Mohamed S. Mohamed Ahmed , Fawzy A. Attaby , Redhab A. J. Alfraiji , Zeinab A. Abdallah
{"title":"Novel thiazole derivatives: Design, synthesis, antibacterial evaluation, DFT, molecular docking and in-silico ADMET investigations","authors":"Mohamed S. Mohamed Ahmed , Fawzy A. Attaby , Redhab A. J. Alfraiji , Zeinab A. Abdallah","doi":"10.1080/00397911.2024.2431989","DOIUrl":"10.1080/00397911.2024.2431989","url":null,"abstract":"<div><div>Thiazole derivatives (<strong>7a-f</strong> and <strong>9a-i</strong>) were synthesized in good yields (up to 98%). The synthetic protocol is achieved through a two-step reaction. The synthesized candidates were then evaluated for their antimicrobial efficacies against gram-positive and gram-negative bacteria. 4-methyl-2-(2-(3-(pentyloxy)benzylidene)hydrazinyl)-5-(p-tolyldiazenyl)thiazole showed significant antimicrobial activity against <em>Staphylococcus aureus</em> (ATCC: 13565) compared to ampicillin. On the other hand, 2-(2-(3-(hexyloxy)benzylidene)hydrazinyl)-4-(4-methoxyphenyl)thiazole shows potent activity against <em>Klebsiella pneumonia</em> (ATCC: 10031) compared to gentamicin as a standard antibiotic. The ADME profile of the prepared compounds indicated favorable pharmacological behaviors. Additionally, docking and in-silico ADMET analyses were performed for the promising derivatives and the results revealed strong antimicrobial activity. DFT calculations were performed, which provided additional insight into the thiazoles’ structure and formation.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 1","pages":"Pages 44-64"},"PeriodicalIF":1.8,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143156694","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Cheng-Yan Wu , Xi Zhang , Tian-Yi Zhang , Zhong-Lin Lu
{"title":"Transition-metal-free and solvent-tolerant decarboxylative iodination of aromatic carboxylic acids","authors":"Cheng-Yan Wu , Xi Zhang , Tian-Yi Zhang , Zhong-Lin Lu","doi":"10.1080/00397911.2024.2428650","DOIUrl":"10.1080/00397911.2024.2428650","url":null,"abstract":"<div><div>Current decarboxylative halogenation methods typically require expensive or toxic transition metal catalysts and have limited solvent compatibility. Herein, we report a novel transition-metal-free and solvent-tolerant decarboxylative iodination method by using iodine monochloride in the presence of potassium phosphate, which are effective to readily available aryl and heteroaryl carboxylic acids, and can be executed in a variety of solvents, including water.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 1","pages":"Pages 84-91"},"PeriodicalIF":1.8,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143156688","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Ahmed A. M. Ahmed , Ahmed E. M. Mekky , Sherif M. H. Sanad
{"title":"Synthesis of new bis(pyrazolo[1,5-a]pyrimidines) linked to different spacers with potential MurB inhibitory activity utilizing 1H-pyrazole-3,5-diamines","authors":"Ahmed A. M. Ahmed , Ahmed E. M. Mekky , Sherif M. H. Sanad","doi":"10.1080/00397911.2024.2428653","DOIUrl":"10.1080/00397911.2024.2428653","url":null,"abstract":"<div><div>Recently, there has been an increased interest in developing new antibacterial agents that target the MurB inhibition, which is necessary for bacterial survival. We developed a two-step tandem protocol to synthesize 15 new bis(pyrazolo[1,5-<em>a</em>]pyrimidines), which are attached to alkane cores by amide linkages. The protocol involved reacting the appropriate bis(2-cyanoacetamides) with dimethylformamide-dimethylacetal in toluene at 80 °C for 3-4 h. The crude bis(2-cyano-3-(dimethylamino)acrylamides) was collected, then reacted with 3,5-diamino-1<em>H</em>-pyrazoles. The reaction gave the desired products in 82-92% yields after 5-6 h of heating at reflux in pyridine. Bis(2,7-diamino-3-(4-methoxybenzyl)pyrazolo[1,5-<em>a</em>]pyrimidine-6-carboxamides) demonstrated comparable efficacy to ciprofloxacin. Their MIC and MBC ranged from 2.8-3.0 and 5.7-6.0 µM, respectively, against <em>S. aureus</em> and <em>E. coli</em>. Moreover, these products displayed promising MurB inhibitory activity with IC<sub>50</sub> ranging from 7.8 to 8.0 µM.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 1","pages":"Pages 19-31"},"PeriodicalIF":1.8,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143156685","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Xin-Hao Hua , Fa-Qi Wang , Zhong-Jin Yang , Yuan Liu , Shu-Han Yang , Dong-Rong Zhu , Yu-Ming Liu
{"title":"Design, synthesis, anti-trypsin and anti-inflammatory evaluation of new guanidinobenzoic acid ester derivatives","authors":"Xin-Hao Hua , Fa-Qi Wang , Zhong-Jin Yang , Yuan Liu , Shu-Han Yang , Dong-Rong Zhu , Yu-Ming Liu","doi":"10.1080/00397911.2024.2420341","DOIUrl":"10.1080/00397911.2024.2420341","url":null,"abstract":"<div><div>Herein, we designed a series of guanidinobenzoic acid ester derivatives on the basis of approved AP drugs, such as nafamostat, gabexate and camostat, and evaluated their inhibitory effects on trypsin and anti-inflammatory activity. Among them, five compounds (<strong>6a</strong>, <strong>6c–6e, 7j</strong>) showed excellent inhibitory effects on trypsin with IC<sub>50</sub> values of 0.0756 μM to 0.1227 μM, which are more potent than nafamostat and gabexate. Moreover, compounds <strong>6a</strong>, <strong>6b</strong> and <strong>6c</strong> also showed significant inhibitory potency against the pro-inflammatory molecule NO with IC<sub>50</sub> values of 1.618 μM, 2.276 μM, and 3.022 μM, respectively. Consequently, the potential lead compounds simultaneously with anti-trypsin and anti-inflammatory activities were identified, which would profit further structural optimization for the treatment of AP.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 23","pages":"Pages 2052-2063"},"PeriodicalIF":1.8,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143175952","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Comparative review on homogeneous and heterogeneous catalyzed synthesis of 1,3-thiazole","authors":"Swapnali Parit , Ajit Manchare , Shrikant Ghodse , Navnath Hatvate","doi":"10.1080/00397911.2024.2399187","DOIUrl":"10.1080/00397911.2024.2399187","url":null,"abstract":"<div><div>Thiazole is a sulfur and nitrogen-containing five-membered heteroaromatic ring in many FDA-approved drugs and numerous experimental leads. To facilitate access to this structure, several novel methodologies have been developed using easily accessible starting materials and more environmentally friendly protocols. This review focuses on all recently developed methods (2013–2024) that utilized homogeneous or heterogeneous catalyzed methods to synthesize 1,3-thiazole and provides thorough information on the diverse therapeutic applicability of thiazole derivatives in drug discovery and development. Furthermore, this review will ameliorate the understanding of synthetic and medicinal chemists in selecting green and ecological methodologies to synthesize thiazoles judicially.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 23","pages":"Pages 2003-2023"},"PeriodicalIF":1.8,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143177692","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Iron (II) catalyzed cyclization of ketoxime acetates with triethyl orthoformate: An easy access to symmetrical pyridines","authors":"Kotyada Satishkumar , Podugu Rajitha Lakshmi , Yettula Kumari , Voosala Christopher , Vidavalur Siddaiah","doi":"10.1080/00397911.2024.2421364","DOIUrl":"10.1080/00397911.2024.2421364","url":null,"abstract":"<div><div>A simple and efficient iron (II) catalyzed approach to the synthesis of symmetrical pyridines has been demonstrated using ketoxime acetates and triethyl orthoformate in DMF at 120 °C under nitrogen environment. In this strategy, significantly, triethyl orthoformate functions as C1 carbon source and which is noteworthy. Other benefits of this process include good yields, high functional group tolerance, low cost of catalyst and avoiding of use of hazardous chemicals.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 23","pages":"Pages 2064-2075"},"PeriodicalIF":1.8,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143175954","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Valeriia V. Pavlova , Pavlo V. Zadorozhnii , Aleksey B. Ryabitsky , Vadym V. Kiselev , Oxana V. Okhtina , Aleksandr V. Kharchenko
{"title":"Synthesis and spectral characteristics of N-(2,2,2-trichloro-1-((5-(R-amino)-1,3,4-thiadiazol-2-yl)amino)ethyl)carboxamides","authors":"Valeriia V. Pavlova , Pavlo V. Zadorozhnii , Aleksey B. Ryabitsky , Vadym V. Kiselev , Oxana V. Okhtina , Aleksandr V. Kharchenko","doi":"10.1080/00397911.2024.2422472","DOIUrl":"10.1080/00397911.2024.2422472","url":null,"abstract":"<div><div>In this paper, we reported the development of an efficient and highly productive synthetic protocol for preparing new 2,5-diamino-1,3,4-thiadiazole derivatives functionalized with <em>N</em>-(2,2,2-trichloroethyl)carboxamide group. The method of their preparation was based on the reaction of oxidative dehydrosulfurization of <em>N</em>-(2,2,2-trichloro-1-(2-(phenylcarbamothioyl)hydrazine-1-carbothioamido)ethyl)carboxamides and <em>N</em>-(1-(2-carbamothioylhydrazine-1-carbothioamido)-2,2,2-trichloroethyl)benzamide under the action of a mixture of iodine and triethylamine in DMF. This reaction took place at room temperature for two hours and allowed obtaining the target products with a 69-75% yield. Using the developed protocol, we obtained ten new derivatives of 1,3,4-thiadiazole. Their structure was proven by IR,<sup>1</sup>H NMR,<sup>13</sup>C NMR, <sup>1</sup>H-<sup>1</sup>H COSY, <sup>1</sup>H-<sup>13</sup>C HSQC, <sup>1</sup>H-<sup>13</sup>C HMBC spectroscopy, and LC/HRMS spectrometry.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 23","pages":"Pages 2076-2087"},"PeriodicalIF":1.8,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143175955","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Sandip J. Detke , Anuja D. Karwande , Sai Srinivas Ponugoti , Shreerang V. Joshi , Prashant S. Kharkar
{"title":"Advancing quinoxaline chemistry: Sustainable and green synthesis using L-arabinose as a catalyst","authors":"Sandip J. Detke , Anuja D. Karwande , Sai Srinivas Ponugoti , Shreerang V. Joshi , Prashant S. Kharkar","doi":"10.1080/00397911.2024.2419861","DOIUrl":"10.1080/00397911.2024.2419861","url":null,"abstract":"<div><div>In the present study, an innovative and eco-friendly methodology for synthesizing quinoxaline derivatives has been introduced, leveraging L-arabinose as a novel catalyst. This approach not only underscores the feasibility of green chemistry in synthesizing high-purity quinoxaline derivatives but also highlights the enhanced sustainability of the process. Detailed mechanistic investigations revealed the synergistic interactions between L-arabinose and the reactants, providing a deeper understanding of the catalytic process. The synthesized compounds, due to their unique structural and electronic properties, may find promising applications in life and material sciences such as optoelectronics. Furthermore, our environmental impact assessment demonstrated significant reduction in generated waste, solvent use, and overall carbon footprint, aligning with the global agenda for sustainable development. This research marks a significant step forward in quinoxaline chemistry, promoting the adoption of green synthesis pathways while reinforcing the principles of sustainable and environment-friendly chemical practices.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 23","pages":"Pages 2024-2037"},"PeriodicalIF":1.8,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143175953","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Najla Altwaijry , Asmaa Saleh , Esam A. Ishak , Hamdi M. D. Nasr , Ismail M. M. Othman
{"title":"One-pot synthesis of new benzo[4,5]imidazo[1,2-a]pyrimidines and pyrazolo[1,5-a] pyrimidines as an eco-friendly and effective method catalyzed by acetic acid with prospective antimicrobial agents","authors":"Najla Altwaijry , Asmaa Saleh , Esam A. Ishak , Hamdi M. D. Nasr , Ismail M. M. Othman","doi":"10.1080/00397911.2024.2419872","DOIUrl":"10.1080/00397911.2024.2419872","url":null,"abstract":"<div><div>A novel set chalcones <strong>3a-d</strong> was efficiently synthesized in elevated produces across the condensing process of Claisen-Schmidt. An eco-friendly and efficient process was designed for creating a novel desired products <strong>5a-f</strong> and <strong>7a-f</strong>, respectively with excellent yields. This synthesis was accomplished by reacting acetophenone derivatives <strong>1a-d</strong>, heteroaromatic aldehydes <strong>2a,b</strong> and aminobenzoimidazole <strong>4</strong> or 3-aminopyrazole <strong>6a,b</strong>, using acetic acid as both the catalyst and solvent. Solvent optimization was performed during the synthesis of the desired compounds <strong>5a</strong> or <strong>7a</strong>, highlighting the benefits of using acetic acid that is harmless for the environment, which offers easy procedure, rapid reaction, elevated efficiency and broad tolerance of starting materials. The preferred products were verified through compatible spectroscopic data. The antimicrobial efficacious for all compounds was successfully evaluated against various microorganisms, revealing that <strong>3b</strong> exhibited significant antimicrobial activity across all tested microbes, with measurements of the minimum inhibitory concentrations being between 4.80 to 63.8 μM.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 23","pages":"Pages 2038-2051"},"PeriodicalIF":1.8,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143175928","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"2,3-Diaminonaphthalene-1,4-dione: Versatile precursor for the synthesis of molecular systems","authors":"Sherif M. H. Sanad","doi":"10.1080/00397911.2024.2435467","DOIUrl":"10.1080/00397911.2024.2435467","url":null,"abstract":"<div><div>The current review investigates the reactivity of 2,3-diaminonaphthalene-1,4-dione in the production of substituted and annulated 1,4-naphthoquinones. 2,3-Diaminonaphthalene-1,4-dione has two adjacent amino functions, allowing for reactions with a variety of electrophilic centers. They are regarded as effective chemical reagents capable of producing a wide range of heterocyclic derivatives with biological applications and favorable electrochemical properties. We reviewed all available papers on the synthesis of substituted 1,4-naphthoquinones via the reactions of 2,3-diaminonaphthalene-1,4-dione with various electrophiles. This review includes all reports in which 2,3-diaminonaphthalene-1,4-dione is annulated, yielding heterocycles with mono-, bi-, tri-, and tetracyclic rings. The review is divided into sections based on the type of annulation system and number of heteroatoms in each system.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 4","pages":"Pages 281-304"},"PeriodicalIF":1.8,"publicationDate":"2024-11-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143378072","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}