxindole-3-carboxylate esters: an alternative approach to 3-hydroxy-2-oxindoles","authors":"Jinge Wang, Siyitemer Osman, Xiaona Lu, Junyi Chen, X. Xia","doi":"10.1515/hc-2019-0114","DOIUrl":"https://doi.org/10.1515/hc-2019-0114","url":null,"abstract":"Abstract A convenient aerobic oxidative hydroxylation of 3-substituted oxindoles under mild reaction conditions is described herein. This process was accomplished by the activation of molecular oxygen in the air in the presence of a photocatalyst under the irradiation of visible light. The desired product was delivered in up to 89% yield without the addition of base or stoichiometric oxidant.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"26 1","pages":"168 - 175"},"PeriodicalIF":2.3,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2019-0114","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42043823","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Huijun Xie, C. Niu, Zeyang Chao, Nuramina Mamat, H. Akber Aisa
{"title":"Synthesis and Activity of New Schiff Bases of Furocoumarin","authors":"Huijun Xie, C. Niu, Zeyang Chao, Nuramina Mamat, H. Akber Aisa","doi":"10.1515/hc-2020-0115","DOIUrl":"https://doi.org/10.1515/hc-2020-0115","url":null,"abstract":"Abstract Furocoumarins, such as 8-MOP, are the most common medications used to relieve the symptoms of vitiligo clinically. Some furocoumarins also showed excellent performance in an anti-bacterial assay. This paper describes the synthesis of a series of novel Schiff bases (6a-6k), and their promotion in melanogenesis and anti-bacterial properties were studied in vitro. The pigment production of B16 cells and bacterial inhibition ring assay were applied for the bioactivity of 6a-6k. According to the results, a stronger promotion on pigment content was observed, when six compounds co-cultured with cells, compared with positive control (8-MOP). Significantly, compound 6k (237%) as the most active was found to increase the amount of melanin more than 1.7 times compared with 8-MOP activation rate (136%). All the compounds could moderately retard C. albicans growth. Interestingly, aldehyde 5, which possessed a broader antibacterial spectrum, showed the highest inhibition against C. albicans as well and much better than the positive control (Amphotericin B). Studies of 6k in animal models of vitiligo and related molecular mechanism are presently under way, with the aim of discovering an anti-vitiligo leading compound.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"26 1","pages":"176 - 184"},"PeriodicalIF":2.3,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2020-0115","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45747461","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Shaikha S. Alneyadi, Naheed Amer, T. Thomas, Ruba Al Ajeil, Priya Breitener, N. Munawar
{"title":"Synthesis, Characterization, and Antioxidant Activity of Some 2-Methoxyphenols derivatives","authors":"Shaikha S. Alneyadi, Naheed Amer, T. Thomas, Ruba Al Ajeil, Priya Breitener, N. Munawar","doi":"10.1515/hc-2020-0112","DOIUrl":"https://doi.org/10.1515/hc-2020-0112","url":null,"abstract":"Abstract Oxidative stress is a causative factor in the pathophysiology of numerous diseases, such as diabetes, atherosclerosis, cancer, and neurodegenerative and cardiovascular diseases. Therapeutic antioxidants are promising candidates for preventing and treating conditions in which oxidative stress is a contributing factor. In this study, we report the design, synthesis and antioxidant activity of six compounds containing the 2-methoxyphenol moiety core structure. The synthesized derivatives were characterized using 1H NMR, 13C NMR, Fourier-transform infrared (FT-IR), and elemental analysis spectroscopy. The antioxidant properties of the compounds were evaluated using the 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH), 2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS), and oxygen radical absorbance capacity (ORAC) assay. New phenolic acid-derived compounds with antioxidant activity were identified.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"26 1","pages":"112 - 122"},"PeriodicalIF":2.3,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2020-0112","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48146420","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
N. Pesyan, Narmin Akhteh, H. Batmani, B. Anıl, E. Şahin
{"title":"A Facile and Catalyst-free Synthesis of Hexahydroacridine-1,8(2H,5H )-dione and Octahydroacridin-10(1H )-yl)thiourea Derivatives: Inter- and Intramolecular Aza-Michael addition","authors":"N. Pesyan, Narmin Akhteh, H. Batmani, B. Anıl, E. Şahin","doi":"10.1515/hc-2020-0005","DOIUrl":"https://doi.org/10.1515/hc-2020-0005","url":null,"abstract":"Abstract An easy and convenient technique for the one-pot synthesis of novel compounds of hexahydroacridine-1,8(2H,5H)-dione and octahydroacridin-10(1H)-yl) thiourea derivatives has been developed by the reaction of the octahydro-1H-xanthenes with hydroxylamine hydrochloride and thiosemicarbazide in ethylene glycol, which is a green solvent, under mild reaction conditions. IR, 1H NMR, 13C NMR spectrometry, and X-ray diffraction analysis were used to identify the structures of these compounds.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"26 1","pages":"26 - 32"},"PeriodicalIF":2.3,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2020-0005","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48587915","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Ball-Type Dioxy-o-Carborane Bridged Cobaltphthalocyanine: Synthesis, Characterization and DFT Studies For Dye-Sensitized Solar Cells as Photosensitizer","authors":"Sevinc Sener","doi":"10.1515/hc-2020-0007","DOIUrl":"https://doi.org/10.1515/hc-2020-0007","url":null,"abstract":"Abstract The synthesis and spectroscopic characterization of an innovative ball-type cobalt metallophthalocyanine 4, bridged by four 1,2-bis(2-hydroxymethyl)-O-carborane (HMOC) 1 units, has been achieved. The synthesized compound 4 was characterized structurally and electronically using elemental analysis, UV-Vis absorption spectroscopy, FT-IR spectroscopy, MALDI-TOF mass spectrometry, EPR spectroscopy and magnetic susceptibility. The photovoltaic performance of the newly synthesized compound in dye-sensitized solar cells was investigated. In order to clarify the effect of dye-sensitization time on photovoltaic performance parameters, the sensitization time was varied from 12 to 60 h and the performance parameters were investigated. It was found that sensitization time had a strong effect on the main performance parameters. The best photovoltaic performance was achieved after sensitization for 36 h (short circuit current density, 5.41 mA cm−2; overall conversion efficiency, 3.42%). Computational UV-Vis absorption spectra of the molecule was calculated using time dependent density functional theory and was found consistent with measured UV-Vis spectra.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"26 1","pages":"37 - 45"},"PeriodicalIF":2.3,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2020-0007","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42030008","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
M. Hawash, A. Eid, N. Jaradat, M. Abualhasan, J. Amer, A. Naser Zaid, Saja Draghmeh, Donia Daraghmeh, Haifa Daraghmeh, Tahrir Shtayeh, Hadeel Sawaftah, A. Mousa
{"title":"Synthesis and Biological Evaluation of Benzodioxole Derivatives as Potential Anticancer and Antioxidant agents","authors":"M. Hawash, A. Eid, N. Jaradat, M. Abualhasan, J. Amer, A. Naser Zaid, Saja Draghmeh, Donia Daraghmeh, Haifa Daraghmeh, Tahrir Shtayeh, Hadeel Sawaftah, A. Mousa","doi":"10.1515/hc-2020-0105","DOIUrl":"https://doi.org/10.1515/hc-2020-0105","url":null,"abstract":"Abstract a series of benzodioxole compounds were synthesized and evaluated for their cytotoxic activity against cervical (Hela), colorectal (Caco-2), and liver (Hep3B) cancer cell lines. Compounds 5a, 5b, 6a, 6b, 7a and 7b showed very weak or negligible anticancer activity with IC50 3.94-9.12 mM. On the contrary, carboxamide containing compounds 2a and 2b showed anticancer activity. Both 2a and 2b reduced Hep3B secretions of α-fetoprotein (α-FP) to 1625.8 ng/ml and 2340 ng/ml, respectively, compared to 2519.17 ng/ml in untreated cells. The results also showed that compound 2a has potent anticancer activity against Hep3B cancer cell line. Furthermore, in cell cycle analysis, compound 2a induced arrest in the G2-M phase in value of 8.07% that was very close to the activity of doxorubicin (7.4%). These results indicate that compound 2a has a potent and promising antitumor activity. However, benzodiazepine derivatives (7a and 7b) showed moderate antioxidant activity with IC50 values of 39.85 and 79.95 μM, respectively compared with the potent antioxidant agent Trolox (IC50 = 7.72 μM).","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"26 1","pages":"157 - 167"},"PeriodicalIF":2.3,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2020-0105","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48141951","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis and antiproliferative activities of polymethoxyflavones aminoalkyl and amino acid derivatives","authors":"Liqiong Ran, Xue-li Li, Manhui Liu, Qiu-an Wang","doi":"10.1515/hc-2020-0010","DOIUrl":"https://doi.org/10.1515/hc-2020-0010","url":null,"abstract":"Abstract Twelve novel aminoalkyl derivatives 3a-3f, 4a-4f and four novel amino acid derivatives 5a, 5b, 6a and 6b of polymethoxyflavones 1 and 2 were synthesized through regioselective demethylation, etherification, amination, EDCl-mediated amide condensation and alkaline hydrolysis, using tangeretin and nobiletin as starting materials. Their antiproliferative activities against four different human cancer cell lines (Aspc-1, SUN5, HepG-2 and HCT116) were evaluated by in vitro CCK-8 assay. The results show that the majority of the synthetic compounds exhibited moderate to good antiproliferative activity. In particular, the antiproliferative activity of compound 5b against HepG-2 cells (IC50 0.057 μM) was equal to the positive control drug Staurosporine (IC50 0.0575 μM).","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"26 1","pages":"68 - 75"},"PeriodicalIF":2.3,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2020-0010","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47632093","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Xiaofeng Yu, Zhen Zhang, Renyuan Song, Li-xin Gou, Guangrong Wang
{"title":"Synthesis of 2-aryl-benzothiazoles via Ni-catalyzed coupling of benzothiazoles and aryl sulfamates","authors":"Xiaofeng Yu, Zhen Zhang, Renyuan Song, Li-xin Gou, Guangrong Wang","doi":"10.1515/hc-2020-0001","DOIUrl":"https://doi.org/10.1515/hc-2020-0001","url":null,"abstract":"Abstract 2-Aryl-benzothiazoles have been successfully synthesized via a simple coupling reaction between benzothiazoles and aryl sulfamates using a nickel catalyst. The nickel catalyst is inexpensive, reusable and commercially available. In addition, the use of highly expensive palladium catalysts and unstable raw materials has been avoided. 2-Aryl-benzothiazoles bearing various substituents on the aryl groups were obtained in good yield.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"26 1","pages":"1 - 5"},"PeriodicalIF":2.3,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2020-0001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48883938","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}