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Synthesis, fungicidal activity and SAR of new amino acid derivatives containing substituted 1-(phenylthio)propan-2-amine moiety 含有取代1-(苯基硫代)丙烷-2胺的新型氨基酸衍生物的合成、杀菌活性和合成孔径(SAR)
Pub Date : 2021-12-20 DOI: 10.1080/10426507.2021.2012471
L. Tian, Yang Gao, Xing-Jie Peng, Cheng Zhang, Wei-Guang Zhao, Xing-Hai Liu
Abstract Fifteen novel amino acid derivatives were designed and synthesized using natural amino acid L-valine and two non-natural amino acids as raw materials. Fungicidal activities of these amino acid derivatives were tested against Phytophthora capsici. Most of these compounds possessed excellent activity against Phytophthora capsici at 50 μg/mL. Interestingly, compound isopropyl ((2S)-1-((1-((4-fluorophenyl)thio)propan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)carbamate 5c (EC50=0.43 μg/mL), isopropyl ((2S)-1-((1-((3,4-dimethoxyphenyl)thio)propan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)carbamate 5g (EC50=0.49 μg/mL), isopropyl ((2S)-1-((1-((4-(ethynyloxy)phenyl)thio)propan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)carbamate 5h (EC50=0.15 μg/mL) and isopropyl ((2S,3S)-1-((1-((4-(ethynyloxy)phenyl)thio)propan-2-yl)amino)-3-methyl-1-oxopentan-2-yl)carbamate 5o (EC50=0.31 μg/mL) exhibited remarkably high activities against Phytophthora capsici, which is better than that of positive control. It is possible that these amino acid derivatives, which possess excellent activity against Phytophthora capsici, may become novel lead compounds for the development of fungicides with further structure modification. Graphical Abstract
摘要以天然氨基酸l -缬氨酸和2种非天然氨基酸为原料,设计合成了15种新型氨基酸衍生物。研究了这些氨基酸衍生物对辣椒疫霉的抑菌活性。这些化合物在50 μg/mL浓度下对辣椒疫霉具有良好的抑制活性。有趣的是,化合物异丙基((2S)-1-((1-(4-氟苯基)硫基)丙基-2-基)氨基)-3-甲基-1-氧丁-2-基)氨基甲酸酯5c (EC50=0.43 μg/mL),异丙基((2S)-1-((3,4-二甲氧基苯基)硫基)丙基-2-基)氨基)-3-甲基-1-氧丁-2-基)氨基甲酸酯5g (EC50=0.49 μg/mL),异丙基((2S)-1-((4-(乙基氧基)苯基)硫基)丙基-2-基)氨基)-3-甲基-1-氧丁-2-基)氨基甲酸酯5h (EC50=0.15 μg/mL)和异丙基((2S,3S)-1-((4-(乙基氧基)苯基)硫基)丙基-2-基)氨基)-3-甲基-1-氧丁-2-基)氨基酯50 (EC50=0.31 μg/mL)对辣椒疫霉表现出极显著的抗疫活性,优于阳性对照。这些氨基酸衍生物具有良好的抗辣椒疫霉活性,有可能成为进一步结构修饰的杀菌剂开发的先导化合物。图形抽象
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引用次数: 1
Syntheses, characterization, and single crystal X-ray analysis of 2-pyridyl aryl selenium (IV) bromides and chlorides 2-吡啶基芳基硒(IV)溴化物和氯化物的合成、表征和单晶x射线分析
Pub Date : 2021-11-02 DOI: 10.1080/10426507.2021.1987898
G. Gujral, Aman K. K. Bhasin, K. Bhasin, Shivani Gulati
Abstract In the present work, a variety of symmetrical and unsymmetrical 2-pyridyl aryl selenium (IV) chlorides or bromides were prepared by the dropwise addition of a dilute solution of bromine or sulfuryl chloride to the corresponding 2-pyridyl aryl selenide in dried organic solvent with continuous stirring at 0 °C. Removal of the solvent under reduced pressure resulted in the synthesis of, 2-pyridyl aryl selenium (IV) bromides or chlorides, respectively, in quantitative yields. The titled dihalides prepared were characterized by elemental analysis, spectroscopic studies, and single crystal X-ray analysis. Single crystal X-ray analysis revealed that the 2-pyridyl aryl selenium (IV) bromides/chlorides have a distorted trigonal bipyramidal structure. The pyridyl and phenyl rings along with a lone pair of electrons on selenium are at equatorial positions whereas chloride/bromide atoms at axial positions of the distorted trigonal bipyramidal structure. Graphical Abstract
在0℃的干燥有机溶剂中,将稀释的溴或硫酰氯溶液滴入相应的2-吡啶基芳基硒化物中,连续搅拌,制备了多种对称和不对称的2-吡啶基芳基硒(IV)氯化物或溴化物。在减压下除去溶剂,分别合成了2-吡啶基芳基硒(IV)溴化物和氯化物。用元素分析、光谱研究和单晶x射线分析对所制备的标题二卤化物进行了表征。单晶x射线分析表明,2-吡啶芳基溴化硒/氯化物具有扭曲的三角双锥体结构。在扭曲的三角双锥体结构中,吡啶环和苯基环以及硒上的孤对电子位于赤道位置,而氯/溴原子位于轴向位置。图形抽象
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引用次数: 0
Transition metal-free domino aryl-aryl coupling/phospha-Michael addition of diarylphosphinite to α,β-unsaturated ketones triggered by alkaline hydrolysis of (4-(2-alkenoyl)phenyl)triarylphosphonium salts (4-(2-烯基)苯基)三芳基磷酸盐碱性水解引发的无过渡金属多米诺芳基-芳基偶联/二芳基亚磷酸酯- michael加成至α,β-不饱和酮
Pub Date : 2021-10-29 DOI: 10.1080/10426507.2021.1995385
Wenhua Huang, Jingfeng Xue
Abstract Alkaline hydrolysis of a variety of (4-(2-alkenoyl)phenyl)triarylphosphonium bromides is reported. This hydrolysis triggers coupling of 4-(2-alkenoyl)phenyl with one aryl via phosphorus(V). Both diarylphosphinite and an α,β-unsaturated ketone are in situ generated and then undergo phospha-Michael addition to provide β-diarylphosphoryl ketones bearing a biaryl moiety in 27–70% yields in the absence of a transition metal. Graphical Abstract
摘要报道了多种(4-(2-烯基)苯基)三芳基溴化磷的碱性水解反应。这种水解通过磷(V)触发4-(2-烯基)苯基与一个芳基的偶联。在没有过渡金属的情况下,原位生成二芳基亚膦酸盐和α,β-不饱和酮,然后进行磷- michael加成,以27-70%的收率得到含有双芳基部分的β-二芳基磷基酮。图形抽象
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引用次数: 0
Cs2CO3-promoted P-N coupling reaction of H-phosphoryl compounds with N-tosylhydrazones to afford N-phosphorylhydrazones via diazo intermediates cs2co3促进h -磷基化合物与n -甲酰基腙的P-N偶联反应,通过重氮中间体生成n -磷酸基腙
Pub Date : 2021-10-27 DOI: 10.1080/10426507.2021.1990923
Can Zhang, Xiaojie Li, Ruwei Shen
Abstract The Cs2CO3-promoted P-N coupling reaction of H-phosphoryl compounds and N-tosylhydrazones is reported. Formally, this transformation represents an interesting example of exchanging the sulfur and phosphorus functionalities to convert N-tosylhydrazones to N-phosphorylhydrazones. The reaction may take place via the nucleophilic interception of the in-situ generated diazo intermediates by H-phosphoryl compounds at the terminal nitrogen atom. GRAPHICAL ABSTRACT
摘要报道了cs2co3促进h -磷酰基化合物与n -甲酰基腙的P-N偶联反应。正式地说,这个转化代表了一个有趣的例子,交换硫和磷的官能团,将n -甲酰基腙转化为n -磷酰腙。该反应可能通过原位生成的重氮中间体被末端氮原子上的h -磷基化合物亲核截获而发生。图形抽象
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引用次数: 0
Ultrasound-assisted a domino three-component reaction to polycyclic selenopyrans synthesis 超声辅助合成多环硒吡喃的多米诺三组分反应
Pub Date : 2021-10-20 DOI: 10.1080/10426507.2021.1991344
Hadi Sedighian, Kaveh Imani, A. Bazgir
Abstract A novel and efficient three-component reaction of substituted benzoyl chlorides, potassium selenocyanate and vinyl malononitriles was developed for the synthesis of polycyclic selenopyrans via an ultrasound-assisted domino vinylogous nucleophilic reaction/intramolecular selenocyclization/imine-enamine tautomerization reaction. Introducing a simple one-step method and use of available starting materials and mild reaction conditions are the most important advantages of this strategy. Graphical Abstract
摘要以取代苯甲酰氯、硒氰酸钾和乙烯基丙二腈为原料,通过超声辅助的多米诺骨牌亲核反应/分子内硒环化反应/亚胺-烯胺互变异构反应合成了多环硒吡喃。引入简单的一步法,使用可用的起始材料和温和的反应条件是该策略最重要的优点。图形抽象
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引用次数: 0
α-Bromination of xanthenediones: A mild and efficient approach using N-bromosuccinimide 用n -溴代琥珀酰亚胺温和有效地催化黄酮二酮的α-溴化反应
Pub Date : 2021-10-11 DOI: 10.1080/10426507.2021.1987432
R. Shashi, N. Begum
Abstract The present work deals with a practically efficient protocol designed for the synthesis of 2,7-dibromoxanthenediones using N-bromosuccinimide (NBS) in the presence of p-toluene sulfonic acid (PTSA). A combination of NBS and PTSA in chloroform is an efficient system for selective α-bromination of xanthenediones under mild reaction conditions. The main advantage of this method is short reaction duration, mild reaction conditions, easy work up and in addition the method provides excellent yields. All the compounds synthesized were characterized by spectroscopic techniques. GRAPHICAL ABSTRACT
摘要:本文研究了在对甲苯磺酸(PTSA)存在下,以n -溴琥珀酰亚胺(NBS)为原料合成2,7-二溴杂蒽二酮的高效工艺。在温和的反应条件下,NBS和PTSA在氯仿中的组合是一种高效的选择性α-溴化体系。该方法的主要优点是反应时间短,反应条件温和,易于操作,收率高。所有合成的化合物都用光谱技术进行了表征。图形抽象
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引用次数: 0
Phosphorus-nitrogen compounds. Part 56. Comparative syntheses and spectral properties of multiheterocyclic 2-cis-4-ansa and spiro-ferrocenyl (N/O)cyclotetraphosphazenes: Antituberculosis and antimicrobial activity and DNA interaction studies Phosphorus-nitrogen化合物。一部分56。多杂环2-顺-4-ansa和螺-二茂铁(N/O)环四磷腈的比较合成和光谱性质:抗结核和抗菌活性及DNA相互作用研究
Pub Date : 2021-10-06 DOI: 10.1080/10426507.2021.1986502
Arzu Binici, Aytuğ Okumuş, M. Yakut, Gamze Elmas, Z. Kılıç, Dila Koyunoğlu, L. Açık, H. Simsek
Abstract In the present study, two types of starting compounds; hexachloro(N/O)-cyclotetraphosphazenes containing mono-ferrocenyl-pendant arm, namely, mono-ferrocenyl-2-cis-4-dichloro-ansa-(2,4-ansa; 2) and mono-ferrocenyl-spiro-(spiro; 3) were prepared by the reaction of N4P4Cl8 (1) with sodium 3-(N-ferrocenylmethylamino)-1-propanoxide (L). Reactions of 2,4-ansa (2) with excess benzylamine and n-hexylamine resulted in the formation of partly substituted 2-cis-4-dichloro-ansa-cyclotetraphosphazenes (2a and 2b). In contrast, spiro (3) gave fully substituted mono-ferrocenyl-spiro-cyclotetraphosphazenes (3a and 3b) with excess benzylamine and n-hexylamine. As expected, the 2,4-ansa cyclotetraphosphazenes (2, 2a, and 2b) have two distinct stereogenic P-centers. The structures of cyclotetraphosphazenes were evaluated by elemental analysis, ESI-MS, FTIR, 1H, 13C, and 31P-NMR techniques. The antibacterial and antifungal activities against some selected bacteria and yeast strains, antituberculosis activities against Mycobacterium tuberculosis H37Rv, and DNA cleavage activities of mono-ferrocenyl-cyclotetraphosphazenes were also discussed. Compounds 2b, 3a, and 3b exhibited antifungal activity against C. albicans (MIC= 156.3 µM) higher than reference antibiotic Ketoconazole. Moreover, four compounds displayed antituberculosis activity against the M. tuberculosis H37RV. Compound 2a (20 μg/mL) is the most potent of the four compounds. Graphical abstract
在本研究中,两类起始化合物;六氯(N/O)-含单二茂铁悬垂臂的环四磷腈,即:单二茂铁-2-顺式-4-二氯-(2,4-);2)和单二茂铁-螺-(螺;3)由N4P4Cl8(1)与3-(n-二茂铁甲胺)-1-丙氧钠(L)反应制得。2,4-ansa(2)与过量的苄胺和正己胺反应生成部分取代的2-顺-4-二氯ansa-环四磷腈(2a和2b)。相反,螺(3)产生了过量的苄胺和正己胺完全取代的单二茂铁-螺环四磷腈(3a和3b)。正如预期的那样,2,4-环四磷腈(2,2a和2b)具有两个不同的立体p中心。采用元素分析、ESI-MS、FTIR、1H、13C和31P-NMR等技术对环四磷腈的结构进行了表征。本文还讨论了单二茂铁环四磷腈对某些选定细菌和酵母菌的抑菌和抗真菌活性、对结核分枝杆菌H37Rv的抗结核活性以及对DNA的裂解活性。化合物2b、3a和3b对白色念珠菌的抑制活性(MIC= 156.3µM)高于对照抗生素酮康唑。此外,4种化合物对结核分枝杆菌H37RV具有抗结核活性。化合物2a (20 μg/mL)是四种化合物中最强的。图形抽象
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引用次数: 3
A review on C-P bonding reactions assisted by manganese(III) acetate 醋酸锰辅助C-P键合反应研究进展
Pub Date : 2021-07-23 DOI: 10.1080/10426507.2021.1945062
Emre Biçer
Abstract This review aims to review the published articles involved with manganese(III) acetate based free radical additions to organic compounds to obtain organophosphorus compounds. As well known, manganese(III) acetate is a long-term initiator used by chemists to form a variety of compounds. Manganese(III) initiated phosphorus-centered radicals which undergo homolytic cleavage of the P-H bond. In follow-up reactions, an addition to unsaturated compounds leads to a wide range of valuable organophosphorus compounds. Based upon the phosphorus reagent, two types of P-centered radicals are formed: Phosphinoyl-radicals result from phosphites and phosphonyl-radicals result from phosphate reagents. According to research results on P-centered radicals, phosphonyl-radicals are more reactive than phosphinoyl radicals. By use of these radicals, many phosphorylated products have been obtained with relatively high yields. The phosphates obtained by radical addition can be used as intermediates to valuable products in organic chemistry, medicinal chemistry, crop science and material chemistry. Graphical Abstract
摘要本文综述了近年来以醋酸锰(III)自由基为基础,在有机化合物中添加有机磷化合物的研究进展。众所周知,醋酸锰(III)是化学家用来形成各种化合物的长期引发剂。锰(III)引发以磷为中心的自由基进行P-H键的均裂裂解。在后续的反应中,对不饱和化合物的添加会产生一系列有价值的有机磷化合物。在磷试剂的基础上,形成了两种以p为中心的自由基:由亚磷酸盐产生的磷酰基自由基和由磷酸盐产生的磷酰基自由基。根据对p中心自由基的研究结果,磷酰自由基比磷酰自由基更具活性。通过使用这些自由基,许多磷酸化产物得到了相对较高的收率。自由基加成得到的磷酸盐可作为有机化学、药物化学、作物科学和材料化学等有价值产品的中间体。图形抽象
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引用次数: 2
Platinum-Pyridine Schiff base complexes immobilized onto silica gel as efficient and low cost catalyst for hydrosilylation 铂吡啶席夫碱配合物在硅胶上固定化作为高效、低成本的硅氢化催化剂
Pub Date : 2021-07-14 DOI: 10.1080/10426507.2021.1871733
Yingpeng Huo, Jiwen Hu, Feng Liu, Jiapei Wu, Yikun Zhang, Ya-lin Zhang, Qianyi Wang
Abstract A heterogeneous platinum catalyst with tridentate pyridine Schiff base ligands supported on silica gel is reported. The catalyst was fully characterized via FTIR, solid-state 13C NMR spectroscopy, X-ray photoelectron spectroscopy (XPS), N2 adsorption/desorption analysis, X-ray diffraction (XRD), scanning electron microscopy (SEM), and transmission electron microscopy (TEM). The catalyst showed potential application in mediating hydrosilylation reactions between olefins and hydrosilanes, and it can be reused for at least five cycles. Graphical Abstract
摘要报道了一种硅胶负载吡啶席夫碱配体的非均相铂催化剂。通过FTIR、固态13C NMR、x射线光电子能谱(XPS)、N2吸附/解吸分析、x射线衍射(XRD)、扫描电子显微镜(SEM)和透射电子显微镜(TEM)对催化剂进行了全面表征。该催化剂在烯烃和氢硅烷之间的硅氢化反应中具有潜在的应用前景,且可重复使用至少5次。图形抽象
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引用次数: 0
Straightforward and simple synthesis of novel pyranodipyrimidine derivatives via reaction of aromatic aldehydes and heterocyclic-1,3-dicarbonyl compound 芳香族醛与杂环-1,3-二羰基化合物反应合成新型吡喃二嘧啶衍生物
Pub Date : 2021-06-07 DOI: 10.1080/10426507.2021.1921775
A. Esmaeili, F. Mesbah, Abbas Moradi, A. Khojastehnezhad, M. Khalili
Abstract An efficient and simple procedure has been described for the synthesis of a novel series of polycyclic compounds containing pyranodipyrimidine core via cyclocondensation reaction of 2,3-dihydro-thiazolo[3,2-a]pyrimidine-5,7-dione and aromatic aldehyde derivatives in the presence of diisopropylethylamine as an organo-base catalyst. This procedure gave the desired products in high yields. Graphical Abstract
摘要以二异丙基乙胺为有机碱催化剂,通过2,3-二氢噻唑[3,2-a]嘧啶-5,7-二酮与芳香醛衍生物的环缩合反应,合成了一系列新的含吡喃二嘧啶核心的多环化合物。该工艺得到了所需产品的高收率。图形抽象
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引用次数: 5
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Phosphorus Sulfur and Silicon and The Related Elements
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