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Published online: 17th June, 2021

Communication | Regular issue | Prepress
DOI: 10.3987/COM-21-14470
Synthesis of Tetraphenyl-Furoindoles via Tandem Reactions

Shi-Yun An,* Jin-Long Zhang, and Gao-Xi Jiang*

*State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. of China

Abstract

We report a novel one-step synthesis of tetraphenyl substituted furoindoles involving acid-catalyzed cascade approach of commercially available m-aminophenols with readily accessible α-hydroxyaldehydes. The tandem reactions involved nucleophilic addition, aldimine condensation, pinacol rearrangement, α-iminol rearrangement, cyclization and dehydration aromatization process. The yield of furoindoles was up to 75%.

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Published online: 17th June, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14482
Diterpenoid Alkaloids from Aconitum Leucostomum and Their Antifeedant Activity

Jue Wang, Jin-bu Xu, Hong-bo Yang, Feng Gao, Xian-li Zhou, Lin Chen,* and Shuai Huang*

*School of Life Science and Engineering, Southwest Jiaotong University, Southwest Jiaotong University, Chengdu, 610031, China

Abstract

Two new diterpenoid alkaloids and eight known ones were isolated from the root of Aconitum leucostomum. Their structures were elucidated on the basis of extensive spectroscopic analyses such as HR-ESI-MS, 1D NMR and 2D NMR spectra. Compounds 1, 2, 5, 6 and 8 were tested for their antifeedant activity against Spodoptera exigua Hübner, and compound 2 showed antifeedant activity with an effective concentration for 50% feeding reduction (EC50) at 1.54 mg/cm2.

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Published online: 17th June, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14484
Three New Anti-Rotavirus Quinoline Alkaloids from the Whole Plant of Thalictrum Glandulosissimum

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

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

Abstract

Three new quinoline alkaloids, 4-acetyl-6-methyl-7-(3-methyl-2-oxobut-3-enyl)quinolin-2(1H)-one (1), 4-acetyl-5-methyl-7-(3-methyl-2-oxobut-3-enyl)quinolin-2(1H)-one (2), and 4-acetyl-6-methyl-7-prenylquinolin-2(1H)-one (3) were isolated from the whole plants of Thalictrum glandulosissimum. 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. Compounds 1-3 exhibited potent anti-rotavirus activity with therapeutic index (TI) valves of 17.6, 15.0, and 23.6 respectively.

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Published online: 17th June, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14496
Natural Osthole-Based Ester Derivates 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

Abstract

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-21-14487
Synthetic Approaches for Nitrogen Bridgehead Pyrido-[1,2-b][1,2,4]triazepines and Annulated Compounds Using 4-(8-Allylchromon-3-yl)-1,6-diamino-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile

Magdy A. Ibrahim*

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

Abstract

Some new nitrogen bridgehead pyrido[1,2-b][1,2,4]triazepines linked 8-allylchromone moiety have been synthesized from reaction of novel 4-(8-allyl-chromon-3-yl)-1,6-diamino-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile (3) with a variety of α,γ-bifunctional electrophiles including dibenzoylmethane, ethyl benzoylacetate, 3-[bis(methylthio)methylidene]pentane-2,4-dione, 2-cyano-3,3-bis(methylthio)acrylonitrile, 2-cyano-3,3-bis(methylthio)prop-2-enamide, 5-chloro-3-methyl-1-phenylpyrazole-4-carboxaldehyde, 2-chloro-3-formyl-quinoline, (p-methoxybenzylidene)malononitrile and ethyl 2-cyano-3-(4-methoxyphenyl)prop-2-enoate. Some novel pyrazolo[3,4-e]pyrido[1,2-b]-[1,2,4]triazepines were also synthesized. Structures of the newly synthesized products have been deduced upon the help of elemental analysis and spectral data (IR, 1H NMR, 13NMR, mass spectra).

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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

Abstract

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: 14th June, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14115
Alternative Approach to the 2-Oxopyrano[3,2-c]quinoline Core

Alexa Redway, Roxanne Higgins, Yvette Jackson, and Nadale Downer-Riley*

*Department of Chemistry, the University of the West Indies, Mona, Kingston 7, Jamaica

Abstract

An alternative route to access the pyrano[3,2-c]quinoline or benzo[7,8]-6-azacoumarin core form readily available quinoline N-oxides is presented. The key reaction involves an unusual rearrangement of tetrahydroquinoline-2-ylacetic acids in the presence of triethylamine and acetic anhydride.

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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

Abstract

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.

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Published online: 8th June, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14481
Synthesis, Characterization, and DRAK2 Inhibitory Activities of Hydroxyaurone Derivatives

Mingsheng Zhao, Chengqiu Dai, Yi Li, Yinan Liu, Jing-Ya Li,* and Xueling Hou*

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

Abstract

We reported the synthesis of 25 derivatives of hydroxyaurone, which were characterized by 1H NMR, 13C NMR, high resolution mass spectrum, and single crystal X-ray diffraction analysis. Their activities on the death-associated protein kinase-related apoptosis-inducing kinase-2 (DRAK2) were evaluated by kinase detection kit at a dosage of 5μM. Most of the synthetic hydroxyaurones exhibited moderate to good inhibitory activities. The IC50 value ranged from 0.81 to 2.42 μM when the structure of aurone's B ring was kept unchanged and its A ring was substituted by hydroxyl groups. On the contrary, modification of the aurone's B-ring with hydroxyl groups lead to the IC50 value ranging from 1.15 to 17.5 μM. This indicates presence of hydroxyl group of the B ring is crucial for aurone's DRAK2 kinase inhibitors. Therefore, hydroxyaurone may serve as a new possible lead compound for the discovery of DRAK2. Further pharmacological investigations are underway and will be reported in due course.

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Published online: 3rd June, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14462
A New Denudatine Type C20-Diterpenoid Alkaloid from Aconitum fischeri var. arcuatum

Lili Qin, Feng Xing, Lin Chen,* and Xianli Zhou*

*School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, Sichuan, People’s Republic of China

Abstract

A new denudatine-type C20-diterpenoid alkaloid bearing a rare C-15 ketone carbonyl and 16,17-epoxy group, named arcutisine (1), together with 24 known compounds (2-25), were obtained from the roots of Aconitum fischeri var. arcuatum. Their structures were established by various spectroscopic analyses. Among them, compounds 1 and 2 were both isolated from a natural source for the first time. Besides, compounds 7 and 10 showed weak effect on anti-inflammatory activity with the inhibition rate of 33.5% and 33.7% at the concentration of 40 µM.

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Published online: 1st June, 2021

Paper | Special issue | Prepress
DOI: 10.3987/COM-21-S(R)2
New Sugar Based γ-Amino Silyl Ether Organocatalysts for Asymmetric Michael Addition of β-Keto Esters with Nitroolefins

Divakar Ganesan, Perumalsamy Parasuraman, Zubeda Begum, Rajkumar Thiyagarajan, Chigusa Seki, Yuko Okuyama, Eunsang Kwon, Koji Uwai, Michio Tokiwa, Suguru Tokiwa, Mitsuhiro Takeshita, and Hiroto Nakano*

*Graduate School of Engineering, Muroran Institute of Technology, 27-1 Mizumoto-cho, Muroran 050-8585

Abstract

New sugar based γ-amino silyl ether organocatalysts were synthesized and their catalytic ability was examined in asymmetric Michael addition of β-keto esters with nitroolefins affording chiral Michael adducts with quaternary carbon stereocenter in good to excellent chemical yields, diastereoselectivities and moderate enantioselectivities (up to 97%, up to dr. 85:15, up to 56% ee).

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Published online: 27th May, 2021

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-21-S(R)1
Lipase-Catalyzed Site-Selective Deacetylation of 2-Methoxy-3-methylnaphthalene-1,4-diol Diacetate for Construction of Characteristic Substituted 1,2,3,4-Tetrahydroisoquinoline Derivative of Novel Ecteinascidin Marine Natural Product

Masashi Yokoya,* Ryo Sato, and Naoki Saito

*Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Abstract

We developed a site-selective deacetylation of 2-methoxy-3-methylnaphthalene-1,4-diol diacetate catalyzed by Candida antarctica lipase B, which furnished 1-hydroxy-2-methoxy-3-methylnaphthalen-4-yl acetate in 88% yield. This product was transformed into 2-methoxy-3-methylnaphthalen-1-ol in a five-step sequence (30.5% overall yield from 7a). It is a novel procedure for preparing a characteristic A ring substituted system for both safracin antibiotics (2) and ecteinascidin marine natural products (1).

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Published online: 27th May, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14479
Multicomponent Reaction for the Synthesis of 1,2,3,4,6-Pentasubstituted Piperidines Catalyzed by NIS

Liu Pengpeng*

*School of Petroleum and Chemical Engineering, Dongying Vocational Institute, Dongying, 257091, China

Abstract

An efficient, suitable and high yielding method has been developed for the synthesis of substituted piperidines via multicomponent, one-pot domino reaction of β-keto ester, aromatic amines, and aromatic aldehydes in the presence of catalytic amount of N-iodosuccinimide (NIS) in ethanol. Atom economy, mild reaction conditions, good to excellent yields, operational simplicity and easy work-up are some of the important features of this method.

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Published online: 26th May, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14467
Biological Evaluation and Synthesis of Thiazole Schiff Base Derivatives

Wei Zhou, Fengyan Wu, and Jinbing Liu*

*School of Food and Chemical Engineering, Shaoyang University, Shao Shui Xi Road, Shaoyang 422100, PRC

Abstract

In this study, we report the synthesis of thiazole Schiff base derivatives (Z1-Z16) and their tyrosinase inhibitory activity, anti-oxidant activities. Mushroom tyrosinase inhibitory assay showed compound Z8 (IC50 = 2.78 ± 0.08 μM) inhibited tyrosinase more than kojic acid (49.39 ± 0.17 μM), and docking study indicated compound Z8 (-7.32 kcal/mol) had stronger binding affinities for tyrosinase than kojic acid (-5.7 kcal/mol). Phenolic hydroxyl group on 4-position (R2) of compound Z8 can form Metal - Acceptor with Cu401. The results of inhibition kinetics studies demonstrated that compound Z8 was mixed type inhibitor. The anti-browning effects manifested compound Z8 expressed satisfactory effects in anti-browning of fresh-cut apples and fresh-cut potato. All the results indicated that thiazole Schiff base derivatives might be promising leading compounds as tyrosinase inhibitors and anti-oxidant agents.

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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

Abstract

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.

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Published online: 25th May, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14457
Preparation of Pyridine Derivatives from the Corresponding 5-Acetal-1-carbonyl Compounds by Acid Promoted Cyclization

Hiromichi Mihara, Yuki Watanabe, and Hiroyuki Konno*

*Department of Biological Engineering, Graduate School of Science and Engineering, Yamagata University, Yonezawa, Yamagata 992-8510, Japan

Abstract

The synthesis of four alkylpyridine derivatives from 5-acetal-1-carbonyl compounds via the one-pot, acid-promoted cyclization of oxime intermediates is described. In addition, a dihydroxypyridine and pyridinium salt were also synthesized. The pyridine formation step was not affected by the stereochemistry of the precursors used.

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Published online: 25th May, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14464
Metal-Free Regioselective Synthesis of 2-Nitro-3-arylimidazo[1,2-a]pyridines via Oxidative Amination under Air Using Silica Sulfuric Acid as an Effective Heterogeneous Catalyst

Divya Sree Uppalapati,* Rama Sekhara Reddy Dachuru,* and Satya Veni Sunkara

*Department of Chemistry, University College of Engineering Kakinada, Jawaharlal Nehru Technological University Kakinada, Kakinada 533003, Andhra Pradesh, India

Abstract

Metal-free regioselective strategy for the synthesis of 2-nitro-3-arylimidazo[1,2-a]pyridines from β-nitrostyrene and 2-aminopyridines under aerobic conditions using silica sulfuric acid (SSA) as heterogeneous catalyst has been developed. The synthetic methodology provides the title compounds with good yields under mild conditions, and complete regioselectivity is observed. Furthermore, SSA was not used previously for this transformation.

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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

Abstract

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.

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Published online: 24th May, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14474
Synthesis and Biological Activity Evaluation of Imidazole Heterocyclic Sulfonylurea Compounds

Wei Li, Jinze Pei, Yang Chen, and Guangshan Xuan*

*College of Chemical Engineering, Qingdao University of Science & Technology, 53 Zhengzhou Road, Shibei District, Qingdao, Shandong Province, China

Abstract

Sulfonylurea herbicides are the most widely used herbicides in the world. They have the advantages of high efficiency, good selectivity, and no toxicity to human and animals. In this study, sulfonylureas containing imidazole heterocycles were synthesized on the basis of computer simulation of molecular docking, and the biological activity was evaluated. It shows that the compound has a good inhibitory effect on the ALS and a certain inhibitory effect on the phytopathogenic fungi of Curvularia lunata and Curvularia mebaldsii. Its inhibitory rate at concentration of 50 mg/L is similar to that of the carbendazim. This research provides the basis for further optimization of the structure of imidazolium heterocyclic sulfonylurea and the synthesis of its derivatives.

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Published online: 21st May, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14463
Synthesis of One Covalent Organic Framework (COF) Based on C=N Bonds and Its Excellent Performance of Iodine Adsorption

Yingbin Zhang, Limei Li, Meige Wang, and Zhongyu Duan*

*School of Chemical Engineering, Hebei University of Technology, 1 Dingzigu Road, Tianjin, 300130, China

Abstract

Radioactive iodine is one of the main substances existed in nuclear wastes. It can quickly diffuse into the atmosphere causing great harm to environment and human health. Therefore, how to capture radioactive iodine efficiently has become a research hotspot. Herein, a covalent organic framework (COF) material (COF-1) has been synthesized by aldimine condensation reaction using the 1,3,5-triazine structure compound and isophthalaldehyde as starting materials. The nitrogen-rich COF-1 possesses medium specific surface area (321.78 m2/g), a pore diameter of 1.98 nm and relatively regular layered stack structure, which provide good conditions for iodine adsorption ability. The maximum iodine uptake of COF-1 is 2647 mg/g, which is higher than most iodine adsorbents reported. Subsequently, the release of iodine can be achieved in methanol indicating the iodine adsorption of COF-1 is a reversible process. It is also shown that COF-1 can be recycled. These characteristics maybe make COF-1 materials as a good iodine capturer in practical applications.

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Published online: 21st May, 2021

Communication | Regular issue | Prepress
DOI: 10.3987/COM-21-14465
Novel Reaction Course of Thiiranes to Vinyloxiranes: Reaction of Benzyne with Thiiranes and Aldehydes

Kentaro Okuma,* Yuxuan Qu, and Noriyoshi Nagahora

*Department of Chemistry, Fukuoka University, Jonan-ku, Fukuoka 814-0180

Abstract

Reaction of 2 molar amount of 2-(trimethylsilyl)phenyl triflate with thiiranes and aldehydes in the presence of CsF afforded vinyloxiranes in one-pot operation. Reaction of benzyne with thiiranes gave the corresponding alkenyl phenyl sulfides, which further reacted with another molar of benzyne to afford sulfonium ylide intermediates. Further treatment of aldehydes gave the corresponding vinyloxiranes.

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Published online: 20th May, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14431
Direct Construction of 9-Amino-7-aryl-6H-benzo[c]chromene-8,10-dicarbonitriles by Means of a Cascade Michael/Cyclization Reaction

Dao-Cal Wang,* Yi Luo, Xi-Xia Chen, and Xiao-Peng Liu*

*Hubei Key Laboratory of Biologic Resources Protection and Utilization, School of Biological Science and Technology, Hubei Minzu University, Enshi 445000, China

Abstract

An easy and practical synthesis method was developed for the preparation of potentially biologically active 9-amino-7-aryl-6H-benzo[c]chromene-8,10-dicarbonitriles. Starting from chroman-4-one derivatives, aldehydes and malononitrile, the one-pot three-component reaction went on smoothly in the presence of DBU at 60 °C for 32 hours using tetrahydrofuran as solvent. More diverse 9-amino-7-aryl-6H-benzo[c]chromene-8,10-dicarbonitriles were synthesized and separated in good yields. The outstanding advantages of this demonstrated method mainly reflects in the easy access to starting materials, high atom economical manner, simple operation steps and wide applicability.

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Published online: 20th May, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14432
Uncommon Reactivity of a Seco-Oxacassane Diterpenoid and Antiproliferative Activity of Some Derivatives

Alexia Hernández-Jiménez, Ledy De-la-Cruz-Martínez, Raúl Velasco-Azorsa, Reyna Zeferino-Díaz, José G. Alvarado-Rodríguez, Luis H. Mendoza-Huizar, J. Jesús Manríquez-Torres, Horacio Almanza-Reyes, Carlos M. Cerda-Garcia-Rojas, Pedro Joseph-Nathan, and J. Martín Torres-Valencia*

*Área Académica de Química, Universidad Autónoma del Estado de Hidalgo, km 4.5 Carretera Pachuca-Tulancingo, Mineral de la Reforma, Hidalgo 42184, México

Abstract

The main diterpenoid of Acacia schaffneri, 7,8-seco-7,8-oxacassa-13,15-dien-7-ol-17-al (1), has two aldehydes of which one is protected as a ε-lactol. The free aldehyde resisted to afford the carboxylic acid using reagents with different oxidative strength, although 1 gave oxime 2 when treated with hydroxylamine, β-hydroxyketone 3 after addition of acetone, aldo-ε-lactone 4 whereby only the lactol was oxidized when using Jones reagent, and epoxyformate 5 after Baeyer-Villiger treatment. Hydrolysis of 5 with NaHCO3 gave 6. Structures 26 followed from physical and spectral data including X-ray diffraction. All compounds showed antiproliferative activity similar to some chemotherapeutic drugs against C2C12, L929, SiHa, and MDA-MB-231 cell lines.

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Published online: 19th May, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14473
Synthesis and Reaction of Novel Spiro Pyrazol-3-ones Containing Oxirane Moiety

Hayate Nagabuchi, Eiichi Masumoto, Fumi Okabe-Nakahara, and Hiroshi Maruoka*

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan

Abstract

An efficient synthesis and reaction of a series of spiro pyrazol-3-one derivatives containing oxirane moiety are described. The convenient substrates, three types of pyrazole-4,5-diones, were reacted with phenacyl bromides in the presence of triethylamine in ethanol at room temperature to give the corresponding spiro epoxide-pyrazol-3-ones in moderate to good yields. Furthermore, thermal treatment of spiro compounds with pyrrolidine in the presence of water caused ring transformation easily to afford the corresponding pyridazinone derivatives. These methods provide several advantages such as operational simplicity, shorter reaction time, and higher yields. All the synthesized compounds were characterized by spectroscopic analysis.

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Published online: 17th May, 2021

Communication | Regular issue | Prepress
DOI: 10.3987/COM-21-14447
Debromooscillatoxins G and I from the Cyanobacterium Moorea producens

Kanon Iguchi, Masayuki Satake, Yutaro Nishio, Bo-Tao Zhang, Kento Kawashima, Hajime Uchida, and Hiroshi Nagai*

*Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan

Abstract

Debromooscillatoxins G and I (1 and 3) were isolated from the marine cyanobacterium Moorea producens collected in Okinawa. Their structures were determined based on spectroscopic data, including nuclear magnetic resonance (NMR) and high resolution mass spectrometry (HRMS). Both the isolated compounds showed moderate cytotoxicity and diatom growth inhibition at a concentration of 10 µg/mL.

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Published online: 14th May, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14456
Synthesis and Biological Activities of Selenium/Thioether Quinazoline Compounds

Canjun Yan, Yuchun Zhang, Guihan Zhao, Xiaohong Jin, Wuwei Yang, Pengpeng Niu, Haojie Wang, and Gang Liu*

*School of Chemistry and Materials Science, Ludong University, Yantai 264025 China

Abstract

In view of the important role of quinazoline skeletons in anti-cancer drugs like Gefitinib and the vital importance of organoselenium compounds in biomedicine field, in this protocol, twenty quinazoline selenium derivatives were designed and synthesized with the aim to develop new anti-cancer drugs by utilizing the synergistic effects of quinazoline skeleton and selenium. In addition, the synthetic method of thioether substituted quinazolines was improved. The biological activities of title compounds were determined against A549 cancer cells in vitro by using MTT assay at 1 μM and 10 μM concentrations. The results showed that most of the title compounds had good anticancer activities. Of note, 6-chloro-4-benzylselenoquinazoline (G5) exhibited better inhibitory activity (67.8% inhibition ratio) than the positive control drug Gefitinib (62.9% inhibition ratio) at the concentration of 10 μM. These findings will provide some clues for further research of anticancer drugs.

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Published online: 14th May, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14480
Total Synthesis of Hyalodendriol C

Ishtiaq Jeelani,* Katsunori Itaya, and Hitoshi Abe

*Graduate School of Innovative Life Science, University of Toyama, 3190 Gofuku 930-8555, Japan

Abstract

We present a total synthesis of hyalodendriol C, a fungal natural product. We have focused on the use of palladium-catalyzed intramolecular biaryl coupling reaction of phenyl benzoate derivatives to synthesize hyalodendriol C. Keeping in view, the indispensable biological values of this compound, we took the advantage of our established strategy to chemically synthesize hyalodendriol C. The total synthesis of hyalodendriol C got accomplished in 10 steps beginning with the preparation of phenol derivative from the commercially available 5-methylbenzene-1,3-diol and synthesis of the corresponding benzoic acid derivative.

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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

Abstract

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.

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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

Abstract

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.

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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

Abstract

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.

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