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Published online: 23rd September, 2020

Paper | Special issue | Prepress
DOI: 10.3987/COM-20-S(K)27
■ Dirhodium(Ii)-Catalyzed Ortho C–H Amination of N-Alkyldiarylamines

Motoki Ito,* Mamiko Mori, Tomoya Nakagawa, Miki Hori, Kazuhiro Higuchi, and Shigeo Sugiyama*

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588,

Abstract

Dirhodium(II)-catalyzed ortho C–H amination of N-alkyldiarylamines has been developed. The C(sp2)–H amination proceeded with high preference over C(sp3)–H amination to provide N-aryl-o-phenylenediamines in up to 80% yield. With the use of unsymmetric diarylamines as substrates, selective amination of one of two distinct aromatic rings was also achieved.

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Published online: 23rd September, 2020

Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14340
■ Stereoselective Synthesis of (Z)-3-Arylidene-2-oxindoles via a Palladium-Catalyzed Tandem Reaction

Sunhwa Park, Kye Jung Shin, and Jae Hong Seo*

*College of Pharmacy, The Catholic University of Korea, 43 Jinong-ro Wonmi-gu Bucheon, Gyeonggi-do, 14662, Korea

Abstract

A novel and efficient synthetic method for the stereoselective preparation of (Z)-3-arylideneoxindoles from simple propiolamide has been developed utilizing a palladium-catalyzed tandem reaction. Two Sonogashira and reductive Heck reactions were successfully combined under microwave irradiation. The E/Z stereoselectivity of the reaction was enhanced by solvent control.

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Published online: 18th September, 2020

Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14330
■ 1-Hydroxyindoles: Production of Feruloylserotonin, an Alkalid of Safflower Seed, Novel Ring System Compound, 1,10-Diaza-9,20-dioxokabutanes, 2,2’-Bisindoles, and (dl)-3a, 3a’-Bispyrrolo[2,3-b]indoles

Mutsuko Tabata, Naoki Oshikiri, Masakazu Hasegawa, Keiichi Satoh, Yoshikazu Fukui, Yoshiyuki Nagahama, Harunobu Morikawa, Fumio Yamada, and Masanori Somei*

*Faculty of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan

Abstract

Methyl 1-hydroxyindole-3-acetate (1a) produced novel hexacyclic 8,17-bis(methoxycarbonylmethyl)-1,10-diaza-9,20-dioxakabutane (3) as a major product by the reaction with 85% formic acid, while its reaction with trifluoroacetic acid generated exclusively another 2,2’-bisindole dimer, 1-hydroxy-3,3’-di(methoxycarbonylmethyl)-2,2’-bisindole (4). Reaction of 1a with mineral acid such as HCl afforded nucleophile substituted 5-chloroindole derivative (6). Products and their distribution changed depending on the structure of 1-hydroxyindole. Species of acid, reaction conditions, side chain structure of 1-hydroxyindole at the 3-position are additional factors for governing the product formation. In the cases that the side chain has a C—C—N structure, nucleophilic substitution reaction occurred effectively, and was applied for the preparation of N-feruloylserotonin (46d), an alkaloid isolated from safflower seed. 1-Hydroxymelatonin (69), having a methoxy group on the benzenoid part, afforded (dl)-3a,3a’-bis(pyrrolo[2,3-b]indole) compound (72) by the treatment with 85% formic acid. Products’ structures are unequivocally determined by X-ray single crystallographic analyses.

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Published online: 18th September, 2020

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14335
■ Chromone Derivatives from the Twigs of Cassia Agnes and Their Anti-Rotavirus Activity

Guang-Hui Kong, Zhen-Yuan Xia, Fan Wu, Ya-Ning Zhu, Jing Li, Wei-Song Kong, Min Zhou, Guang-Yu Yang, Qiu-Fen Hu,* and Yu-Ping Wu*

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

Abstract

Three new (1 - 3), together with four known chromone derivatives (4 - 7) were isolated from the twigs of Cassia agnes. Their structures were elucidated by spectroscopic methods, including extensive 1D- and 2D-NMR techniques. Compounds 1 - 7 were evaluated for their anti-rotavirus activity. The results revealed that compounds 1 - 7 exhibited potent anti-rotavirus activity with TI valves in the range of 9.4 - 14.5, respectively.

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Published online: 16th September, 2020

Paper | Special issue | Prepress
DOI: 10.3987/COM-20-S(K)23
■ Synthesis of (Trifluoromethyldiazirinyl)phenyl-boronic Acid Derivatives for Photoaffinity Labeling

Manami Hashinoki, Natsumi Kurokawa, Yuta Murai, Zetryana Puteri Tachrim, Yasuko Sakihama, Takeyuki Suzuki, and Makoto Hashimoto*

*Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita-9, Nishi-9, Kita-ku, Sapporo, Hokkaido 060-8589, Japan

Abstract

Trifluoromethylphenyldiazirine is one of the most reliable photophores for photoaffinity labeling during functional analysis of biologically active compounds. Phenylboronic acid derivatives containing trifluoromethyldiazirinyl moiety have not yet been reported. The construction of the photophore was achieved using (3-formylphenyl)boronic acid and (4-formylphenyl)boronic acid pinacol esters effectively.

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Published online: 15th September, 2020

Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14302
■ Synthesis of 4,7-Dibromobenzo[b]thiophene Derivatives via 2-(1-Adamantylsulfanyl)-1,4-dibromo-3-(ethynyl)benzenes and Their Reactions

Kozo Toyota,* Shinichi Mikami, Hiroki Tanaka, Shuhei Yoshida, Kazuma Iwai, Kenta Takahashi, Hiroki Kishi, Yota Kikuchi, Koya Saito, Homa Yamaguchi, and Hirotaka Mutoh

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

Abstract

Mild Corey-Fuchs reaction conditions using dimethyl sulfoxide - aqueous KOH solution at room temperature were applied to preparation of 2-(1-adamantylsulfanyl)-1,4-dibromo-3-(ethynyl)benzene. Various substituents were introduced to the terminal alkyne moiety of the (ethynyl)(sulfanyl)benzene, either by substitution reaction or by Sonogashira cross coupling. The alkynes thus obtained were converted to the corresponding 4,7-dibromobenzo[b]thiophene derivatives by the ‘silica gel-assisted cyclization’ method. Reactions of 4,7-dibromobenzo[b]thiophene and 2,4,7-tribromobenzo[b]thiophene were also investigated.

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Published online: 14th September, 2020

Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14316
■ Synthesis of Novel (Thiazol-5-Yl)pyrazoles and Their Antimicrobial Evaluation

Sanjay U. Deshmukh,* Raghunath B. Toche,* Sushama J. Takate, Supriya P. Salve, and Ram W. Sabnis

*Department of Chemistry, KRT Arts, BH Commerce & AM Science College, Nashik 422002, India.

Abstract

A series of novel (thiazol-5-yl)pyrazoles were designed and synthesized. All the synthesized compounds were characterized by spectroscopic analysis and were evaluated for their antimicrobial activity in vitro against Gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus, Gram-negative bacteria, Salmonella abony and Escherichia coli and fungi, Aspergillus flavus and Fusarium oxysporum.

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Published online: 11th September, 2020

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-20-S(K)26
■ Transition Metal-Free O-Arylation of Quinoxalin-2-ones with Diaryliodonium Salts

Masami Kuriyama,* Yuki Mochizuki, Tsubasa Miyagi, Kosuke Yamamoto, Yosuke Demizu, and Osamu Onomura*

*Graduate School of Biomedical Sciences, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

The transition metal-free O-arylation reactions of quinoxalin-2-ones with diaryliodonium salts have been achieved, and desired 2-aryloxyquinoxalines were readily obtained in moderate to high yields. This method proved to be compatible with a series of diaryliodonium salts as well as a set of quinoxalin-2-ones.

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Published online: 9th September, 2020

Paper | Special issue | Prepress
DOI: 10.3987/COM-20-S(K)19
■ An Alternative Approach to the Development of Near-Infrared Fluorescent Dyes Based on Fluorescein

Akane Katori, Akari Yamagami, Sae Wakabayashi, Kouji Kuramochi, Ayumi Imayoshi, and Kazunori Tsubaki*

*Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, Japan

Abstract

In xanthene dyes the upper aryl moiety is often a benzene ring, but in this work an L-shaped dibenzoxanthene dye (4) was synthesized with a five-membered (benz)imidazole ring as the upper aryl moiety. Although 4 was designed with the π-face of the dibenzoxanthene and the π-plane of the aryl moiety as coplanar, the reactivity of the compound at the triaryl carbon was quite high and easily attacked by solvent, such as methanol. The consequent discoloration is caused not only by the external exposure of the triaryl carbon, but also by the greatly reduced LUMO level and increased reactivity to nucleophilic attack when the π-system of the xanthene ring is expanded. The introduction of the 2,6-dimethylphenyl group was found to be effective to avoid nucleophilic attack by solvent. A compound, labeled 9c, with a 2,6-dimethylphenyl group as the aryl moiety, had sufficient stability to solvent, an emission maximum at 828 nm in DMF, and a fluorescence quantum yield of 8%.

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Published online: 9th September, 2020

Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14317
■ Synthesis and Evaluation of β-Galactosidase-Targeting Spin-Label Probe: 5-O-β-D-Galactosyl-5-hydroxy-1,1,3,3-tetramethylisoindoline-2-oxyl

Koya Sugawara, Hiroyuki Konno, Tomohiro Ito, and Shingo Sato*

*Graduate School of Science and Engineering, Yamagata University, Jonan 4-3-16, Yonezawa-shi, Yamagata 992-8510, Japan

Abstract

In this study, 3-hydroxymethyl-2,2,5,5-tetramethylpyrrolidine-1-oxyl, 4-hydroxy-2,2,6,6-tetramethylpyperidine-1-oxyl, and 5-hydroxy-1,1,3,3-tetramethylisoindoline-2-oxyl O-galactosides (PG, TG, and IG) were synthesized. Moreover, their reduction reactivity (RR) for ascorbic acid and hydrolysis reactivity (HR) for β-galactosidase were measured via electron paramagnetic resonance (EPR) spectroscopy and high-performance liquid chromatography (HPLC), respectively. The both rate constants for these two reactions were found to exhibit the following order: RR: TG > IG > PG, and HR: IG > PG > TG. Based on the results of the in vitro assay, IG was selected as the candidate for the bioassay. The bioassay of IG by HeLa cells (cancer cells) and PC12 cells (normal cells) indicated that after 20 min of IG addition, more nitroxide radicals were located in the cancer cells than in the normal cells, while their EPR intensity was low.

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Published online: 8th September, 2020

Review | Regular issue | Prepress
DOI: 10.3987/REV-20-938
■ 9,9'-Bi(Xanthene)-Type Hexaphenylethane Derivatives as Advanced Organic Electrochromic Systems

Takanori Suzuki,* Yusuke Ishigaki, Masaki Takata, Jun-ichi Nishida, and Takanori Fukushima

*Department of Chemistry, Faculty of Science, Hokkaido University, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan

Abstract

9-Phenylxanthenyl radical can undergo facile C-C bond formation at C9-position when the two units of the radical are connected at C2'-positions to give stable intramolecular dimer (1), which is a clamped hexaphenylethane derivative with an elongated C-C bond. The newly formed bond in 1 can be cleaved easily upon two-electron oxidation to give bis(9-xanthenylium)-type dication (22+), from which the diradical is generated upon two-electron reduction. This review account describes the dynamic redox ("dyrex") pair of colorless 1 and yellow-orange 22+, which provides a versatile scaffold to develop multi-functional electrochromic systems. Both of 1 and 22+ are sterically challenged molecules and thus adopt characteristic skewed geometries. Electrochiroptical response was realized by suppressing the chiral inversion of helicity in 1 and axial chirality in 22+ whereas redox-induced fluorescence switching was attained by attaching the fluorophore whose emission is quenched by xanthenylium in 22+ but not by spiro(xanthene) unit in 1. By the molecular design that allows intramolecular chiral transmission, the spectral changes were also induced by the external stimuli (e.g. heat, pH) other than redox input, which made it possible to construct less well-explored multi-input-multi-output response systems. More advanced functions could be endowed, such as chiral redox memory or reversible O2-storage, by further modification of the prototype.

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Published online: 4th September, 2020

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-20-S(K)25
■ Palladium on Carbon–Catalyzed Oxidative Transformation of Benzylic Ethers

Ryoya Takakura, Shoko Kuwata, Kouki Nakano, Naoki Yasukawa, Hironao Sajiki,* and Yoshinari Sawama*

*Laboratory of Organic Chmistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi 501-1196, Japan

Abstract

Palladium on carbon (Pd/C)-catalyzed oxidative transformations of primary and secondary benzylic ethers in ethylene glycol as a solvent and reagent in an oxygen atmosphere produced the corresponding hydroxyethyl esters and cyclic ketals, respectively. Commercially-available and heterogeneous Pd/C was easily removed by filtration, and molecular oxygen was used as a clean oxidant.

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Published online: 3rd September, 2020

Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14327
■ Synthesis and Evaluation of Biological Properties of 2-(2-(Phenoxy)pyridin-3-YL)quinazolin-4(3H)-one Derivatives

Li-qiong Zhang, Jia-min Liu, Yi-yuan Gan, Li-hui Shao, Yi-hong Fu, Zhen-chao Wang,* and Gui-ping Ouyang*

*College of Pharmacy, Guizhou University, Huaxi St., Guiyang 550025, China

Abstract

A series of novel 2-(2-(phenoxy)pyridin-3-yl)quinazolin-4(3H)-one derivatives were designed, synthesized as antitumor agents. The antitumor activities of target compounds were evaluated and compared with positive drug Gefitinib employing standard MTT assay against A549 (human lung adenocarcinoma cell), PC-3 (prostate cancer cells), K562 (human chronic myeloid leukemia cells), HepG2 (human liver cancer cell) cancer cell lines in vitro. The pharmacological screening results revealed that many compounds exhibited moderate levels of antitumor activities against four cancer cell lines, especially 6-chloro-2-(2-(3,5-dimethylphenoxy)pyridin-3-yl)-3,8-dimethylquinazolin-4(3H)-one (z8) displayed promising activities against A549 (IC50 = 12.47±2.86 μM) than Gefitinib (IC50 = 17.37±6.01 μM). The mechanism and the apoptosis inducing effect of z8 against A549 cell line were studied. The results showed that z8 could inhibit migration and motility of cancer cells, induce cell apoptosis and exhibit the typical apoptotic morphology.

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Published online: 2nd September, 2020

Paper | Special issue | Prepress
DOI: 10.3987/COM-20-S(K)16
■ The Effect of the Base Triplets Adjacent to a T•CG or 5-MethylC•CG Triplet in the Triplex DNA

Yuta Ito, Chisa Hama, Takashi Osawa, and Yoshiyuki Hari*

*Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan

Abstract

The effect of the base triplets adjacent to an X•CG triplet [X = T, 5-methylcytosine (C), or their LNA and ENA counterparts] in a triplex DNA was examined through the UV-melting experiments. Whereas the triplex containing a T•CG triplet, sandwiched by T•AT triplets, was stable, the replacement of T•AT with C•GC at the 5ʹ-adjacent site significantly destabilized the stability. When one or both of the adjacent T•AT triplets were replaced with C•GC, the triplexes containing a C•CG triplet were generally more stable than those containing a T•CG triplet. Further increases in the thermal stability of the triplexes were observed by LNA and ENA modifications. These results suggested that a C•CG triplet rather than a T•CG triplet would be suitable for triplex formation when C•GC triplets existed at its adjacent site.

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Published online: 27th August, 2020

Communication | Special issue | Prepress
DOI: 10.3987/COM-20-S(K)20
■ Transition-Metal-Free Aziridination of Alkenes with Sulfamate Esters Using tert-Butyl Hypoiodite

Kensuke Kiyokawa,* Shogo Nakamura, and Satoshi Minakata*

*Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

Abstract

The transition-metal-free aziridination of alkenes with sulfamate esters in the presence of tert-butyl hypoiodite (t-BuOI) is reported. The reaction can be used in intra- and intermolecular reactions, offering a practical and environmentally benign method for the synthesis of valuable aziridine compounds.

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Published online: 27th August, 2020

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14288
■ Design and Synthesis of Pentacycloundecane Cage Compound Containing Oxazole Moiety

Sambasivarao Kotha* and Subba Rao Cheekatla

*Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India

Abstract

Here, we have established a new and simple synthetic approach to the pentacycloundecane containing cage oxazole unit in four steps. The synthesis begun with a cheap and readily available materials such as 2,5-dimethoxybenzaldehyde and endo-dicyclopentadiene. This approach relies on Van Leusen oxazole synthesis and [2+2] photocycloaddition as key steps. To the best of our knowledge, this is the first example of Cookson’s dione containing oxazole ring system. Some of these oxazole motifs are useful in bioorganic chemistry and our results are likely to draw the attention of medicinal chemists

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Published online: 26th August, 2020

Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14321
■ Facile Preparation of 5-Alkyl-1-aryltetrazoles with Arenes, Acyl Chlorides, Hydroxylamine, and Diphenylphosphoryl Azide

Kaho Shibasaki and Hideo Togo*

*Graduate School of Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

Successive treatment of arenes with acyl chlorides and AlCl3, the addition of water and removal of solvent, the reaction with NH2OH•HCl and K2CO3, and the reaction with diphenylphosphoryl azide and DBU under warming conditions gave the corresponding 5-alkyl-1-aryltetrazoles efficiently in good to moderate yields. The present method is one-pot transformation of arenes into 5-alkyl-1-aryltetrazoles using the Friedel-Crafts acylation and the Beckmann rearrangement under transition-metal-free conditions.

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Published online: 25th August, 2020

Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14333
■ Synthesis and Reactivity of Dimethoxy Activated Benzothiazoles

Mahiuddin Alamgir, Hao Jiang, Mohan Bhadbhade, Naresh Kumar, and David StC. Black*

*School of Chemistry, The University of New South Wales, Sydney 2052, Australia

Abstract

A range of 2-substituted-5,7-dimethoxybenzothiazoles and 2-substituted-4,6-dimethoxybenzothiazoles have been synthesized by oxidative cyclization of the corresponding thioamides. These activated benzothiazoles display nucleophilic reactivity at C4 and C7 respectively and undergo formylation, acetylation and related reactions. Some 5,7-dimethoxybenzothiazoles with functionalization in a 2-aryl substituent are also reported as potential precursors for so far unsuccessful formation of macrocycles containing two benzothiazoles and two benzimidazoles.

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Published online: 21st August, 2020

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14298
■ Synthesis and Antibacterial Survey of Some New Pyridine-Based Heterocycles

Ebrahim Abdel-Galil, Moged A. Berghot, Alshimaa I. Zaki, and Ehab Abdel-Latif*

*Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, Egypt

Abstract

Treatment of ethyl 2-((3-cyano-4,6-dimethylpyridin-2-yl)thio)acetate (4) with hydrazine hydrate furnished 2-((3-cyano-4,6-dimethylpyridin-2-yl)thio)-acetohydrazide (5) which underwent condensation with five benzaldehydes to afford the corresponding N'-arylidene-2-((3-cyano-4,6-dimethylpyridin-2-yl)thio)-acetohydrazides 6a-e. The reaction of hydrazide 5 with ethyl acetoacetate yielded the expected 2-((2-(3-methyl-5-oxo-pyrazolyl)-2-oxoethyl)thio)nicotinonitrile derivative 7 which diazo-coupled with different diazonium chlorides to furnish the corresponding 2-(4-(2-arylhydrazono)pyrazolyl)-2-oxoethyl)thio)nicotinonitriles 8a-c. In addition, the nucleophilic substitution of chlorine from 2-chloroacetamide derivative 16 by various types of nucleophiles (salicylaldehyde, ethyl thioglycolate, 2-mercaptobenzoxazole, ammonium thiocyanate and/or malononitrile) was investigated. In general, all synthesized pyridine scaffolds revealed better activity against the Gram-positive bacterium (Bacillus subtilis) rather than the Gram-negative bacterium (Escherichia coli).

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Published online: 20th August, 2020

Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14300
■ An Efficient Synthesis of Some New Coumarin Hybrids Endowed with Expected Biological Activity

Mohamed A. Raslan,* Noura Sh. Hagaggi, Kamal M. Dawood, Hany A. Abdel Atty, and Ayman Nafady

*Department of Chemistry, Faculty of Science, Aswan University, Aswan 81528, Egypt

Abstract

Reactions of 5-bromo-2-hydroxybenzaldehyde with cyanoacetic acid hydrazide derivatives in refluxing ethanol afforded some new chromene-based polyfunctionally substituted heteroaromatics. The antimicrobial activity of some of the obtained products was evaluated. The structures of the newly synthesized compounds were elucidated based on their elemental analyses and spectral data.

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Published online: 20th August, 2020

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14305
■ Identification and Characterization of Chlorine-Containing Briaranes from a Cultured Octocoral Briareum excavatum (Briareidae)

Yi-Lin Zhang, Liang-Mou Kuo, Lo-Yun Chen, Gene-Hsiang Lee, Bo-Rong Peng, You-Ying Chen, Yu-Hsin Chen, Tsong-Long Hwang,* Jyh-Horng Sheu,* and Ping-Jyun Sung*

*Department of Planning and Research, National Museum of Marine Biology and Aquarium, 2 Houwan Road, Checheng, Pingtung, Taiwan 944, Taiwan

Abstract

Six chlorine-containing briaranes, including two new compounds, briarenols M (1) and N (2), as well as four known metabolites solenolide E (3), briarenolide R (4), excavatolide A (5), and briaexcavatolide F (6), have been isolated from a cultured octocoral identified as Briareum excavatum. The structures of 1 and 2 were established by spectroscopic methods and the absolute configurations of 5 and 6 were confirmed by single-crystal X-ray diffraction analysis. These compounds were subjected into the inhibitory effects on fMLF/CB stimulated superoxide anion generation and elastase release in human neutrophils.

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Published online: 20th August, 2020

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14306
■ Synthesis and Reactions of 3,8-Diphenyl-5-(4-methoxyphenyl)pyrrolo[1,2-c][1,3]thiazolo[3,2-a]pyrimidine-6-carbohydrazide

Kamelia M. El-mahdy and Azza M. El-kazak*

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

Abstract

The reaction of 2-mercaptopyrimidine 1 with phenacyl bromide gave pyrrolothiazolopyrimidine 2, which underwent hydrazinolysis to produce the novel pyrrolo[1,2-c][1,3]thiazolo[3,2-a]pyrimidine-6-carbohydrazide 3. Compound 3 used as a key intermediate for the synthesis of poly fused and isolated systems bearing pyrrolo[1,2-c][1,3]thiazolo[3,2-a]pyrimidine moiety via its reactions with some heterocyclization reagents. Structures of the newly synthesized compounds were established by elemental analysis and spectral data (IR, 1H NMR, Mass spectra and 13C NMR). The prepared compounds would be expected to have biological activities.

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Published online: 20th August, 2020

Review | Regular issue | Prepress
DOI: 10.3987/REV-20-937
■ Pyrrolotetrazoles and Ring-Fused Derivatives

Dietrich Moderhack*

*Institute of Medicinal and Pharmaceutical Chemistry, Technical University, Braunschweig, Beethovenstrasse 55, D-38106, Germany

Abstract

The preparative chemistry of seven types of pyrrolotetrazoles (formally: pyrrolo[1,2-d]tetrazoles) A–G including five ring-fused derivatives such as B', B'', C', C'', and E' is surveyed in this article. Theoretical work on annular tautomerism and pyrrolotetrazole–azidopyrrole isomerism is dealt with complementarily.

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Published online: 20th August, 2020

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14315
■ Amphirionins-3 and -6, New Polyketides from the Cultured Marine Dinoflagellate Amphidinium Species

Masashi Tsuda,* Ryui Makihara, Mika Minamida, Masayuki Tsuda, Mai Akakabe, Keiko Kumagai, Eri Fukushi, Jun Kawabata, and Takeyuki Suzuki

*Center for Advanced Marine Core Research , Kochi University, Nankoku, Kochi 783-8502, Japan

Abstract

Amphirionins-3 (1) and -6 (2) have been isolated from the marine dinoflagellate Amphidinium species. The structures were elucidated by detail analyses of the spectroscopic data, and chemical conversions. Compounds 1 and 2 exhibited moderate cytotoxic activity against human cervix adenocarcinoma HeLa cells.

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Published online: 20th August, 2020

Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14324
■ Efficient Synthesis and Anticancer Activities of Some Novel Functionalized (4-Oxo-4H-chromen-3-Yl)-2-selenoxo-1,2-dihydropyrimidines

Tarik E. Ali,* Mohammed A. Assiri, Mamdouh M. Ali, Abeer E. M. Ali, Ibrahim S. Yahia, and Heba. Y. Zahran

*Department of Chemistry, Faculty of Science, King Khalid University, Abha, Saudi Arabia

Abstract

Some novel functionalized 2-selenoxo-1,2-dihydropyrimidines bearing a chromone ring 2a-h were synthesized in excellent yields via a simple one-pot reaction. The simple method depended on one-pot three-component the reaction of 3-formylchromone (1) and selenourea with some active methylene compounds in the presence of sodium benzoate as a basic catalyst in a mixture of ethanol and water. The reactions were completed in 1.5–2.5 h in 88-94% yields. Structures of the synthesized compounds were based on elemental analysis, IR, 1H- and 13C-NMR and mass spectrometry. The anticancer properties of the synthesized compounds were evaluated against five cancer cell lines. Compounds 2a-d displayed the most potent anticancer activities against A549, MCF-7 and HepG2 cell lines in comparison with doxorubicin as the standard drug.

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Published online: 19th August, 2020

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14325
■ Synthesis of Some Novel Antimicrobial and Antioxidant Agents of Functionalized Pyrazolo[4',3':5,6]pyrano[3,2-d]- [1,2]azaphospholes and Pyrazolo[4',3':5,6]pyrano[2,3-d][1,3,2]diazaphosphinines

Noha M. Hassanin,* Tarik E. Ali, Hafez M. El-Shaaer, Somaia M. Abdel-Kariem, Somaya M. El-Edfawy, and Wafaa R. Abdel-Monem

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

Abstract

We have demonstrated facile synthetic approach for some novel functionalized pyrazolo[4',3':5,6]pyrano[3,2-d]-[1,2]azaphospholes and pyrazolo[4',3':5,6]pyrano[2,3-d][1,3,2]diazaphosphinines via treatment of 6-amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile with some phosphorus halides. The structure of the products was characterized by elemental analysis and spectral tools. The antimicrobial and antioxidant activities of the products were also evaluated.

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Published online: 18th August, 2020

Review | Regular issue | Prepress
DOI: 10.3987/REV-20-936
■ An Overview of Quantitative and Qualitative Approaches on the Synthesis of Heterocyclic Kojic Acid Scaffolds through the Multi-Component Reactions

Fatemeh Mohajer and Ghodsi Mohammadi Ziarani*

*Department of Chemistry, Alzahra University, Vanak Square, 1993893973, Tehran, Iran

Abstract

Multi-component reactions as powerful synthetic methods were developed to provide efficient complex scaffolds, including kojic acid, through the one-pot one-step fashion. This review highlights the progress of multicomponent reactions covering kojic acid under different conditions through, short reaction time, higher yields, and environmental friendliness via producing various molecules. The aim of this paper is to review the literature from 2015 to 2020 via quantitative and qualitative approaches.

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Published online: 13th August, 2020

Review | Regular issue | Prepress
DOI: 10.3987/REV-20-933
■ Recent Development of Stereoselective Glycosylation Reactions

Shino Manabe*

*Laboratory of Functional Molecule Chemistry, Pharmaceutical Department and Institute of Medicinal Chemistry, Hoshi University, 2-4-41 Ebara, Shinagawa, Tokyo, 142-8501, Japan

Abstract

Carbohydrates are the most abundant class among biological molecules. Advances in glycobiology have revealed the vital roles played by glycosides and glycoconjugates in biological events. In this context, access to homogenous oligosaccharides and glycoconjugates is critical for various biological investigations. Glycosylation is the cornerstone of glycoside synthesis, and during glycosylation, the control of stereoselectivity at the anomeric position is highly important. In this review, recent progresses in 1,2-cis-glycosylation reactions are summarized, with a focus on the influence of the protecting groups on the conformations of the glycosyl donors, role of reaction mixture additives, and synthetic utility of endocyclic cleavage of glycoside. Development of robust glycosylation reaction will contribute to biologically active oligosaccharide synthesis.

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Published online: 13th August, 2020

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14329
■ Four-Component Domino Reaction for the Synthesis of Novel 8-Methyl-9-substituted-2,10-diaryl-2,3-dihydro-10H-pyrano[3,2-e][1,2,4,3]triazaphospholo[1,5-c]pyrimidines

Dina A. Bakhotmah and Tarik E. Ali*

*Department of Chemistry, Faculty of Science, King Khalid University, Abha, Saudi Arabia

Abstract

A novel four-component domino reaction for the synthesis of 8-methyl-9-substituted-2,10-diaryl-2,3-dihydro-10H-pyrano[3,2-e]-[1,2,4,3]triazaphospholo[1,5-c]pyrimidines has been established. The reaction was performed in THF using readily available 5-substituted-2-amino-6-methyl-4-phenyl-4H-pyran-3-carbonitrile, dimethyl-formamide dimethyl acetal, hydrazine hydrate and aryldichlorophosphine. The simple and efficient one-pot four-component approach, catalyst free and mild reaction conditions made the present methodology a good synthetic procedure.

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Published online: 12th August, 2020

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-20-14308
■ Some New C3- and Cs-Symmetrical Trialkylamino-substituted 1,3,5-Triazines and Their Biological Evaluation

Shunsuke Shimomura, Yusuke Inoue, Yuki Kawano, Yuka Fujita, Kanae Yamada, Yumemi Matsumoto, Kazumi Yokomizo, Jian-Rong Zhou, Kaori Ota, Nobuko Mibu, Makoto Furutachi, and Kunihiro Sumoto*

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

Abstract

We report the preparation of some new additionally synthesized symmetrical 1,3,5-triazines (TAZ) and the results of biological evaluation of their anti-herpes simplex virus type 1 (anti-HSV-1) activity and cytotoxic activity against Vero cells. All of the new trisubstituted TAZ derivatives 3a-3e showed considerable levels of anti-HSV-1 activity (EC50 = 4.4 ~ 30.3 μM). Among the tested compounds, two compounds (3c-2 and 3d) that have three 3,4-methylenedioxyphenylalkylamino groups showed low levels of cytotoxicity (CC50 > 200 μM) against Vero cells. On the other hand, the C3-symmetrical TAZ derivatives 3a-2, 3b-2 and 3e　showed considerably high levels of cytotoxicity (CC50 = 8.91 ~ 15.2 μM). The structure-activity relationships for anti-HSV-1 activity and cytotoxicity of synthesized single-drug type 2,4,6-trisubstituted TAZ derivatives are also discussed.

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