Pub Date : 2024-05-20DOI: 10.2174/0113852728309735240513053527
Maurizio D’Auria, F. Langerame
The reaction of pyridinium chlorochromate (PCC) with furan derivatives gives the corresponding enediones. However, the reaction of pyridinium chlorochromate with furan to give enedione derivatives cannot be performed by using commercial PCC. XRD and XPS analysis of the reagents coupled with DFT calculations can allow us to explain this different behavior. Homemade and commercial PCC have different colors and show some differences in the XRD spectrum. XPS shows the presence of a relevant amount of Cr(III) in the homemade reagent. DFT calculations demonstrate that Cr(III) impurities in the reagent could catalyze the reaction with furan derivatives if an oxygen atom in the Cr(III) derivative attacks the furan ring while it is reoxidized by PCC through the migration of a chlorine atom.
{"title":"The Synthesis of Trans-Enediones from Furan Derivatives Using Pyridinium\u0000Chlorochromate: An Explanation","authors":"Maurizio D’Auria, F. Langerame","doi":"10.2174/0113852728309735240513053527","DOIUrl":"https://doi.org/10.2174/0113852728309735240513053527","url":null,"abstract":"\u0000\u0000The reaction of pyridinium chlorochromate (PCC) with furan derivatives gives the corresponding\u0000enediones. However, the reaction of pyridinium chlorochromate with furan to give enedione derivatives cannot\u0000be performed by using commercial PCC. XRD and XPS analysis of the reagents coupled with DFT calculations\u0000can allow us to explain this different behavior. Homemade and commercial PCC have different colors and show\u0000some differences in the XRD spectrum. XPS shows the presence of a relevant amount of Cr(III) in the homemade\u0000reagent. DFT calculations demonstrate that Cr(III) impurities in the reagent could catalyze the reaction\u0000with furan derivatives if an oxygen atom in the Cr(III) derivative attacks the furan ring while it is reoxidized by\u0000PCC through the migration of a chlorine atom.\u0000","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141118973","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-20DOI: 10.2174/0113852728306222240513112937
E. R. Lachter, Rosane Aguiar da Silva San Gil, Luis G. Valdivieso
Important organic reactions require the use of catalysts. The Friedel-Crafts reactions were discovered by Charles Friedel and James Mason Crafts in 1887. They are an essential catalytic process since they are widely applied in different areas such as fuels, cleaning, and pharmacological products. The reaction is usually carried out in the presence of Lewis acids or Brønsted acids in a homogeneous medium, with the nucleophilic aromatic substrate in excess. Although there is still work in the literature on the Friedel-Crafts reaction in a homogeneous medium using metal halides, the tendency is to replace these catalysts, which generate effluents that are harmful to the environment. Heterogeneous catalysts using solid acids show advantages over homogeneous catalysts, especially concerning separating products from the reaction medium, recycling, and reusing. This paper presents a mini-review focusing on the use of solid acids in Friedel-Crafts reactions.
{"title":"Friedel Crafts Reactions Revisited: Some Applications in Heterogeneous Catalysis","authors":"E. R. Lachter, Rosane Aguiar da Silva San Gil, Luis G. Valdivieso","doi":"10.2174/0113852728306222240513112937","DOIUrl":"https://doi.org/10.2174/0113852728306222240513112937","url":null,"abstract":"\u0000\u0000Important organic reactions require the use of catalysts. The Friedel-Crafts reactions were discovered\u0000by Charles Friedel and James Mason Crafts in 1887. They are an essential catalytic process since they are\u0000widely applied in different areas such as fuels, cleaning, and pharmacological products. The reaction is usually\u0000carried out in the presence of Lewis acids or Brønsted acids in a homogeneous medium, with the nucleophilic\u0000aromatic substrate in excess. Although there is still work in the literature on the Friedel-Crafts reaction in a\u0000homogeneous medium using metal halides, the tendency is to replace these catalysts, which generate effluents\u0000that are harmful to the environment. Heterogeneous catalysts using solid acids show advantages over homogeneous\u0000catalysts, especially concerning separating products from the reaction medium, recycling, and reusing.\u0000This paper presents a mini-review focusing on the use of solid acids in Friedel-Crafts reactions.\u0000","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141121153","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-20DOI: 10.2174/0113852728305580240429100851
A. K. Seth, Ghanshyam Parmar, C. Aundhia, Nirmal Shah, D. Gohil
Recently, pharmaceutical industries have placed considerable emphasis on formulating drug delivery systems that precisely target specific sites, optimize drug utilization, minimize excipient usage, and mitigate side effects. Smart polymers hold tremendous promise in the design of innovative formulations tailored to deliver drugs with enhanced precision, efficacy, and therapeutic benefits while minimizing adverse effects. Within drug delivery, smart polymers demonstrate exceptional potential in achieving controlled and targeted release profiles, ensuring drug delivery to specific receptors, and minimizing off-target effects. This comprehensive review article focuses on the latest developments in smart polymers, primarily in the domains of drug delivery. By intelligently responding to external stimuli, smart polymer-based materials offer various applications, making them pivotal in modern pharmaceutical research. By utilizing the remarkable attributes of smart polymers, researchers and industry stakeholders can forge a path toward personalized, efficient, and patient-centric therapies with reduced side effects, propelling the pharmaceutical field into an era of unprecedented advancements.
{"title":"Smart Polymer Systems: A Futuristic Approach to Enhance Therapeutic Efficacy","authors":"A. K. Seth, Ghanshyam Parmar, C. Aundhia, Nirmal Shah, D. Gohil","doi":"10.2174/0113852728305580240429100851","DOIUrl":"https://doi.org/10.2174/0113852728305580240429100851","url":null,"abstract":"\u0000\u0000Recently, pharmaceutical industries have placed considerable emphasis on formulating drug delivery\u0000systems that precisely target specific sites, optimize drug utilization, minimize excipient usage, and mitigate\u0000side effects. Smart polymers hold tremendous promise in the design of innovative formulations tailored to deliver\u0000drugs with enhanced precision, efficacy, and therapeutic benefits while minimizing adverse effects. Within\u0000drug delivery, smart polymers demonstrate exceptional potential in achieving controlled and targeted release\u0000profiles, ensuring drug delivery to specific receptors, and minimizing off-target effects. This comprehensive\u0000review article focuses on the latest developments in smart polymers, primarily in the domains of drug delivery.\u0000By intelligently responding to external stimuli, smart polymer-based materials offer various applications, making\u0000them pivotal in modern pharmaceutical research. By utilizing the remarkable attributes of smart polymers,\u0000researchers and industry stakeholders can forge a path toward personalized, efficient, and patient-centric therapies\u0000with reduced side effects, propelling the pharmaceutical field into an era of unprecedented advancements.\u0000","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141119383","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-20DOI: 10.2174/0113852728307241240430055059
C. Aundhia, Ghanshyam Parmar, Chitrali Talele, Sunil Kardani, Rajesh Maheshwari
Photoresponsive polymers have emerged as innovative tools in the domain of drug delivery, presenting advanced solutions for controlled and targeted release of therapeutic agents. This review explores recent advances in the design and application of photoresponsive polymers, focusing on their pivotal role in lighttriggered drug delivery systems. It also encompasses organic synthesis methodologies, key advancements in polymer design, and the integration of photoresponsive elements into drug carriers. Moreover, this review also focuses on the applications, challenges, and future prospects, providing a comprehensive overview of the evolving landscape of light-responsive drug delivery technologies. The information about the synthesis presented herein aims to contribute to the understanding and advancement of this dynamic field, offering insights for researchers and practitioners engaged in the development of next-generation drug delivery systems.
{"title":"Light-Responsive Polymers: Developments in Drug Delivery Systems","authors":"C. Aundhia, Ghanshyam Parmar, Chitrali Talele, Sunil Kardani, Rajesh Maheshwari","doi":"10.2174/0113852728307241240430055059","DOIUrl":"https://doi.org/10.2174/0113852728307241240430055059","url":null,"abstract":"\u0000\u0000Photoresponsive polymers have emerged as innovative tools in the domain of drug delivery, presenting\u0000advanced solutions for controlled and targeted release of therapeutic agents. This review explores recent\u0000advances in the design and application of photoresponsive polymers, focusing on their pivotal role in lighttriggered\u0000drug delivery systems. It also encompasses organic synthesis methodologies, key advancements in\u0000polymer design, and the integration of photoresponsive elements into drug carriers. Moreover, this review also\u0000focuses on the applications, challenges, and future prospects, providing a comprehensive overview of the evolving\u0000landscape of light-responsive drug delivery technologies. The information about the synthesis presented\u0000herein aims to contribute to the understanding and advancement of this dynamic field, offering insights for researchers\u0000and practitioners engaged in the development of next-generation drug delivery systems.\u0000","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141121829","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-14DOI: 10.2174/0113852728317263240510114622
Zetryana Puteri Tachrim, Makoto Hashimoto
The Friedel-Crafts acylation of natural or unnatural amino acids in stereo-retarded manner is willing to prescribed here. Depending on its main skeleton, the typical intra- and intermolecular Friedel-Crafts reaction of amino acids can be differentiated. The unique amino acid’s general structure can contribute to the reaction between its carboxyl group and the side chain. Depending on the Friedel-Crafts reaction condition, the amino acid’s optical retention can be retarded. This perspective can contribute to the development of this one-century reaction in the field of organic chemistry.
{"title":"The Intra- and Intermolecular Friedel-Crafts Acylation of Amino Acid Derivatives in Stereo-Retarded Manner","authors":"Zetryana Puteri Tachrim, Makoto Hashimoto","doi":"10.2174/0113852728317263240510114622","DOIUrl":"https://doi.org/10.2174/0113852728317263240510114622","url":null,"abstract":"\u0000\u0000The Friedel-Crafts acylation of natural or unnatural amino acids in stereo-retarded manner is willing\u0000to prescribed here. Depending on its main skeleton, the typical intra- and intermolecular Friedel-Crafts reaction\u0000of amino acids can be differentiated. The unique amino acid’s general structure can contribute to the reaction\u0000between its carboxyl group and the side chain. Depending on the Friedel-Crafts reaction condition, the amino\u0000acid’s optical retention can be retarded. This perspective can contribute to the development of this one-century\u0000reaction in the field of organic chemistry.\u0000","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140981675","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-13DOI: 10.2174/0113852728313438240429052927
Caterina Testa, Chiara M.A. Gangemi, Giuseppe Trusso Sfrazzetto, Martina Ricceri, Alessandro Giuffrida, Valentina Greco, Ambra Maria Cancelliere, Fausto Puntoriero, Andrea Pappalardo
A luminescent calix[5]arene with a covalently linked dansyl chromophore substituent has been successfully used, both in solution and in the gas phase (ESI-MS), for the recognition of biogenic amines that contain linear alkylammonium structural unit. Binding constant values, determined by fluorescence spectroscopy, revealed a greater affinity for cadaverine, spermidine, and L-lysine, in which the terminal ammonium group allows for additional stabilizing interactions with the dansyl moiety. the recognition of selected biogenic amines both in solution and in the gas phase (ESI-MS), and determining the relative binding constant values by fluorescence spectroscopy
{"title":"Luminescent Dansyl-Calix[5]arene for the Recognition of Biogenic Amines","authors":"Caterina Testa, Chiara M.A. Gangemi, Giuseppe Trusso Sfrazzetto, Martina Ricceri, Alessandro Giuffrida, Valentina Greco, Ambra Maria Cancelliere, Fausto Puntoriero, Andrea Pappalardo","doi":"10.2174/0113852728313438240429052927","DOIUrl":"https://doi.org/10.2174/0113852728313438240429052927","url":null,"abstract":"\u0000\u0000A luminescent calix[5]arene with a covalently linked dansyl chromophore substituent\u0000has been successfully used, both in solution and in the gas phase (ESI-MS), for the\u0000recognition of biogenic amines that contain linear alkylammonium structural unit. Binding\u0000constant values, determined by fluorescence spectroscopy, revealed a greater affinity for\u0000cadaverine, spermidine, and L-lysine, in which the terminal ammonium group allows for\u0000additional stabilizing interactions with the dansyl moiety.\u0000\u0000\u0000\u0000the recognition of selected biogenic amines both in solution and in the gas phase (ESI-MS), and determining the relative binding constant values by fluorescence spectroscopy\u0000","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140985406","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-13DOI: 10.2174/0113852728296495240409062733
A. Soldatenko, M. Molokeev, N. Lazareva
Synthesis of new hybrid organosilicon compounds based on the amides 1-naphthylacetic acid was described. N-Organyl-2-(1-naphthyl)-N-[(triethoxysilyl) methyl]acetamides were obtained by the reaction of 1- naphthylacetyl chloride with α-silylamines RNHCH2Si(OEt)3 (R = Me, i-Pr and Ph). Their subsequent interaction with N(CH2CH2OH)3 led to the formation of N-organyl-2-(1-naphthyl)-N-(silatranylmethy) acetamides. The structure of these hybrid compounds wascharacterized by 1H, 13C, and 29Si NMR spectroscopy. The structure of N-methyl- and N-isopropyl-2-(1-naphthyl)-N-(silatranylmethy)acetamides was confirmed by X-ray diffraction analysis. Results of computational screening showed that these silatranes are bioavailable and have drug-likeness. Silatranes XSi(OCHRCH2)3N belong to a widely known class of pentacoordinated silicon compounds with intramolecular dative bond Si←N. Their unique structure in combination with properties of the X substituent provide high and diverse physiological and pharmacological activities: immunomodulatory, antitumor, growth stimulating, antimicrobial and other]. Over the last 15 years, several papers have been published on the study of growth-regulating activity of compounds containing silatranyl group. However, there is no systematic study of phytohormones containing the silicon group in the molecule. N-organyl-2-(1-naphthyl)-N-(silylmethyl)acetamides NMR spectroscopy, X-ray diffraction analysis, computational screening, PASS, ADME
{"title":"N-Silylmethyl-2-(1-Naphthyl)Acetamides: Synthesis, Structure and Computational Screening","authors":"A. Soldatenko, M. Molokeev, N. Lazareva","doi":"10.2174/0113852728296495240409062733","DOIUrl":"https://doi.org/10.2174/0113852728296495240409062733","url":null,"abstract":"\u0000\u0000Synthesis of new hybrid organosilicon compounds based on the amides 1-naphthylacetic acid was\u0000described. N-Organyl-2-(1-naphthyl)-N-[(triethoxysilyl) methyl]acetamides were obtained by the reaction of 1-\u0000naphthylacetyl chloride with α-silylamines RNHCH2Si(OEt)3 (R = Me, i-Pr and Ph). Their subsequent interaction\u0000with N(CH2CH2OH)3 led to the formation of N-organyl-2-(1-naphthyl)-N-(silatranylmethy) acetamides.\u0000The structure of these hybrid compounds wascharacterized by 1H, 13C, and 29Si NMR spectroscopy. The structure\u0000of N-methyl- and N-isopropyl-2-(1-naphthyl)-N-(silatranylmethy)acetamides was confirmed by X-ray diffraction\u0000analysis. Results of computational screening showed that these silatranes are bioavailable and have\u0000drug-likeness.\u0000\u0000\u0000\u0000Silatranes XSi(OCHRCH2)3N belong to a widely known class of pentacoordinated silicon compounds with intramolecular dative bond Si←N. Their unique structure in combination with properties of the X substituent provide high and diverse physiological and pharmacological activities: immunomodulatory, antitumor, growth stimulating, antimicrobial and other]. Over the last 15 years, several papers have been published on the study of growth-regulating activity of compounds containing silatranyl group. However, there is no systematic study of phytohormones containing the silicon group in the molecule.\u0000\u0000\u0000\u0000N-organyl-2-(1-naphthyl)-N-(silylmethyl)acetamides\u0000\u0000\u0000\u0000NMR spectroscopy, X-ray diffraction analysis, computational screening, PASS, ADME\u0000","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140983059","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: Anthraquinone moiety is very common among naturally occurring bioactive compounds. Many commercially available drug molecules also possess anthraquinone moiety. In recent times, among many other anthraquinone derivatives, specifically, 2-substituted-1H-anthra[1,2-d]imidazole-6,11-diones are gaining extra attention due to their significant anti-cancer, anti-HIV, anti-inflammatory activities, etc. This study aimed to report a simple, straightforward, organocatalyzed method for the efficient synthesis of a series of 2- aryl/heteroaryl/alkyl-1H-anthra[1,2-d]imidazole-6,11-diones from the reactions of 1,2-diaminoanthraquinone and various aldehydes using a catalytic amount of camphorsulfonic acid as an efficient organocatalyst in aqueous ethanol under refluxed conditions. Under the same optimized reaction conditions, along with aryl or heteroaryl aldehydes, aliphatic aldehydes also underwent a smooth reaction and afforded the desired products in excellent yields. All the synthesized compounds were obtained pure in excellent yields by simple filtration and washing subsequently with ethanol. The use of less toxic solvent, low-cost, commercially available metal-free organocatalyst, no column chromatographic separation, good yields, and easy isolation procedure are some of the major advantages of this newly developed protocol.
{"title":"Camphorsulfonic Acid-Catalyzed Synthesis of a Series of 2-Aryl/heteroaryl/alkyl-1Hanthra[1,2-d]imidazole-6,11-dione Derivatives","authors":"Bubun Banerjee, Anu Priya, Arvind Singh, Aditi Sharma, Manmeet Kaur, Kinkar Biswas","doi":"10.2174/0113852728301570240405033544","DOIUrl":"https://doi.org/10.2174/0113852728301570240405033544","url":null,"abstract":": Anthraquinone moiety is very common among naturally occurring bioactive compounds. Many commercially available drug molecules also possess anthraquinone moiety. In recent times, among many other anthraquinone derivatives, specifically, 2-substituted-1H-anthra[1,2-d]imidazole-6,11-diones are gaining extra attention due to their significant anti-cancer, anti-HIV, anti-inflammatory activities, etc. This study aimed to report a simple, straightforward, organocatalyzed method for the efficient synthesis of a series of 2- aryl/heteroaryl/alkyl-1H-anthra[1,2-d]imidazole-6,11-diones from the reactions of 1,2-diaminoanthraquinone and various aldehydes using a catalytic amount of camphorsulfonic acid as an efficient organocatalyst in aqueous ethanol under refluxed conditions. Under the same optimized reaction conditions, along with aryl or heteroaryl aldehydes, aliphatic aldehydes also underwent a smooth reaction and afforded the desired products in excellent yields. All the synthesized compounds were obtained pure in excellent yields by simple filtration and washing subsequently with ethanol. The use of less toxic solvent, low-cost, commercially available metal-free organocatalyst, no column chromatographic separation, good yields, and easy isolation procedure are some of the major advantages of this newly developed protocol.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140937487","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-13DOI: 10.2174/0113852728303168240424052507
Tanushree Sen, Suman Adhikari, Nabajyoti Baildya, Kumaresh Ghosh
: Three receptors 1-3, built on adenine, have been synthesized, structurally characterized, and successfully employed for the recognition of monocarboxylic acids. The adenine-based receptors 1-3 have been found to bind monocarboxylic acids via the Hoogsteen (HG) binding site or the Watson-Crick (WC) binding site and form 1:1 complexes in CHCl3. Detailed binding of the receptors 1-3, in the presence of the monocarboxylic acids, corroborates that there is a distinct propensity of the HG site for aromatic carboxylic acids, for example, (S)-mandelic acid and benzoic acid. Aliphatic acids, for example, propanoic acid and rac-lactic acid, on the other hand, prefer to bind at the WC site. The monocarboxylic acid bindings to 1-3 were examined by UV–Vis, fluorescence, and 1 H NMR spectroscopic methods, and DFT study.
{"title":"Functionalized Adenine-Based Receptors for Monocarboxylic Acids’ Recognition","authors":"Tanushree Sen, Suman Adhikari, Nabajyoti Baildya, Kumaresh Ghosh","doi":"10.2174/0113852728303168240424052507","DOIUrl":"https://doi.org/10.2174/0113852728303168240424052507","url":null,"abstract":": Three receptors 1-3, built on adenine, have been synthesized, structurally characterized, and successfully employed for the recognition of monocarboxylic acids. The adenine-based receptors 1-3 have been found to bind monocarboxylic acids via the Hoogsteen (HG) binding site or the Watson-Crick (WC) binding site and form 1:1 complexes in CHCl3. Detailed binding of the receptors 1-3, in the presence of the monocarboxylic acids, corroborates that there is a distinct propensity of the HG site for aromatic carboxylic acids, for example, (S)-mandelic acid and benzoic acid. Aliphatic acids, for example, propanoic acid and rac-lactic acid, on the other hand, prefer to bind at the WC site. The monocarboxylic acid bindings to 1-3 were examined by UV–Vis, fluorescence, and 1 H NMR spectroscopic methods, and DFT study.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140937494","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-13DOI: 10.2174/0113852728248318240418092208
Sayed K. Ramadan, Sameh A. Rizk, Eman A.E. El-Helw
: This survey provides information on the synthesis and biological applications of coumarinylchalcones. Chalcones are unsaturated ketones involving the reactive keto-ethylenic group (CO-CH=CH). Chalcones are naturally abundant in many medical plants, including vegetables, fruits, and foods. Natural and synthetic chalcone compounds exhibit a broad spectrum of biological properties like anticancer, antiinflammatory, anti-HIV, antioxidant, antimalarial, and antimicrobial. Some conventional, microwave, and grinding techniques have been utilized for the synthesis of chalcones. Noteworthy, the Claisen-Schmidt condensation reaction remains the most popular and effective method for synthesis. It summarizes information about its synthetic methods as building blocks in some reactions like cyclization reactions and medical applications. This review article presents an overview of approaches and biological data for chalcones bearing a coumarin scaffold.
{"title":"Synthesis and Biological Applications of Coumarinyl-Chalcones","authors":"Sayed K. Ramadan, Sameh A. Rizk, Eman A.E. El-Helw","doi":"10.2174/0113852728248318240418092208","DOIUrl":"https://doi.org/10.2174/0113852728248318240418092208","url":null,"abstract":": This survey provides information on the synthesis and biological applications of coumarinylchalcones. Chalcones are unsaturated ketones involving the reactive keto-ethylenic group (CO-CH=CH). Chalcones are naturally abundant in many medical plants, including vegetables, fruits, and foods. Natural and synthetic chalcone compounds exhibit a broad spectrum of biological properties like anticancer, antiinflammatory, anti-HIV, antioxidant, antimalarial, and antimicrobial. Some conventional, microwave, and grinding techniques have been utilized for the synthesis of chalcones. Noteworthy, the Claisen-Schmidt condensation reaction remains the most popular and effective method for synthesis. It summarizes information about its synthetic methods as building blocks in some reactions like cyclization reactions and medical applications. This review article presents an overview of approaches and biological data for chalcones bearing a coumarin scaffold.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140937370","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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