Background: Background: Heterocyclic compounds and their derivatives epitomize the building blocks of many biological entities, e.g., alkaloids, antibiotics, enzymes, hormones, vitamins, and others that are abundant in nature. The Vilsmeier-Haack reaction has fascinated organic chemists due to its significant use in the synthesis of numerous heterocycles. This analytical evaluation provides a scrutinized overview of the literature on the synthesis of heterocyclic compounds by Method: A comprehensive review of the literature related to Vilsmeier- Haack reagents and reactions is done from PubMed and other sources like google scholar and Google websites. Result: This precise analytic evaluation provides a revolutionary update on the Vilsmeier-Haack reaction and its applications in the synthesis of natural and synthetic compounds. Conclusion: Presently researchers are developing and looking for unconventional reagents that are inexpensive, have high chemical yields, are environmentally benign, recyclable, and robust. The information incorporated in this review paper may inspire more research on the Vilsmeier-Haack reagent and its usage in heterocycle synthesis.
{"title":"Vilsmeier Haack Reaction: An Exemplary Tool for Synthesis of Different Heterocycles","authors":"Shivani Tyagi, Rakhi Mishra, Avijit Mazumder, Varsha Jindaniya","doi":"10.2174/1570178620666230911152937","DOIUrl":"https://doi.org/10.2174/1570178620666230911152937","url":null,"abstract":"Background: Background: Heterocyclic compounds and their derivatives epitomize the building blocks of many biological entities, e.g., alkaloids, antibiotics, enzymes, hormones, vitamins, and others that are abundant in nature. The Vilsmeier-Haack reaction has fascinated organic chemists due to its significant use in the synthesis of numerous heterocycles. This analytical evaluation provides a scrutinized overview of the literature on the synthesis of heterocyclic compounds by Method: A comprehensive review of the literature related to Vilsmeier- Haack reagents and reactions is done from PubMed and other sources like google scholar and Google websites. Result: This precise analytic evaluation provides a revolutionary update on the Vilsmeier-Haack reaction and its applications in the synthesis of natural and synthetic compounds. Conclusion: Presently researchers are developing and looking for unconventional reagents that are inexpensive, have high chemical yields, are environmentally benign, recyclable, and robust. The information incorporated in this review paper may inspire more research on the Vilsmeier-Haack reagent and its usage in heterocycle synthesis.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"365 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136023988","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}
Background: The recent energy shortage has drawn much attention to synthesizing active pharmaceutical ingredients (API) using green chemistry concepts like renewable energy sources and solvents. The concentrated solar radiation (CSR) technique has several advantages, including simple, affordable, energy and time-efficient for synthesizing active pharmaceutical ingredients and new chemical entities. Here, we successfully developed a two-step, one-pot synthesis of levodropropizine for the first time using CSR as a clean energy source and in a green solvent. Objective: To synthesize levodropropizine using concentrated solar radiations to save energy and improve yields while maintaining essential properties like chirality and physical properties. Methods: Levodropropizine was synthesized in two steps and in one pot method in a glass apparatus under concentrated solar radiation using a Fresnel lens measuring 20 cm (l) X 20 cm (b). The outcome was compared with the one obtained from the conventional heating method. X-ray crystallography, FTIR, NMR, polarimetry, HPLC-MS, chiral HPLC, DSC, and DTA characterized the Levodropropizine produced by CSR and conventional heating. The product synthesized by CSR was in agreement with the one synthesized by conventional heating. Results: As shown in scheme-1 a two step, one pot synthetic protocol for Levodropropizine using concentrated solar radiations resulted in 87% yield in 38 minutes while conventional heating method took about 6 hours with 77% yield. Conclusion: A two-step, one-pot, environmentally friendly, and straightforward approach to synthesizing Levodropropizine using concentrated solar radiation has been established; this method minimized the reaction time from 6.08 h. to 38 minutes, saving up to 90.89% of the energy. Different analytical techniques for physical characterization, such as x-ray crystallography, DSC, DTA, and chemical identity and purity by FTIR, NMR, Polarimetry, chiral HPLC, and LC-MS, thoroughly characterized Levodropropizine synthesized by CSR.
背景:近年来能源短缺引起了人们对利用可再生能源和溶剂等绿色化学概念合成活性药物成分(API)的关注。集中太阳辐射(CSR)技术具有简单、经济、节能、省时等优点，可用于药物活性成分和新型化学实体的合成。在这里，我们首次成功地利用CSR作为清洁能源，在绿色溶剂中两步一锅合成左丙丙嗪。目的:利用太阳辐射合成左丙丙嗪，在保持手性和物理性质的前提下，节约能源，提高产率。方法:采用20 cm (l) × 20 cm (b)的菲涅耳透镜，在太阳集中辐射下，在玻璃装置中分两步一锅法合成左丙丙嗪，并与常规加热法合成结果进行比较。采用x射线晶体学、FTIR、NMR、极化、HPLC- ms、手性HPLC、DSC和差热分析对CSR法和常规加热法制备的左丙哌嗪进行了表征。CSR合成的产物与常规加热合成的产物基本一致。结果:如方案-1所示，采用两步一锅法合成左丙丙嗪，38分钟产率87%，而常规加热法需6小时左右，产率77%。结论:建立了一种两步、一锅、环境友好、简便的利用太阳辐射合成左旋丙哌嗪的方法;该方法将反应时间从6.08 h缩短至38 min，节约能量达90.89%。不同的物理表征分析技术，如x射线晶体学、DSC、DTA，以及FTIR、NMR、极化、手性HPLC、LC-MS等化学性质和纯度，全面表征了CSR合成的左旋丙哌嗪。
{"title":"Concentrated Solar Radiation (CSR) assisted two-step, one-pot synthesis of (S)-3-(4-phenylpiperazin-1-yl) propane-1,2-diol (Levodropropizine)","authors":"Pawan Kudale, Santosh Chikane, Dipak Pinjari, Ganesh Chaturbhuj","doi":"10.2174/1570178620666230907115917","DOIUrl":"https://doi.org/10.2174/1570178620666230907115917","url":null,"abstract":"Background: The recent energy shortage has drawn much attention to synthesizing active pharmaceutical ingredients (API) using green chemistry concepts like renewable energy sources and solvents. The concentrated solar radiation (CSR) technique has several advantages, including simple, affordable, energy and time-efficient for synthesizing active pharmaceutical ingredients and new chemical entities. Here, we successfully developed a two-step, one-pot synthesis of levodropropizine for the first time using CSR as a clean energy source and in a green solvent. Objective: To synthesize levodropropizine using concentrated solar radiations to save energy and improve yields while maintaining essential properties like chirality and physical properties. Methods: Levodropropizine was synthesized in two steps and in one pot method in a glass apparatus under concentrated solar radiation using a Fresnel lens measuring 20 cm (l) X 20 cm (b). The outcome was compared with the one obtained from the conventional heating method. X-ray crystallography, FTIR, NMR, polarimetry, HPLC-MS, chiral HPLC, DSC, and DTA characterized the Levodropropizine produced by CSR and conventional heating. The product synthesized by CSR was in agreement with the one synthesized by conventional heating. Results: As shown in scheme-1 a two step, one pot synthetic protocol for Levodropropizine using concentrated solar radiations resulted in 87% yield in 38 minutes while conventional heating method took about 6 hours with 77% yield. Conclusion: A two-step, one-pot, environmentally friendly, and straightforward approach to synthesizing Levodropropizine using concentrated solar radiation has been established; this method minimized the reaction time from 6.08 h. to 38 minutes, saving up to 90.89% of the energy. Different analytical techniques for physical characterization, such as x-ray crystallography, DSC, DTA, and chemical identity and purity by FTIR, NMR, Polarimetry, chiral HPLC, and LC-MS, thoroughly characterized Levodropropizine synthesized by CSR.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"30 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135096563","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}
Abstract: The 1,2,5-oxadiazole framework has garnered a lot of interest among many nitrogen heterocycles because of its capacity to give off NO under physiological circumstances. Because of this, major efforts by chemical scientists have been made to create novel drug possibilities in medicinal, material, and agriculture science that include the NO-donor 1,2,5-oxadiazole N-oxide subunit coupled to a known drug or a possible pharmacophore by C-C/C-N links or by using a suitable spacer. In the last few years, 1,2,5-oxadiazole and its derivatives have been reported as good pharmacophores as carbonic anhydrase inhibitors, antibacterial, vasodilating agents, antimalarial, anticancer, etc. In the presented manuscript, we reviewed granted patents (last 10 years), different synthetic strategies (last 27 years) of 1,2,5-oxadiazoles and their N-oxide derivatives synthesis such as cycloaddition, dimerization, cyclodehydration, condensation, thermolysis, nitration, oxidation, ring-conversion, etc. These synthetic methods have also been analyzed for their merits and demerits. The manuscript also highlighted various applications of 1,2,5-oxadiazole and its derivatives. We hope that researchers across the scientific streams will benefit from the presented review articles for designing their work related to 1,2,5-oxadiazoles.
{"title":"Synthetic Protocols and Applications of 1,2,5-Oxadiazoles: A Review","authors":"Greesh Kumar, Rajnish Kumar, Avijit Mazumder, Salahuddin Salahuddin, Upendra Kumar","doi":"10.2174/1570178620666230905145050","DOIUrl":"https://doi.org/10.2174/1570178620666230905145050","url":null,"abstract":"Abstract: The 1,2,5-oxadiazole framework has garnered a lot of interest among many nitrogen heterocycles because of its capacity to give off NO under physiological circumstances. Because of this, major efforts by chemical scientists have been made to create novel drug possibilities in medicinal, material, and agriculture science that include the NO-donor 1,2,5-oxadiazole N-oxide subunit coupled to a known drug or a possible pharmacophore by C-C/C-N links or by using a suitable spacer. In the last few years, 1,2,5-oxadiazole and its derivatives have been reported as good pharmacophores as carbonic anhydrase inhibitors, antibacterial, vasodilating agents, antimalarial, anticancer, etc. In the presented manuscript, we reviewed granted patents (last 10 years), different synthetic strategies (last 27 years) of 1,2,5-oxadiazoles and their N-oxide derivatives synthesis such as cycloaddition, dimerization, cyclodehydration, condensation, thermolysis, nitration, oxidation, ring-conversion, etc. These synthetic methods have also been analyzed for their merits and demerits. The manuscript also highlighted various applications of 1,2,5-oxadiazole and its derivatives. We hope that researchers across the scientific streams will benefit from the presented review articles for designing their work related to 1,2,5-oxadiazoles.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"33 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135362251","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}
Pub Date : 2023-09-01DOI: 10.2174/1570178620666230901101009
David Fuentes-Ríos, Manuel Doña, J. López-Romero, Rodrigo Rico
1,3-dimethyl-4,5-diaminouracil has been used as an efficient protecting group for the carbonyl moiety in sugars by the formation of the imine group. The protection reaction is carried out under mild conditions, the yields are quantitative in most of the cases, and the protecting group is completely recovered and reused. After per-acetylation, deprotection is accomplished at room temperature with aqueous formic acid to produce acyclic acetylated sugars in good global yield.
{"title":"Acyclic aldehydo sugars: 1,3-dimethyl-4,5-diamino uracil as recoverable carbonyl protecting group","authors":"David Fuentes-Ríos, Manuel Doña, J. López-Romero, Rodrigo Rico","doi":"10.2174/1570178620666230901101009","DOIUrl":"https://doi.org/10.2174/1570178620666230901101009","url":null,"abstract":"\u0000\u00001,3-dimethyl-4,5-diaminouracil has been used as an efficient protecting group for the carbonyl moiety in sugars by the formation of the imine group. The protection reaction is carried out under mild conditions, the yields are quantitative in most of the cases, and the protecting group is completely recovered and reused. After per-acetylation, deprotection is accomplished at room temperature with aqueous formic acid to produce acyclic acetylated sugars in good global yield.\u0000","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":0.8,"publicationDate":"2023-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45627114","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}
Pub Date : 2023-08-31DOI: 10.2174/1570178620666230831162320
Areveli Srinivas, A. Shree, S. Goud
Pyrazolo bridged quinolones scaffolds are an important building block in many of the medicinally active new chemical entities. In the current work, synthesis of phenyl-4-(1H-pyrazol-5-yl) conjugated with 1H-pyrazolo[3,4-b]quinolin-5(4H)-ones derivatives has been achieved by one-pot three-component reaction of 3-methyl-1-phenyl-1H-pyrazol-5-amine 1, 5,5-dimethylcyclohexane-1,3-diones 2, and 1H-pyrazole-5-carbaldehydes 3 using [BMIM]BF4 as green reaction medium with good yields. Furthermore, the synthesized compounds were evaluated for cytotoxic potential towards HeLa and DU145 cells. Of the eight derivatives, compound 4d exhibited good cytotoxicity with an IC50 value of 8.5 and 8.9 µM against DU145 and HeLa cells, respectively. The molecular docking studies revealed that compound 4d displayed good binding energy (-8.4 kcal/mol) against human checkpoint kinase 1.
{"title":"[BMIM]BF4 Mediated Multi-component Synthesis of Phenyl-4-(1H-pyrazol-5-yl)-1H-pyrazolo[3,4-b]quinolin-5(4H)-ones and Evaluation of their Anti-cancer Activity","authors":"Areveli Srinivas, A. Shree, S. Goud","doi":"10.2174/1570178620666230831162320","DOIUrl":"https://doi.org/10.2174/1570178620666230831162320","url":null,"abstract":"\u0000\u0000Pyrazolo bridged quinolones scaffolds are an important building block in many of the medicinally active new chemical entities. In the current work, synthesis of phenyl-4-(1H-pyrazol-5-yl) conjugated with 1H-pyrazolo[3,4-b]quinolin-5(4H)-ones derivatives has been achieved by one-pot three-component reaction of 3-methyl-1-phenyl-1H-pyrazol-5-amine 1, 5,5-dimethylcyclohexane-1,3-diones 2, and 1H-pyrazole-5-carbaldehydes 3 using [BMIM]BF4 as green reaction medium with good yields. Furthermore, the synthesized compounds were evaluated for cytotoxic potential towards HeLa and DU145 cells. Of the eight derivatives, compound 4d exhibited good cytotoxicity with an IC50 value of 8.5 and 8.9 µM against DU145 and HeLa cells, respectively. The molecular docking studies revealed that compound 4d displayed good binding energy (-8.4 kcal/mol) against human checkpoint kinase 1.\u0000","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":0.8,"publicationDate":"2023-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49117551","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}
Pub Date : 2023-08-30DOI: 10.2174/1570178620666230830125327
T. Yamanoi, Kenji Koike, Yoshiki Oda
In this study, a new fluorous aza-crown ether derivative (1) conjugated with two Bfp (bisfluorous chain type propionyl) groups was prepared; then, the partition ratios of 1 in biphasic systems using FC 72 and several organic solvents were investigated. Next, the activities of 1 in an FC 72/acetonitrile biphasic system were assessed via the SN2-type acetoxylation reaction using 2-(bromomethyl)naphthalene and potassium acetate. Finally, the recyclability of 1 in a two-layer system based on its immobilization in an FC 72 solvent was examined during acetoxylation reactions.
{"title":"Preparation of fluorous aza-crown ether with two bisfluorous chain type propionyl groups: An investigation of its partition ratios in fluorous biphasic systems and recyclability during SN2-type acetoxylation reactions","authors":"T. Yamanoi, Kenji Koike, Yoshiki Oda","doi":"10.2174/1570178620666230830125327","DOIUrl":"https://doi.org/10.2174/1570178620666230830125327","url":null,"abstract":"\u0000\u0000In this study, a new fluorous aza-crown ether derivative (1) conjugated with two Bfp (bisfluorous chain type propionyl) groups was prepared; then, the partition ratios of 1 in biphasic systems using FC 72 and several organic solvents were investigated. Next, the activities of 1 in an FC 72/acetonitrile biphasic system were assessed via the SN2-type acetoxylation reaction using 2-(bromomethyl)naphthalene and potassium acetate. Finally, the recyclability of 1 in a two-layer system based on its immobilization in an FC 72 solvent was examined during acetoxylation reactions.\u0000","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":0.8,"publicationDate":"2023-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48016230","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}
Pub Date : 2023-08-25DOI: 10.2174/1570178620666230825153812
A. Camacho-Dávila, J. Espinoza-Hicks, G. Zaragoza-Galán
An improved synthesis of the monoterpene cyclic ketone karahanaenone, an ingredient in cosmetics, perfumery, and pest-control agents, is reported. The synthesis uses linalyl acetate as the starting material, which is converted to the epoxide with m-CPBA and submitted to an anhydrous lithium perchlorate catalyzed rearrangement to the corresponding ketone. Hydrolysis and thermolysis of the ketone afford karahanaenone in good yield. The catalyst can be recycled by simple dehydration and reused without affecting the yield for the rearrangement.
{"title":"An improved synthesis of Karahanaenone","authors":"A. Camacho-Dávila, J. Espinoza-Hicks, G. Zaragoza-Galán","doi":"10.2174/1570178620666230825153812","DOIUrl":"https://doi.org/10.2174/1570178620666230825153812","url":null,"abstract":"\u0000\u0000An improved synthesis of the monoterpene cyclic ketone karahanaenone, an ingredient in cosmetics, perfumery, and pest-control agents, is reported. The synthesis uses linalyl acetate as the starting material, which is converted to the epoxide with m-CPBA and submitted to an anhydrous lithium perchlorate catalyzed rearrangement to the corresponding ketone. Hydrolysis and thermolysis of the ketone afford karahanaenone in good yield. The catalyst can be recycled by simple dehydration and reused without affecting the yield for the rearrangement.\u0000","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":0.8,"publicationDate":"2023-08-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47095272","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}
Pub Date : 2023-08-21DOI: 10.2174/1570178620666230821143013
V. Srivastava
The preparation and characterization of SBA-15 supported Ni catalysts with varying metal loading (1, 2, and 3% by weight) was carried out using the impregnation technique, followed by a rigorous characterization using advanced analytical techniques. The catalytic performance of the synthesized catalysts was evaluated for the Wittig-type olefination reaction, and it was found that the SBA-15-3Ni catalyst exhibited superior activity for this reaction under mild reaction conditions (70 °C and 1 hour). The corresponding stilbenes were obtained in good yield, although with low to average diastereoselectivity. An important feature of this protocol is that the proposed methodology is especially efficient for the synthesis of stilbenes since no additives are required to serve as a hydrogen acceptor. Moreover, the new catalytic system was successfully employed for the synthesis of polymethoxylated and polyhydroxylated stilbenes, including resveratrol and DMU-212, with high yield and easy product isolation. A key advantage of this protocol is that the catalysts can be reused for up to 5 runs without significant loss in catalytic activity, which makes this approach highly sustainable and cost-effective. Additionally, the ligand-free approach proposed in this study is an added advantage, which makes it more attractive for large-scale synthesis of biologically active compounds.
{"title":"Silica-supported active Ni Nanocatalyst for Wittig Reaction","authors":"V. Srivastava","doi":"10.2174/1570178620666230821143013","DOIUrl":"https://doi.org/10.2174/1570178620666230821143013","url":null,"abstract":"\u0000\u0000The preparation and characterization of SBA-15 supported Ni catalysts with varying metal loading (1, 2, and 3% by weight) was carried out using the impregnation technique, followed by a rigorous characterization using advanced analytical techniques. The catalytic performance of the synthesized catalysts was evaluated for the Wittig-type olefination reaction, and it was found that the SBA-15-3Ni catalyst exhibited superior activity for this reaction under mild reaction conditions (70 °C and 1 hour). The corresponding stilbenes were obtained in good yield, although with low to average diastereoselectivity. An important feature of this protocol is that the proposed methodology is especially efficient for the synthesis of stilbenes since no additives are required to serve as a hydrogen acceptor. Moreover, the new catalytic system was successfully employed for the synthesis of polymethoxylated and polyhydroxylated stilbenes, including resveratrol and DMU-212, with high yield and easy product isolation. A key advantage of this protocol is that the catalysts can be reused for up to 5 runs without significant loss in catalytic activity, which makes this approach highly sustainable and cost-effective. Additionally, the ligand-free approach proposed in this study is an added advantage, which makes it more attractive for large-scale synthesis of biologically active compounds.\u0000","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":0.8,"publicationDate":"2023-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46660275","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}
Pub Date : 2023-08-21DOI: 10.2174/1570178620666230821142342
Qinghan Li, Meng Liang, Jiaxia Pu, X. Jia, Lirong Han
An alternative method for the synthesis of 2-heteroaryl or alkynyl benzo[b]thiophene or furan derivatives via direct palladium-catalyzed cross-coupling of 2-benzo[b]thiophene or furan aluminum with heteroaryl or alkynyl bromides, respectively, has been successfully developed. This case is remarkable as the same catalytic system could simultaneously produce either 2-substituted benzo[b]thiophene or furan derivatives.
{"title":"Palladium-catalyzed Cross-coupling of 2-Benzo[b]thiophene or 2-Benzo[b]furan Aluminum with Heteroaryl or Alkynyl Bromides for the Synthesis of 2-Hetroaryl or Alkynyl Benzo[b]thiophene or Benzo[b]furan Derivatives","authors":"Qinghan Li, Meng Liang, Jiaxia Pu, X. Jia, Lirong Han","doi":"10.2174/1570178620666230821142342","DOIUrl":"https://doi.org/10.2174/1570178620666230821142342","url":null,"abstract":"\u0000\u0000An alternative method for the synthesis of 2-heteroaryl or alkynyl benzo[b]thiophene or furan derivatives via direct palladium-catalyzed cross-coupling of 2-benzo[b]thiophene or furan aluminum with heteroaryl or alkynyl bromides, respectively, has been successfully developed. This case is remarkable as the same catalytic system could simultaneously produce either 2-substituted benzo[b]thiophene or furan derivatives.\u0000","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":0.8,"publicationDate":"2023-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44462459","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}
Pub Date : 2023-08-18DOI: 10.2174/1570178620666230818105236
F. Moosavi, N. Hasanzadeh, H. Yahyaei, A. Rayatzadeh
Using single-wall carbon nanotubes (SWCNTs) and boron nitride nanotubes (BNNTs), this study evaluated the interactions between Capecitabine (CAP) and Gemcitabine (GEM). Molecular mechanics and quantum mechanics were used in the analysis. The interaction between CP and GM with SWCNTs and BNNTs under various solvents was analyzed using the self-consistent reaction field (SCRF) as a model and DFT as the analytical method. Additionally, the effect of temperature on the stability of the molecule interactions during the experiment was examined. The thermodynamic properties of the title compounds were analyzed based on theoretical calculations. It included the calculation of Frontier Molecular Orbitals (FMOs) and Total Density of States (DOS). In addition to studying the ionization potential (I), we also examined the other molecular properties of the structures, such as electrophilicity (ω), electron affinity (A), chemical hardness (η), and electronic chemical potential (μ). To investigate the interaction between CAP and GEM with SWCNTs and BNNTs, molecular mechanics methods (MM) including AMBER, OPLS, CHARMM, and MM+ force fields, were employed. Monte Carlo simulation techniques were used to calculate the results at different temperatures. The effects of the liquid phase and mixed solvent media with varying dielectric constants (Water, DMSO, Methanol, and Ethanol) on the interaction between CAP and GEM using the force fields described above were examined in this study. The correlation between data generated by Monte Carlo, Quantum Mechanics, and Molecular Mechanics was demonstrated. There was a striking similarity in the thermodynamic properties and conformer populations of all three materials.
{"title":"Study of Interactions of Nucleoside Anticancer Drugs, Capecitabine and Gemcitabine, with SWNT and BNNT using Molecular and Quantum Mechanical Calculations","authors":"F. Moosavi, N. Hasanzadeh, H. Yahyaei, A. Rayatzadeh","doi":"10.2174/1570178620666230818105236","DOIUrl":"https://doi.org/10.2174/1570178620666230818105236","url":null,"abstract":"\u0000\u0000Using single-wall carbon nanotubes (SWCNTs) and boron nitride nanotubes (BNNTs), this study evaluated the interactions between Capecitabine (CAP) and Gemcitabine (GEM). Molecular mechanics and quantum mechanics were used in the analysis.\u0000\u0000\u0000\u0000The interaction between CP and GM with SWCNTs and BNNTs under various solvents was analyzed using the self-consistent reaction field (SCRF) as a model and DFT as the analytical method. Additionally, the effect of temperature on the stability of the molecule interactions during the experiment was examined. The thermodynamic properties of the title compounds were analyzed based on theoretical calculations. It included the calculation of Frontier Molecular Orbitals (FMOs) and Total Density of States (DOS). In addition to studying the ionization potential (I), we also examined the other molecular properties of the structures, such as electrophilicity (ω), electron affinity (A), chemical hardness (η), and electronic chemical potential (μ).\u0000\u0000\u0000\u0000To investigate the interaction between CAP and GEM with SWCNTs and BNNTs, molecular mechanics methods (MM) including AMBER, OPLS, CHARMM, and MM+ force fields, were employed. Monte Carlo simulation techniques were used to calculate the results at different temperatures.\u0000\u0000\u0000\u0000The effects of the liquid phase and mixed solvent media with varying dielectric constants (Water, DMSO, Methanol, and Ethanol) on the interaction between CAP and GEM using the force fields described above were examined in this study. The correlation between data generated by Monte Carlo, Quantum Mechanics, and Molecular Mechanics was demonstrated. There was a striking similarity in the thermodynamic properties and conformer populations of all three materials.\u0000","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":0.8,"publicationDate":"2023-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46980693","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}
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