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4-(2-(5-(2-(tert-Butoxycarbonyl)hydrazinecarbonyl)-2-methylthiophen-3-yl)cyclopent-1-enyl)-5-methylthiophene-2-carboxylic Acid 4-(2-(5-(2-(叔丁氧羰基)肼羰基)-2-甲基噻吩-3-基)环戊-1-烯基)-5-甲基噻吩-2-羧酸
IF 0.6 Q4 CHEMISTRY, ORGANIC Pub Date : 2024-01-11 DOI: 10.3390/m1760
Marija Matković
Diarylethene (DAE) molecular photoswitches draw attention as building units in the preparation of diverse photoactive molecules. An interesting class of these molecules are photoactive peptides. A way to build DAE moiety into peptides/peptidomimetics is via DAE amino acids, an example of which has been demonstrated in bioactive cyclic peptides, wherein the DAE Fmoc-amino acid was prepared and used. Herein, the preparation of DAE Boc-amino acid is presented using a modified method of synthesis. This contribution to the DAE amino acid collection could be useful in the further enhancement of diversity in designing different routes to photoactive peptides.
作为制备各种光活性分子的构建单元,二元蒽(DAE)分子光开关备受关注。其中一类有趣的分子是光活性肽。在肽/拟肽中加入 DAE 分子的一种方法是通过 DAE 氨基酸,生物活性环肽就是一个例子,其中制备并使用了 DAE Fmoc 氨基酸。在此,我们将介绍使用改进的合成方法制备 DAE Boc 氨基酸。这是对 DAE 氨基酸系列的贡献,有助于进一步提高光活性肽设计不同路线的多样性。
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引用次数: 0
(1R/S,7aS/R)-1-Benzyl-1-[2,8-bis(trifluoromethyl)quinolin-4-yl]-hexahydro-oxazolo[3,4-a]pyridin-3-one (1R/S,7aS/R)-1-苄基-1-[2,8-双(三氟甲基)喹啉-4-基]-六氢恶唑并[3,4-a]吡啶-3-酮
IF 0.6 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-12-30 DOI: 10.3390/m1756
Dawid J Kucharski, Przemysław J. Boratyński
An unexpected diastereoselective C-alkylation of a mefloquine derivative in up to 57% yield was the result of an attempted Williamson etherification of Boc-mefloquine. The domino reaction involved oxazolidinone ring closure, deprotonation, and stereoselective carbon–carbon bond formation. The structure was confirmed with 2D NMR experiments.
威廉姆森尝试对 Boc-甲氟喹进行醚化反应,意外地对甲氟喹衍生物进行了非对映选择性 C-烷基化反应,收率高达 57%。多米诺反应涉及噁唑烷酮的闭环、去质子化和立体选择性碳-碳键形成。二维核磁共振实验证实了这一结构。
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引用次数: 0
Unexpected Formation of the Iodobismuthate Salt (C14H15S2N2)2(C9H10SN)2[Bi4I16] upon Reaction of the Unsaturated Ligand Z-PySCH2CH=CHCH2Spy with BiI3 不饱和配体 Z-PySCH2CH=CHCH2Spy 与 BiI3 反应意外生成碘铋盐 (C14H15S2N2)2(C9H10SN)2[Bi4I16]
IF 0.6 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-12-29 DOI: 10.3390/m1755
Marwa Essid, Chakib Hrizi, Salah Ammar, A. Khatyr, M. Knorr, Annika Schmidt, Carsten Strohmann
The olefinic dithioether (Z)-1,4-bis(pyridin-2-ylthio)but-2-ene Z-PyS(CH2CH=CHCH2)SPy (L) was prepared by the treatment of cis-ClCH2CH=CHCH2Cl with in situ generated potassium pyridine-2-thiolate Py-SK and analyzed by IR and NMR spectroscopy. To investigate the chemistry of polynuclear iodobismuthate complexes, two equivalents of BiI3 were reacted with L in the MeOH solution to afford the anionic tetranuclear title compound (C14H15S2N2)2(C9H10SN)2[Bi4I116] with a N-protonated (Z)-1,4-bis(pyridin-2-ylthio)but-2-ene as a counterion. Compound 1 was characterized by IR and UV spectroscopy; the formation of a tetranuclear framework was ascertained by a single-crystal X-ray diffraction study performed at 100 K. Furthermore, an unusual Bi(III)-meditated cyclization of one Z-PyS(CH2CH=CHCH2)SPy ligand occurred, affording the bicyclic pyridinium salt 3-vinyl-2,3-dihydrothiazolo[3,2-a]pyridinium bearing a terminal vinyl group, compensating the second negative charge of the Bi4I164− cluster anion. The SCXRD characterization was completed by a Hirshfeld surface analysis, revealing some secondary interactions occurring in the crystal.
通过原位生成的吡啶-2-硫酸钾 Py-SK 处理顺式-ClCH2CH=CHCH2Cl,制备了烯烃二硫醚 (Z)-1,4-双(吡啶-2-硫基)丁-2-烯 Z-PyS(CH2CH=CHCH2)Spy(L),并通过红外光谱和核磁共振光谱进行了分析。为了研究多核碘铋酸盐络合物的化学性质,在 MeOH 溶液中将两当量的 BiI3 与 L 反应,得到阴离子四核标题化合物 (C14H15S2N2)2(C9H10SN)2[Bi4I116],并以 N-质子化 (Z)-1,4- 双(吡啶-2-基硫基)丁-2-烯作为反离子。通过红外光谱和紫外光谱对化合物 1 进行了表征;在 100 K 温度下进行的单晶 X 射线衍射研究确定了四核框架的形成。此外,一个 Z-PyS(CH2CH=CHCH2)Spy配体在 Bi(III)-meditated cyclization 的作用下发生了不寻常的环化反应,产生了带有一个末端乙烯基的双环吡啶鎓盐 3-乙烯基-2,3-二氢噻唑并[3,2-a]吡啶,补偿了 Bi4I164- 簇阴离子的第二负电荷。Hirshfeld 表面分析完成了 SCXRD 表征,揭示了晶体中发生的一些次级相互作用。
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引用次数: 0
New Antimicrobial Accramycins from Streptomyces sp. MA37 Variant 来自链霉菌 MA37 变异株的新型抗菌药 Accramycins
IF 0.6 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-12-28 DOI: 10.3390/m1754
Aziz Alabed, K. Kyeremeh, Hai Deng
In our continued desire to isolate more bioactive compounds from the Streptomyces sp. MA37 variant, ΔaccJ, three new accramycin derivatives have been successfully characterised. The structures of accramycin L-N (1–3) were established by high-resolution mass spectrometry and 1D and 2D nuclear magnetic resonance. The antimicrobial evaluation of accramycin L-N against Staphylococcus aureus, Klebsiella pneumoniae, and Enterobacter cloacae showed minimum inhibitory concentration (MIC) values ranging from 0.77 to 13.02 µg/mL. Accramycin L exhibited the most significant activity against S. aureus. In addition, accramycin L-N (1–3) displayed significant activity against K. pneumoniae at the MIC values of 0.81, 0.77, and 0.79 µg/mL, respectively.
我们一直希望从链霉菌 MA37 变异株 ΔaccJ 中分离出更多具有生物活性的化合物,现已成功鉴定出三种新的安克拉霉素衍生物。通过高分辨率质谱分析以及一维和二维核磁共振,确定了阿克拉霉素 L-N (1-3)的结构。对阿克拉霉素 L-N 针对金黄色葡萄球菌、肺炎克雷伯菌和泄殖腔肠杆菌的抗菌评估显示,其最低抑菌浓度 (MIC) 值介于 0.77 至 13.02 µg/mL 之间。阿克拉霉素 L 对金黄色葡萄球菌的活性最强。此外,阿克拉霉素 L-N (1-3) 对肺炎双球菌也有显著的活性,其 MIC 值分别为 0.81、0.77 和 0.79 µg/mL。
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引用次数: 0
N,N′-Dipropyloxamide 产品名称
IF 0.6 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-12-22 DOI: 10.3390/m1753
E. Podda, Eleanor Dodd, M. Arca, M. Aragoni, Vito Lippolis, S. Coles, Anna Pintus
N,N′-Dipropyloxamide (1) was synthesised by the reaction between diethyloxalate and n-propylamine in ethanol. Compound 1 was fully characterised by both microanalytical (elemental analysis, melting point determination) and spectroscopic means (FT-IR and NMR spectroscopy). Crystals suitable for single crystal X-ray diffraction were isolated by the slow evaporation of a methyl alcohol solution of the compound. The resulting crystal structure shows the prominent role exerted by intermolecular hydrogen bonds in the crystal packing.
N,N′-Dipropyloxamide (1) 是通过二乙氧基丙酸盐和正丙胺在乙醇中的反应合成的。通过微量分析(元素分析、熔点测定)和光谱分析(傅立叶变换红外光谱和核磁共振光谱)对化合物 1 进行了全面鉴定。通过缓慢蒸发化合物的甲醇溶液,分离出了适合进行单晶 X 射线衍射的晶体。由此得到的晶体结构表明,分子间氢键在晶体堆积中发挥了重要作用。
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引用次数: 0
Bis(2,6-di(pyridin-2-yl)pyridin-4-yl)-6,6′-(1,2-diselanediyl)dihexanoate 双(2,6-二(吡啶-2-基)吡啶-4-基)-6,6′-(1,2-二壬二基)二己酸酯。
IF 0.6 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-12-20 DOI: 10.3390/m1752
E. Popa, A. Andelescu, Valentin Badea, Paula Svera M Ianăşi, Elisabeta I. Szerb
The present paper describes the preparation and characterization of a new dinuclear ligand based on terpyridine featuring a diselenide unit. This new compound was synthesized in a two-step procedure that first involved the insertion of the diselenide moiety on a carboxylic acid and was followed by a Steglich esterification reaction between the biscarboxylic acid containing the diselenide unit and 2,6-di(pyridin-2-yl)pyridin-4-ol (tpyOH). The title compound was characterized via FT-IR, Raman, NMR (1D and 2D), and UV-Vis spectroscopies and elemental analysis. Emission properties were investigated.
本文介绍了一种新的双核配体的制备和表征,该配体以具有二硒化单元的三联吡啶为基础。这种新化合物的合成分两步进行,首先将二硒化物插入羧酸中,然后在含有二硒化物单元的双羧酸和 2,6-二(吡啶-2-基)吡啶-4-醇 (tpyOH) 之间进行斯特克里奇酯化反应。通过傅立叶变换红外光谱、拉曼光谱、核磁共振(一维和二维)光谱、紫外-可见光谱和元素分析对标题化合物进行了表征。还对发射特性进行了研究。
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引用次数: 0
(Z)-1-Benzyl-5-(4-bromophenyl)-5-hydroxy-4-(2-oxomorpholin-3-ylidene)pyrrolidine-2,3-dione (Z)-1-苄基-5-(4-溴苯基)-5-羟基-4-(2-氧代吗啉-3-亚基)吡咯烷-2,3-二酮
IF 0.6 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-12-18 DOI: 10.3390/m1751
N. A. Tretyakov, A. N. Maslivets
The reaction of 8-(4-bromobenzoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-1,6,7-trione with benzylamine in acetonitrile at room temperature afforded a good yield of (Z)-1-benzyl-5-(4-bromophenyl)-5-hydroxy-4-(2-oxomorpholin-3-ylidene)pyrrolidine-2,3-dione. The compound was fully characterized.
室温下,8-(4-溴苯甲酰基)-3,4-二氢-1H-吡咯并[2,1-c][1,4]恶嗪-1,6,7-三酮与苄胺在乙腈中反应,得到了收率很高的(Z)-1-苄基-5-(4-溴苯基)-5-羟基-4-(2-氧代吗啉-3-亚基)吡咯烷-2,3-二酮。该化合物已完全定性。
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引用次数: 0
4-(5-Benzyl-3-((4-fluorophenyl)sulfonyl)-5-methyl-4,5-dihydrofuran-2-yl)-2-nitrobenzamide 4-(5-苄基-3-((4-氟苯基)磺酰基)-5-甲基-4,5-二氢呋喃-2-基)-2-硝基苯甲酰胺
IF 0.6 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-12-15 DOI: 10.3390/m1750
Oscar Leonardo Avendaño Leon, Christophe Curti, Hussein El-Kashef, Youssef Kabri, S. Redon, Patrice Vanelle
As part of our ongoing attempt to broaden the applications of the amidoxime moiety as a potential source of new antileishmanial agents, this study focuses on the product 4-(5-Benzyl-3-((4-fluorophenyl)sulfonyl)-5-methyl-4,5-dihydrofuran-2-yl)-2-nitrobenzamide. This unexpected amide was obtained in an 85% yield as the major product with a conventional amidoxime synthesis protocol (Ethanol/Na2CO3) involving the reaction of hydroxylamine and a nitrile group. The formation of this amide derivative instead of the expected amidoxime can be attributed to two complementary effects: the strong electron effect of the nitro group and the influence of ethanol, a polar protic solvent. Alternatively, the desired amidoxime derivative, 4-(5-benzyl-3-((4-fluorophenyl)sulfonyl)-5-methyl-4,5-dihydrofuran-2-yl)-N′-hydroxy-2-nitrobenzimidamide, was obtained in an 80% yield by an alternative protocol (DMSO/KOtBu). This original compound, featuring a nitro group in the ortho position to the amidoxime, will be further evaluated, both in the field of medicinal chemistry and in other relevant areas, highlighting an unusual method to access amidoximes from hindered substrates.
我们一直在努力拓宽脒肟分子作为新型抗利什曼病药潜在来源的应用范围,本研究的重点是产品 4-(5-苄基-3-((4-氟苯基)磺酰基)-5-甲基-4,5-二氢呋喃-2-基)-2-硝基苯甲酰胺。采用传统的脒肟合成工艺(乙醇/Na2CO3),通过羟胺和腈基的反应,以 85% 的收率获得了这种意想不到的酰胺作为主要产物。这种酰胺衍生物而非预期的脒肟的形成可归因于两种互补效应:硝基的强电子效应和乙醇这种极性原生溶剂的影响。另外,通过另一种方案(DMSO/KOtBu),也可以得到所需的脒肟衍生物 4-(5-苄基-3-((4-氟苯基)磺酰基)-5-甲基-4,5-二氢呋喃-2-基)-N′-羟基-2-硝基苯甲脒,收率为 80%。这种原始化合物的特点是在脒肟的正交位置上有一个硝基,我们将在药物化学领域和其他相关领域对其进行进一步评估,以突出从受阻底物中获得脒肟的不寻常方法。
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引用次数: 0
3-Benzoyl-2-hydroxy-3a-[(3-methylquinoxalin-2-yl)methyl]-1H-pyrrolo[2,1-c][1,4]benzothiazine-1,4(3aH)-dione 3-Benzoyl-2-hydroxy-3a-[(3-methylquinoxalin-2-yl)methyl]-1H-pyrrolo[2,1-c][1,4]benzothiazine-1,4(3aH)-dione
IF 0.6 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-12-13 DOI: 10.3390/m1749
E. A. Lystsova, E. E. Khramtsova
The reaction of 3-benzoylpyrrolo[2,1-c][1,4]benzothiazine-1,2,4-trione with 2,3-dimethylquinoxaline afforded 3-benzoyl-2-hydroxy-3a-[(3-methylquinoxalin-2-yl)methyl]-1H-pyrrolo[2,1-c][1,4]benzothiazine-1,4(3aH)-dione in a moderate yield. The compound was fully characterized.
通过 3-苯甲酰基吡咯并[2,1-c][1,4]苯并噻嗪-1,2,4-三酮与 2,3-二甲基喹喔啉的反应,得到了 3-苯甲酰基-2-羟基-3a-[(3-甲基喹喔啉-2-基)甲基]-1H-吡咯并[2,1-c][1,4]苯并噻嗪-1,4(3aH)-二酮,收率中等。该化合物已完全定性。
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引用次数: 0
Building Triazolated Macrocycles from Bis-Propargylated Calix[4]arenes and Bis-Azidomethylated Azobenzene or Stilbene 从双-丙炔化钙[4]烯和双-叠氮甲基化偶氮苯或二苯乙烯构建三唑大环
IF 0.6 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-12-07 DOI: 10.3390/m1748
Ivan Lentin, Ilia Korniltsev, A. Gorbunov, Dmitry Cheshkov, S. Bezzubov, Vladimir Kovalev, I. Vatsouro
Copper(I)-catalyzed azide-alkyne cycloaddition was employed to construct biscalixarene assemblies from the calix[4]arene dipropargyl ethers and 4,4′-bis-azidomethylated azobenzene or stilbene. Three bis(calixarenes) having the calix[4]arene cores linked to each other by pairs of (E)-azobenzene/stilbene units through four triazole groups were obtained as confirmed by NMR, HRMS and X-ray diffraction data. Nevertheless, the formation of larger macrocycles and polymeric/oligomeric products was found to be the major competing process that seriously limited the applicability of the one-step macrocyclization approach for the construction of photoresponsive biscalixarene assemblies linked by pairs of azobenzene/stilbene units.
以杯[4]芳烃二丙基醚和4,4′-双叠氮甲基化偶氮苯或二苯乙烯为原料,采用铜(I)催化叠氮化物-炔环加成法制备了双杯芳烃组合物。经核磁共振、HRMS和x射线衍射数据证实,得到了3个杯芳烃[4]核心由(E)-偶氮苯/苯乙烯单元通过4个三唑基团相互连接的双(杯芳烃)。然而,更大的大环和聚合物/低聚产物的形成被发现是主要的竞争过程,严重限制了一步大环化方法用于构建由偶氮苯/苯乙烯单元对连接的光响应性双杯芳烃组合的适用性。
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引用次数: 0
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Molbank
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