Regular Issues

25 data found. 1 - 25 listed

Published online: 5th August, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14518
An Efficient Synthesis of 2-Amino-4-(Guaiazulen-1-Yl)-4H-chromenes via Cycloaddition of 1-Hydroxy-2-(3-Guaiazulenylium)benzenes with Malononitrile/Ethyl Cyanoacetate

Shuang Yang, Xin-Shuang Xiong, and Dao-Lin Wang*

*College of Chemistry and Material Science, Bohai University, Jinzhou, China


An efficient two-step method developed for the synthesis of 2-amino-4-(guaiazulen-1-yl)-4H-chromenes is described. The construction of these compounds was achieved by the reaction of guaiazulene and 2-hydroxy-benzaldehydes in the presence of perchloric acid, followed by cycloaddition of the resulting 1-hydroxy-2-(3-guaiazulenylmethylium)benzenes which allowed access to the title heterocycles.


Published online: 3rd August, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14515
A Convenient Synthesis of Novel 6-Aryl-5-phenyl-5-oxido-6,7-dihydro[1,3,4,2]thiadiazaphospholo[5,4-c][1,2,4,5]triazaphosphinines

Tarik E. Ali,* Mohammed A. Assiri, Abdullah Y. Alzahrani, and Mohamed A. Salem

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


A convenient method for design of novel 6-aryl-5-phenyl-5-oxido-6,7- dihydro[1,3,4,2]thiadiazaphospholo[5,4-c][1,2,4,5]triazaphosphinines was achieved. This method depended on three-component reaction of 5-hydrazino-1,3,4,2-thiadiaza- phosphole with aromatic aldehydes and phenyldichlorophosphine in dry THF. The methodology was easy, efficient, catalyst-free and good synthetic procedure.


Published online: 29th July, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14503
Design and One-Pot Synthesis of Some New [3,5-di(4’,5’-diphenyl-2’-substituted)-1H-imidazol-1-yl)]-1H-1,2,4-triazole Derivatives: in silico Admet and Docking Study, Antibacterial and Antifungal Activities Evaluation

Nadia Hadhoum,* Fatima Zohra Hadjadj-Aoul, Smain Hocine, Souhila Bouaziz-Terrachet, Amar Abdoun, Nacera Seklaoui, Fella Boubrit, Wissem Abderrahim, and Lamine Redouane Mekacher

*Department of Pharmacie, University Mouloud mammeri, Tizi Ouzou, Algeria


In this paper, a new series of some [3,5-di(4’,5’-diphenyl-2’- substituted)-1H-imidazol-1-yl)]-1H-1,2,4-triazole derivatives (C1-C9) were efficiently synthesized by a one-pot three component reaction via a coupling of benzil, aldehydes and 3,5-diamino-1,2,4-triazole and using ceric ammonium nitrate as a catalyst. The structures of the newly compounds were investigated by IR, 1H NMR, 13C NMR and UV-visible spectroscopy. The in vitro antibacterial and antifungal activities showed that the C9 is the most active compound. The C9 docking study revealed the best mode of binding in the active site of the cytochrome P450 lanosterol 14α-demethylase. All the synthesized compounds were predicted as non-carcinogens and demonstrated acceptable pharmacokinetic profile in blood brain barrier (BBB) and human intestinal absorption (HIA).

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Published online: 29th July, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14513
Microwave-assisted Synthesis of 2-Aminothiophene Derivatives via Improved Gewald Reactions

Bankang Ruan, Zhiyan Zhang, Lei Huang, Chao Xu, and Luolan Li*

*Shizhen College of Guizhou University of Traditional Chinese Medicine, Shizhen College, Guiyang, China


In this paper, a new and efficient method was developed to prepare 2-aminothiophene derivatives through improved Gewald reaction. Thirty-one final products were synthesized under microwave radiation for 30 min with 57%-95% isolated yield. All the products were could be used as building blocks in drug discovery.

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Published online: 27th July, 2021

Communication | Regular issue | Prepress
DOI: 10.3987/COM-21-14502
A Long-Wavelength Emission Fiuorescent Probe Based on TCF Derivatives for High-Sensitivity Detection of Hg2+

Yuan Sun, Keli Zhong, Lijun Tang,* and Xiaomei Yan*

*College of Chemistry and Materials Engineering, Bohai University, Jinzhou, 121013, China


A new fluorescent probe 1 that derived from 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (TCF) has been developed. Probe 1 displays selective recognition toward Hg2+ in MeOH/Tris (1:1, v/v, Tris 20 mM, pH = 7.4) solution through fluorescence turn on behavior. The Hg2+ sensing mechanism underwent Hg2+-triggered removal of thiocarbonyl moiety of probe 1, which resulting in releasing of the highly emissive compound 2. The Hg2+ recognition process holds some advantages including rapid response (<3 min), low detection limit (1.06 nM), and a large Stokes shift (160 nm). Cell imaging studies showed that probe 1 has membrane permeability and low toxicity to cells, and can be used to detect Hg2+ in living cells.

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Published online: 27th July, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14504
Four-Component Synthesis of Functionalized 1, 3, 4-Oxadiazole Derivatives Bearing the 2-Amino Benzothiazole Moiety

Milad Bazaz Rastkar, Bita Mohtat,* Gholam Bagheri Marandi, and Hoorieh Djahaniani

*Department of Chemistry, School of Sciences, Islamic Azad University Karaj Branch, Moazen St., Karaj 31485-313, Iran


A one-pot sixteen derivatives of N-((5-(aryl)-4H-pyrazol-3-yl)(aryl)methyl)benzo[d]thiazol-2-amine (5a–p) were synthesized from 2-aminobezothiazole, aromatic aldehyde, N-isocyaniminotriphenylphosphorane on reaction with aryl carboxylic acid derivatives under a catalyst-free condition in CH2Cl2 by a Ugi-4CR/aza-Wittig cyclization at room temperature in fairly good yields. The newly synthesized compounds were confirmed and deduced based on IR, 1H NMR, 13C NMR, and mass spectroscopy, and elemental analysis.

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Published online: 19th July, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14506
When Hydrazonoyl Chlorides Meet Allenes: a Site- and Regio-Selective Copper(I)-Catalysed Approach to 5-Substituted Pyrazoles

Giorgio Molteni,* Stefano Baroni, Marco Manenti, and Alessandra Silvani

*Department of Chemistry, University of Milano, Via Golgi 19, 20133 Milano, Italy


The reaction between hydrazonoyl chlorides and monosubstituted allenes in the presence of catalytic amounts of copper(I) chloride gives 1,3,5-substituted pyrazoles under mild conditions and very short reaction times. This site- and regioselective process involves first the complexation of copper(I) on the external double bond of the allene moiety, followed by nucleophilic attack on the central carbon atom of the so-formed copper(I)-complexed allene by the terminal nitrogen of the hydrazonoyl chloride. Subsequent ring closure to thetarget pyrazole ring is possible in the presence of electron-attracting groups on theallene moiety. A catalytic cycle has been proposed on the basis of the experimental results.

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Published online: 19th July, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14512
A Facile, Efficient and Catalyst Free Synthesis of Imidazole, Tetrazole and Pyrimidine Combined Moiety as Potential AntiMicrobial and AntiTubercular Agents

Nayankumar M. Panchani* and Hitendrakumar S. Joshi

*Department of Chemistry, Goverment Science College, Gariyadhar, C/O M.D. Patel Highschool, Nani Vavdi Road, Gariyadhar, Dis- Bhavnagar, India


The tetrazole fused pyrimidine system possesses a broad spectrum of biological activities. So, we have synthesized 5-(substitutedphenyl)-7-(1H- imidazol-4-yl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine derivatives (5a-n) by reaction of chalcones with 5-aminotetrazole without catalyst in appropriate solvent. The structural elucidation of these compounds is based on MS, IR, 1H-NMR and 13C-NMR spectral data. The in vitro anti-microbial activity was investigated against Gram-positive and Gram-negative bacterial and fungal strains. It was found that the compounds 5a, 5b, 5c, 5d, 5e showed significant activities against tested organisms as compared to standard drugs (Ampicillin and Griseofulvin) while compounds 5a, 5c, 5i, and 5k showed good percentage of average inhibition in the dormant and active stage of tuberculosis.

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Published online: 7th July, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14454
Application of a New 4'‎‎‒‎‎‎Functionalized 2,2': 6',2''‎‎‒‎‎‎Terpyridine Ruthenium(II) Complex as a Sensitizer in Dye Sensitized Solar Cells

Azam Nasirian,* Valiollah Mirkhani,* Majid Moghadam,* Shahram Tangestaninejad, and Iraj Mohammadpoor-Baltork

*Department of Chemistry, Catalysis Division, University of Isfahan, 81746‎‎‒‎‎‎73441, Isfahan, Iran


In this work, the synthesis of a Ru(II) complex derived from 4'‎‎‒‎‎‎functionalized‎‎‒‎‎‎2,2':6',2''‎‎‒‎‎‎terpyridine ligand was described and the its spectral property of this complex was investigated. We synthesized this ligand and used that for the synthesis of Ru(II) complex. Ligand and complex were characterized by UV–vis, FT‎‎‒‎‎‎IR, ESI-MS, CHN analysis and NMR methods. After synthesis and characterization of this complex, we investigated the application of this complex as a photosensitizer in manufacturing of dye-sensitized solar cells. A sandwich cell was prepared using the dye anchored TiO2 film as a working electrode and a second conducting glass coated with chemically deposited platinum as a counter electrode. The application of this complex in a dye-sensitized nanocrystalline TiO2 solar cell has demonstrated a short-circuit current density of 12.84 mA, with an open circuit potential of 0.69 V. The total efficiency of this dye-sensitized solar cell with this complex was 4.97%.

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Published online: 6th July, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14505
Three New Anti-Rotavirus Chromeno[3,2-c]pyridines from the Whole Plant of Thalictrum scabrifolium

Qiu-Fen Hu, Fan Wu, Tao Zhou, Min Zhou, Ya-Ning Zhu, Bing-Biao Cai, Ming-Xin Liu, Man-Fei Li, Guang-Yu Yang,* and Yin-Ke Li*

*Key Laboratory of Chemistry in Ethnic Medicinal Resources, Yunnan Minzu University, Kunming 60500, P. R. China


Three new chromeno[3,2-c]pyridines (1-3) were isolated from the whole plants of Thalictrum scabrifolium. Their structures were elucidated by spectroscopic methods, including extensive 1H, 13C, and 2D-NMR techniques. Compounds 1-3 were also tested for their anti-rotavirus activity, and they exhibited potent anti-rotavirus activity with therapeutic index (TI) valves of 23.7, 18.3, and 19.2 respectively.

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Published online: 2nd July, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14499
New and Practical Synthesis of GS-441524, the Key Intermediate of Remdesivir

Bo Li, Han Wang,* Cong Sun, Sheng Lu, LinLin Kang, and Shun Jiang

*College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620, China


A new and practical synthesis of GS-441524, the key intermediate for remdesivir, is developed. 4-Amino-7-iodopyrrolo[2,1-f][1,2,4]triazine is protected by DMF-DMA, and reacted with 2,3,5-tri-O-benzyl-D-ribonolactone to give the product in 61% isolated yield. The next cyanation and debenzylation are carried out at −30 °C successively in 67% yield over two steps with >99% purity (HPLC). Purification methods of the intermediates and the final product involved in the route are developed.

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Published online: 2nd July, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14500
New Synthesis of Abexinostat

Xiaolei Zhu, Han Wang,* Sheng Lu, Cong Sun, Zhiyong Xu, and Jingli Xu

*College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620, China


A practical and convergent synthetic route of abexinostat was developed successfully. The key intermediate 3-((dimethylamino)methyl)- benzofuran-2-carboxylic acid (16) was prepared from 1-(2-hydroxyphenyl)ethan-1-one in 76.6% yield over 4 steps. Methyl 4-(2-aminoethoxy)benzoate hydrochloride (20) was synthesized from methyl 4-hydroxybenzoate in 97.0% yield over 2 steps. Abexinostat was obtained from 16 and 20 in 72.4% yield over 2 steps and 98.7% purity. Purification methods of the intermediates and the final product involved in the route were developed.

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Published online: 25th June, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14494
Synthesis, Antimicrobial and Antitumor Study of New Pyrido[2,1-a]isoquinolines via Isoquinoline-1-acetonitrile

Mohamed A. Mohamed Teleb, Hamdi M. Hassaneen,* Hyam A. Abdelhadi, Yara N. Laboud, and Fatma M. Saleh

*Department of chemistry, Faculty of science, University of Cairo, Giza 12613, Egypt


Refluxing of enaminonitrile 3 with arylacetonitriles 2 in ethanol in the presence of piperidine afforded 4H-pyrido[2,1-a]isoquinoline-1-carbonitriles 6. Refluxing of 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile 1 with ethyl 3-aryl-2-cyanoacrylates 9 in acetonitrile in the presence of piperidine gave the corresponding 4H-pyrido[2,1-a]isoquinoline-1,3-dicarbonitriles 13. All the new synthesized compounds were identified by elemental analysis and spectral data. Cytotoxic assay was investigated for in vitro antitumor screening against MCF7, HepG2 and HCT-116 cell lines. Molecular docking using software was carried out for the most potent compound 6b. The results are compared with doxorubicin standard anticancer drug. Antimicrobial activities were investigated, and all compounds revealed no antimicrobial activities against all tested strains except compounds 13b and 13e.

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Published online: 22nd June, 2021

Review | Regular issue | Prepress
DOI: 10.3987/REV-21-964
Synthesis of Multisubstituted Benzofurans/Indoles Using Multichlorinated Phenols/Anilines via Palladium-Catalyzed Site-Selective Sonogashira Coupling

Miyuki Yamaguchi and Kei Manabe*

*School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga, Shizuoka 422-8526, Japan


Multisubstituted benzofurans/indoles are a critical class of compounds in the fields of pharmaceuticals and natural products. A useful method of preparing 2-substituted benzofurans/indoles is the Pd-catalyzed Sonogashira coupling of 2-halophenols/2-haloanilines and terminal alkynes, followed by cyclization. For the syntheses of multisubstituted benzofurans/indoles, the use of multichlorinated phenols/anilines as coupling partners is powerful because the synthetic steps required are reduced and all dichlorophenol and dichloroaniline positional isomers are commercially available and inexpensive. However, their use in benzofuran/indole synthesis is limited because of their low reactivity compared with those of the corresponding iodo or bromo compounds. Furthermore, site-selective Sonogashira coupling at the 2-position of the multihalogenated phenols/anilines is sterically and electronically challenging. To overcome these problems, dihydroxyterphenylphosphine (DHTP) has been developed as a ligand that enables the highly ortho-selective Sonogashira coupling of 2-chlorophenols/2-chloroanilines with terminal alkynes. Using the Pd–DHTP catalyst, chlorinated benzofurans/indoles are successfully obtained, which are easily converted to other derivatives by substitution of the chloro group. In this review, we summarize this and related studies to demonstrate the utility of this method.


Published online: 17th June, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14496
Natural Osthole-Based Ester Derivatives as Potential Fungicidal Agents: Design, Synthesis and Quantitative Structure-Activity Relationship (QSAR)

Yong-Ling Wu,* Yong Yan, Tin-Tin Pan, and Dou-dou Wang

*College of Biology Pharmacy and Food Engineering, Shangluo University, Shangluo 726000, Shaanxi, China


Turning potential natural products into value-added fungicides is a bioactivity-guided mixed synthesis method. Thirty-two derivatives were designed and synthesized to improve the potential use of the osthole, a natural coumarin pharmacophore. Compound Os14 with 3-ClPh showed a high in vitro and in vivo antifungal activity than other derivatives. The preliminary structure-activity relationships (SARs) demonstrated that compounds with a short aliphatic chain or electron-withdrawing groups on phenyl ring would have more desirable potency. Meanwhile, the quantitative structure-activity relationship (QSAR) model (R2 = 0.928, F = 83.54, S2 = 0.0042) were performed using Gaussian and CODESSA software with optimal conformers and heuristic regression analysis, which revealed a correlation of antifungal activity and molecular structures. Thus, these results laid the foundation for further design of improved crop-protection agents based on osthole scaffold.

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Published online: 15th June, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14493
Concise Synthesis of Eutigoside C

Shiqiang Yan, Yueyue Zhu, Lisha Wu, Liqun Chi,* and Wei Zhang*

*School of Pharmacy, Fudan University, Shanghai, 201203, China


Eutigoside C, a new glucoside with a variety of biological activities, was synthesized via regioselective Me2SnCl2-catalyzed O-6 acylation and mild oxidation strategy. Through this route, eutigoside C was obtained from inexpensive starting materials in a linear 5-step sequence with an overall yield of 35.2%.

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Published online: 11th June, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14488
Organocatalyzed Three-Component Synthesis of Isoxazol-5(4H)-ones under Aqueous Conditions

Zeinab Faramarzi and Hamzeh Kiyani*

*School of Chemistry, Damghan University, 36719-41167 Damghan, Iran


The three-component cyclocondensation was performed using various frequently available aryl/heteroaryl aldehydes, hydroxylamine hydrochloride, and β-ketoesters in water as a green reaction medium at 80 °C. In this reaction, isoxazol-5(4H)-ones were obtained in the presence of 2-aminopyridine as an efficient and low-cost organocatalyst. The present methodology offers sustainable approach with appreciable yields of the desired heterocycles. This procedure has expectant features, including shorter reaction times, easy separation of pure products, avoiding the hazardous organic solvents, simplicity experimental procedure, operationally simple, and eco-friendly. The heterocyclic structures were characterized using physical properties and analysis of spectral data.


Published online: 26th May, 2021

Review | Regular issue | Prepress
DOI: 10.3987/REV-21-962
Chemical Transformation of Chromones into Coumarins

Aya Ahmed, Magdy A. Ibrahim, and Al-Shimaa Badran*

*Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, 11711, Cairo-Egypt


The essential focus of the present review is to collect the chemical reactions of chromone derivatives involving their transformation into coumarin derivatives. A diversity of coumarins was efficiently synthesized from the reactions of chromones with some nucleophilic reagents. This review includes the reactions of chromone derivatives with nitrogen and carbon nucleophiles, (acyclic and cyclic) leading to coumarins.


Published online: 24th May, 2021

Review | Regular issue | Prepress
DOI: 10.3987/REV-21-960
Synthesis and Chemistry of Phosphorus Compounds Substituted by 1,2,4-Triazine Moieties as Medicinal Probes

Abdulrahman S. Alharbi* and Reda M. Abdel-Rahman

*Department of Chemistry, Faculty of Science, King Abdul Aziz University, P.O. Box. 42805 Jeddah, 21551, Saudi Arabia


Design, synthesis, and chemical behaviors of various phosphorus compounds containing and/ or bearing 1,2,4-triazine moieties are received. Besides, the medicinal, biocidal, and biological activities of these targets were reported. A relation between P-C, P-O, P-N, and P-S bonds was also studied.


Published online: 10th May, 2021

Review | Regular issue | Prepress
DOI: 10.3987/REV-21-956
Synthetic Approaches toward Certain Structurally Related Antimicrobial Thiazole Derivatives (2010-2020)

Abdelfattah Hassan, Heba A. Hassan, Dalia Abdelhamid, and Gamal El-Din A. Abuo-Rahma*

*Medicinal Chemistry Department, Faculty of Pharmacy, Minia University, Minia, Egypt & Pharmaceutical Chemistry Department, Faculty of Pharmacy, Deraya University, New Minia, Minia, Egypt


In the present literature review, we comprehensively discuss different methods of synthesis of published antimicrobial thiazole derivatives in the last decade mainly those which showed antibacterial, antimycobacterial and/or antifungal activity. Owing to the great diversity of thiazole-derived antimicrobial agents, we organized most of them chemically in stipulated classes. In each class, we mentioned common methods of thiazole ring closure and indicated antimicrobial activity of the most active derivatives in clear and simple way.


Published online: 28th April, 2021

Review | Regular issue | Prepress
DOI: 10.3987/REV-20-953
Recent Achievements in the Synthesis of Heterocyclic Compounds by Phthalhydrazide-Based Multicomponent Reactions

Ghodsi Mohammadi Ziarani,* Negar Jamasbi, and Fatemeh Mohajer

*Department of Chemistry, Faculty of Physic and Chemistry, Alzahra University, Tehran, Iran. P. O. Box 1993893973


Phthalhydrazide is one of the useful starting material toward the synthesis of heterocyclic compounds, and considered as a valuable structural unit in organic synthesis due to its significant pharmacological and biological activities. There are many multicomponent reactions using phthalhydrazide under different conditions. This review article aims to give an overview of recent applications of phthalhydrazide in the multicomponent reactions during the period of 2006 to 2021.


Published online: 15th April, 2021

Review | Regular issue | Prepress
DOI: 10.3987/REV-21-958
Recent Advances in 1,2,4-Triazole Ring Construction via Cycloaddition Reactions

Nataliya Korol,* Mikhailo Slivka, and Oksana Holovko-Kamoshenkova

*Organic synthesis laboratory, Faculty of Chemistry, Uzhhorod National University, Uzhhorod 88000, Ukraine


The sources, describing cycloaddition reactions that lead to obtaining of substituted 1,2,4-triazoles and their fused derivatives were reviewed. The review article covers the literature data published in the period 2011-2021. Synthetic particularities of cycloaddition products, the optimization of reaction conditions, factors that influence on the direction of the reaction are reasonably mentioned. Cycloaddition reactions are presented as convenient method for obtaining of as functional 1,2,4-triazoles, as well as their fused derivatives.


Published online: 12th April, 2021

Review | Regular issue | Prepress
DOI: 10.3987/REV-20-950
Iodine-Containing 4,7-Dihalobenzo[b]thiophene Building Blocks and Related Iodobenzo[b]thiophenes: Promising Molecular Scaffolds for Bio-Inspired Molecular Architecture

Kozo Toyota* and Shinichi Mikami

*Department of Chemistry, Graduate School of Science, Tohoku University, Aoba, Sendai, Miyagi 980-8578, Japan


This review describes preparations and reactions of 4,7-dihalobenzo[b]thiophenes bearing iodine atom(s). A short survey of typical preparative methods for iodobenzo[b]thiophenes and relatively simple benzo[b]thiophenes is included. Reactions of the iodine-containing 4,7-dihalobenzo[b]thiophenes are shown and their application to α helix-inspired artificial molecular architecture is referred.


Published online: 30th March, 2021

Review | Regular issue | Prepress
DOI: 10.3987/REV-21-955
The Fascinating Chemistry of Mesoionic 4-Trifluoroacetyl-1,3-oxazolium-5-olates and Related Compounds

Ryosuke Saijo and Masami Kawase*

*Faculty of Pharmaceutical Sciences, Matsuyama University, 4-2 Bunkyo-cho, Matsuyama, Ehime 790-8578, Japan


This review illustrates the unexpected and unique transformation of mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (4-TFMK-münchnones) on treatment with different nucleophiles. A trifluoromethyl group that cannot be synthesized by the usual methods is incorporated in the products. The research discussed in this review is focused on the rich chemistry of 4-TFMK-münchnones. In particular, we highlight the recent advances in their use in contemporary organic synthesis, primarily of trifluoromethyl-substituted heterocycles. The chemistry of related mesoionic compounds is also discussed.


Published online: 23rd March, 2021

Review | Regular issue | Prepress
DOI: 10.3987/REV-21-957
Synthesis and Structure−Activity Relationship Study of Intervenolin, an Antitumor and Anti-Helicobacter Pylori Quinolone Natural Product

Takumi Watanabe*

*Institute of Microbial Chemistry, Tokyo (BIKAKEN), 3-14-23 Kamiosaki Shinagawa-ku, Tokyo 141-0021, Japan


This review article overviews the chemistry and biology of intervenolin, a quinolone natural product bearing unusual substituents. Intervenolin was isolated as a modulator of tumor–stroma interactions, communication between tumor cells and surrounding normal cells to regulate tumor-associated events including proliferation. The synthesis of intervenolin by the author employs thiocyanate–isothiocyanate rearrangement and Suzuki–Miyaura cross coupling as key reactions, which was utilized in structure–activity relationship studies. The SAR studies generated analogs that are effective in vivo. Moreover, several intervenolin and analogs also showed anti-Helicobacter pylori activity. Mechanistic aspects of these biological activities, and synthetic study on structurally related natural products by Spring and co-workers are also discussed.

25 data found. 1 - 25 listed