{"title":"Three-Component Synthesis of Trisubstituted Pyridine-2(1H)-ones","authors":"G. M. Talybov","doi":"10.1134/S1070428024050099","DOIUrl":"10.1134/S1070428024050099","url":null,"abstract":"<p>The condensation of aryl cyanides with chloromethyl propargyl(allyl) ethers and ethyl phenylpropiolate in the presence of pyridine leads to trisubstituted pyridin-2(1<i>H</i>)-ones.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141865160","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}
Nedime Çalişkan, Emre Menteşe, Fatih Yilmaz, Muhammed Süleyman Ilhan
{"title":"Synthesis and Anticancer Activities of Amide-Bridged Coumarin–Quinazolinone Hybrid Compounds","authors":"Nedime Çalişkan, Emre Menteşe, Fatih Yilmaz, Muhammed Süleyman Ilhan","doi":"10.1134/S1070428024050142","DOIUrl":"10.1134/S1070428024050142","url":null,"abstract":"<p>Some novel 3-aminoquinazolin-4(<i>3H</i>)-one derivatives were synthesized by the reaction of 2-aminobenzhydrazide and corresponding iminoester hydrochlorides and then reacted with coumarin-3-carbonyl chloride to obtain novel coumarin–quinazolinone hybrids. The synthesized hybrid compounds were screened for their anticancer activity against various human cancer and normal cell lines. <i>N</i>-{2-[(4-Bromo- and <i>N</i>-{2-[(3-bromo-phenyl)methyl]-4-oxoquinazolin-3(4<i>H</i>)-yl}-2-oxo-2<i>H</i>-1-benzopyran-3-carboxamides exhibited the highest cytotoxic effect on the PC-3 prostate cancer cell line: IC<sub>50</sub> 35.3 ± 0.6 and 36.8 ± 0.8 µg/L, respectively. <i>N</i>-{2-[(4-Fluoro-, <i>N</i>-{2-[(4-bromo-, and <i>N</i>-{2-[(3,4-dichloro-phenyl)methyl]-4-oxoquinazolin-3(4<i>H</i>)-yl}-2-oxo-2<i>H</i>-1-benzopyran-3-carboxamides showed the highest activity against the MCF-7 breast cancer cell line: IC<sub>50</sub> 48.5 ± 0.4, 44.8 ± 0.4 and 46.1 ± 0.5 µg/L, respectively.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141865051","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}
O. A. Petrov, G. A. Gamov, N. V. Chizhova, N. Zh. Mamardashvili
{"title":"Reactivity of Octa(2,6-fluorophenyl)porphyrazine in Acid–Base Reactions with Nitrogenous Organic Bases","authors":"O. A. Petrov, G. A. Gamov, N. V. Chizhova, N. Zh. Mamardashvili","doi":"10.1134/S1070428024050051","DOIUrl":"10.1134/S1070428024050051","url":null,"abstract":"<p>Reactions between octa(2,6-fluorophenyl)porphyrazine and pyridine, 2-methylpyridine, morpholine, piperidine, butylamine, <i>tert</i>-butylamine, diethylamine, and triethylamine in a benzene medium have been studied. The acid–base reactions between the macroheterocycle and piperidine or butylamine are slow processes leading to the formation of kinetically stable proton-transfer complexes. The structures of these complexes have been optimized using CAM-B3LYP/cc-pVTZ. The changes in the reactivity of octa(2,6-fluorophenyl)porphyrazine are analyzed as a function of the steric structure and proton-acceptor power of the nitrogenous base.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141865157","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}
Prabhakar Chavan, Prashant C. Hanamshetty, Balaji Biradar, M. M. Nagabhushan
{"title":"Design and Synthesis of Novel 1,4-Dihydropyridine Derivatives as Antioxidant and Antimicrobial Agents","authors":"Prabhakar Chavan, Prashant C. Hanamshetty, Balaji Biradar, M. M. Nagabhushan","doi":"10.1134/S1070428024050130","DOIUrl":"10.1134/S1070428024050130","url":null,"abstract":"<p>1,4 Dihydropyridines are one of the most used scaffolds in drug development. The present paper describes the autocatalytic four-component reactions of heterocyclic aldehydes, malononitrile, and piperidine, leading to novel 2-amino-1,4-dihydro-6-[pyridin-1(4<i>H</i>)-yl]-4-(hetero-2/3-yl)pyridine-3,5-dicarbonitrile derivatives in good yields. The structure of the synthesized compounds was confirmed by IR and <sup>1</sup>H and <sup>13</sup>C NMR and mass spectrometry. 4-(1<i>H</i>-Indol-3-yl)-substituted 1,4-dihydropyridine exhibited good radical scavenging activity, while its thiophen-2-yl-substituted analog proved to be potent antimicrobial agent.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141865050","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}
Vishwa B. Das, Boja Poojary, Vinuta Kamat, Ankita Sharma, Rajdeep Chowdhury, Shanavaz Hamzad
{"title":"Synthesis, In Silico Docking Study, and Biological Evaluation of S-Alkylated 1,3,4-Oxadiazole Hybrids","authors":"Vishwa B. Das, Boja Poojary, Vinuta Kamat, Ankita Sharma, Rajdeep Chowdhury, Shanavaz Hamzad","doi":"10.1134/S1070428024050154","DOIUrl":"10.1134/S1070428024050154","url":null,"abstract":"<p>A library of 3-(5-[(substituted benzyl)sulfanyl]-1,3,4-oxadiazol-2-yl)-<i>N</i>-substituted pyridine-2-amines and 2-[(5-{2-[(substituted phenyl)amino]pyridin-3-yl}-2,3-dihydro-1,3,4-oxadiazol-2-yl)sulfanyl]-<i>N</i>-substituted phenylacetamides were synthesized by the multistage procedure, starting from 2-chloronicotinic acid. The newly synthesized compounds were tested for <i>in vitro</i> cytotoxicity against the MCF-7 breast cancer cell line. Significant cell death rates were demonstrated by all the test compounds in a concentration-dependent manner. The active compounds <i>N</i>-(4-fluorophenyl)-3-{5-[(4-nitrobenzyl)sulfanyl]-1,3,4-oxadiazol-2-yl}pyridin-2-amine and 2-[(5-{2-[(3-chloro-4-fluorophenyl)amino]pyridin-3-yl}-1,3,4-oxadiazol-2-yl)sulfanyl]-<i>N</i>-(2,4-dichlorophenyl)-acetamide were further subjected to DAPI staining to assess their effect on nuclear fragmentation. Additionally, the synthesized compounds were screened for anti-inflammatory and antioxidant activities, yielding promising results. A molecular docking study was conducted to assess the binding affinities of the synthesized compounds to PDB 3ERT (human estrogen receptor-α in complex with 4-hydroxytamoxifen). For all the compounds, good binding energies with the target protein were predicted. An ADME screening showed that the majority of the synthesized compounds have good pharmacokinetic profiles.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141865054","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":"Design, Synthesis, Antimicrobial, Anticancer, and Molecular Docking of Novel Quinoline Derivatives","authors":"Kurls E. Anwer, Galal H. Sayed","doi":"10.1134/S107042802405018X","DOIUrl":"10.1134/S107042802405018X","url":null,"abstract":"<p>A variety of novel pyrimidopyridoquinazoline, pyrazoloquinoline, and thiazoloquinoline derivatives were synthesized starting from 2,5,7-triamino-4-(4-methoxyphenyl)quinoline-3,8-dicarbonitrile under conventional heating. The same products were also prepared under microwave irradiation to improve the yield and time of the reactions. The structures of all newly synthesized compounds were proved by elemental analysis and IR, <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy and mass spectrometry. The products were screened for their in vitro antimicrobial activity and showed moderate to high activity. They were also evaluated for anticancer activity against the HePG-2, HCT-116, and MCF-7 cell lines. Molecular docking was used to explore the molecular mechanism of the anticancer activity of 6-(4-methoxyphenyl)-3,9-dihydrodipyrazolo[3,4-<i>b</i>:3',4'-<i>h</i>]quinoline-1,5,7-triamine, which showed the highest cytotoxicity against all the test tested cancer cell lines.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141865056","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}
A. V. Bobrova, E. I. Golenko, A. V. Oberenko, T. Y. Ivanenko, E. V. Root, G. A. Suboch
{"title":"Modification of N-Functionalized 4-Nitroso-1H-pyrazoles","authors":"A. V. Bobrova, E. I. Golenko, A. V. Oberenko, T. Y. Ivanenko, E. V. Root, G. A. Suboch","doi":"10.1134/S1070428024050063","DOIUrl":"10.1134/S1070428024050063","url":null,"abstract":"<p>The behavior of <i>N</i>-Substituted 3,5-dimethyl-4-nitroso-1<i>H</i>-pyrazoles in oxidation, condensation, and reduction reactions was studied. The synthesized 4-aminopyrazole was acylated and diazotized with further azo coupling or the replacement of the amino group by iodine, as well as subjected to condensation with 4-nitrobenzaldehyde. The first condensation of nitrosopyrazole with 2,4-dinitrotoluene was demonstrated. As a result, new functionalized pyrazole derivatives were isolated. The structure of the novel pyrazoles was confirmed by IR and <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, gas chromatography-mass spectrometry, and elemental analysis. The synthesized compounds hold promise for further research in medicine and pharmaceutical chemistry.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141865158","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}
A. Mathakiya, G. G. Dubal, K. Kapadiya, K. Raval, J. Dhalani
{"title":"Carbamoyl 1,4-Dihydropyridine Derivatives: Synthesis and Impressive Antidiabetic Activity","authors":"A. Mathakiya, G. G. Dubal, K. Kapadiya, K. Raval, J. Dhalani","doi":"10.1134/S1070428024050166","DOIUrl":"10.1134/S1070428024050166","url":null,"abstract":"<p>1,4-Dihydropyridine is known as one of the most important heterocyclic frameworks found in numerous pharmaceuticals and drugs. A series of novel methyl 5-[(substituted phenyl)carbamoyl]-1-(2,2-dimethoxyethyl)-3-methoxy-4-oxo-1,4-dihydropyridine-2-carboxylates were synthesized by an in situ two-step procedure, starting from 1-(2,2-dimethoxyethyl)-5-methoxy-6-(methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid. The compositions and structures of the synthesized diverse compounds were confirmed by elemental analysis and IR and <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy and mass spectrometry. Screening for in vitro α-amylase inhibitor activity revealed a high inhibitory activity of methyl 1-(2,2-dimethoxyethyl)-3-methoxy-5-[(4-methoxyphenyl)carbamoyl]-4-oxo-1,4-dihydro pyridine-2-carboxylate, comparable with that of the standard drug Acarbose (IC<sub>50</sub> = 28.83 and 26.81 μg/mL, respectively).</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141865052","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}
V. A. Polikarchuk, M. S. Derkachev, Kh. S. Shikhaliev
{"title":"Synthesis of 7-[2-(Dimethylamino)vinyl]pyrazolo[1,5-a]pyrimidine-6-carbonitriles and Their Heterocyclizations with N1 Synthons","authors":"V. A. Polikarchuk, M. S. Derkachev, Kh. S. Shikhaliev","doi":"10.1134/S1070428024050087","DOIUrl":"10.1134/S1070428024050087","url":null,"abstract":"<p>The use of new 7-methylazolo[1,5-<i>a</i>]pyrimidine-6-carbonitriles for the construction of heterocyclic systems annulated at the pyrimidine ring has been demonstrated. Cascade cyclizations are carried out via the intermediate dimethylaminovinyl derivatives. The specific features of the cascade reactions with ammonia or aliphatic amines as N1 synthons, depending on the reaction conditions, are demonstrated.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141865161","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":"Features of F2-BODIPY Synthesis (A Review)","authors":"A. I. Krasnopyorov, E. A. Larkina","doi":"10.1134/S1070428024050026","DOIUrl":"10.1134/S1070428024050026","url":null,"abstract":"<p>BODIPY derivatives (4,4-difluoro-4-boron-3<i>a</i>,4<i>a</i>-diaza-<i>S</i>-indacene), due to their high molar extinction coefficients, fluorescence quantum yields, and photochemical stability, have gained popularity as optical sensors for bioimaging and detection of various analytes. BODIPY molecules have different substituents not only at the <i>meso</i>-carbon atom, but also at the boron atom. The review describes various synthetic approaches to BODIPY derivatives and «classical» BODIPY, in which the boron atom bears 2 fluorine substituents (F<sub>2</sub>-BODIPY). The advantages and limitations of the methods of synthesis are considered, as well as the use of reagents and their popularity are analyzed. Based on the literature, the mechanisms for the synthesis of BODIPY derivatives are proposed, with focus on the reasons affecting the yield of BODIPY derivatives, including a low stability of reagents, by-products formation, and the influence of water.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141865153","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}