Regular & Special Issues

25 data found. 1 - 25 listed

Published online: 17th September, 2021

Review | Regular issue | Prepress
DOI: 10.3987/REV-21-965
Recent Progress on Synthesis of Spirochromanone and Spirochromane Derivatives

S. Chakroborty,* P. Panda, S. C. Ramírez-Lopìez, M. A. Garcia Eleno, E. C. Yañez, L. Strekowski, and M. V. B. Unnamatla*

*School of Sciences, Auro University, earthspace, Hazira Road, opp. ONGC, Surat, Gujarat 394510, India


Nature offers plenty of opportunities to the researchers of different communities to explore heterocyclic compounds. Among the various magic heterocyclic scaffolds, chromane and chromanone are the most privileged heterocycles due to their omnipresence in most value-added chemical entities. On the other hand, spirocyclic heterocyclic moieties offer unique three-dimensional frameworks which can fit into the cavity of the proteins, including enzymes, thereby enhancing the biological properties. Considering the remarkable significance of spirocyclic systems of chromanes and chromanones, various novel strategies such as Kabbe condensation, organocatalyzed reactions, oxa/sulfa-Michael-Aldol cascade reaction, oxa-Michael/addition and 1,3-dipolar cycloaddition, among others, have emerged to access this precious heterocyclic architecture in good to excellent yields. This review summarizes the synthesis of a variety of spirochromane and spirochromanone derivatives covering the literature from 1991-2020.


Published online: 15th September, 2021

Review | Regular issue | Prepress
DOI: 10.3987/REV-21-969
Total Synthesis of Natural Products and Medicinal Molecules via Chelation-Controlled Diastereoselective Hydride Reduction of Amino Ketones

Tian Jin,* Lu Zhao, Chichong Lu,* Zhe-Bin Zheng, and Won-Hun Ham*

*Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610106, People’s Republic of China


The chiral β-amino alcohols are widely presented in the natural products, privileged ligands, and medicinal molecules. In the past decades, the construction of anti-β-amino alcohols have attracted in the interest of synthetic chemists. A number of studies indicated that the chelation-controlled hydride reduction approach is straightforward for the preparation of anti-β-amino alcohol motifs in high yield with excellent diastereoselectivity and they can be used as chiral building block in the total synthesis of natural products and medicinal molecules. The aim of this review is to highlight application of chelation-controlled hydride reduction in total synthesis of natural products and medicinal molecules on the basis of a collection of recent literature studies.


Published online: 15th September, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14531
Five New Compounds from Arenga pinnata (Wurmb.) Merr. Fruits

Ji-Fei Liu, Xin Cai, Feng-Jin Li, Chang Wang, Jin-Hai Huo,* and Wei-Ming Wang*

*Institute of Chinese Materia Medica, HeilongJiang Academy of Chinese Medicine Sciences, Harbin 150036, China


Phytochemical investigation of Arenga pinnata (Wurmb.) Merr. fruits led to the isolation of 5 new compounds, designated A. pinnata A-E (1–5), and 13 known compounds (6–18). All compounds were isolated from A. pinnata for the first time. Their chemical structures were identified based on extensive spectroscopic methods, including HR-ESI-MS, 1D and 2D-NMR. To the best of our knowledge, this is the first systematic scientific study on the chemical composition of the Arenga genus.

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Published online: 14th September, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14538
Oscillatoxin E and Its C7 Epimer Show Distinct Growth Inhibition Profiles against Several Cancer Cell Lines

Yusuke Hanaki,* Yusuke Araki, Toshio Nishikawa, and Ryo C. Yanagita

*Faculty of Agriculture, Kagawa University, Kagawa 761-0795, Japan


Oscillatoxins (OTXs) are naturally occurring polyketides produced by some marine cyanobacteria. We have recently reported the total synthesis and in vitro biological activities of OTX-D, E, and F. Their spiro-ether structure was synthesized with an intramolecular Mukaiyama aldol reaction as a key step. Although the desired isomer was stereoselectively obtained, some amount of its C7 epimer was also produced as a byproduct. Using the C7 epimer, we investigated the effect of stereochemistry at the spiro-center of OTX-E (1) on its antiproliferative activity against several cancer cell lines. Growth inhibitory activity of 1 and its C7 epimer 2 was not strong, but they showed different efficacy profiles from each other. This result suggests that our synthetic method for OTXs would contribute to not only total synthesis of natural products but also to construction of chemical libraries containing unique biologically active compounds.

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Published online: 8th September, 2021

Paper | Special issue | Prepress
DOI: 10.3987/COM-21-S(R)6
Application of Reversible Detection Method for N-terminus Amino Groups: Solid Phase Synthesis of Stylissatin B

Ao Tan, Keigo Takamatsu, Fusheng Xu, Seren Osanai, and Hiroyuki Konno*

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


The first synthesis of the proline-rich cyclic heptapeptide stylissatin B is described. Reversible detection method of N-terminus amino groups using tetrachloro-N-hydroxyphthalimide was applied as the Fmoc-solid phase peptide synthesis. The end points of all reactions of solid support could be pursued by the detection methods.

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Published online: 7th September, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14526
Sythesis and Bioligical Evaluation of New Pyrimidine Derivatives as Fak Inhibitors for Development of Antitumor Agents

Di Zhang, Qin Wang, Jing Yang, Qing Zhang, Yi Le, Li Liu, and Longjia Yan*

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


In this paper, a set of new pyrimidine derivatives was designed and synthesized. Subsequently, all the final targets were evaluated for antitumor activities in vitro on four human cancer cell lines including U-87 MG, MDA-MB-231, PC-3, and MCF-7, which were high expressed with focal adhesion kinase (FAK). The results were shown that these compounds performed well antitumor activities. Especially 2-((2-((4-((2-((2-acrylamidoethyl)amino)-3,4-dioxocyclobut-1-en-1-yl)amino)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)amino)-N-methylbenzamide (7b) exhibited the highest antitumor activities with 2.16 μM, 2.03 μM, 6.19 μM, and 21.31 μM, respectively. In addition, all the compounds were tested activities against FAK and compound 7b was also the best candidate with IC50 value of 5.9 nM.

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Published online: 7th September, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14541
Detection of New 3,4-Dimethylpyrrole Derivatives upon the Incubation of Exogenous Amines with Extract of Onion (Allium cepa) and Crude Alliinase from Garlic (A. sativum)

Taichi Yoneda, Seikou Nakamura,* Shogo Okui, Sayaka Okazaki, Souichi Nakashima, and Hisashi Matsuda

*Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8414, Japan


Seven new N-substituted 3,4-dimethylpyrroles were obtained in situ through the reaction of an amine ((L)-phenylalanine, (L)-tryptophan, (L)-leucine, (L)-methionine, 1-phenethylamine, aniline or dodecylamine) and a mixture of unstable sulfur-containing compounds derived from the reaction of amino acids in Allium cepa and plant enzyme alliinase. In addition, a plausible reaction mechanism for the synthesis of N-substituted 3,4-dimethylpyrroles was displayed.

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Published online: 3rd September, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14530
Synthetic Approaches for Construction of Novel 3-Heteroarylchromeno[2,3-b]pyridines and Annulated Chromenopyridopyrazolopyrimidines

Magdy A. Ibrahim* and Youssef A. Alnamer

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


Hydrazinolysis of ethyl 2,5-dioxo-1,5-dihydro-2H-chromeno[2,3-b]- pyridine-3-carboxylate (2) afforded chromeno[2,3-b]pyridine-3-carbohydrazide 3 which utilized as a precursor for building a diversity of heterocyclic compounds at position 3. Condensation of carbohydrazide 3 with 3-formylchromone produced the condensation product 4, while addition of carbohydrazide 3 to phenyl isothiocyanate gave hydrazinecarbothioamide derivative 5 which upon cyclization afforded 3-thiadiazolylchromeno[2,3-b]pyridine-2,5(1H)-dione 6. Condensation of carbohydrazide 3 with some monoelectrophilic reagents namely ethyl chloroformate, carbon disulfide, acetyl chloride and benzoyl chloride and chromone-3-carboxylic acid gave a variety of novel 3-oxadiazolylchromeno-[2,3-b]pyridines 7-10 and 12. Treatment of carbohydrazide 3 with a variety of 1,3-bielectrophiles such as acetylacetone, ethyl acetoacetate and diethyl malonate yielded 3-(pyrazolyl)carbonylchromeno[2,3-b]pyridines 13-15. Finally, reaction of carbohydrazide 3 with ethyl cyanoacetate and (ethoxymethylene)malononitrile afforded heteroannulated chromeno[2``,3``:6`,5`]pyrido[2`,3`-d]pyrazolo[1,5-a]-pyrimidines 17 and 18. Structures of the synthesized products were confirmed based on their analytical and spectral data.


Published online: 2nd September, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14521
Quinoline Alkaloids from the Leaves of Cigar Tobacco and Their Anti-Tobacco Mosaic Virus Activity

Guang-Hui Kong, Guang-Hai Zhang, Zhong-Long Lin, Gao-Kun Zhao, Yin-Ke Li, Heng Yao, Guang-Yu Yang, Qiu-Fen Hu,* and Yu-Ping Wu*

*Yunnan Academy of Tobacco Agricultural Sciences, Kunming, Yunnan 650031, P. R. China


Three new (1-3), together with three known (4-6) quinoline alkaloids were isolated from the leaves of cigar tobacco (a variety of Nicotiana tabacum). Their structures were elucidated by spectroscopic methods, including extensive 1H, 13C, and 2D-NMR techniques. Compounds 1-6 were tested for their anti-tobacco mosaic virus (anti-TMV) activity. The results showed that compound 3 exhibited high anti-TMV activity with inhibition rate of 42.2% at the concentration of 20 μM. This rate in higher than that of positive control (with inhibition rate of 32.5% at the concentration of 20 μM). Compounds 1, 2, 4~6 also showed potential anti-TMV activity with inhibition rates of 28.2, 31.0, 22.8, 26.6, and 29.5% at the concentration of 20 μM, respectively. These rates are slightly lower than that of positive control.

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Published online: 2nd September, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14529
Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazole by the Reaction of 2-Amino-4,5-dihydro-3-furancarbonitrile and o-Substituted Anilines in the Catalysis of Trimetylamine Hydrochloride

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

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


Efficient synthesis of benzimidazoles, benzoxazoles and benzothiazole from the reaction of 2-amino-4,5-dihydro-3-furancarbonitrile with o-substituted anilines in the catalysis of trimethylamine hydrochloride was achieved. The structures of the obtained products were established by spectroscopic data.

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Published online: 27th August, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14534
Synthesis, Characterization, Antibacterial and Cytotoxic Evaluation of New 6-(Chlorothiophenyl)-2-(2-oxopropoxy)pyridine-3-carbonitrile Derivatives and Their Corresponding Furo[2,3-b]pyridine Derivatives

Ala’a B. Said, Mahmoud Al-Refai,* Armin Geyer, Iman A. Mansi, and Basem Fares Ali*

*Department of Chemistry, Al al-Bayt University, Mafraq 25113, Jordan


The synthesis of a new series of 6-(chlorothiophenyl)-2-(2-oxopropoxy)pyridine-3-carbonitrile compounds 2 and 5 and their furo[2,3-b]pyridines bearing heteroaryl substituents 3 and 6 in high yield is reported. The 6-(chlorothiophenyl)-2-(2-oxopropoxy)pyridine-3-carbonitrile derivatives (2a-f) and (5a-d) were prepared from the corresponding 3-cyano-(2H)-pyridones (1a-f) and (4a-d) followed by the Thorpe-Ziegler ring cyclization in the presence of sodium methoxide to give the target furo[2,3-b]pyridine derivatives (3a-f) and (6a-d). Proposed structures of the new compounds are based on NMR and mass spectral data. Antibacterial evaluation of (2a-d), (2f), (5a-d), (3a-d), (3f), and (6a-d) derivatives against eight different microorganisms shows no activity towards any of the tested bacteria while compounds (6a) and (6c) showed weak antibacterial activity with inhibition zone of 10 mm. Cytotoxic assessment against MCF7 breast cancer cells reveals that 10 of the derivatives were found to decrease cell viability in a dose dependent manner at concentration of 100 μM, but six of them decreased it to less than 50% and had IC50’s ranging from 23.3 to 41.2 μM.

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Published online: 23rd August, 2021

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14527
New Synthesis of Lumateperone Tosylate

Cong Sun, Yongjun Mao,* Bo Li, Zhiyong Xu, Shun Jiang, Linlin Kang, and Han Wang

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


A new and practical synthesis of lumateperone tosylate is developed. The intermediate, ethyl (4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydro-2H-pyrido-[4,3-b]indole-2-carboxylate (12), is prepared on kilograms scale in 31% overall yield and >99% ee. (6bR,10aS)-3-Methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline hydrochloride (16-HCl) is obtained through reductamination reaction, palladium catalyzed cyclization and ester hydrolysis in 60% yield over 3 steps and >98% purity. Lumateperone tosylate is produced on 20 g scale in 65% yield over 2 steps and >99% purity (HPLC). Purification methods of the intermediates and the final product involved in the route are developed.

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Published online: 19th August, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14519
Ruthenium(II) Complexes with Chelating N-Heterocyclic Carbenes and a Ruthenate(II) Complex as Catalysts for the Anti-Markovnikov Hydroaminations of Styrene

Murat Yiğit,* Yetkin Gök, Özlem Özeroğlu Çelikal, and Beyhan Yiğit

*Department of Chemistry and Chemical Processing Technologies, Vocational School of Technical Sciences, Adiyaman University, 02040-Adıyaman, Turkey


New ruthenium chelate and ruthenate complexes were synthesized through the reaction of benzimidazolium salts and [RuCl2(p-cymene)]2 in toluene and characterized by elemental analysis, 1H NMR and 13C NMR spectroscopy. These ruthenium complexes were tested as catalysts in the intermolecular hydroamination reactions between styrene with aromatic amines in ionic liquid. All of these complexes tested here showed good catalytic activity in these reactions. The hydroamination reactions regioselectively produced anti-Markovnikov addition products in moderate to good yields by using 1 mol% of the ruthenium complex.


Published online: 18th August, 2021

Paper | Regular issue | Prepress
DOI: 10.3987/COM-21-14514
A Simple Route for Synthesis of New Triazole Derivatives via Reaction between Arylglyoxals, Acetylacetone and Sodium Azide

Fereshteh Nejad-Shahrokhabadi and Mohammad Anary-Abbassinejad*

*Department of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan, Rafsanjan 7718897111, Iran


A fast and green way to preparation of a new series of triazole derivatives is reported using the three-component reaction between arylglyoxals, acetylacetone and sodium azide in water as solvent.

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Published online: 17th August, 2021

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-21-S(R)4
Isolation of Ikahonone, 4-methyl-2,4-dihydroxy-3-pentanone from Bacillus cereus IFM12235

Yasumasa Hara, Mareno Chiba, Keiichiro Watanabe, and Masami Ishibashi*

*Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba 260-8675, Japan


A new ketone, ikahonone (1), and five known compounds (2-6) were isolated from Bacillus cereus IFM12235 collected in Japan. The structure of compound 1 was elucidated using spectral studies, including NMR. The absolute configurations of 1 and 2 were determined by comparing electronic circular dichroism (ECD) spectra with known compounds and calculating the ECD spectra of 1 and 2. Three compounds (2-4) were previously prepared by synthesis, and first isolated as natural products in the present study.

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Published online: 11th August, 2021

Paper | Special issue | Prepress
DOI: 10.3987/COM-21-S(R)5
Azuleno[6,5-b]indoles: Palladium-Catalyzed Oxidative Ring-Closing Reaction of 6-(Arylamino)azulenes

Taku Shoji,* Yukino Ariga, Shunji Ito, and Masafumi Yasunami

*Department of Science, Graduate School of Science and Technology, Shinshu University, Matsumoto 390-8621, Nagano, Japan


6-Bromoazulene derivative with two n-butoxycarbonyl groups was prepared by the modification procedure of Nozoe’s azulene synthesis. The aromatic nucleophilic substitution reaction of the 6-bromoazulene derivatives having two-ester functions with aniline derivatives proceeded to give the corresponding 6-(arylamino)azulene derivatives. Palladium-catalyzed oxidative ring-closing reaction of the 6-(arylamino)azulene derivatives provided the azuleno[6,5-b]indoles in moderate to good yields.


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: 22nd June, 2021

Communication | Special issue | Prepress
DOI: 10.3987/COM-21-S(R)3
Synthesis and Optical Properties of Azuleno[1,2-b]benzothiophene and Selenophene

Mio Matsumura,* Taiki Kamiya, Masato Kawakubo, Yukako Hayashi, Tadashi Hyodo, Yuki Murata, Kentaro Yamaguchi, and Shuji Yasuike*

*School of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, Japan


Benzothiophene- and benzoselenophene-fused azulene derivatives were synthesized by Cu-catalyzed tandem cyclization via the Ullmann-type S/Se– arylation and Csp2–H chalcogenation of 2-(2′-bromophenyl)azulene. The maximum absorption of tetracyclic products was red-shifted from that of 2-phenylazulene, which does not contain a bridged chalcogen atom. Single-crystal X-ray analysis of azuleno[1,2-b]benzoselenophene revealed that the benzo[b]selenophene and azulene rings are almost coplanar.

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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: 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


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


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).


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: 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.

25 data found. 1 - 25 listed