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Organocatalytic Synthesis of γ-Amino Acid Precursors via Masked Acetaldehyde under Micellar Catalysis 胶束催化下掩蔽乙醛有机催化合成γ-氨基酸前体
IF 2.5
SynOpen Pub Date : 2022-11-15 DOI: 10.1055/a-1996-8940
Maria Edith Casacchia, G. Giorgianni, E. Allegritti, L. Giansanti, Armando Carlone, Fabio Pesciaioli
{"title":"Organocatalytic Synthesis of γ-Amino Acid Precursors via Masked Acetaldehyde under Micellar Catalysis","authors":"Maria Edith Casacchia, G. Giorgianni, E. Allegritti, L. Giansanti, Armando Carlone, Fabio Pesciaioli","doi":"10.1055/a-1996-8940","DOIUrl":"https://doi.org/10.1055/a-1996-8940","url":null,"abstract":"The development of micellar catalysis offers a sustainable alternative to organic solvents representing an environmental milestone in organic synthesis. Here the first Michael addition of masked acetaldehyde under neutral, cationic and anionic micellar catalysis is reported, affording the products in high yields and enantiomeric excess in spite the use of water as solvent.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2022-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49430670","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Synthesis of Acidiphilamide A–C: Secondary Metabolites from the Genus Streptacidiphilus 嗜酸酰胺A-C的合成:链杆菌属次生代谢产物
IF 2.5
SynOpen Pub Date : 2022-11-10 DOI: 10.1055/a-2035-9753
P. Mallesham, K. Raghavulu, Venkatesh Miriyala, Raju Doddipalla, Satyanarayana Yennam, P. Sanasi, M. Behera
{"title":"Synthesis of Acidiphilamide A–C: Secondary Metabolites from the Genus Streptacidiphilus","authors":"P. Mallesham, K. Raghavulu, Venkatesh Miriyala, Raju Doddipalla, Satyanarayana Yennam, P. Sanasi, M. Behera","doi":"10.1055/a-2035-9753","DOIUrl":"https://doi.org/10.1055/a-2035-9753","url":null,"abstract":"The paper describes the efficient total syntheses of naturally occurring tripeptides Acidiphilamides A–C and epi-Acidiphilamides A-C, which were prepared from commercially available L-phenyl alanine using Hexafluorophosphate Azabenzotriazole Tetramethyl Uronium (HATU) as peptide coupling reagent. The structures of the natural Acidiphilamides A, B and C were characterized by NMR, MS & SOR data which were matching with those of natural products, whereas the structures of epi-Acidiphilamides A, B and C were confirmed by 2D NMR studies.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2022-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44064262","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Science through the Lens of Nature: Recent Advances in Biomimetic Approaches towards Pesticide Degradation 从自然视角看科学：农药降解仿生方法的最新进展
IF 2.5
SynOpen Pub Date : 2022-11-03 DOI: 10.1055/a-2004-7289
Shikha Jyoti Borah, Akanksha Gupta, P. Sahu, N. Dheer, Vinod Kumar
{"title":"Science through the Lens of Nature: Recent Advances in Biomimetic Approaches towards Pesticide Degradation","authors":"Shikha Jyoti Borah, Akanksha Gupta, P. Sahu, N. Dheer, Vinod Kumar","doi":"10.1055/a-2004-7289","DOIUrl":"https://doi.org/10.1055/a-2004-7289","url":null,"abstract":"Pesticides are widely used to prevent bug infestation in agricultural crops and to get rid of other pests and disease-carrying creatures including mice, rats, ticks, and mosquitoes from various environment and h In response to this environmental and human health hazard, a dire need for remediation has emerged in the last few decades. Green approaches for the remediation of pesticides can boost sustainable development. A biomimetic approach for degradation of pesticides can have high potential to generate ripples of positive outcomes. Biomimetic catalysts are synthetic chemical molecules which have been inspired by natural processes to mimic their structural and functional properties. This short review concisely focuses on the synthesis of various biomimetic catalysts including metal-based materials, carbon-based materials and others. In this context, recent advances achieved by such biomimetic catalysts for the degradation of pesticides have been covered. It highlights the importance of adopting a biomimetic approach as it provides a green and efficient method for pesticides degradation","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2022-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48953414","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Design, Synthesis and Biological Evaluation of Imidazole-Substituted/Fused Aryl Derivatives Targeting Tubulin Polymerization as Anticancer Agents 咪唑取代/稠合芳基衍生物的设计、合成及抗癌活性评价
IF 2.5
SynOpen Pub Date : 2022-10-18 DOI: 10.1055/s-0042-1751835
K. Goel, S. Rajput, Rajeev Kharb
{"title":"Design, Synthesis and Biological Evaluation of Imidazole-Substituted/Fused Aryl Derivatives Targeting Tubulin Polymerization as Anticancer Agents","authors":"K. Goel, S. Rajput, Rajeev Kharb","doi":"10.1055/s-0042-1751835","DOIUrl":"https://doi.org/10.1055/s-0042-1751835","url":null,"abstract":"The development of new pharmacologically active molecules targeting tubulin polymerization has recently attracted great interest in research groups. In efforts to develop new potent anticancer compounds, imidazole-tethered/fused pharmacologically active aryl derivatives possessing different substitution patterns targeting tubulin polymerization have been rationally designed and synthesized. The target molecules (P1-5 and KG1-5) were synthesized by multistep syntheses involving the reaction of intermediate 2-aminophenyl-tethered imidazoles with appropriate reactants in the presence of p-TsOH under different conditions. The synthesized compounds displayed moderate to good cytotoxicity, comparable to that of colchicine, against four cancer cell lines (MCF-7, MD-MBA-231, A549, and HCT-116). Compounds P2 and P5, with an imidazoloquinoxaline moiety, emerged as potential leads with cytotoxicity profiles against these cell lines similar to colchicine. Compounds P2 and P5 arrested cell division at the G2/M phase and prevented cancerous cell growth through induced apoptosis. These results favored the hypothesis that the compounds might act by binding to the colchicine binding site, which was further confirmed with the help of a tubulin polymerization inhibition assay. The results encourage the further exploration of imidazoloquinoxalines as promising leads that deserve advanced clinical investigation.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2022-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44631179","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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 α-Sulfoximino Tetrazoles via Azido-Ugi Four-Component Reaction 叠氮-乌吉四元反应合成α-磺酰氨基四唑
IF 2.5
SynOpen Pub Date : 2022-10-12 DOI: 10.1055/a-1981-9151
C. I. Jesin, R. Kataria, G. Nandi
{"title":"Synthesis of α-Sulfoximino Tetrazoles via Azido-Ugi Four-Component Reaction","authors":"C. I. Jesin, R. Kataria, G. Nandi","doi":"10.1055/a-1981-9151","DOIUrl":"https://doi.org/10.1055/a-1981-9151","url":null,"abstract":"The sulfoximine based tetrazoles have been synthesized via Azido-Ugi four component reactions of sulfoximines, isocyanides, aldehydes, and TMS-azide in MeOH at 70 ℃ in the presence of InCl3. Replacement of sulfoximine with sulfonimidamide (SIA) have delivered corresponding SIA based tetrazole. Interestingly, SIA is also acting as a surrogate amine to accomplish corresponding aminotetrazole as by-product.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2022-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41999580","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Zn/ZnBr2 Catalysed Reaction of Aldehydes with Allylbromide: Synthesis of 2,6-Disubstituted 4-Bromotetrahydropyrans Zn/ZnBr2催化醛与烯基溴反应:合成2,6-二取代4-溴四氢吡喃
IF 2.5
SynOpen Pub Date : 2022-10-01 DOI: 10.1055/s-0042-1751374
A. Narsaiah, D. Biradar, Y. Mane, Y. P. Sarnikar, S. G. Kulkarni, B. Reddy
{"title":"Zn/ZnBr2 Catalysed Reaction of Aldehydes with Allylbromide: Synthesis of 2,6-Disubstituted 4-Bromotetrahydropyrans","authors":"A. Narsaiah, D. Biradar, Y. Mane, Y. P. Sarnikar, S. G. Kulkarni, B. Reddy","doi":"10.1055/s-0042-1751374","DOIUrl":"https://doi.org/10.1055/s-0042-1751374","url":null,"abstract":"An efficient approach for the one-pot synthesis of 4-bromotetrahydropyrans in a highly diastereoselective manner via the alkynylation followed by Prins cyclisation is described. The method employs aldehydes and allyl bromide as reactants, with a Zn/ZnBr2 catalytic system in CH2Cl2. A variety of 2,6-disubstituted 4-bromotetrahydropyran derivatives were obtained in good yields.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2022-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42620193","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent progress on the [3+2] cycloaddition route for the synthesis of all-carbon quaternary stereocentres [3+2]环加成法合成全碳四元立体中心的研究进展
IF 2.5
SynOpen Pub Date : 2022-09-20 DOI: 10.1055/a-1947-3351
A. Deepthi, Maneesh Mohan, C. Meenakshy
{"title":"Recent progress on the [3+2] cycloaddition route for the synthesis of all-carbon quaternary stereocentres","authors":"A. Deepthi, Maneesh Mohan, C. Meenakshy","doi":"10.1055/a-1947-3351","DOIUrl":"https://doi.org/10.1055/a-1947-3351","url":null,"abstract":"Construction of all-carbon quaternary centres is an important task in organic synthesis. In spite of the challenges associated with the Csp3-Csp3 bond constructions in a sterically constrained environment, significant advances have been made in this area. Among the latter, catalytic and non-catalytic [3+2] cycloaddition approach has gained wide attention recently. This short review summarizes the [3+2] cycloaddition reactions reported during the period 2016-2022 for the synthesis of molecules possessing one or more all-carbon quaternary stereocentre","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2022-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46870331","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic Acid 实用的、多克的从奎宁酸制备合成有用的、对映体纯的构建块
IF 2.5
SynOpen Pub Date : 2022-09-19 DOI: 10.1055/a-1952-4557
Shen Tan, P. Lan, M. Banwell, L. V. White
{"title":"Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic Acid","authors":"Shen Tan, P. Lan, M. Banwell, L. V. White","doi":"10.1055/a-1952-4557","DOIUrl":"https://doi.org/10.1055/a-1952-4557","url":null,"abstract":"The naturally abundant, enantiomerically pure cyclitol quinic acid (1) has been converted into the synthetically useful enone 2 in nearly quantitative yield using the operationally straightforward and reproducible protocols reported herein. The latter compound, which was obtained in multigram quantities, engages in a diastereoselective 1,2-addition reaction with a hydrazone-based nucleophile. Furthermore, the readily derived α-iodoenone 3 participates in both cross-coupling and α,β-annulation reactions. The results reported here emphasize that the now practically accessible cyclohexenones 2 and 3 are useful, enantiomerically pure building blocks for organic synthesis.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2022-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49066720","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Total synthesis of marine-derived azole resistant antifungal agent (-)-melearoride A and antibiotic (-)-PF1163B 海洋衍生抗真菌药(-)-melearoride A和抗生素(-)- pf1163b的全合成
IF 2.5
SynOpen Pub Date : 2022-09-14 DOI: 10.1055/a-1942-6969
Srihari Pabbaraja, Bharath Yasam
{"title":"Total synthesis of marine-derived azole resistant antifungal agent (-)-melearoride A and antibiotic (-)-PF1163B","authors":"Srihari Pabbaraja, Bharath Yasam","doi":"10.1055/a-1942-6969","DOIUrl":"https://doi.org/10.1055/a-1942-6969","url":null,"abstract":"A flexible stereoselective and convergent cum divergent approach to the synthesis of two 13-membered macrolides through a common skeleton present in their structure is described in two different routes, with good overall yield. The key synthetic reactions utilized include Keck allylation, Evans asymmetric methylation, Grubbs metathesis and Julia-Kocienski olefination reaction.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2022-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43659489","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Zinc acetate catalyzed stereoselective 1,2 trans glycosylation using glycosyl chlorides 乙酸锌催化糖基氯化物立体选择性1,2反式糖基化反应
IF 2.5
SynOpen Pub Date : 2022-09-12 DOI: 10.1055/a-1941-3801
Mohammad Saif Ali, Ramesh P.I, Subhash Ghosh, M. Tatina
{"title":"Zinc acetate catalyzed stereoselective 1,2 trans glycosylation using glycosyl chlorides","authors":"Mohammad Saif Ali, Ramesh P.I, Subhash Ghosh, M. Tatina","doi":"10.1055/a-1941-3801","DOIUrl":"https://doi.org/10.1055/a-1941-3801","url":null,"abstract":"We report the strategy for the stereoselective synthesis of 1,2-trans glycosides in the absence of NGP (neighboring group participation). Present protocol for the selective glycosylation mainly rely on catalyst control rather than protecting group selection. Using this protocol, several glycosides were prepared. Cost effective zinc acetate was found to be the best catalyst that provided desired 1,2-trans glycosides from glucose and mannose derived glycosyl halides at room temperature unlike traditional cryogenic conditions.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2022-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41415840","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
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