Regular Issues

9 data found. 1 - 9 listed

Published online: 17th November, 2022

Paper | Regular issue | Prepress
DOI: 10.3987/COM-22-14764
Synthesis and Antitumor Activity of Heterocylic Aurone and Its Analogue Indanone Derivatives

Heng Wu, Ayitila Maimaitijiang, Dan Tang, Baoxing Xie, Chao Niu,* and Haji Akber Aisa*

*State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, CAS Key Laboratory of Chemistry of Plant Resources in Arid Regions, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011 China


Based on non-classical bioisosterism and the rule of alkene insertion, thirty-five heterocyclic aurones and its analogue indanones derivatives were designed and synthesized. They were evaluated for inhibitory activity against HELA, HT-29 and A549 and HepG2 human cancer cell lines. Among them, twenty-five compounds exhibited moderate to excellent antitumor activity. The minimum value of IC50 was 1.649±0.083 μM (compound B1). The SAR showed that aurone with B ring as aromatic heterocycles such as 4-bromothiophene, quinoline, carbazole and indanone derivatives and some or indanone were more potent than others. Besides, the introduction of acetylated glycosides was beneficial to the activity. Compounds A1, B1, C5, C8, C10, C11, C12 and D1 were promising antitumor agents. Among them, compounds molecular docking studies were performed between B1, C8 and potential targets Aurora B (PBD: 2BFY). On the basis, the chemical and physical properties, as well as ADMET of active compounds were predicted and analyzed. And it showed that most of compounds had good pharmacokinetic profiles and high safety profiles.

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Published online: 17th November, 2022

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-22-14768
Direct Arylation of Benzothiophene and Benzofuran Catalyzed by a Dinuclear Palladium Complex

Takuma Mochizuki, Keiryu Seto, Yuma Sugiyama, and Naofumi Tsukada*

*Department of Chemistry, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan


Direct arylation of benzothiophene and benzofuran with iodoarenes proceeded in the presence of a dinuclear palladium complex formed by a chelate-bridging ligand. In the reaction of benzothiophene, β-arylbenzothiophenes were selectively obtained by using silver acetate as an additive. In the reaction of benzofuran, α-arylbenzofurans were selectively obtained by using silver sulfonate as an additive.

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Published online: 15th November, 2022

Paper | Regular issue | Prepress
DOI: 10.3987/COM-22-14760
Comprehensive Synthesis of 20 Fentanyl Derivatives for Their Rapid Differentiation by GC-MS Analysis

Takashi Kurohara, Takahito Ito, Genichiro Tsuji,* Takashi Misawa,* Hidetomo Yokoo, Maiko Kawamura, Takuji Shoda, Ruri Hanajiri-kikura, and Yosuke Demizu

*National Institute of Health Sciences, 3-25-26, Tonomachi, Kawasaki, Kanagawa 210-9501, Japan


Fentanyl, a selective agonist of opioid μ receptors, is a broadly used clinical agent for anesthesia and pain relief. Despite its clinical benefits, the abuse of fentanyl and its derivatives causes a number of health concerns, which are increasing at an alarming rate; its abuse has become a serious social problem. These compounds are often difficult to obtain as reagents, which hinders forensic toxicological analysis. Therefore, it is important to address their unavailability by synthesizing the structural derivatives of fentanyl. In this study, we synthesized 20 fentanyl derivatives, such as o- or p-fluorofentanyl and furanylfentanyl, and determined their purities using HPLC (95.2%−100%). Moreover, the GC-MS analysis of the synthesized fentanyl derivatives was performed for the rapid differentiation of the synthesized fentanyl derivatives. We demonstrate that our method achieves a convenient and efficient synthesis of fentanyl derivatives.

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Published online: 14th November, 2022

Paper | Regular issue | Prepress
DOI: 10.3987/COM-22-14770
Synthesis and Characterization of Some Novel Heteroannulated Chromeno[4,3-b]quinolines

Najla A. Alshaye and Magdy A. Ibrahim*

*Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Heliopolis 11757, Cairo, Egypt


The recently synthesized 1-chloro-11-oxo-3,4-dihydro-11H-chromeno[4,3-b]quinoline-2-carboxaldehyde (1) was efficiently utilized as a key precursor to construct a diversity of polyfused systems containing chromeno[4,3-b]quinoline. Reaction of compound 1 with some substituted hydrazines afforded pyrazoles annulated chromeno[4,3-b]quinoline. Treatment of compound 1 with a diversity of 1,3-N,N-binucleophiles led to pyrimidines annulated chromeno[4,3-b]quinoline. In addition, a diversity of fused pyridines annulated chromeno[4,3-b]quinoline were synthesized from condensation of compound 1 with a variety of 1,3-C,N-binucleophiles. Finally, the reactivity of compound 1 was tested towards a diversity of 1,4-binucleophilic reagents. Structures of the new compounds were established using spectral and analytical data.


Published online: 8th November, 2022

Paper | Regular issue | Prepress
DOI: 10.3987/COM-22-14745
Design, Synthesis and Biological Evaluation of Pyrimidinamine Derivatives Containing Urea Moiety

Weiqin Liu, Mi Hou, Qin Wang, Huayuan Tan, Litao Ji, Congyu Wang, Xuesha Long, Zhenchao Wang,* and Guiping Ouyang*

*School of Pharmaceutical Sciences, Guizhou University, Guizhou Guiyang, 550025, China


New series of 17 pyrimidinamine derivatives containing urea moiety were designed and synthesized. Their antitumor activity was investigated by MTT method. The results showed that some of these compounds exhibited moderate to good antitumor activities against all four cancer cell lines. The IC50 value of compound HD-6 on PC-3 cells was better 2.37 μM than the positive control drug sorafenib (3.66 μM). The inhibitory activity of most target compounds on HepG2 cells was better than that of positive drug sorafenib (10.70 μM). Among them, the IC50 value of compound HD-6 on K562 cells was 6.80 μM, which close to solafinib (4.62 μM). Further studies revealed that compound HD-6 clearly possessed apoptosis inducing effects, increased the level of reactive oxygen species, arrested the cycle in the G2/M phase and regulated the expression of tyrosine kinase EGFR in PC-3 cells.

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Published online: 25th October, 2022

Review | Regular issue | Prepress
DOI: 10.3987/REV-22-992
Recent Advances in the Synthesis of 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazole Compounds: A Mini-Review

Jin Luo,* Puqing Chen, and Chonghu Song

*Analytical and Testing Center, Jiangxi Normal University, Nanchang, Jiangxi 330022, China


1,2,4-Triazolo[3,4-b][1,3,4]thiadiazoles are important sulphur- and nitrogen-containing fused heterocycles that can act as promising scaffolds exhibiting outstanding biological activities. Herein, we focused on the major synthetic pathways and methodologies for the synthesis of 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole compounds in an attempt to facilitate the discovery of unique 1,2,4-triazolo[3,4-b]-[1,3,4]thiadiazole derivatives with improved biological activities.


Published online: 7th October, 2022

Review | Regular issue | Prepress
DOI: 10.3987/REV-22-993
Hydroxychloroquine: Chemistry and Medicinal Applications

Nidhi Yadav, Yogesh Kumar Tyagi,* and Ram Singh*

*Department of Applied Chemistry, Delhi Technological University, Delhi - 110042, India


Hydroxychloroquine (HCQ) is a molecule from the 4-aminoquinoline family which is utilized for the treatment of many diseases. This is one of the essential drugs, as per WHO. HCQ has been an anti-malarial drug and is also used for the treatment of autoimmune and rheumatic diseases. This molecule is repurposed for many types of diseases, either alone or in combination with other drugs. This review article discusses its synthetic methodologies and approved applications along with repurposed studies. This article covers HCQ applications in anti-cancer activity, anti-rheumatic activity, epigenetic activity, systemic lupus erythematosus, and COVID-19.


Published online: 6th September, 2022

Review | Regular issue | Prepress
DOI: 10.3987/REV-22-990
Mini Review on Pyrido[2,3-c]coumarins Backbone of Santiagonamine Antibiotics

Prasanta Patra* and Susanta Patra

*Chemisty, Jhargram Raj College, West Bengal, Jhargram College Rd, Jhargram, West Bengal, India


Santiagonamine is a natural coumarin fused pyridine, specifically pyrido[2,3-c]coumarin derivative having wound-healing activities and is extracted from stems and branches of the South American shrub Berberis darwinii Hook. It was isolated by Shamma et al. in 1984. Both coumarin and pyridine represent an important class of a multi tasking and multi functional scaffolds in organic synthesis. So, the syntheses of coumarin fused pyridine derivatives have an immense impact in the field of organic and pharmaceutical chemistry due to various biological activities displayed by such classes of compounds as well as for their natural occurrences. The main purpose of this review is to focus on different synthetic methodologies for the synthesis of specifically pyrido[2,3-c]coumarins as it is the backbone of santiagonamine antibiotics. Several methods for the synthesis of pyrido[2,3-c]coumarins have been described in the literature, most of which use 3-aminocoumarin as the starting material.


Published online: 22nd August, 2022

Review | Regular issue | Prepress
DOI: 10.3987/REV-22-988
The Azalogues of Pyrrolotetrazole – An Overview

Dietrich Moderhack*

*Institute of Medicinal and Pharmaceutical Chemistry, Technical University, D-38106 Braunschweig, Germany


This overview is dealing with the seven azalogues of pyrrolotetrazole, i.e., the systems AG, in all their manifold forms. Major interest is directed to the preparative chemistry, but theoretical work, in particular on the azolotetrazole–azidoazole isomerism ('ring–chain tautomerism'), will be looked at as well.

9 data found. 1 - 9 listed