Synthetic Communications最新文献

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Green synthesis, molecular docking and in vitro biological evaluation of novel hydrazones, pyrazoles, 1,2,4-triazoles and 1,3,4-oxadiazoles 新型肼、吡唑、1,2,4-三唑和 1,3,4-恶二唑的绿色合成、分子对接和体外生物学评价

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2024-10-24 DOI: 10.1080/00397911.2024.2417362

Ultrasonic waves were used for synthesis of novel hydrazones, bishydrazones, pyrazoles, 1,2,4-triazole and 1,3,4-oxadiazole. The structural formulae of the synthesized compounds were elucidated in terms of elemental and spectroscopic analyses. All synthesized compounds were estimated by testing total antioxidant capacity, iron‐reducing power, the scavenging activity against ABTS and DPPH radicals in addition to testing anti‐diabetic, anti‐Alzheimer and anti‐arthritic activities. All compounds displayed good to potent bioactivity. Compounds 6, 10 exhibit the highest antioxidant and free radicals scavenging activities. Furthermore, compounds 6, 10 demonstrate the strongest inhibition of α‐amylase and α-glucosidase. Compound 12 exhibit strongest acetylcholinesterase inhibition among prepared compounds. However, compounds 18a,b, 19 show a significantly higher inhibition percentage for protein denaturation and proteinase. The most bioactive prepared compounds 6, 10 and 12 were investigated toward docking methodology against appropriate protein.

利用超声波合成了新型肼、双肼、吡唑、1,2,4-三唑和 1,3,4-恶二唑。通过元素分析和光谱分析，阐明了合成化合物的结构式。通过测试总抗氧化能力、铁还原力、ABTS 和 DPPH 自由基清除活性以及抗糖尿病、抗老年痴呆和抗关节炎活性，对所有合成化合物进行了评估。所有化合物都显示出良好甚至强效的生物活性。化合物 6 和 10 的抗氧化和清除自由基活性最高。此外，化合物 6 和 10 对 α 淀粉酶和 α 葡萄糖苷酶的抑制作用最强。在制备的化合物中，化合物 12 对乙酰胆碱酯酶的抑制作用最强。然而，化合物 18a、b 和 19 对蛋白质变性和蛋白酶的抑制率明显更高。对生物活性最强的 6、10 和 12 号化合物进行了与相应蛋白质的对接研究。

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引用次数: 0

Synthesis and structural characterization of a novel large type double-layered cyclophanes based on the reaction of bis(N-alkylene benzothiazolium) dibromide and triethylamine 基于双（N-亚烷基苯并噻唑）二溴化物和三乙胺反应的新型大型双层环烷的合成及其结构特征

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2024-10-18 DOI: 10.1080/00397911.2024.2415435

The synthesis of a novel large type double-layered cyclophanes has been successfully accomplished by free radical coupling reaction with the bis(N-alkylene benzothiazolium) dibromide salts as their important synthetic intermediates. The structures of the two-layered cyclophanes and the synthetic intermediates have been elucidated based on the NMR data and X-ray structural analysis, respectively. The two-layered cyclophanes consist of two different geometries, anti-two cyclic lactam amide rings inside and two bridges of disulfide bonds outside, which are unique and novel structures. Their physical properties were investigated by UV–Vis and redox potential, too.

以双（N-亚烷基苯并噻唑）二溴化盐为重要合成中间体，通过自由基偶联反应成功合成了一种新型的大型双层环烷。根据核磁共振数据和 X 射线结构分析，分别阐明了二层环烷和合成中间体的结构。双层环烷由两种不同的几何结构组成，内含两个反双环内酰胺酰胺环，外含两个二硫键桥，结构独特新颖。此外，还通过紫外可见光和氧化还原电位研究了它们的物理性质。

引用次数: 0

Solvent-free and efficient heterogeneous Biginelli reactions catalyzed by copper (II)-incorporated iminophenol-based porous organic polymer 铜(II)掺杂亚氨基苯酚基多孔有机聚合物催化的无溶剂高效异相比吉内利反应

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2024-10-16 DOI: 10.1080/00397911.2024.2416529

The copper (II)-incorporated iminophenol containing porous polymer (Cu-TAzo-TAPB), which was reported to be a recyclable catalyst for click reactions, is now exploited as an efficient catalyst in the solvent-free one-pot process to make 3,4-dihydropyrimidinone derivatives (DHPMs) by a three-component condensation reaction of urea/thiourea, aldehydes, and active methylene compounds. Usually, these reactions are complicated to carry out in a neutral medium. We describe here an eco-friendly method to produce Biginelli products with 5 mol% catalyst loading with a simple isolation technique. The high product yields show the effective Biginelli reaction technique. The catalyst is highly stable and easily recoverable for reuse without significant loss of catalytic efficiency.

铜 (II) 嵌合含亚胺苯酚的多孔聚合物（Cu-TAzo-TAPB）曾被报道为点击反应的可循环催化剂，现在被用作一种高效催化剂，通过脲/硫脲、醛和活性亚甲基化合物的三组分缩合反应，在无溶剂一锅工艺中制造 3,4-二氢嘧啶酮衍生物 (DHPM)。通常，这些反应在中性介质中进行比较复杂。我们在此介绍一种生态友好型方法，利用简单的分离技术，在催化剂负载量为 5 摩尔% 的情况下生产 Biginelli 产品。产品的高产率显示了比吉奈利反应技术的有效性。催化剂高度稳定，易于回收再利用，且不会明显降低催化效率。

引用次数: 0

Cobalt(II) catalyzed Michael-type hydroamination of activated olefins 钴（II）催化活化烯烃的迈克尔型加氢反应

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2024-10-16 DOI: 10.1080/00397911.2024.2414410

The aza-Michael addition reaction of primary and secondary amines to α,β-unsaturated olefins viz; acrylonitrile, phenyl vinyl sulfone and dimethyl maleate has been carried out using 5–10 mol% Co(NO₃)₂.6H₂O as a catalyst in t-BuOMe at 80–100 °C, giving rise to the desired β-aminocarbonyl compounds or sulfones in moderate to good yields. A wide range of aromatic amines, even those bearing electron withdrawing groups could be added to activated olefins via this strategy. Addition of (hetero)aromatic amines were also feasible, while in case of 2-aminopyridine the reaction was found to be effective only when AgOTf was added along with the catalyst. The aliphatic amines; benzylamine, dibenzylamine, di-n-butylamine were also smoothly added to acrylonitrile and phenyl vinyl sulfone. The methodology describes cobalt(II) nitrate as an eco-friendly, cheap and shelf available catalyst suitable for performing the Michael-type hydroamination reactions.

以 5-10 mol% 的 Co(NO3)2.6H2O 为催化剂，在 80-100 °C 的 t-BuOMe 溶液中进行了伯胺和仲胺与α,β-不饱和烯烃（即丙烯腈、苯基乙烯基砜和马来酸二甲酯）的氮杂迈克尔加成反应，得到了所需的β-氨基羰基化合物或砜，收率中等至良好。通过这种方法可以将多种芳香胺，甚至是那些带有取电子基团的芳香胺添加到活化烯烃中。添加（杂）芳香胺也是可行的，但对于 2-氨基吡啶，只有在添加 AgOTf 和催化剂时反应才有效。脂肪族胺；苄胺、二苄胺、二正丁胺也能顺利地加入到丙烯腈和苯乙烯砜中。该方法说明硝酸钴（II）是一种环保、廉价且可在货架上购买到的催化剂，适用于进行迈克尔型氢化反应。

引用次数: 0

Copper(II)-catalyzed dehydration of primary amides to nitriles with the aid of trichloroacetonitrile 铜(II)催化伯胺在三氯乙腈帮助下脱水成腈纶

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2024-10-15 DOI: 10.1080/00397911.2024.2415442

A method for the preparation of nitriles from primary amides using trichloroacetonitrile and a catalytic amount of cupric acetate is described. Using this method, amides including aromatic amides, aromatic heterocyclic amides and aliphatic amides were converted into the corresponding nitriles in moderate to good yields. Trichloroacetonitrile reacted with amide in the presence of cupric acetate to form trichloroacetamide, which has been isolated and confirmed.

介绍了一种使用三氯乙腈和催化量的乙酸铜从伯胺制备腈的方法。利用这种方法，包括芳香族酰胺、芳香族杂环酰胺和脂肪族酰胺在内的酰胺被转化为相应的腈，产率为中等到良好。三氯乙腈与酰胺在醋酸铜存在下反应生成三氯乙酰胺，该反应已被分离和确认。

引用次数: 0

Synthesis and biological evaluation of 1, 2, 3-triazole incorporated pyrrole derivatives as anticancer agents 作为抗癌剂的 1, 2, 3-三唑并吡咯衍生物的合成和生物学评价

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2024-10-15 DOI: 10.1080/00397911.2024.2408605

A new series of 1,2,3-triazole skeleton incorporated pyrrole derivatives (11a–j) were developed and their chemical structures were confirmed by analytical data. Further, the anticancer profile of these newly derived compounds 11a–j was assessed against four types of human cancer cell lines such as human breast cancer (MCF-7), lung cancer (A549), colon cancer (Colo-205) and ovarian cancer (A2780) by employing of the MTT method and was compared with etoposide used as a positive control. Most of the examined derivatives displayed moderate to good activity compared with the positive control. Among them, five compounds 11a, 11b, 11c, 11d, and 11e showed more potent activity. Particularly, compound 11a showed superior activity.

我们开发了一系列新的 1,2,3- 三唑骨架结合吡咯衍生物（11a-j），并通过分析数据确认了它们的化学结构。此外，还采用 MTT 法评估了这些新衍生化合物 11a-j 对四种人类癌细胞系（如人类乳腺癌（MCF-7）、肺癌（A549）、结肠癌（Colo-205）和卵巢癌（A2780））的抗癌作用，并与作为阳性对照的依托泊苷进行了比较。与阳性对照相比，大多数受检衍生物显示出中等至良好的活性。其中，5 个化合物 11a、11b、11c、11d 和 11e 显示出更强的活性。特别是化合物 11a 显示出更强的活性。

引用次数: 0

Sequential Knoevenagel condensation/cyclization reaction using Meldrum’s acid 使用梅尔德鲁姆酸的克诺文纳格尔缩合/环化顺序反应

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2024-10-11 DOI: 10.1080/00397911.2024.2413165

Sequential Knoevenagel condensation/cyclization using cyclic active methylene compounds such as Meldrum’s acid have been studied. The reaction of 2-(1-phenylvinyl)benzaldehyde and Meldrum’s acid, dimedone, or 1,3-indandione with piperidine/AcOH or L-proline at room temperature for 17–18 h gave cyclized indene derivatives in 63–80% yield. The reaction of 2-(3,5-dimethoxyphenyl)benzaldehyde and Meldrum’s acid at room temperature for 17 h gave a fluorene derivative in 98% yield. Furthermore, the reaction of 2-(3,5-dimethoxybenzyl)benzaldehyde and Meldrum’s acid with piperidine at room temperature for 18 h gave a dihydroanthracene derivative bearing Meldrum’s acid in 83% yield. The reaction of 2-(3,5-dimethoxybenzyl)benzaldehyde and Meldrum’s acid with piperidine at 110 °C for 2 h gave Meldrum’s acid fragmentated dihydroanthracene derivative in 48% yield. The reaction mechanisms of the cyclization steps and Meldrum’s acid fragmentation have been examined by the DFT calculations.

研究人员利用环状活性亚甲基化合物（如梅尔德鲁姆酸）进行了顺序克诺文那格尔缩合/环化反应。在室温下，2-（1-苯基乙烯基）苯甲醛和梅尔杜姆酸、二美酮或 1,3-茚二酮与哌啶/AcOH 或 L-脯氨酸反应 17-18 小时，可得到环化茚衍生物，产率为 63-80%。2-（3,5-二甲氧基苯基）苯甲醛与 Meldrum's 酸在室温下反应 17 小时，可得到一种芴衍生物，收率为 98%。此外，2-(3,5-二甲氧基苄基)苯甲醛和梅氏酸与哌啶在室温下反应 18 小时后，生成了一种含梅氏酸的二氢蒽衍生物，收率为 83%。将 2-(3,5-二甲氧基苄基)苯甲醛和梅氏酸与哌啶在 110 °C 下反应 2 小时，可得到梅氏酸片段化的二氢蒽衍生物，收率为 48%。通过 DFT 计算研究了环化步骤和梅尔杜姆酸破碎的反应机理。

引用次数: 0

An efficient synthesis, characterization, and in silico studies of novel chromenes, thiophenes, pyrazolo[1,5-a]pyrimidines, and pyrimidines as potential antimicrobial and anticancer agents using the bio-buffer tris(hydroxymethyl)aminomethane (THAM) 使用生物缓冲剂三（羟甲基）氨基甲烷（THAM）高效合成、表征和硅学研究新型铬、噻吩、吡唑并[1,5-a]嘧啶和嘧啶，将其作为潜在的抗菌剂和抗癌剂

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2024-10-10 DOI: 10.1080/00397911.2024.2410933

Novel 2-imino-6-(aryldiazenyl)-2H-chromene-3-carboxamides 6a–e, 2-amino-4H-cyclopenta or benzo[b]thiophene-3-carboxamides 10a,b, 2,7-diaminopyrazolo[1,5-a]pyrimidine-6-carboxamides 13a–e, pyrimidine-5-carboxamides 14, 15 and 3-amino-1H-pyrazole-4-carboxamide 16 were synthesized from the reaction of 2-cyano-N-(1,3-dihydroxy-2-(hydroxyl-methyl) propan-2-yl) acetamide 2 with 4-arylazosalicylaldehydes 5a-e, cyclopentanone and/or cyclohexanone, guanidine derivatives and hydrazine hydrate, respectively. Some new compounds were evaluated for antibacterial activity in vitro, and exhibited good efficacy compared to gentamicin. Compound 4c showed greater activity against gram negative bacteria (Klebsiella pneumonia and Pseudomonas aeruginosa) than standard antibiotic. Compound 4c with two withdrawing groups also showed the higher activity (38.7 ± 0.6) against fungi (Candida albicans) than the Nystatin (20 ± 0.5). On the other hand, compounds 13a, 13c, and 13e have strong cytotoxic activity among the tested compounds in the three selected cancer cell lines (HePG2, MCF7 and Hela). Physicochemical characterization by Swiss ADME predication was also performed for some synthesized compounds exhibiting better biological and antimicrobial properties.

新型 2-亚氨基-6-(芳基二氮)-2H-苯并吡喃-3-甲酰胺 6a-e、2-氨基-4H-环戊二烯或苯并[b]噻吩-3-甲酰胺 10a,b、2,7-二氨基吡唑并[1,5-a]嘧啶-6-甲酰胺 13a-e、嘧啶-5-甲酰胺 14、15 和 3-氨基-1H-吡唑-4-甲酰胺 16 分别由 2-氰基-N-（1,3-二羟基-2-（羟基甲基）丙-2-基）乙酰胺 2 与 4-芳基水杨醛 5a-e、环戊酮和/或环己酮、胍衍生物和水合肼反应合成。对一些新化合物进行了体外抗菌活性评估，结果表明，与庆大霉素相比，这些化合物具有良好的疗效。与标准抗生素相比，化合物 4c 对革兰氏阴性菌（肺炎克雷伯氏菌和铜绿假单胞菌）的活性更高。化合物 4c 的两个提取基团对真菌（白色念珠菌）的活性（38.7 ± 0.6）也高于奈司他丁（20 ± 0.5）。另一方面，在所测试的化合物中，13a、13c 和 13e 对三种选定的癌细胞系（HePG2、MCF7 和 Hela）具有很强的细胞毒性活性。此外，还通过瑞士 ADME 预测法对一些合成化合物进行了理化表征，结果表明这些化合物具有更好的生物和抗菌特性。

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引用次数: 0

Synthesis, antiproliferative activity, and in silico studies of quinoline-based pyrimidinedione and thiazolidinedione derivatives 基于喹啉的嘧啶二酮和噻唑烷二酮衍生物的合成、抗增殖活性及硅学研究

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2024-10-04 DOI: 10.1080/00397911.2024.2409872

Cancer affects millions of people worldwide. PDK1 enzyme (co-crystallized with BIM-1) controls the proliferation of breast cancer cells. Aiming to resemble BIM-1’s binding, quinoline-based pyrimidinediones and thiazolidinediones were synthesized starting from 2-chloro-3-formylquinoline. Compared with doxorubicin (reference), in vitro antiproliferative activity against MCF7 and HCT116 cancer cell lines showed the most potency of thiobarbiturate 3 and thiazolidinedione 4. In silico molecular docking, DFT, and pharmacokinetics simulations supported the findings. The docking analysis toward PDK1 enzyme showed that most amino acids interacting with co-crystallized ligand (BIM-1) were successfully bonded to our docked substances, especially thiobarbiturate 3 with highest S-score closer to BIM-1. In DFT calculations, this compound exhibited the lowest energy gap and highest softness leading to more response to radical surface interactions. The compounds with significant antiproliferative activity exhibited high electrophilicity values. ADME analysis showed its desirable drug-likeness and oral bioavailability. This work may contribute to developing new potent antiproliferative agents.

癌症影响着全球数百万人。PDK1 酶（与 BIM-1 共同结晶）控制着乳腺癌细胞的增殖。为了类似于 BIM-1 的结合，研究人员从 2-氯-3-甲酰基喹啉开始，合成了喹啉基嘧啶二酮和噻唑烷二酮。与多柔比星（参照物）相比，硫代巴比妥酸 3 和噻唑烷二酮 4 对 MCF7 和 HCT116 癌细胞株的体外抗增殖活性最强。硅学分子对接、DFT 和药代动力学模拟证实了这些发现。与 PDK1 酶的对接分析表明，与共晶体配体（BIM-1）相互作用的大多数氨基酸都成功地与我们对接的物质结合在一起，尤其是硫代巴比妥酸 3，其 S 分数最高，更接近 BIM-1。在 DFT 计算中，该化合物表现出最低的能隙和最高的软度，因此对自由基表面相互作用的响应更强。具有显著抗增殖活性的化合物表现出较高的亲电性。ADME 分析表明，该化合物具有理想的药物亲和性和口服生物利用度。这项工作可能有助于开发新的强效抗增殖剂。

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引用次数: 0

Potential MRSA inhibitory activity of some new benzofuran-pyrazolo[1,5-a]pyrimidine hybrids attached to arene units via methylene or azo linkage 通过亚甲基或偶氮连接与炔单元相连的一些新型苯并呋喃-吡唑并[1,5-a]嘧啶杂化物的潜在 MRSA 抑制活性

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2024-09-28 DOI: 10.1080/00397911.2024.2409875

MRSA, a resistant bacteria causing severe infections, is targeted by researchers developing new anti-resistance compounds. The study aimed to investigate the MRSA inhibitory activity of two series of benzofuran-pyrazolo[1,5-a]pyrimidines 1 and 2, attached to arene units via methylene or azo linkage, respectively. The desired products were prepared, in 82–92% yields, by reacting benzofuran-based enaminone 4 with the appropriate 1H-pyrazole-3,5-diamines 5 in pyridine at reflux for 5–6 h. The new hybrids showed a wide spectrum of antibacterial activity against different ATCC strains. Products with azo linkage and para-substituted arene units with electron-releasing groups demonstrated higher antibacterial activity. 3-((4-Methoxyphenyl)diazenyl)-linked pyrazolo[1,5-a]pyrimidine 2e demonstrates activity that exceeded the reference ciprofloxacin with MIC/MBC values of 1.8/3.6 µM against S. aureus and E. coli strains. Also, it demonstrated more effective MRSA inhibitory activity than the reference linezolid, with MIC/MBC values of 3.6/14.4 and 1.8/7.2 µM against MRSA ATCC:33591 and ATCC:43300 strains, respectively.

MRSA 是一种导致严重感染的抗药性细菌，是研究人员开发新型抗药性化合物的目标。本研究旨在研究两个系列的苯并呋喃吡唑并[1,5-a]嘧啶 1 和 2 的 MRSA 抑制活性，这两个系列的苯并呋喃吡唑并[1,5-a]嘧啶分别通过亚甲基或偶氮连接到炔单元上。通过将苯并呋喃基烯丙酮 4 与适当的 1H-吡唑-3,5-二胺 5 在吡啶中回流反应 5-6 小时，制备出了所需的产品，产率为 82-92%。具有偶氮连接和带有电子释放基团的对位取代炔单元的产品表现出更高的抗菌活性。3-((4-Methoxyphenyl)diazenyl)-linked pyrazolo[1,5-a]pyrimidine 2e 对金黄色葡萄球菌和大肠杆菌菌株的 MIC/MBC 值为 1.8/3.6 µM，其活性超过了参照物环丙沙星。此外，它对 MRSA ATCC:33591 和 ATCC:43300 菌株的 MIC/MBC 值分别为 3.6/14.4 µM 和 1.8/7.2 µM，显示出比参考药物利奈唑胺更有效的 MRSA 抑制活性。

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