Manoj N. Bhoi , Mayuri A. Borad , Ankita P. Solanki , Hitesh D. Patel
{"title":"Novel 4H-pyrimido[2,1-b]benzothiazoles derivatives: Camphorsulphonic acid catalyzed enantioselective synthesis, optimization, and biological study","authors":"Manoj N. Bhoi , Mayuri A. Borad , Ankita P. Solanki , Hitesh D. Patel","doi":"10.1080/10426507.2023.2199994","DOIUrl":"https://doi.org/10.1080/10426507.2023.2199994","url":null,"abstract":"<div><p>An efficient, highly convergent route for the synthesis of novel fourteen single isomer derivatives of ethyl-2-methyl-4-(pyridin-2-yl)-4<em>H</em>-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylate have been developed by one-pot, three-component reaction between pyridine 2-aldehyde, <em>β</em>-ketoester and various derivatives of 2-amino benzothiazole in the presence of D-(+)-10-camphorsulphonic acid (D-(+)-10-CSA) as an effective chiral acid catalyst. Under the optimized conditions with 20 mol% catalyst loading, a wide range of optically active 4<em>H</em>-pyrimido[2,1-b]benzothiazole derivatives were obtained in good yields (up to 82%) with good to excellent enantioselectivities (84-99%ee). Their structures were elucidated by various spectroscopic methods such as <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, Chiral HPLC, mass and elemental analysis. The attractive feature of this approach is one-pot synthesis, good yield, environment benign, mild reaction condition, simple, efficient, excellent stereoselectivity, water soluble catalyst and easy workup. All the final scaffolds have been screened for antibacterial activity. Among them, <strong>4a’, 4c’, 4d’, 4e’, 4f’, 4g’, 4j’,4m’</strong> and <strong>4n’</strong> were proven to possess enhanced antibacterial properties as compared to the standard drug.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 10","pages":"Pages 822-835"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49729622","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
G.B. Venkatesh , S. HariPrasad , A.S. Jeevan Chakravarthy
{"title":"One-pot synthesis of a new class of alkynyl anionic synthons: the 4-(2',2-trimethylsilylethynylphenoxymethyl)-2H-chromen-2-ones","authors":"G.B. Venkatesh , S. HariPrasad , A.S. Jeevan Chakravarthy","doi":"10.1080/10426507.2022.2150851","DOIUrl":"https://doi.org/10.1080/10426507.2022.2150851","url":null,"abstract":"<div><p>An efficient approach for the synthesis of a new class of anionic synthons: the 4-(2<em>'</em>,2-trimethylsilylethynylphenoxymethyl)-2<em>H</em>-chromen-2-ones employing a one-pot three-component reaction is reported. Reaction of trimethylsilylacetylene, <em>o</em>-iodophenol and nine different bromomethylcoumarins in THF solvent at 80<!--> <!-->°C under sealed tube conditions gave nine novel 4-(2<em>'</em>,2-trimethylsilylethynylphenoxymethyl)-2<em>H</em>-chromen-2-ones in greater than 90% isolated yields. All compounds were spectroscopically characterized by elemental analysis, FT-IR, MS, <sup>1</sup>H-, and <sup>13</sup>C-NMR techniques.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 4","pages":"Pages 330-335"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49700487","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Stephany González-González , Marco Franco-Pérez , Christiaan Jardínez , Jorge Jairo Cariño-Moreno , María Guadalupe Ramírez-Sotelo , Angel Zamudio-Medina
{"title":"Synthesis, characterization, and quantum chemistry local chemical reactivity description of new phosphorylated derivatives of piperazine","authors":"Stephany González-González , Marco Franco-Pérez , Christiaan Jardínez , Jorge Jairo Cariño-Moreno , María Guadalupe Ramírez-Sotelo , Angel Zamudio-Medina","doi":"10.1080/10426507.2023.2193404","DOIUrl":"https://doi.org/10.1080/10426507.2023.2193404","url":null,"abstract":"<div><p>We report a fast, safe, and efficient procedure for the synthesis of phosphorylated derivatives of piperazines through a multicomponent reaction (MCR) strategy. Our key reagents were the piperazines 1-(2-methoxyphenyl) piperazine and 3-(4- (2-methoxyphenyl) piperazin-1-yl) propan-1-amine which reacted with five different phosphorous chlorides. A total of ten new derivatives were obtained, all confirmed by NMR spectroscopy (<sup>1</sup>H, <sup>13</sup>C, and <sup>31</sup>P) and mass spectrometry. Then, the reactivity profile of our new compounds was characterized through the new theoretical framework of the Local Electronic Temperature of Atoms in Molecules (LT-AIMs), from which we identified the most reactive sites of each of our derivatives. Furthermore, some of the quantities defined within this context were used to reproduce trends observed in our NMR records. A brief discussion about the advantages of performing a combined experimental and theoretical chemical characterization of recently synthesized compounds is also presented, particularly for those compounds with potential therapeutic features.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 8","pages":"Pages 693-703"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49712604","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Aromatic metamorphosis of thiophenes: replacing endocyclic sulfur with a different atom or group of atoms","authors":"Hideki Yorimitsu","doi":"10.1080/10426507.2023.2190978","DOIUrl":"https://doi.org/10.1080/10426507.2023.2190978","url":null,"abstract":"<div><p>This account deals with our research about the development of synthetic approaches to replace the endocyclic sulfur in thiophenes with a different atom or group of atoms, that is, an aromatic metamorphosis of thiophenes, as a game-changer in organic synthesis. The aromatic metamorphosis has allowed thiophenes and their benzo-analogs to be converted to a variety of cyclic compounds such as triphenylenes, carbazoles, dibenzophospholes, fluorenes, dibenzoazepines, siloles, germoles, and boroles, some of which are difficult to synthesize by conventional methods. The transformations have been achieved by using one of the following dearomatization tricks for enhancing the reactivity of the stable thiophene cores: (1) alkylation at the sulfur atom to yield sulfonium salts; (2) oxidation into sulfones; (3) reduction into 1,4-dianions.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 6","pages":"Pages 478-480"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49863682","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of aza-S(VI) motifs","authors":"James A. Bull","doi":"10.1080/10426507.2023.2175827","DOIUrl":"https://doi.org/10.1080/10426507.2023.2175827","url":null,"abstract":"<div><p>Sulfoximines and sulfonimidamides are of interest as design options for medicinal chemists. This article describes the development of methods for the synthesis of sulfoximines by metal-free NH-transfer to sulfoxides, and NH/O transfer to sulfides, using convenient sources of ammonia and hypervalent iodine reagents. Similarly, sulfonimidamides are prepared from sulfenamides. Methods for the preparation of enantioenriched sulfonimidoyl fluorides are also described, as are their stereospecific reactions with amines and Grignard reagents. This work was presented at the 29<sup>th</sup> International Symposium on the Organic Chemistry of Sulfur (Guelph, July 2022).</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 6","pages":"Pages 471-477"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49863683","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Basal application of different sources of silicon fertilizers to enhance biochemical factors in sugarcane (Saccharum officinarum L.)","authors":"Veeran Sivakumar Indhumathi , Periyakaman Chandramani , Peyandi Paraman Mahendran , Jayachandran Jayaraj","doi":"10.1080/10426507.2022.2145607","DOIUrl":"https://doi.org/10.1080/10426507.2022.2145607","url":null,"abstract":"<div><p>Four silicon sources <em>viz.,</em> rice husk ash, bagasse ash, calcium silicate, sodium metasilicate each at the rate of 500 and 1000 kg/ha were incorporated as basal application in two sugarcane fields of Poovanthi and Silaiman village of Sivagangai and Madurai district respectively. Leaves from the silicon treated plants were collected at 90,180 and 270 d after planting for analysis of biochemical factors which revealed that the silicon content in the Poovanthi village was ranged from 1.18 to 1.77% and that of Silaiman village was 1.28 to 1.78%. Similarly phenol content ranged from 7.68 to 10.33 mg/g and 10.49 to 12.85 mg/g, tannin content ranged from 4.21 to 6.32 and 4.70 to 7.03 mg/g, peroxidase activity ranged from 32.18 to 38.60 and 38.07 to 44.38 Δ<sub>460</sub>/min/mg and phenylalanine ammonia lyase activity ranged from 29.93 to 36.85 and 36.31 to 44.48 Δ<sub>290</sub>/µmol m<sup>−1</sup>mL<sup>−1</sup>g<sup>−1</sup> in the fields of Poovanthi and Silaiman village respectively. Among the four sources of silicon fertilizers tested, basal application of calcium silicate at 500 kg/ha was found effective in facilitating the maximum accumulation of silicon content along with phenol, tannin content, peroxidase and phenylalanine ammonia lyase activity.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 4","pages":"Pages 311-320"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49700535","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Fangfang Luo , Le Wang , Xiao Zhang , Ping Xu , Xiao Wang , Yi Qu
{"title":"Ratiometric H2S probe that can be recognized by the naked eye and its application in cell imaging","authors":"Fangfang Luo , Le Wang , Xiao Zhang , Ping Xu , Xiao Wang , Yi Qu","doi":"10.1080/10426507.2023.2199995","DOIUrl":"https://doi.org/10.1080/10426507.2023.2199995","url":null,"abstract":"<div><p>A ratiometric dual-mode probe NI-SH based on 1,8-Naphthalimide was prepared for H<sub>2</sub>S detection. When treated with H<sub>2</sub>S, the fluorescence of NI-SH changes from blue (456 nm) to green (540 nm), and displays significant color variation (colorless to yellow) that can visible to the naked eye. Further investigation shows that the NI-SH has high sensitivity, selectivity, and low detection limit at about 0.2 μM, and with large Stokes shift (84 nm). The intermolecular charge transfer (ICT) response mechanism of NI-SH was further studied by analyzing the distributions of the molecular orbital. Besides, NI-SH exhibits a ratiometric fluorescence response in living Hela cells.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 10","pages":"Pages 836-843"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49704463","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Direct synthesis of γ,γ-diketophosphonates from pentacovalent 1,2λ5-oxaphosphorane","authors":"Tae Woo Kim , Chung-Min Park , Kang-Yeoun Jung","doi":"10.1080/10426507.2023.2198713","DOIUrl":"https://doi.org/10.1080/10426507.2023.2198713","url":null,"abstract":"<div><p>Pyrazole phosphonate derivatives are receiving increasing attention in the pharmaceutical field due to their wide range of biological activities. However, the syntheses of diketophosphonates, as precursors of α-pyrazole phosphonates, require high temperatures and excess of reactants to proceed. Therefore, a simple and efficient procedure to prepare γ,γ-diketophosphonates <em>via</em> reactions between 1,2λ<sup>5</sup>-oxaphospholene and aromatic acid chlorides under mild conditions is proposed herein. The formation of the keto phosphonium ion of 1,2λ<sup>5</sup>-oxaphospholenes is favored at −10 °C, and these ions react with aromatic acid chlorides to yield γ,γ-diketophosphonates in 83–89% yields. This reaction may be readily applied for the preparation of γ,γ-derivatives of α-diketophosphonates as precursors of α-pyrazole phosphonates, which are molecules of immense medical significance.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 10","pages":"Pages 783-788"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49704494","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Yanle Men , Zijian Li , Hongying Wang , Yuming Liu , Xuguang Liu , Baoquan Chen
{"title":"Synthesis and antiproliferative evaluation of novel 1,3,4-thiadiazole-S-alkyl derivatives based on quinazolinone","authors":"Yanle Men , Zijian Li , Hongying Wang , Yuming Liu , Xuguang Liu , Baoquan Chen","doi":"10.1080/10426507.2023.2176500","DOIUrl":"https://doi.org/10.1080/10426507.2023.2176500","url":null,"abstract":"<div><p>Thirty-five novel 1,3,4-thiadiazole-S-alkyl derivatives based on quinazolinone have been designed and synthesized. The structures of the target compounds <strong>5a</strong> − <strong>5p</strong> and <strong>6a</strong> − <strong>6s</strong> were confirmed by their IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, HR-ESI-MS spectroscopic data. This study detected their cytotoxicity for mouse fibroblast (normal cells, L929) and their <em>in vitro</em> antiproliferative activities against human cancer cell lines (Hela, MCF-7 and A549) by using CCK-8 assay. The results of all the tested compounds <strong>5a</strong> − <strong>5p</strong> and <strong>6a</strong> − <strong>6s</strong> showed that the growth and reproduction of cells were impeded to a certain extent. Compared with the reference drug 5-FU, some compounds even showed better proliferation inhibition against various cancer cells. Among these, most of the compounds had relatively less cytotoxicity to L929 cells. 6-Chloro-2-(2-(benzylthio)-1,3,4-thiadiazol-5-yl)-quinazolin-4(3<em>H</em>)-one (<strong>6a</strong>) gave expression to the strongest inhibitory activity on Hela cells with IC<sub>50</sub> value of 1.40 µM. 6-Chloro-2-[2-(4-trifluoromethylbenzylthio)-1,3,4-thiadiazol-5-yl]-quinazolin-4(3<em>H</em>)-one (<strong>6s</strong>) displayed high antitumor activities against MCF-7 cells with IC<sub>50</sub> values of 3.01 µM. 2-[2-(Benzylthio)-1,3,4-thiadiazol-5-yl]-quinazolin-4(3<em>H</em>)-one (<strong>5a</strong>) revealed excellent antitumor activities against A549 cells with IC<sub>50</sub> values of 2.21 µM.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 7","pages":"Pages 591-601"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49728039","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Sulfur chemistry in action. New perspectives for organic synthesis","authors":"Samir Z. Zard","doi":"10.1080/10426507.2023.2173755","DOIUrl":"https://doi.org/10.1080/10426507.2023.2173755","url":null,"abstract":"Abstract The radical chemistry based on organosulfur derivatives constitutes a powerful tool for solving synthetic problems. The present short overview discusses a method for the contra-thermodynamic isomerization of trisubstituted cycloalkenes into the less stable disubstituted regioisomer. It also describes the use of xanthates as radical precursors for the synthesis and modification of ketones and for accessing a wide range of boronates. Graphical Abstract","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 6","pages":"Pages 456-465"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49863679","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}