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Sustainable Organocatalyzed Enantioselective Catalytic Michael Additions in Betaine-Derived Deep Eutectic Solvents 甜菜碱衍生的深度共晶溶剂中可持续的有机催化对映选择性催化Michael加成
IF 2.5 Q2 CHEMISTRY, ORGANIC Pub Date : 2023-03-23 DOI: 10.1055/a-2117-9971
Daniela Fonseca, Ana C. Amorim, Elisabete P. Carreiro, J. Ramalho, G. Hermann, H. Federsel, A. Duarte, A. Burke
The catalyst cinchonidine-squaramide was immobilized within three different deep eutectic solvents (DES): (Betaine: D-Sorbitol: Water), (Betaine: D-Xylitol: Water) and (Betaine: D-Mannitol: Water) and evaluated in a well-known asymmetric Michael addition. These reactions provided excellent yields (up to 99%) and enantioselectivities (up to 98%) using only 1 mol% of catalyst. It was also possible to achieve 9 cycles in reactions with DES (Betaine: D-Sorbitol: Water), proving the high recyclability of this system. In the reactions realized with only 0.5 mol% of catalyst, it was possible to achieve 5 cycles and the products were obtained with high yields (up to 95%) and excellent enantioselectivities (up to 94%), using DES (Betaine: D-Sorbitol: Water).
将催化剂辛可尼丁方酰胺固定在三种不同的深共晶溶剂(DES)中:(甜菜碱:D-山梨醇:水)、(甜菜碱:D-木糖醇:水)和(甜菜碱:D-甘露醇:水),并在众所周知的不对称Michael加成中进行评价。这些反应仅使用1mol%的催化剂就提供了优异的产率(高达99%)和对映选择性(高达98%)。在与DES(甜菜碱:D-山梨醇:水)的反应中也可以实现9个循环,证明了该系统的高可回收性。在仅用0.5mol%催化剂实现的反应中,可以实现5个循环,并且使用DES(甜菜碱:D-山梨醇:水)以高产率(高达95%)和优异的对映选择性(高达94%)获得产物。
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引用次数: 1
Click-Chemistry-Assisted Alteration of Glycosaminoglycans for Biological Applications 生物应用中糖胺聚糖的点击化学辅助修饰
IF 2.5 Q2 CHEMISTRY, ORGANIC Pub Date : 2023-03-03 DOI: 10.1055/s-0040-1720072
Smritilekha Bera, D. Mondal
This short review describes the assistance of click chemistry in the chemical modification of glycosaminoglycans. Through an alkyne-azide 1,3-dipolar cycloaddition reaction, the chemically and physiologically stable triazole unit connects glycosaminoglycans with other labelled or attached functionalities. The synthesized glycosaminoglycan (GAG) conjugates act as drug carriers, forming hydrogels or nanohydrogels for localized drug delivery or injectable GAGs and so on. These are used in research on antithrombotic agents, protein binding, and hepatocyte growth factors, as well as in mechanistic studies of glycosaminoglycans biosynthesis and wound healing.1 Introduction2 Synthetic Modification of GAGS3 Click Chemistry4 Modification of GAGS Applying Click Chemistry5 Conclusions6 Abbreviations
本文简要介绍了点击化学在糖胺聚糖化学改性中的作用。通过炔-叠氮化1,3偶极环加成反应,化学上和生理上稳定的三唑单元将糖胺聚糖与其他标记或附加的官能团连接起来。合成的糖胺聚糖(GAG)偶联物作为药物载体,形成水凝胶或纳米水凝胶,用于局部药物递送或可注射的GAG等。它们被用于抗血栓药物、蛋白质结合和肝细胞生长因子的研究,以及糖胺聚糖生物合成和伤口愈合的机制研究引言2 GAGS的合成修饰s3 Click化学4应用Click化学修饰GAGS 5结论6缩写
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引用次数: 0
Conversion of α-Diazoketones into 1-Bromo-2-alkyl- or 2-arylpent-4-en-2-ols using Tin-Mediated Allylation/Propargylation 使用锡介导的烯丙基化/丙炔基化将α-二唑酮转化为1-溴-2-烷基-或2-芳基戊-4-烯-2-醇
IF 2.5 Q2 CHEMISTRY, ORGANIC Pub Date : 2023-03-02 DOI: 10.1055/a-2068-5625
S. Biswas, Sipak Joyasawal
High yielding and mild conditions to prepare of 1-bromo-2-alkyl- or 2-arylpent-4-en-2-ols/1-bromo-2-alkyl-or 2-arylpent-4-yn-2-ols from α-diazoketones which involves allylation/propargylation with successive bromide insertion using in-situ generated allyltin bromide/or propargyltin bromide from activated tin metal and allyl/or propargyl bromide.
α-重氮酮制备1-溴-2-烷基或2-芳基戊-4-烯-2-醇/1-溴-2-烷基或2-芳基戊-4-烯-2-醇/1-溴-2-烷基或2-芳基戊-4-炔-2-醇的高产温和条件。
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引用次数: 0
Synthesis of Calix[4]arene Appended Lactosylated G 1 and Galactosylated G 2 Generation Glycodendrimers using a ‘CuAAC’ Click Approach CuAAC点击法合成杯[4]芳烃连接的乳糖基G1和半乳糖基G2代糖树状大分子
IF 2.5 Q2 CHEMISTRY, ORGANIC Pub Date : 2023-01-31 DOI: 10.1055/a-2063-4139
Sunil Kumar, Mangal S Yadav, Sumit Kumar Singh, S. Rajkhowa, V. Tiwari
A modular click-approach is applied for the expeditious synthesis of lactose- and galactose-coated calixarene cored G1 and G2 generation glycodendrimers, respectively. The developed calixarene glycodendrimers has been characterized by using extensive spectral analysis including NMR (1H and 13C), MS, IR and SEC data.
模块化点击法分别用于快速合成乳糖和半乳糖包被的杯芳烃核G1代和G2代糖树状大分子。通过广泛的光谱分析,包括NMR(1H和13C)、MS、IR和SEC数据,对所开发的杯芳烃糖树枝状聚合物进行了表征。
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引用次数: 0
Synthesis of Bioactive Macrocycles Involving Ring-Closing Metathesis Strategy 采用闭合环复合策略合成生物活性大环
IF 2.5 Q2 CHEMISTRY, ORGANIC Pub Date : 2023-01-31 DOI: 10.1055/s-0042-1751453
N. Jahan, Inul Ansary
This review reports the synthesis of various bioactive macrocycles, involving ring-closing metathesis as a key step, developed since ca. 2000. These macrocycles exhibited biological activities such as antiviral, antifungal, antibacterial, and anticancer activities, and more. Thus, their syntheses and utilization are essential for both synthetic organic and medicinal chemists.
这篇综述报道了自2000年以来发展起来的各种生物活性大环的合成,包括闭环复分解作为关键步骤。这些大环具有抗病毒、抗真菌、抗菌和抗癌等生物活性。因此,它们的合成和利用对于合成有机化学家和药物化学家来说都是必不可少的。
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引用次数: 0
Recent Advancements in Triazole-based Click Chemistry in Cancer Drug Discovery and Development 基于三唑的点击化学在癌症药物发现和开发中的最新进展
IF 2.5 Q2 CHEMISTRY, ORGANIC Pub Date : 2023-01-28 DOI: 10.1055/s-0042-1751452
Arun Kumar, A. Yadav, V. Mishra, Deepak Kumar
Triazole-based compounds possess a broad range of activity and can be synthesized using click chemistry. Many new chemotherapeutic agents have been developed in recent years by exploiting click chemistry and these are covered in this review.
三唑类化合物具有广泛的活性,可通过化学反应合成。本文就近年来利用点击化学开发出的许多新型化疗药物进行综述。
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引用次数: 6
Highly Efficient Synthesis of 3,3-Disubstituted Oxindoles through Direct Oxidative Alkylarylation of N -Arylacrylamides with Simple Alkanes N -芳烯酰胺与简单烷烃直接氧化烷基化高效合成3,3-二取代氧吲哚
IF 2.5 Q2 CHEMISTRY, ORGANIC Pub Date : 2023-01-26 DOI: 10.1055/s-0042-1751451
Y. Chen, Weihong Song, Zhi Zhou, Ziye Zhang, Kai Liu, Xiaofei Zeng, Xiaoyu Han
A direct oxidative alkylarylation reaction of N-arylacrylamides with simple alkanes for the synthesis of 3,3-disubstituted oxindoles under metal-free conditions was demonstrated. By using PhI(OAc)2 [(diacetoxy)iodobenzene] as an oxidant, a series of 3,3-disubstituted oxindoles bearing different aryl or alkyl substituents were generated in moderate to excellent chemical yields via a radical-initiated alkylation/cyclization process. The reported method features good functional group tolerance and wide substrate range, and provides an effective method for the preparation of various alkyl substituted 3,3-disubstituted oxindoles.
研究了n -芳基丙烯酰胺与简单烷烃在无金属条件下直接氧化烷基化合成3,3-二取代氧吲哚的反应。以PhI(OAc)2[(二乙酰氧基)碘苯]为氧化剂,通过自由基引发的烷基化/环化反应,生成了一系列含有不同芳基或烷基取代基的3,3-二取代氧吲哚,收率中等至优异。该方法具有官能团耐受性好、底物范围广的特点,为制备各种烷基取代3,3-二取代氧吲哚提供了一种有效的方法。
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引用次数: 0
Emergent Strategies for Catalytic Enantioselective Direct Thiocyanation and Selenocyanation Reactions 催化对映选择性直接硫氰化和硒氰化反应的紧急策略
IF 2.5 Q2 CHEMISTRY, ORGANIC Pub Date : 2023-01-24 DOI: 10.1055/a-2041-0188
Floris Buttard, T. Besset
The publisher announces that this article has been temporarily removed. An edited version will be published under the same DOI as soon as possible. We thank you for your understanding. If you have any questions, please contact am-query@thieme.com.
出版商宣布这篇文章已被暂时删除。编辑后的版本将尽快在相同的DOI下发布。我们感谢您的理解。如果您有任何问题,请联系am-query@thieme.com。
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引用次数: 1
A Chitosan Hydrochloride Mediated, Simple and Efficient Approach for the Synthesis of Hydrazones, their in vitro Antimycobacterial Evaluations, and Molecular Modeling Studies (Part III) 壳聚糖盐酸盐介导的简单有效的腙合成方法、体外抗菌评价和分子模型研究(第三部分)
IF 2.5 Q2 CHEMISTRY, ORGANIC Pub Date : 2023-01-16 DOI: 10.1055/a-2035-6493
Suraj N. Mali, Anima Pandey, B. Thorat
A simple, eco-friendly and straightforward synthesis of hydrazones have been devised in the presence of Chitosan Hydrochloride as catalyst in aqueous-ethanol medium at room temperature. The current protocol offers metal-free synthesis, adaptability to large-scaleup, good yields, and quicker reaction time. All synthesized hydrazones (3a-3j) were also depicted good antimycobacterial activity with MICs (minimum inhibitory concentrations) ranging from 3.12-6.25 µg/mL. Compound 3b represented strong binding affinity against M. tuberculosis pantothenate synthetase (pdb id: 3IVX) with a Glide docking score of -8.803 kcal/mol. Molecular dynamics simulation analysis of the complex 3b:3IVX retained good stability over the simulation period of 20 ns.
在室温下,以壳聚糖盐酸盐为催化剂,在乙醇水介质中合成了一种简单、环保、直接的腙。目前的方案提供了无金属合成、大规模放大的适应性、良好的产率和更快的反应时间。所有合成的腙(3a-3j)也显示出良好的抗分枝杆菌活性,MIC(最小抑制浓度)范围为3.12-6.25µg/mL。化合物3b表现出对结核分枝杆菌泛酸合成酶(pdb-id:3IVX)的强结合亲和力,Glide对接得分为-8.803 kcal/mol。配合物3b:3IVX的分子动力学模拟分析在20ns的模拟周期内保持了良好的稳定性。
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引用次数: 0
Red-Shifting Blue Light Photoredox Catalysis for Organic Synthesis: A Graphical Review 有机合成中红移蓝光光氧化还原催化:图解综述
IF 2.5 Q2 CHEMISTRY, ORGANIC Pub Date : 2023-01-11 DOI: 10.1055/s-0040-1720060
Logan R. Beck, Katherine Xie, Samantha L. Goldschmid, Stavros K. Kariofillis, C. Joe, Trevor C. Sherwood, Melda Sezen-Edmonds, T. Rovis
Photoredox catalysis has revolutionized synthetic chemistry in recent decades. However, the field has traditionally used high-energy blue/ultraviolet light to activate chromophores. High-energy irradiation is associated with several drawbacks (e.g., activation of sensitive functional groups, undesired metal-ligand homolysis, background activation of molecules, and poor penetration), which has led researchers to develop alternative systems with lower energy deep red (DR) or near-infrared (NIR) light. This graphical review provides a concise overview of photophysical principles relevant to photoredox catalysis. Several applications that benefit from low-energy irradiation, such as large-scale batch reactions, photodynamic therapy, biological labeling, and multi-photon excitation are reviewed.
近几十年来,光氧化还原催化已经彻底改变了合成化学。然而,该领域传统上使用高能蓝光/紫外光来激活发色团。高能辐射与几个缺点有关(例如,敏感官能团的活化、不希望的金属配体均聚、分子的背景活化和较差的穿透性),这导致研究人员开发了具有较低能量深红色(DR)或近红外(NIR)光的替代系统。这篇图表综述简要概述了与光氧化还原催化相关的光物理原理。综述了低能辐照的几种应用,如大规模批量反应、光动力治疗、生物标记和多光子激发。
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引用次数: 2
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