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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":"60 9","pages":"1777 - 1783"},"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":"60 9","pages":"1630 - 1637"},"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":"60 9","pages":"1698 - 1704"},"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":"60 9","pages":"1647 - 1653"},"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":"60 9","pages":"1725 - 1729"},"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
Synthesis, Identification, and Evaluation of New Pyrimidine and Pyrazole Derivatives Bearing a Quinazolin-4(3H)-one Moiety, Including Antibacterial, Antifungal, and Antioxidant Effects 含有喹唑啉-4(3H)-酮分子的新型嘧啶和吡唑衍生物的合成、鉴定和评估，包括抗菌、抗真菌和抗氧化作用
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI: 10.1134/S1070428024090239
N. N. Saeed, S. M. H. Al-Majidi
{"title":"Synthesis, Identification, and Evaluation of New Pyrimidine and Pyrazole Derivatives Bearing a Quinazolin-4(3H)-one Moiety, Including Antibacterial, Antifungal, and Antioxidant Effects","authors":"N. N. Saeed,&nbsp;S. M. H. Al-Majidi","doi":"10.1134/S1070428024090239","DOIUrl":"10.1134/S1070428024090239","url":null,"abstract":"<p>New azo pyrimidine and pyrazole derivatives containing a quinazolin-4(3<i>H</i>)-one moiety were synthesized, and their antioxidant and antimicrobial effects were studied. The target compounds were obtained starting from ethyl 2-[2-(4-methoxyphenyl)-4-oxo-3,4-dihydroquinazolin-3-yl]acetate which was reacted with <i>p</i>-phenylenediamine, followed by diazotization, coupling with acetylacetone, and condensation with urea, thiourea, and substituted hydrazines. The synthesized compounds were characterized by melting points, FT-IR and <sup>1</sup>H and <sup>13</sup>C NMR spectra, and elemental analyses. Some of them showed high antioxidant activity compared to ascorbic acid as standard drug, while the others exhibited moderate to low activity. The title compounds were also evaluated for antimicrobial activity by the well diffusion method and were found to be effective against Gram-positive and Gram-negative bacteria such as <i>Escherichia</i> <i>coli</i>, <i>Bacillus</i> <i>cereus</i>, and <i>Staphylo­coccus aureus</i>, as well as against the fungi <i>Candida albicans</i> and <i>Rhizopus microsporum</i>, at a concentration of 80 µg/mL.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 9","pages":"1791 - 1798"},"PeriodicalIF":0.8,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142595333","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
Three-Component Synthesis of Tetrahydroisoquinolines via SNVin Reaction 通过 SNVin 反应三组分合成四氢异喹啉
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI: 10.1134/S107042802409001X
I. V. Dyachenko, V. D. Dyachenko, P. V. Dorovatovskii, V. N. Khrustalev, V. G. Nenajdenko
{"title":"Three-Component Synthesis of Tetrahydroisoquinolines via SNVin Reaction","authors":"I. V. Dyachenko,&nbsp;V. D. Dyachenko,&nbsp;P. V. Dorovatovskii,&nbsp;V. N. Khrustalev,&nbsp;V. G. Nenajdenko","doi":"10.1134/S107042802409001X","DOIUrl":"10.1134/S107042802409001X","url":null,"abstract":"<p>The three-component reaction of carbocyclic enamino ketones, CH acids, and electrophiles has been studied. Previously unknown 5,6,7,8-tetrahydroisoquinoline derivatives have been synthesized via nucleophilic vinylic substitution (S<sub>N</sub>Vin). The structures of some of the obtained compounds have been determined by X-ray analysis.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 9","pages":"1619 - 1629"},"PeriodicalIF":0.8,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142595256","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
Efficient Route to N-Substituted β-Amido Ketone Scaffold Using Bismuth Nitrate-Catalyzed One-Pot MCR Protocol 利用硝酸铋催化的一锅 MCR 程序制备 N-取代的 β-氨基酮支架的高效路线
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI: 10.1134/S1070428024090197
K. S. Sini, S. Arun, V. S. Shinu
{"title":"Efficient Route to N-Substituted β-Amido Ketone Scaffold Using Bismuth Nitrate-Catalyzed One-Pot MCR Protocol","authors":"K. S. Sini,&nbsp;S. Arun,&nbsp;V. S. Shinu","doi":"10.1134/S1070428024090197","DOIUrl":"10.1134/S1070428024090197","url":null,"abstract":"<p>A new catalytic one-pot synthesis of N-substituted β-amido carbonyl compounds has been developed using bismuth nitrate as highly efficient, commercially available, recyclable, and reusable acid catalyst. The efficiency of the proposed protocol was demonstrated by 17 examples including various functionalized N-substituted β-amido carbonyl compounds. The reaction utilized easily available and cost-effective starting materials and proceeded at room temperature in a short period of time, followed by aqueous workup.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 9","pages":"1761 - 1768"},"PeriodicalIF":0.8,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142595251","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
Chemoselective Baeyer–Villiger Oxidation of R-(+)-Camphor with Caroʼs Acid R-(+)- 樟脑与 Caroʼs 酸的化学选择性 Baeyer-Villiger 氧化反应
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI: 10.1134/S1070428024090069
V. A. Vydrina, M. P. Yakovleva, G. Yu. Ishmuratov
{"title":"Chemoselective Baeyer–Villiger Oxidation of R-(+)-Camphor with Caroʼs Acid","authors":"V. A. Vydrina,&nbsp;M. P. Yakovleva,&nbsp;G. Yu. Ishmuratov","doi":"10.1134/S1070428024090069","DOIUrl":"10.1134/S1070428024090069","url":null,"abstract":"<p>Chemoselective Baeyer–Villiger oxidation of <i>R</i>-(+)-camphor with Caroʼs acid afforded a mixture of 1,2- and 3,4-campholactones.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 9","pages":"1663 - 1666"},"PeriodicalIF":0.8,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142595428","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
Novel Thiazolinone Derivatives: Synthesis, Biological Evaluation, and In Silico Studies 新型噻唑啉酮衍生物：合成、生物学评价和硅学研究
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI: 10.1134/S1070428024090136
W. O. Alsulami, Z. M. Al-Amshany, N. Y. Tashkandi, R. M. El-Shishtawy
{"title":"Novel Thiazolinone Derivatives: Synthesis, Biological Evaluation, and In Silico Studies","authors":"W. O. Alsulami,&nbsp;Z. M. Al-Amshany,&nbsp;N. Y. Tashkandi,&nbsp;R. M. El-Shishtawy","doi":"10.1134/S1070428024090136","DOIUrl":"10.1134/S1070428024090136","url":null,"abstract":"<p>A series of novel thiazolinone derivatives have been synthesized and characterized, and their biological activities have been studied. The title compounds were synthesized by condensation of different aldehydes <b>11a</b>–<b>11e</b> with thiosemicarbazide to give thiosemicarbazones <b>12a</b>–<b>12e</b>, which were cyclized with ethyl bromoacetate in the presence of sodium acetate to afford new thiazolinone derivatives <b>13a</b>–<b>13e</b>. The structure of all newly synthesized compounds was elucidated by elemental analysis and FT<b>–</b>IR and multinuclear NMR (<sup>1</sup>H and <sup>13</sup>C) spectroscopy. Newly synthesized compounds <b>13a</b>–<b>13e</b> showed weak or no antimicrobial activity against bacterial strains <i>Escherichia coli</i> and <i>Staphylococcus aureus</i> and fungal strain <i>Candida albicans</i>. Furthermore, the ADME properties of compounds <b>13a</b>–<b>13e</b> were examined, and derivatives <b>13a</b> and <b>13b</b> but not <b>13c</b>–<b>13e</b> were found to conform to Lipinskiʼs and Veberʼs rules without violations. The promising compounds <b>13a</b> and <b>13b</b> were docked against EGFR and VEGFR-2 binding sites with reduced energy scores, higher fitting, and stability.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 9","pages":"1705 - 1719"},"PeriodicalIF":0.8,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142595250","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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