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Synthesis and Antihypoxic Properties of New 2-(1,4-Benzodioxan-2-yl)-1,3,4-oxadiazole Derivatives 新型 2-(1,4-苯并二恶烷-2-基)-1,3,4-恶二唑衍生物的合成与抗缺氧特性
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI: 10.1134/S1070428024090100
S. O. Vardanyan, A. S. Avagyan, A. B. Sargsyan, H. A. Panosyan, S. A. Harutyunyan, H. V. Gasparyan, A. A. Aghekyan
{"title":"Synthesis and Antihypoxic Properties of New 2-(1,4-Benzodioxan-2-yl)-1,3,4-oxadiazole Derivatives","authors":"S. O. Vardanyan,&nbsp;A. S. Avagyan,&nbsp;A. B. Sargsyan,&nbsp;H. A. Panosyan,&nbsp;S. A. Harutyunyan,&nbsp;H. V. Gasparyan,&nbsp;A. A. Aghekyan","doi":"10.1134/S1070428024090100","DOIUrl":"10.1134/S1070428024090100","url":null,"abstract":"<p>The condensation of previously described 1,4-benzodioxane-2-carbohydrazide with various 1-(sub­stituted phenyl)cycloalkan-1-carbonyl chlorides, as well as 4-aryltetrahydropyran-4-carbonyl chloride gave <i>N</i>,<i>N</i>′-diacylhydrazines which were cyclized by the action of phosphoryl chloride to the corresponding 2-(1,4-benzodioxan-2-yl)-1,3,4-oxadiazole derivatives. The synthesized compounds were evaluated for anti­hypoxic activity.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142595465","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}
引用次数: 0
1-(3-Methylthiophene-2-yl)-N-(3,4,5-trimethoxyphenyl)­methanimine: Synthesis, Spectroscopic Characterization, Antileishmanial Activity, and DFT and In Silico Studies 1-(3-甲基噻吩-2-基)-N-(3,4,5-三甲氧基苯基)甲亚胺：合成、光谱特性、抗利什曼病活性以及 DFT 和 In Silico 研究
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI: 10.1134/S1070428024090240
M. Evecen, F. Çelik, H. İ. Güler, Ş. Direkel, Y. Ünver
{"title":"1-(3-Methylthiophene-2-yl)-N-(3,4,5-trimethoxyphenyl)­methanimine: Synthesis, Spectroscopic Characterization, Antileishmanial Activity, and DFT and In Silico Studies","authors":"M. Evecen,&nbsp;F. Çelik,&nbsp;H. İ. Güler,&nbsp;Ş. Direkel,&nbsp;Y. Ünver","doi":"10.1134/S1070428024090240","DOIUrl":"10.1134/S1070428024090240","url":null,"abstract":"<p>1-(3-Methylthiophen-2-yl)-<i>N</i>-(3,4,5-trimethoxyphenyl)methanimine (<b>1</b>, MTM) was synthesized from 3-methylthiophene-2-carbaldehyde and 3,4,5-trimethoxyaniline and characterized by FTIR and <sup>1</sup>H and <sup>13</sup>C NMR spectra. The geometric structure of the title compound was optimized, and its electronic (FMO, NLO, MEP, NBO), spectroscopic (NMR, IR, UV), and thermodynamic properties were calculated by quantum chemicial methods. The calculated and experimental geometric parameters were compared with each other. Compound <b>1</b> was tested for leishmanicidal activity against <i>Leishmania infantum</i> by the broth microdilution method and was found to be efficient against <i>Leishmania infantum</i> promastigotes in the concentration range studied. Possible interactions responsible for the antileishmanial activity were determined by molecular docking analysis against trypanothione reductase (TRe). The docking results demonstrated high inhibition constant of the title compound and supported its antileishmanial activity.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142595258","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}
引用次数: 0
Design, Synthesis, Molecular Docking, and Anti-inflammatory Activity of 2-[(E)-{1-[4-(4-Chlorophenyl)-1,3-thiazol-2-yl]-1H-pyrazol-4-yl}(hydroxyimino)methyl]phenol and {1-[4-(4-Chlorophenyl)-1,3-thiazol-2-yl]-1H-pyrazol-4-yl}(2-hydroxyphenyl)methanone Derivatives 2-[(E)-{1-[4-(4-氯苯基)-1,3-噻唑-2-基]-1H-吡唑-4-基}(羟基亚氨基)甲基]苯酚和{1-[4-(4-氯苯基)-1,3-噻唑-2-基]-1H-吡唑-4-基}(2-羟基苯基)甲酮衍生物的设计、合成、分子对接和抗炎活性
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI: 10.1134/S1070428024090264
N. R. Darekar, S. J. Takate, H. N. Akolkar, M. H. Shaikh, V. M. Khedkar, D. N. Raut, S. D. Mhaske
{"title":"Design, Synthesis, Molecular Docking, and Anti-inflammatory Activity of 2-[(E)-{1-[4-(4-Chlorophenyl)-1,3-thiazol-2-yl]-1H-pyrazol-4-yl}(hydroxyimino)methyl]phenol and {1-[4-(4-Chlorophenyl)-1,3-thiazol-2-yl]-1H-pyrazol-4-yl}(2-hydroxyphenyl)methanone Derivatives","authors":"N. R. Darekar,&nbsp;S. J. Takate,&nbsp;H. N. Akolkar,&nbsp;M. H. Shaikh,&nbsp;V. M. Khedkar,&nbsp;D. N. Raut,&nbsp;S. D. Mhaske","doi":"10.1134/S1070428024090264","DOIUrl":"10.1134/S1070428024090264","url":null,"abstract":"<p>A series of {1-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-1<i>H</i>-pyrazol-4-yl}(2-hydroxyphenyl)metha­nones <b>5</b> were synthesized from 1-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]hydrazine <b>3</b> and substituted 3-formyl­chromones <b>4</b>. Compounds <b>5</b> were converted into 2-[(<i>E</i>)-{1-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-1<i>H</i>-pyrazol-4-yl}(hydroxyimino)methyl]phenols <b>6</b>. The synthesized compounds were characterized by spectral techniques screened for their anti-inflammatory activity. Compounds <b>6c</b> and <b>6e</b> showed good percent inhibition of haemolysis when compared with the standard drug celecoxib. The molecular docking study explored the essential binding mode and possible thermodynamic interactions within the binding site of COX-2 enzyme.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142595260","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}
引用次数: 0
Synthesis and Photophysical and Electrochemical Properties of Conjugated Donor–Acceptor–Donor Systems Based on 1,3,4-Thiadiazole and Fused Naphtho[2,1-b]thiophene Derivatives 基于 1,3,4-噻二唑和融合萘并[2,1-b]噻吩衍生物的共轭供体-受体-供体系统的合成及其光物理和电化学性质
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI: 10.1134/S1070428024090033
E. B. Uliankin, A. S. Kostyuchenko, A. S. Fisyuk
{"title":"Synthesis and Photophysical and Electrochemical Properties of Conjugated Donor–Acceptor–Donor Systems Based on 1,3,4-Thiadiazole and Fused Naphtho[2,1-b]thiophene Derivatives","authors":"E. B. Uliankin,&nbsp;A. S. Kostyuchenko,&nbsp;A. S. Fisyuk","doi":"10.1134/S1070428024090033","DOIUrl":"10.1134/S1070428024090033","url":null,"abstract":"<p>A series of 2,5-diaryl-1,3,4-thiadiazole derivatives have been synthesized from fused benzothio­phene-2-carboxylates and alkyl-substituted 2,2′-bithiophene-5-carboxylate. Photophysical and electrochemical properties of the synthesized compounds have been studied. Extension of the conjugation chain in the donor moiety of substituted 1,3,4-thiadiazoles has been found to narrow the energy band gap due mainly to increase of the HOMO energy.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142595330","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}
引用次数: 0
Synthesis, Biological Evaluation, and Computational Study of Novel 1,2,3‐Triazole‐Tethered Chalcone Derivatives 新型 1,2,3-三唑系链查耳酮衍生物的合成、生物学评价和计算研究
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI: 10.1134/S1070428024090161
R. A. Kawale, M. H. Shaikh, H. N. Akolkar, V. M. Khedkar, D. N. Raut, S. N. Shelke
{"title":"Synthesis, Biological Evaluation, and Computational Study of Novel 1,2,3‐Triazole‐Tethered Chalcone Derivatives","authors":"R. A. Kawale,&nbsp;M. H. Shaikh,&nbsp;H. N. Akolkar,&nbsp;V. M. Khedkar,&nbsp;D. N. Raut,&nbsp;S. N. Shelke","doi":"10.1134/S1070428024090161","DOIUrl":"10.1134/S1070428024090161","url":null,"abstract":"<p>In search of novel anti-inflammatory and antioxidant agents with improved potency, a small focused library of 1,2,3-triazole-based chalcone derivatives has been efficiently prepared via the click chemistry approach. All synthesized compounds’ Structures were characterized with the help of IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and mass spectroscopic techniques. All the synthesized novel derivatives were evaluated for their anti-inflammatory activity. Molecular docking studies against COX-2 gave valuable insights into the mechanistic basis of the demonstrated anti-inflammatory activity. Further, the synthesized compounds were found to have potential antioxidant activity.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142595248","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}
引用次数: 0
Design, Synthesis, and Evaluation of Imidazole Derivatives as Potential Antimalarial Drugs 设计、合成和评估作为潜在抗疟药物的咪唑衍生物
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI: 10.1134/S1070428024090215
D. P. Upadhyay, C. P. Somaiya
{"title":"Design, Synthesis, and Evaluation of Imidazole Derivatives as Potential Antimalarial Drugs","authors":"D. P. Upadhyay,&nbsp;C. P. Somaiya","doi":"10.1134/S1070428024090215","DOIUrl":"10.1134/S1070428024090215","url":null,"abstract":"<p>A highly effective approach has been proposed for the synthesis of unique imidazole aniline compounds via a reaction sequence including acylation of substituted anilines with 2-chloroacetyl chloride, alkylation of 2-butyl-5-chloro-1<i>H</i>-imidazole-4-carbaldehyde with the resulting 2-chloroacetanilides, and con­densa­tion of 2-(2-butyl-5-chloro-4-formyl-1<i>H</i>-imidazol-1-yl)-<i>N</i>-(substituted phenyl)acetamides with 4-{4-[5-(amino­methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one. The newly synthesized compounds have been screened for their in vitro antimalarial potential against <i>Plasmodium falciparum</i> and found to exhibit incredibly impressive half-maximum inhibitory concentration (IC<sub>50</sub>) values. Molecular docking has been performed for the most active compound and dihydrofolate reductase–thymidylate synthase (DHFR-TS) from the wild-type <i>Plasmodium falciparum</i>, and hydrogen bond interactions between the amino acid residues Ser167 and Ser111 and azomethine and imidazole nitrogen atoms, respectively, have been revealed.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142595253","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}
引用次数: 0
Synthesis, Structure, and Reactions of Substituted 2-Aminotetrahydroquinoline-3-carbonitriles 取代的 2-氨基四氢喹啉-3-甲腈的合成、结构和反应
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI: 10.1134/S1070428024090021
A. V. Nikulin, N. O. Vasilkova, A. P. Krivenko
{"title":"Synthesis, Structure, and Reactions of Substituted 2-Aminotetrahydroquinoline-3-carbonitriles","authors":"A. V. Nikulin,&nbsp;N. O. Vasilkova,&nbsp;A. P. Krivenko","doi":"10.1134/S1070428024090021","DOIUrl":"10.1134/S1070428024090021","url":null,"abstract":"<p>A series of substituted 2-aminotetrahydroquinolinecarbonitriles have been synthesized by the three-component condensation of diaryl(hetaryl)methylidenecyclohexanones, malononitrile, and ammonium acetate. Factors responsible for the reaction selectivity and product formation pathway have been revealed. The reaction of aminoquinolinecarbonitriles with acetic anhydride under acidic conditions afforded substituted hexahydro­pyrimido[4,5-<i>b</i>]quinolinones. The structure of the synthesized compounds has been determined by IR and <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, including HSQC two-dimensional correlation technique.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142595329","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}
引用次数: 0
Iodination of Phenylacetylene and Some Transformations of the Resulting Iodo Derivatives 苯乙炔的碘化作用和由此产生的碘衍生物的一些转化作用
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI: 10.1134/S1070428024090124
N. G. Hobosyan, K. V. Balyan, H. R. Pogosyan, L. A. Movsisyan, V. S. Hovsepyan, H. B. Sargsyan
{"title":"Iodination of Phenylacetylene and Some Transformations of the Resulting Iodo Derivatives","authors":"N. G. Hobosyan,&nbsp;K. V. Balyan,&nbsp;H. R. Pogosyan,&nbsp;L. A. Movsisyan,&nbsp;V. S. Hovsepyan,&nbsp;H. B. Sargsyan","doi":"10.1134/S1070428024090124","DOIUrl":"10.1134/S1070428024090124","url":null,"abstract":"<p>An efficient procedure has been proposed for the reaction of molecular iodine with phenylacetylene in the presence of cadmium(II) acetate in DMSO at room temperature, and the reactant ratio has been optimized for the iodination process. Mercuration–demercuration of iodoethynylbenzene with molecular iodine and oxidative homocoupling in the presence of dilithium tetrachlorocuprate have been performed.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142595249","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}
引用次数: 0
Synthesis of 3-Substituted 1-(Dichloromethyl)adamantanes 合成 3-取代的 1-(二氯甲基)金刚烷
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI: 10.1134/S1070428024090045
V. A. Shiryaev, D. O. Eremeev, Yu. N. Klimochkin
{"title":"Synthesis of 3-Substituted 1-(Dichloromethyl)adamantanes","authors":"V. A. Shiryaev,&nbsp;D. O. Eremeev,&nbsp;Yu. N. Klimochkin","doi":"10.1134/S1070428024090045","DOIUrl":"10.1134/S1070428024090045","url":null,"abstract":"<p>Transformations of 1-(dichloromethyl)adamantane and its derivatives in strongly acidic media have been studied. The nitroxylation of the title compound has been found not to be accompanied by nitrolysis of the dichloromethyl group. A series of 3-substituted 1-(dichloromethyl)adamantanes have been obtained via genera­tion of tertiary carbenium ion; the conservation of the dichloromethyl group in the products makes them promising for further modification.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142595331","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}
引用次数: 0
Synthesis and Characterization of Nucleoside Analogues via Mannich Reaction of Benzimidazole and Their Biological Activity 通过苯并咪唑的曼尼希反应合成核苷类似物并确定其特性及其生物活性
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI: 10.1134/S107042802409015X
H. J. Al-Adhami, D. J. Mehdi
{"title":"Synthesis and Characterization of Nucleoside Analogues via Mannich Reaction of Benzimidazole and Their Biological Activity","authors":"H. J. Al-Adhami,&nbsp;D. J. Mehdi","doi":"10.1134/S107042802409015X","DOIUrl":"10.1134/S107042802409015X","url":null,"abstract":"<p>New nucleoside analogues have been synthesized through the Mannich reaction starting from 4-methoxybenzaldehyde and α-D-mannose. The aromatic aldehyde was condensed with <i>o</i>-phenylene diamine to obtain 2-(4-methoxyphenyl)-1<i>H</i>-benzimidazole, and the subsequent Mannich reaction with protected α-D-mannofuranosyl bromide afforded new protected nucleoside analogues. Hydrolysis of the latter with sodium methoxide in methanol gave the target free nucleoside analogues. The synthesized compounds were identified by FT-IR and <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, and their in vitro antibacterial activity against four bacterial and fungal strains was evaluated.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142595430","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}
引用次数: 0
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