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Effect of Laterally Substituted Methoxy Group on the Mesomorphic Behavior of Novel Ester Derivatives
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100154
N. K. Baku, K. D. Ladva, A. Y. Cholera, J. J. Travadi
{"title":"Effect of Laterally Substituted Methoxy Group on the Mesomorphic Behavior of Novel Ester Derivatives","authors":"N. K. Baku,&nbsp;K. D. Ladva,&nbsp;A. Y. Cholera,&nbsp;J. J. Travadi","doi":"10.1134/S1070428024100154","DOIUrl":"10.1134/S1070428024100154","url":null,"abstract":"<p>To understand how molecular structure affects liquid crystal behavior with reference to the lateral methoxy group, a novel homologous series of liquid crystal derivatives was synthesized and analyzed. The homologous series consists of 12 derivatives (C<sub>1</sub>–C<sub>16</sub>), of which the first five homologs (C<sub>1</sub>–C<sub>5</sub>) are not liquid crystals, while the remaining homologs (C<sub>6</sub>–C<sub>16</sub>) are enantiotropically smectogenic liquid crystals without exhibiting the nematic phase. The average thermal stability of the smectic phase is 77.85°C, and the mesophase length ranges from 4 to 17°C. The molecular structures were verified by analytical and spectral data. The liquid crystal properties of the novel series were compared with those of structurally similar known homologous series. The transition temperatures were determined by an optical polarizing microscope equipped with a heating stage.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1991 - 1998"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859693","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 (S)-2-{(R)-Hydroxy[2-(trifluoromethyl)phenyl]­methyl}cyclohexan-1-one Using (1R,2R)-2-(Piperidin-1-yl)­cyclohexan-1-amine as a Catalyst
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100166
C. L. Li, S. Y. Wang, M. R. Zhan, C. C. Chen, Z. X. Wang
{"title":"Synthesis of (S)-2-{(R)-Hydroxy[2-(trifluoromethyl)phenyl]­methyl}cyclohexan-1-one Using (1R,2R)-2-(Piperidin-1-yl)­cyclohexan-1-amine as a Catalyst","authors":"C. L. Li,&nbsp;S. Y. Wang,&nbsp;M. R. Zhan,&nbsp;C. C. Chen,&nbsp;Z. X. Wang","doi":"10.1134/S1070428024100166","DOIUrl":"10.1134/S1070428024100166","url":null,"abstract":"<p>Chiral monosubstituted cyclohexanediamine catalyst, namely (1<i>R</i>,2<i>R</i>)-2-(piperidin-1-yl)cyclo­hexan-1-amine (<b>Cat1</b>) has been efficiently synthesized and used to catalyze the aldol reaction of cyclohexanone and 2-(trifluoromethyl)benzaldehyde to obtain (<i>R</i>)-2-{(<i>S</i>)-hydroxy[2-(trifluoromethyl)phenyl]methyl}cyclo­hexan-1-one. The catalyst (20 mol %) provided high yield (up to 85%) and excellent enantioselectivity (95.6% <i>ee</i>) in water solution in three parallel tests.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1999 - 2003"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858726","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
A Concise Method for Constructing Pyrrolo[1,2-a]quinoxaline Derivatives via Pictet–Spengler Type Cyclization
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100178
X. Yu, Y. Liu, J. Chen, F. Liu, X. Zhu, Y. Zhang
{"title":"A Concise Method for Constructing Pyrrolo[1,2-a]quinoxaline Derivatives via Pictet–Spengler Type Cyclization","authors":"X. Yu,&nbsp;Y. Liu,&nbsp;J. Chen,&nbsp;F. Liu,&nbsp;X. Zhu,&nbsp;Y. Zhang","doi":"10.1134/S1070428024100178","DOIUrl":"10.1134/S1070428024100178","url":null,"abstract":"<p>A simple and efficient method for concise synthesis of pyrido[3,2-<i>e</i>]pyrrolo[1,2-<i>a</i>]pyrazine deriva­tives based on Pictet–Spengler type cyclization reaction has been successfully developed. This procedure tolerates different types of aldehydes and ketones as starting materials in the presence of trifluoroacetic acid to provide the desired heterocyclic products with medium to excellent yields. The heterocycle containing bromine could be further used as a building block to synthesize more complex compounds. This strategy is characterized by simple operation and environmental friendliness and is a reliable tool for synthesizing bioactive substances.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"2004 - 2013"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858727","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
A Convenient Synthesis of 7-Methyladenine
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100245
A. N. Du, Y. L. Feng, Y. H. Yan, T. J. Chen
{"title":"A Convenient Synthesis of 7-Methyladenine","authors":"A. N. Du,&nbsp;Y. L. Feng,&nbsp;Y. H. Yan,&nbsp;T. J. Chen","doi":"10.1134/S1070428024100245","DOIUrl":"10.1134/S1070428024100245","url":null,"abstract":"<p>7-Methyladenine is a biomarker of DNA damage from exposure to methylating agents. Also, it is a partial agonist for the G protein-coupled receptor in rats. So far, the reported synthetic methods for 7-methyl­adenine are not convenient enough. We herein report an improved four-step synthesis of 7-methyladenine via cyanation, Raney Ni catalytic reduction, cyclization, and bis(pinacolato)diboron (Bpin)<sub>2</sub> reduction. The advan­tages of this procedure include the avoidance of precious metal catalysts, simple operation, and good yields.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"2048 - 2051"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859594","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
Quantum Chemical Study of Mechanisms of Organic Reactions: XIII. Reaction of Propargyl Chloride with Dipotassium Ethane-1,2-bis(thiolate) in the System Hydrazine Hydrate–Potassium Hydroxide. Heterocyclization Pathways
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100075
E. A. Chirkina, V. A. Grabelnykh, N. A. Korchevin, L. B. Krivdin, I. B. Rozentsveig
{"title":"Quantum Chemical Study of Mechanisms of Organic Reactions: XIII. Reaction of Propargyl Chloride with Dipotassium Ethane-1,2-bis(thiolate) in the System Hydrazine Hydrate–Potassium Hydroxide. Heterocyclization Pathways","authors":"E. A. Chirkina,&nbsp;V. A. Grabelnykh,&nbsp;N. A. Korchevin,&nbsp;L. B. Krivdin,&nbsp;I. B. Rozentsveig","doi":"10.1134/S1070428024100075","DOIUrl":"10.1134/S1070428024100075","url":null,"abstract":"<p>The reaction of propargyl chloride with ethane-1,2-bis(thiolate) in the system hydrazine hydrate–potassium hydroxide has been simulated using the combined CCSD(T)/6-31+G*//B3LYP/6-311++G** approach. Elementary steps of the process and possible heterocyclization pathways of the primary intermediates have been identified. Under experimental conditions (40–42°C, 6 h), the title reaction produced 25% of 2-methyl-5,6-dihydro-1,4-dithiine and 24% of 4,7-dithiadeca-2,8-diyne. No cyclic products were formed at –10 to –15°C.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1932 - 1944"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1134/S1070428024100075.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858648","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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":"60 9","pages":"1685 - 1691"},"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":"60 9","pages":"1799 - 1809"},"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":"60 9","pages":"1818 - 1827"},"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":"60 9","pages":"1638 - 1646"},"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":"60 9","pages":"1730 - 1743"},"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
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