Synthetic Communications最新文献

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Hybrids of thiophene, pyrazole and oxadiazol: Synthesis, DFT calculations, molecular docking studies and biological evaluation for anticancer and antimicrobial activity 噻吩、吡唑和恶二唑的杂合体：合成、DFT计算、分子对接研究及抗癌和抗菌活性的生物学评价

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2026-01-17 DOI: 10.1080/00397911.2026.2613352

Dhavalkumar M. Bhatt (Data curation Resources Software Writing – original draft) , Gaurav B. Patel (Data curation Formal analysis Resources) , Yogesh O. Bhola (Methodology Software Supervision Writing – review & editing) , Piyush V. Dholaria (Supervision Visualization) , Amitkumar M. Patel (Data curation Resources Validation)

Nine novel pyrazole-thiophene-oxadiazole hybrid compounds (8a–i) were synthesized, characterized using spectroscopic techniques, and evaluated for anticancer and antimicrobial activities using molecular docking, DFT calculations, and ADMET profiling. Compound 8i exhibited the most potent anticancer activity against HepG2 (IC₅₀ = 1.3 ± 1 μM) and MCF-7 (IC₅₀ = 10.6 ± 1 μM) cell lines, comparable to that of doxorubicin. Antimicrobial screening revealed that compound 8b exhibited the highest antibacterial activity (40.6 ± 0.8 mm zone against S. aureus). In contrast, compound 8c demonstrated superior broad-spectrum activity against bacteria (32.2 mm against S. aureus and 30.1 mm against E. coli) and fungi (12.3 mm against C. albicans), surpassing that of the reference drugs. Molecular docking showed compound 8i with the highest binding affinity to Human Topoisomerase IIα (−7.6030 kcal/mol vs. −5.4560 kcal/mol for doxorubicin). In comparison, compound 8c exhibited optimal binding to the Candida albicans target 5AEZ (−6.055 kcal/mol), which correlated with the experimental results. DFT calculations (B3LYP/6–311++G(d,p)) revealed that compound 8i possessed the smallest HOMO-LUMO gap (3.9464 eV), highest reactivity, and optimal softness (0.4998). The RDG analysis confirmed the extensive noncovalent interactions that contribute to molecular stability. ADMET profiling indicated low gastrointestinal absorption and CYP3A4 inhibition for all compounds, with compound 8g exhibiting the most favorable metabolic profile. These findings establish pyrazole-thiophene-oxadiazole hybrids as promising dual anticancer and antimicrobial scaffolds for further development of novel therapeutic agents.

合成了9个新的吡唑-噻吩-恶二唑杂化化合物（8a-i），利用光谱技术对其进行了表征，并利用分子对接、DFT计算和ADMET分析对其抗癌和抗菌活性进行了评价。化合物8i对HepG2 （IC50 = 1.3±1 μM）和MCF-7 （IC50 = 10.6±1 μM）细胞的抑癌活性与阿霉素相当。抗菌筛选结果显示，化合物8b对金黄色葡萄球菌的抑菌活性最高（40.6±0.8 mm区）。相比之下，化合物8c对细菌（对金黄色葡萄球菌32.2 mm，对大肠杆菌30.1 mm）和真菌（对白色念珠菌12.3 mm）的广谱活性优于对照药物。分子对接表明，化合物8i与人拓扑异构酶i α的结合亲和力最高（−7.6030 kcal/mol，而阿霉素为−5.4560 kcal/mol）。相比之下，化合物8c与白色念珠菌靶点5AEZ的结合效果最佳（- 6.055 kcal/mol），这与实验结果相关。DFT计算（B3LYP/ 6-311 ++G(d,p)）表明，化合物8i具有最小的HOMO-LUMO间隙（3.9464 eV）、最高的反应活性和最佳的柔软度（0.4998）。RDG分析证实了广泛的非共价相互作用有助于分子稳定性。ADMET分析表明，所有化合物的胃肠道吸收低，CYP3A4抑制，化合物8g表现出最有利的代谢谱。这些发现表明，吡唑-噻吩-恶二唑复合物是一种有前景的抗癌和抗菌双重支架，可用于进一步开发新的治疗药物。

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引用次数: 0

Copper-catalyzed annulation of oxime acetates with benzimidates: a new access to substituted pyridines 铜催化醋酸肟与苯并咪酯的环化：取代吡啶的新途径

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2026-01-17 DOI: 10.1080/00397911.2026.2613768

Boniface Opio (Conceptualization Investigation Methodology Project administration) , Kumari Yettula (Data curation Formal analysis) , Satishkumar Kotyada (Data curation Formal analysis) , Meenakshi Tamara (Formal analysis Software) , Rajeswari Karnati (Formal analysis) , Kamala Pamula (Data curation Formal analysis Validation) , Siddaiah Vidavalur (Conceptualization Supervision)

A copper-catalyzed annulation of oxime acetates and benzimidates has been developed via the reductive cleavage of the N–O bond. The reaction proceeds smoothly with a broad range of substrates, giving access to a variety of substituted pyridine derivatives in moderate to good yields. This methodology features the use of inexpensive catalysts and the avoidance of additional ligands and additives.

通过N-O键的还原裂解，制备了一种铜催化的醋酸肟酸酯和苯并咪甲酸酯环。该反应在广泛的底物上顺利进行，以中等到较高的产率获得各种取代吡啶衍生物。这种方法的特点是使用廉价的催化剂和避免额外的配体和添加剂。

引用次数: 0

A comprehensive review on prasugrel: Industrial synthesis, impurity profiling, pharmacokinetics & FDA assessment 综述普拉格雷的工业合成、杂质分析、药代动力学和FDA评价

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2026-01-17 DOI: 10.1080/00397911.2025.2593997

Ankita A. Kanhere (Conceptualization Investigation Methodology Resources Software Visualization Writing – original draft) , Yashwanti D. Suryawanshi (Conceptualization Methodology Resources Validation Writing – original draft) , Nitin D. Arote (Conceptualization Supervision Writing – review & editing)

Prasugrel, a Thienopyridine-class antiplatelet agent, is extensively used to prevent thrombus formation in people at high risk of cardiovascular disease. With a projected market CAGR of 8.0%, the global demand for Prasugrel continues to rise. The current review gives an extensive overview of industrial synthesis, focusing on patented strategies to enhance yield and minimize impurities such as CATP and OXTP. The standard industrial synthetic route involves the condensation of the thienopyridine moiety with 2-bromo-1-cyclopropyl-2-(2-fluorophenyl) ethenone, followed by an acetylation step. In addition, the review aims to assess Prasugrel’s key pharmacological aspects, including its mechanism of action, pharmacokinetic profile, and comparison with Clopidogrel. The polymorph forms of Prasugrel hydrochloride are also discussed in detail, alongside a critical evaluation of the risk-benefit profile, to provide a comprehensive understanding of its clinical and regulatory positioning.

普拉格雷是一种噻吩吡啶类抗血小板药物，广泛用于预防心血管疾病高危人群血栓形成。预计市场复合年增长率为8.0%，全球对普拉格雷的需求将继续上升。当前的综述对工业合成进行了广泛的概述，重点介绍了提高收率和减少杂质（如CATP和OXTP）的专利策略。标准的工业合成路线包括噻吩吡啶部分与2-溴-1-环丙基-2-（2-氟苯基）乙烯酮缩合，然后是乙酰化步骤。此外，本综述旨在评估普拉格雷的关键药理学方面，包括其作用机制、药代动力学特征以及与氯吡格雷的比较。本文还详细讨论了盐酸普拉格雷的多形态，并对其风险-收益概况进行了关键评估，以全面了解其临床和监管定位。

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引用次数: 0

Simple, efficient and one-pot synthetic protocol for highly versatile 4-formylpyrazole derivatives: A step toward sustainable development 4-甲酰吡唑衍生物的简单、高效和一锅合成方案：迈向可持续发展的一步

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2026-01-17 DOI: 10.1080/00397911.2026.2613767

Aman Kumar (Conceptualization Investigation Methodology Validation Writing – original draft) , Arpan Das (Investigation Validation) , Pratima Kumari (Investigation Validation) , Manshu Choudhary (Investigation Validation) , Ramesh Kataria (Data curation Formal analysis Writing – review & editing) , Vinod Kumar (Conceptualization Supervision Writing – review & editing)

4-Formylpyrazole derivatives are an important class of building blocks for various heterocycles, including drugs. They have wide applications in the fields of synthetic and medicinal chemistry, in addition to acting as antibacterial, anti-inflammatory, antiparasitic, and anti-diabetic agents. Here, we report a new one-pot synthetic protocol for highly versatile 4-formylpyrazole derivatives in which differently substituted acetophenones and phenyl hydrazine were treated with Vilsmeier–Haack reagent. The present protocol offers a straightforward, highly efficient, practical, and cost-effective approach for synthesizing 4-formylpyrazole derivatives in excellent yields, including an important intermediate of the drug, Lonazolac. All the synthesized compounds were characterized based on spectroscopic data (UV-Vis, ¹H, ¹³C NMR, FT-IR, and Mass).

4-甲酰基吡唑衍生物是包括药物在内的各种杂环化合物的重要组成部分。除具有抗菌、抗炎、抗寄生虫、抗糖尿病等作用外，在合成化学和药物化学等领域有着广泛的应用。在这里，我们报告了一种新的一锅合成方案，高度通用的4-甲酰吡唑衍生物，其中不同取代的苯乙酮和苯基肼用维斯迈耶-哈克试剂处理。本方案提供了一种简单、高效、实用和经济的方法，以优异的收率合成4-甲酰吡唑衍生物，包括药物的重要中间体Lonazolac。所有合成的化合物都通过光谱数据（UV-Vis, 1H, 13C NMR， FT-IR和Mass）进行了表征。

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引用次数: 0

Synthesis, biological evaluation, and in silico studies of imidazole-linked 1,2,3-triazole heterocycles as antimicrobial agents 咪唑- 1,2,3-三唑类杂环抗菌药物的合成、生物学评价和硅片研究

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2026-01-17 DOI: 10.1080/00397911.2026.2613310

Pratibha Periwal (Formal analysis Validation Writing – original draft) , Vikramjeet Singh (Data curation Software) , Samridhi Thakral (Software) , Sonia Rohilla (Data curation) , Meenakshi Bhatia (Validation) , Vikas Verma (Conceptualization Methodology Supervision Writing – review & editing)

In the current research, a novel series of imidazole-linked 1,2,3-triazole heterocycles (5a–5j) was synthesized via copper(I)-catalyzed azide-alkyne click chemistry. The synthesized compounds were characterized and further assessed for their in vitro antimicrobial activity. All the targeted compounds displayed antimicrobial potency with MIC values ranging from 0.0054 to 0.0459 μmol/mL. Among all the synthesized compounds, compounds 5e and 5j were found to be most active against S. aureus and E. coli, with MIC values of 0.0057 and 0.0054 μmol/mL, respectively. Moreover, all the compounds (5a–5j) displayed better antifungal activity against C. albicans than standard fluconazole. Furthermore, the binding energies of all the synthesized compounds were predicted using a molecular docking study. The compounds 5i and 5j exhibited good 3D and 2D binding interaction with active residues PDB:5V5Z and PDB:2XCT, respectively. The ADMET analysis supported the compound’s (5a–5j) potential as a drug-like candidate with a significant pharmacokinetic profile.

本研究通过铜(I)催化叠氮-炔键化学合成了一系列咪唑- 1,2,3-三唑杂环（5a-5j）。对合成的化合物进行了表征并进一步评价了其体外抗菌活性。所有目标化合物的MIC值均在0.0054 ~ 0.0459 μmol/mL之间。在所合成的化合物中，化合物5e和5j对金黄色葡萄球菌和大肠杆菌的活性最高，其MIC值分别为0.0057和0.0054 μmol/mL。此外，所有化合物（5a-5j）对白色念珠菌的抗真菌活性均优于标准氟康唑。此外，利用分子对接研究预测了所有合成化合物的结合能。化合物5i和5j分别与活性残基PDB:5V5Z和PDB:2XCT表现出良好的3D和2D结合作用。ADMET分析支持该化合物（5a-5j）作为具有显著药代动力学特征的候选药物的潜力。

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引用次数: 0

Recent synthetic methodologies for transition metal-catalyzed S-arylation reactions 过渡金属催化s -芳基化反应的最新合成方法

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2026-01-02 DOI: 10.1080/00397911.2025.2582183

Saeeda Mubashra (Data curation Methodology Software Visualization Writing – original draft) , Matloob Ahmad (Conceptualization Investigation Supervision Writing – original draft Writing – review & editing) , Nasir Rasool (Conceptualization Investigation Writing – review & editing) , Sana Aslam (Conceptualization Investigation Writing – original draft Writing – review & editing)

Organosulfur compounds have emerged as an important class of bioactive molecules in drug discovery. The S-arylated compounds using various sulfur surrogates act as precursors for drugs and biologically active compounds. This review article offers a dynamic discussion on S-arylation reactions of organosulfur compounds reported in the literature during 2020–2025. The synthetic approaches include multicomponent reaction, nucleophilic substitution, reductive and deoxygenative cross-coupling, Sandmeyer-type arylation, Ullmann, and Chan-Evan-Lam type cross-coupling reactions to afford S-arylated compounds. The key purpose of this review is to offer a concise summary of recently reported methods using mild, selective, and sustainable transition metal-catalyzed approaches for S-arylation, overcoming the challenges of harsh conditions, toxicity, and regioselectivity.

有机硫化合物已成为一类重要的生物活性分子。使用各种硫代物的s -芳基化化合物作为药物和生物活性化合物的前体。本文对2020-2025年间文献报道的有机硫化合物s -芳基化反应进行了动态讨论。合成方法包括多组分反应、亲核取代、还原和脱氧交叉偶联、sandmeyer型芳基化、Ullmann和Chan-Evan-Lam型交叉偶联反应，以获得s-芳基化化合物。本综述的主要目的是简要总结最近报道的使用温和、选择性和可持续的过渡金属催化方法进行s -芳基化的方法，克服了苛刻的条件、毒性和区域选择性的挑战。

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引用次数: 0

Synthesis and cytotoxic evaluation of 2-aminobenzothiazole amide derivatives inspired by hydroxamate structural motifs 基于羟基甲酸酯结构基序的2-氨基苯并噻唑酰胺衍生物的合成及细胞毒性评价

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2026-01-02 DOI: 10.1080/00397911.2026.2616660

Dinh Thi Cuc (Writing – review & editing) , Hoai Thu Pham (Formal analysis) , Nguyen Thi Hien (Formal analysis) , Luu Duc Phuong (Methodology) , Tran Quang Hung (Formal analysis) , Dang Thi Mai (Validation) , Tran Dang Thuan (Methodology) , Nguyen Thi Le Huyen (Supervision) , Ba Thi Duong (Methodology) , Nguyen Thi Ngoan (Formal analysis)

In this study, a series of amide derivatives based on the 2-aminobenzothiazole scaffold, structurally inspired by hydroxamic acid (hydroxamate) frameworks, were successfully synthesized in good yields. Their structures were confirmed by spectroscopic techniques, and the compounds were evaluated for cytotoxic activity against MCF-7 and KB human cancer cell lines using the MTT assay. Among the synthesized compounds, compound 3d exhibited notable cytotoxic effects, with IC₅₀ values ranging from 27.06 to 85.28 µM. Preliminary structure–activity observations suggest that modifications of the amide functionality and the benzothiazole ring influence the observed cytotoxicity. These findings provide preliminary insights into the cytotoxic potential of benzothiazole-based amide derivatives and support further mechanistic investigations.

在本研究中，以2-氨基苯并噻唑为骨架，在结构上受到羟肟酸框架的启发，成功合成了一系列酰胺衍生物。通过光谱技术确定了它们的结构，并利用MTT法评估了化合物对MCF-7和KB人癌细胞的细胞毒活性。在所合成的化合物中，化合物3d表现出明显的细胞毒作用，IC50值为27.06 ~ 85.28µM。初步的结构活性观察表明，酰胺功能和苯并噻唑环的修饰影响观察到的细胞毒性。这些发现为苯并噻唑基酰胺衍生物的细胞毒性潜力提供了初步的见解，并支持进一步的机制研究。

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引用次数: 0

Cyclocondensation of bromoacetaldehyde diethyl acetal with 2-amino-N-(aryl/alkyl)-2-thioxoacetamides: a novel synthesis of N-(aryl/alkyl)thiazole-2-carboxamides 溴乙醛缩二乙醛与2-氨基-N-（芳基/烷基）-2-硫氧乙酰胺的环缩合反应：N-（芳基/烷基）噻唑-2-羧酰胺的新合成方法

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2026-01-02 DOI: 10.1080/00397911.2025.2608344

Kanaka Vijayashankar Honnabandar (Conceptualization) , Nagarakere C. Sandhya (Conceptualization) , Chaitra G. Reddy (Conceptualization) , Toreshettahally R. Swaroop (Supervision Writing – original draft) , Kempegowda Mantelingu (Supervision Writing – review & editing)

In this article, we report an important extended work of the Hantzsch synthesis of thiazoles by reacting novel 2-amino-N-(aryl/alkyl)-2-thioxoacetamides with bromoacetaldehyde diethyl acetal in DMF at 80 °C. We synthesized required 2-amino-N-(aryl/alkyl)-2-thioxoacetamides by reacting 2-oxo-2-(aryl/alkylamino)ethanedithioates with ammonia, which is generated in situ by mixing ammonium chloride and sodium acetate in acetonitrile at room temperature. We have also proposed a possible mechanism of formation of thiazoles. High yields, comparatively less reaction times and mild conditions are the important features of this procedure.

在这篇文章中，我们报道了Hantzsch在DMF中80°C下用新型2-氨基- n -（芳基/烷基）-2-硫氧乙酰胺与溴乙醛缩二乙醛反应合成噻唑的重要扩展工作。在室温下，氯化铵和乙酸钠在乙腈中混合原位生成2-氧-2-（芳基/烷基）-2-硫代乙硫代酸盐与氨反应，合成了所需的2-氨基- n -（芳基/烷基）-2-硫代乙酰胺。我们还提出了一种可能形成噻唑的机制。收率高、反应时间短、条件温和是该工艺的重要特点。

引用次数: 0

Synthesis, antimicrobial evaluation, and molecular docking study of fenchol- and menthol-based derivatives 芬醇和薄荷醇衍生物的合成、抗菌评价及分子对接研究

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2026-01-02 DOI: 10.1080/00397911.2026.2613299

Fatma Salaheldin Mohamed (Data curation Methodology Software Validation Writing – original draft Writing – review & editing) , Ahmed I. Hashem (Supervision Visualization Writing – review & editing) , Mahmoud F. Ismail (Supervision Writing – review & editing) , Mamdouh A. Abu-Zaied (Data curation Investigation Methodology Supervision Validation Writing – original draft Writing – review & editing) , Galal A. M. Nawwar (Conceptualization Methodology Project administration Supervision Validation Writing – review & editing)

A new series of substituted heterocyclic compounds was synthesized through the reaction of cyanoacetyl derivatives 3a,b with various reagents, including substituted aldehydes 4a–e, aryl diazonium salts 7a–b, 2-cyano-3-(5-methylfuran-2-yl)acrylic acid ethyl ester 11a, and 2-(5-methylfuran-2-ylmethylene)malononitrile 11b under basic condition. The structures of the obtained compounds were confirmed by elemental and spectral analyses. Additionally, the mechanisms of their formation were considered. The antimicrobial activities of the synthesized compounds were evaluated against six microbial strains, including Gram-positive and Gram-negative bacteria as well as fungi. The tested compounds exhibited different degrees of antibacterial activity compared with the standard drugs. Compounds 3b and 10b displayed broad-spectrum activity, with compound 10b showing the highest efficacy; its inhibition zones were nearly twice those of the reference drugs. In silico molecular docking analyses of compounds 10a and 10b revealed comparable binding affinities toward Escherichia coli DNA gyrase B.

在碱性条件下，以氰乙酰基衍生物3a、b与取代醛4a-e、芳基重氮盐7a-b、2-氰-3-（5-甲基呋喃-2-基）丙烯酸乙酯11a、2-（5-甲基呋喃-2-基亚甲基）丙二腈11b反应，合成了一系列新的取代杂环化合物。所得化合物的结构经元素分析和光谱分析证实。并对其形成机理进行了探讨。合成的化合物对革兰氏阳性菌和革兰氏阴性菌以及真菌等6种微生物进行了抑菌活性评价。与标准药物相比，被试化合物表现出不同程度的抗菌活性。化合物3b和10b具有广谱活性，其中化合物10b的药效最高；其抑制范围是参比药的近两倍。化合物10a和10b的硅分子对接分析显示其与大肠杆菌DNA旋切酶B的结合亲和力相当。

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引用次数: 0

6-Amino-7-fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one, a crucial intermediate in the synthesis of herbicides, flumioxazin and thidiazimin 6-氨基-7-氟- 2h -苯并[b][1,4]恶嗪-3(4H)- 1，是合成除草剂氟恶嗪和噻嗪的重要中间体

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications

Pub Date : 2026-01-02 DOI: 10.1080/00397911.2025.2612513

Prakash Suman Behera (Data curation Formal analysis Investigation Methodology Validation Visualization Writing – original draft) , Devendra Nagineni (Data curation Methodology Validation Visualization Writing – original draft) , Naga Pranathi Abburi (Data curation Formal analysis Methodology Visualization Writing – review & editing) , Srinivas Kantevari (Conceptualization Formal analysis Funding acquisition Investigation Methodology Project administration Supervision Writing – original draft Writing – review & editing)

An efficient synthesis of 6-amino-7-fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one, a key intermediate in the preparation of the herbicides flumioxazin and thidiazimin, is accomplished in three steps from readily available 1,3-difluorobenzene. The key steps of nitration, condensation, and reductive cyclization were optimized to obtain the product in 78% overall yield with 99.4% purity.

以易得的1,3-二氟苯为原料，三步合成了6-氨基-7-氟- 2h -苯并[b][1,4]恶嗪-3(4H)- 1，它是制备除草剂氟恶嗪和噻嗪的关键中间体。优化了硝化、缩合、还原环化等关键步骤，产品总收率为78%，纯度为99.4%。

引用次数: 0

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