Regular & Special Issues

71 data found. 1 - 30 listed Next Last

Published online: 19th October, 2016

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)16
Design and Synthesis of 1,3,5-Triazine Derivatives as Novel Inverse Agonists of Nuclear Retinoic Acid Receptor-Related Orphan Receptor-γ

Kazuma Kaitoh, Hirozumi Toyama, Yuichi Hashimoto, and Shinya Fujii*

*Institute of Molecular and Cellular Biosciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-0032, Japan


1,3,5-Triazine structure is a versatile chemical species for development of functional molecules, including biologically active compounds. We report herein the design, synthesis and biological evaluation of novel inverse agonists of nuclear retinoic acid receptor-related orphan receptor-γ (RORγ), in which the 2-anilino-1,3,5-triazine moiety was used as a scaffold for structural development. Among the synthesized compounds, 13b exhibited potent and selective inverse agonistic activity toward RORγ, being more potent than the lead compound T0901317 (7). The results suggest that the 2-anilino-1,3,5-triazine moiety is a useful scaffold for development of inhibitory ligands of nuclear receptors.

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Published online: 19th October, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)13
One-Pot Synthesis of Fused 2-Pyridones from Heteroarylacrylic Acid via Curtius Rearrangement and Microwave-Assisted Thermal Electrocyclization

Takashi Nishiyama, Noriyuki Hatae, Kaori Hayashi, Manami Obata, Kimiko Taninaka, Masahiro Yamane, Shota Oda, Takumi Abe, Minoru Ishikura, Satoshi Hibino, and Tominari Choshi*

*Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan


We investigated the one-pot synthesis of several fused 2-pyridone ring systems based on a Curtius rearrangement, followed by a microwave-assisted thermal electrocyclization of a 2-aza-6π-electron system including isocyanate. We synthesized seven heterocyclic compounds containing a fused 2-pyridone ring. In these results, the one-pot synthesis of fused 2-pyridone ring system 5 from (E)-acrylic acids 1 under microwave irradiation conditions was more effective than the conventional reaction conditions in terms of the yield and the reaction time.

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Published online: 19th October, 2016

Review | Regular issue | Prepress
DOI: 10.3987/REV-16-847
Syntheses of Triazoloquinoxalines

Mohammed A. Baashen, Bakr F. Abdel-Wahab,* and Gamal A. El-Hiti*

*Applied Organic Chemistry Department, National Research Center, Dokki 12622, Giza, Egypt


This review summarizes the synthetic procedures for the production of various types of triazoloquinoxaline derivatives. Synthesis of triazolo[1,5-a]-, triazolo[4,3-a]-, triazolo[4,5-g]- and bis-triazoloquinoxalines are given. The main synthetic methods involve diazotization of 2-nitroanilines, then reaction with acid chloride derivatives followed by reduction of nitro groups and ring closure; ring closure of N-(2-alkynyl)-2-azido-anilines; reaction of 2,3-dichloroquinoxalines with acid hydrazides, or hydrazine hydrates and carbonyl compounds and reaction of 1,2-diaminobenzenes with hydrazonoyl halides. Triazoloquinoxalines are important intermediates for the design of novel biologically active molecules.

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Published online: 18th October, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)14
Synthesis of Unsymmetrical Heterobiaryls with Winding Vine-Shaped Molecular Asymmetry through a Condensation Pathway

Atsunori Mori,* Daichi Matsuoka, Shiomi Ashida, Ryo Inoue, Kazuki Maruhashi, Yoichi Okayama, Guan Hong Jin, and Kentaro Okano

*Chemical Science & Technology, Graduate School of Engineering, Kobe University, 1-1 Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan


Oxidative condensation of N-(3-buten-1-yl)-1,2-phenylenediamine with a formylated heteroarene bearing 3-buten-1-yl substituent gives unsymmetrical heterobiaryl in 42-86% yields. Ring-closing metathesis of the thus obtained product affords the cyclized product, which resulted in separation of each enantiomer by HPLC with a chiral column showing molecular asymmetry.

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Published online: 18th October, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)19
Synthesis of Enantioenriched Indolopiperazinones via Iridium(I) N-Heterocyclic Carbene Complex Catalyzed Asymmetric Intramolecular Allylic Amination Reaction

Ke-Yin Ye, Ke-Jia Wu, Guo-Tai Li, Li-Xin Dai, and Shu-Li You*

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, 345 Lingling Road, Shanghai 200032, China


Systematic study on employing the D-camphor derived carbenes as the chiral ligands in iridium-catalyzed intramolecular allylic amination reaction was carried out. Under mild reaction conditions, enantioenriched indolopiperazinones were obtained in good yields (75-95%) and high enantioselectivity (88-94% ee).

Supporting Info. (1.9MB)PDF (528KB)

Published online: 18th October, 2016

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)20
Synthesis of β-Dihydropyrrolyl and β-Pyrrolyl Acrylates and Their Antiproliferative Activity against HCT-116 and HL-60 Cells

Noriyuki Hatae,* Yoko Sakai, Kohei Yorozu, Chiaki Okada, Mitsuhiro Yoshimatsu, and Teruki Yoshimura*

*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan


The α,β-unsaturated carbonyl derivatives have been reported as bioactive substances, in particular acting as antiproliferative and antifungal agents. In this study, β-dihydropyrrolyl and β-pyrrolyl acrylates were synthesized by copper-mediated 5-endo cyclization of isolable Blaise-type β-enamino esters and were assessed for antiproliferative activity against HCT-116 and HL-60 cells. Some β-dihydropyrroles and β-pyrroles showed such activities, which were found to be due to different mechanisms: the β-dihydropyrroles act as cytotoxic agents, whereas the β-pyrroles act as cell cycle inhibitors.

Supporting Info. (1.7MB)PDF (287KB)

Published online: 17th October, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13532
Synthesis of Some Isoxazolidine and Isoxazoline Derivatives Using Nitrone-Derived (‒)-Menthone via 1,3-Dipolar Cycloaddition with Alkenes, Alkynes and Cycloalkenes

Heithem Abda, Kaïss Aouadi,* Moncef Mssadek, and Sébastien Vidal*

*Department of Chemistry, Faculté des Sciences de Monastir, Av de l'environnement 5019, Tunisia


Cycloaddition reactions between a menthone-based chiral nitrone and alkenes or alkynes under microwave activation afforded a series of enantiopure cycloadducts in good yields and with high stereoselectivity. Removal of the chiral auxiliary under acid-catalysis led to a new series of isoxazolidines and isoxazolines with the control of one, two or three stereogenic centers.

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Published online: 17th October, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13569
A Simplified Green Chemistry Approach to Synthesis of Azolo[1,5-a]pyrimidine Incorporated Thiophene Moiety

Tamer S. Saleh* and Abdullah S. Al-Bogami

*Green Chemistry Department, National Research Centre, El-Tahrir Street, Dokki, Giza 12622, Egypt


A highly efficient and environmentally friendly protocol has been developed for a facile synthesis of novel azolo[1,5-a]pyrimidines incorporated thiophene moiety under microwave irradiation. The advantages of short reaction time, high efficiency, no separation of in situ generated intermediate, using cheap, non-corrosive sodium persulfate as the oxidant, together with a very simple work-up procedure, make this one-pot and solvent-free protocol a green and powerful alternative to traditional methods for the synthesis of these kinds of compounds.

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Published online: 14th October, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13544
Synthesis of New 3-Substituted 1-Hydroxy-2-phenylindoles Using Sulfur-Containing Nucleophiles

Hyejin Kim and Sang Hyup Lee*

*College of Pharmacy and Innovative Drug Center, Duksung Women's University, Seoul 01369, Korea


The synthesis of new 3-[(acyl(or alkyl)thio)methyl]-1-hydroxy-2- phenylindoles 1 are presented. The substrates 2 obtained by each efficient three-step synthesis were treated, in the presence of SnCl2·2H2O, with nucleophiles such as thiocarboxylic acids and thiols to provide target compounds 1 by successive processes of nitro reduction and intramolecular condensation, followed by addition of nucleophile. Analyses of the reaction mechanism, including the effects of substituents along with the reactivity of nucleophiles, are described.

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Published online: 14th October, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13551
Facile Synthesis of Imidazo[1,5-a]pyrazin-8(7H)-ones from Mesoionic 1,3-Oxazolium-5-olates via a Multistep One-Pot Transformation

Ryosuke Saijo, Hidemitsu Uno, and Masami Kawase*

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


A novel one-pot conversion of mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates into imidazo[1,5-a]pyrazin-8(7H)-ones by the reaction with TosMIC is described. The structure of the product was determined by single-crystal X-ray analysis.

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Published online: 13th October, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13556
Two New Atisine-Type C20-Diterpenoid Alkaloids from Aconitum leucostomum

Wenliang Xu, Lin Chen, Lianhai Shan, Feng Gao, Shuai Huang, and Xianli Zhou*

*School of Life Science and Engineering, Southwest Jiaotong University, NO.111, North Second Ring Road Chengdu 610031, Sichuan, China


Two new atisine-type C20-diterpenoid alkaloids, leucostomine A (1) and leucostomine B (2) were isolated from the root of Aconitum leucostomum. Their structures were determined by spectroscopic methods including 1D-, 2D-NMR, and HR-ESI–MS.

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Published online: 12th October, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13546
Intermolecular Hydroamination of Styrene Catalyzed by Palladium(II) N-Heterocyclic Carbene Complexes in Ionic Liquid

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

*Department of Chemistry, Faculty of Science and Art, Adıyaman University, 02040 Adıyaman, Turkey


PdCl2(NHC)2 complexes have been synthesized by the reaction of palladium acetate with a series of benzimidazolium and imidazolinium salts and characterized by elemental analysis, 1H NMR and 13C NMR spectroscopy. These complexes were used as catalysts for the intermolecular hydroamination reactions between styrene with various anilines in ionic liquid at 160 oC and corresponding anti-Markovnikov products were obtained with a selectivity of 100% in good yields.

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Published online: 11th October, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)18
The Synthesis of Polyfunctionalized, Cyclohexene-Based Chirons from Tartaric Acid

Joshua N. Buckler, Brett D. Schwartz, and Martin G. Banwell*

*Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia


Compound ent-1 as well as certain related homochiral and polyfunctionalized cyclohexenes have been prepared from the 1,2-diacetal 4 that is itself readily derived from L-tartaric acid (3). Grignard addition and ring-closing metathesis processes constitute the key steps associated with the reaction sequences involved. This work provides a method for obtaining a range of potentially useful cyclohexenone-containing chirons that are enantiomerically related to those that have been prepared from the homochiral cis-1,2-dihydrocatechol 2, the product of the microbial biotransformation of bromobenzene.

Supporting Info. (1.2MB)PDF (654KB)

Published online: 11th October, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13538
A Concise and Highly Efficient Synthesis of Praziquantel as an Anthelmintic Drug

Zhezhou Yang, Lin Zhang, Huirong Jiao, Rusheng Bao, Weiwei Xu, and Fuli Zhang*

*Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, 285 Gebaini Road, Shanghai 201203, China


A concise and practical synthesis of praziquantel as anthelmintic drug is described. The key steps include a monoalkylation of ethanolamine for the preparation of 2-(2-hydroxyethylamino)-N-phenethylacetamide and a mild oxidation protocol with SO3-Py/DMSO as oxidant to transform alcohol into the corresponding aza-acetal. The telescoped synthesis is composed of five steps without purification of the intermediates, providing an overall yield of 80% with 99.8% purity after crystallization.

Supporting Info. (4.9MB)PDF (363KB)

Published online: 7th October, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)24
Synthesis of the 5-Methyluridine Monomer of 3’-O,4’-C-Ethyleneoxy-bridged Nucleic Acid

Takashi Osawa, Masakazu Dohi, Yuka Hitomi, Yuta Ito, Satoshi Obika,* and Yoshiyuki Hari*

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


A novel bridged nucleic acid, 3ʹ-O,4ʹ-C-ethyleneoxy-bridged nucleic acid (3ʹ,4ʹ-EoNA), forming 2ʹ,5ʹ-linkage with the flanking nucleotides in oligonucleotides was designed. The 3ʹ,4ʹ-EoNA is expected to improve the biophysical properties of the oligonucleotides (e.g., binding affinity with complementary single-stranded oligonucleotides and resistance against nuclease digestion) because of the presence of the 6ʹ-oxygen atom. In this study, the synthesis of the 5-methyluridine monomer of 3ʹ,4ʹ-EoNA was achieved via Lewis acid-mediated C4ʹ-iodoethoxylation followed by intramolecular 1,4-dioxane ring formation. Here, we describe, in detail, the results of the study.

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Published online: 5th October, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13533
Structure-Activity Relationship of Phenylethanoid Glycosides on the Inhibition of Amyloid β Aggregation

Eri Kidachi, Manami Kurisu, Yusaku Miyamae, Mizuho Hanaki, Kazuma Murakami, Kazuhiro Irie, and Hideyuki Shigemori*

*Graduate School of Life and Environmental Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Japan


The structure-activity relationship of the inhibitory activity of Aβ aggregation and antioxidant activity for phenylethanoid glycosides, acteoside (1), oraposide (2), and their derivatives which isolated from Orobanche minor was investigated. Acteoside (1) and oraposide (2) containing two catechol moieties exhibit strong activities for inhibition of Aβ aggregation and antioxidant. These results suggested that existence of the catechol moieties of the phenylethanoid glycosides were important roles for these activities.

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Published online: 3rd October, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)17
Kinetic Resolution of Racemic 2-Hydroxyacetals by Asymmetric Esterification Using a Mixed Anhydride Protocol

Kenya Nakata,* Eri Tokumaru, Takahiro Saitoh, Takayoshi Nakahara, Keisuke Ono, Takatsugu Murata, and Isamu Shiina*

*Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan


The non-enzymatic kinetic resolution of racemic 2-hydroxyacetals via asymmetric esterification with diphenylacetic acid and pivalic anhydride catalyzed by the chiral acyl transfer catalyst (R)-BTM is reported. The reaction transition states were elucidated using theoretical calculations; it was found that 1,3-dioxolane is a suitable reagent for attaining high selectivity.

Supporting Info. (25.8MB)PDF (1.2MB)

Published online: 3rd October, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13560
Titanium Tetraiodide Induced Cyclization of Cyanoketones into 3-Aryl-1-iodoisoquinolines

Kai Yashiro, Keito Sakata, Iwao Hachiya, and Makoto Shimizu*

*Department of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Kurimamachiya-cho Tsu, Mie 514-8507, Japan


3-Aryl-1-iodoisoquinoline synthesis is developed using titanium tetraiodide induced cyclization of cyanoketones. The method is applied to the short step formal synthesis of CWJ-a-5 having a topoisomerase I inhibitory activity. 3-Iodo-1-phenylisoquinoline synthesis is also reported under the similar reaction conditions.

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Published online: 29th September, 2016

Communication | Regular issue | Prepress
DOI: 10.3987/COM-16-13562
An Organocatalytic Asymmetric Diels-Alder Strategy for the Enantioselective Synthesis of Spirocyclic Oxindole-Cyclohexenones

Aoi Matsugi, Shiori Nunokawa, Naruhisa Watanabe, Yuya Nakata, Keiji Nakano, Yoshiyasu Ichikawa, and Hiyoshizo Kotsuki*

*Laboratory of Natural Products Chemistry, Faculty of Science, Kochi University, 2-5-1, Akebono-cho, Kochi 780-8520, Japan


An efficient method for the asymmetric synthesis of spirocyclic oxindole-cyclohexenone conjugates was developed. A chiral thiourea-catalyzed asymmetric Diels-Alder reaction between 3-alkylidene-oxindoles and Rawal’s diene was used as the key strategy for construction of the desired products in moderate to good yields with good diastereo- and enantioselectivities.

Supporting Info. (4.6MB)PDF (479KB)

Published online: 27th September, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13548
Synthesis and Evaluation of the Antitumor Activities of Two Series of Jaspine B Analogues Bearing 2-Alkyloxymethyl Group

En Zhang,* Shang Wang, Jie Gao, Xiao-Jing Shi, Ming-Ming Wang, Shuai-Min Xu, and Hong-Min Liu*

*School of Pharmaceutical Sciences, Zhengzhou University, Ke xue DaDao 100, Zhengzhou 450001, China


Two series of jaspine B analogues bearing 2-alkyloxymethyl group have been synthesized and evaluated for their cytotoxicity against four cancer cell lines, including Eca-109, EC-9706, B16-F10 and MCF-7 cells. Most of the compounds exhibited potent cytotoxic activity against all four cell lines. The results also revealed that some of the analogues prepared in the current study exhibited comparable or better in vitro antitumor activity to jaspine B. Compound 9g, in particular, displayed the most potent antitumor activity of all of the compounds prepared in the current study with an IC50 value of 2.0 ± 0.4 μM towards B16-F10 cells, which was better than that of jaspine B (IC50 = 5.08 ± 0.6 μM). The results of a structure–activity relationship study showed that the oxygen atom and the length of the alkyl chain have an effect on the cytotoxic activity of these compounds.

Supporting Info. (8.2MB)PDF (295KB)

Published online: 20th September, 2016

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)21
Palladium-Catalyzed Cross-Coupling of Aryl Chlorides with Arylsilatranes

Yutaro Yamamoto, Alexandre Baralle, Anaïs Godefroy, Kei Murakami, Hideki Yorimitsu,* and Atsuhiro Osuka

*Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan


The cross-coupling reactions of arylsilatranes with readily available and inexpensive aryl chlorides were carried out in toluene/THF at 100 ºC for 3 h in the presence of tetrabutylammonium fluoride as an activator for smooth transmetalation and catalytic amounts of palladium(II) acetate and XPhos.

Supporting Info. (3.1MB)PDF (421KB)

Published online: 16th September, 2016

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)27
Synthesis of 4-Substituted-pyridine-2,6-dicarboxylic Acid Derivatives from Pyruvates and Aldehydes in One Pot

Pandurang V. Chouthaiwale, Sébastien Lapointe, and Fujie Tanaka*

*Chemistry and Chemical Bioengineering Unit, Okinawa Institute of Science and Technology Graduate University, 1919-1 Tancha, Onna, Okinawa 904-0495, Japan


4-Substituted-pyridine-2,6-dicarboxylic acid derivatives were synthesized in one pot under mild conditions via the formation of dihydropyran derivatives from pyruvates and aldehydes catalyzed by pyrrolidine-acetic acid, followed by the reaction with ammonium acetate.

Supporting Info. (3.5MB)PDF (475KB)

Published online: 5th August, 2016

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)12
Synthesis of γ-Trifluoromethyl Tetronate Derivatives from Squarates

Yoshihiko Yamamoto,* Yosuke Takamizu, Takashi Kurohara, and Masatoshi Shibuya

*Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8601, Japan


Squarates and semisquarates were treated with TMSCF3 in the presence of a catalytic amount of AcONa in DMF at room temperature to afford 4-trifluoromethyl-4-hydroxycyclobutenones. Subsequent oxidative ring expansion of these products was performed using Pb(OAc)4 in the presence of MS 4A in 1,2-dichloroethane at 50 °C to afford γ-trifluoromethyl tetronate derivatives.

Supporting Info. (7MB)PDF (714KB)

Published online: 3rd August, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)7
[3+2] Cycloadditions of N-Protected ‘(S)-Diazoproline’ with Selected Acetylenes

Grzegorz Mlostoń,* Paulina Pipiak, and Heinz Heimgartner*

*Department of Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland


Acetylene carboxylates and an acetylene phosphonate reacted with N-protected (S)-2-(diazoacetyl)pyrrolidines ((S)-diazoprolines) to give optically active bis-heterocyclic pyrazole derivatives in a regioselective [3+2] cycloaddition. The reactions occurred at 60 °C in THF solution in the absence of a catalyst. However, diethyl ethynylphosphonate reacted significantly slower than the carboxylates. The obtained products were shown to exist in CDCl3 solution at room temperature as mixtures of rotamers. The reactions of diethyl ethynylphosphonate with a selected cyclic α-oxodiazo compound, i.e. 2-diazoacenaphthen-1-one, yielded a fused tricyclic pyrazole derivative.

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Published online: 1st August, 2016

Communication | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)11
Oxidative Self-Annulation of 2,5-Diaryl-3,4-diaminothiophene via C–C and C–S Bond Cleavage of the Thiophene Ring: A New Synthesis of an Amino-Substituted Triarylthieno[3,4-b]pyrazines and Their Photophysical Properties

Youhei Takeda,* Satoshi Ueta, and Satoshi Minakata*

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


A novel oxidative self-annulation of 2,5-diaryl-3,4-diaminothiophenes that accompanies C–C and C–S bonds cleavage of a thiophene ring to produce 3,5,7-triaryl-2-aminothieno[3,4-b]pyrazines in moderate to good yields has been discovered. Photophysical properties of this new family of thienopyrazines have also been disclosed.

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Published online: 1st August, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)10
Total Synthesis of Fargesine Using a Platinum-Catalyzed Intramolecular Friedel-Crafts-Type C–H Coupling–Allylic Amination Cascade

Yuito Tanaka, Yuta Suzuki, Yasumasa Hamada, and Tetsuhiro Nemoto*

*Pharmaceutical Chemistry, Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo, Chiba, Japan


Total synthesis of fargesine was described herein. The synthesis was based on the platinum-catalyzed intramolecular Friedel-Crafts-type C–H coupling–allylic amination cascade to construct the 3,4-fused tricyclic indole skeleton.

Supporting Info. (306KB)PDF (415KB)

Published online: 28th July, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)8
N-Heterocyclic Carbene-Promoted [3+2] Cycloaddition of Allenyl Sulfone and Arylidenemalononitriles

Satoru Kuwano,* Toshinobu Masuda, Koki Yamaguchi, and Takayoshi Arai

*Department of Chemistry, Graduate School of Science, Chiba University, , Japan


N-Heterocyclic carbenes promote the [3+2] cycloaddition of allenyl sulfone and arylidenemalononitriles, accompanied by 1,2-migration of the sulfonyl group. This reaction provides a new route to highly substituted cyclopentenes.

Supporting Info. (4.9MB)PDF (402KB)

Published online: 13th July, 2016

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)9
Preparation and Biological Activity of Novel Twin-Drug Type C2-Symmetrical Cyclic Phenylboronic Acid Derivatives

Makoto Furutachi, Ayumi Ejima, Reika Tsuru, Saho Goto, Toshiaki Gondo, Kenta Ako, Saho Fuchigami, Saya Fujii, Arisa Okumura, Ayumi Tozuka, Kazumi Yokomizo, Jian-Rong Zhou, Hiroshi Inao, Yutaro Ono, Nobuhiro Kashige, Fumio Miake, and Kunihiro Sumoto*

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


We here report the results of evaluation of antibacterial and anti-herpes simplex virus-1 (HSV-1) activities of a novel twin-drug type C2-symmetrical boronic acid and its pinacol ester derivatives. By using a primitive amide bond formation reaction, various targeted C2-symmetrical cyclic phenylboronic acid derivatives were obtained from the reactions of commercially available amino-substituted phenylboronic acid derivatives and diacid dichlorides. The C2-symmetrical bivalent molecule 3bd containing two cyclic phenylboronic acid pinacol ester moieties and a flexible hexamethylene linker showed both antibacterial activity (S. aureus) and anti-HSV-1 activity. The corresponding boronic acid derivative 3dd showed neither antibacterial nor anti-HSV-1 activity, indicating the importance of two pinacol ester functionalities.

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Published online: 30th June, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)4
Isolation and Evaluation of Hedgehog Inhibitors from Christmas Grass (Themeda arguens)

Tatsuro Yoneyama, Midori A. Arai,* Takashi Koyano, Thaworn Kowithayakorn, and Masami Ishibashi*

*Department of Natural Products Chemistry, Graduate School of Pharmaceutical Science, Chiba University, 1-8-1 Inohana, Chuo, Chiba, Japan


The hedgehog (Hh) signaling pathway is an important regulator of embryonic development, tissue patterning, cellular proliferation and differentiation. However, aberrant activation of the pathway is associated with tumorigenesis. In this study, the Hh signal inhibitory activity of plant extracts was measured with a cell-based assay system that targets GLI1-mediated transcription. Activity guided analysis of MeOH extracts of christmas grass (Themeda arguens) led to the isolation of four inhibitory compounds: aciculatin (1), 7-de-O-methylaciculatin (2), 8-C-β-D-boivinopyranosylapigenin (3) and aciculatinone (4). Compound 1 strongly inhibited Hh/GLI1-mediated transcriptional activity with an IC50 value of 1.8 μM, and disrupted the formation of the GLI1-DNA complex by EMSA. 1 and 3 were cytotoxic for human prostate (DU-145) and breast (MCF-7) cancer cells. These compounds may serve as new tools for the molecular dissection of Hh pathway activation.

Supporting Info. (129KB)PDF (1.6MB)

Published online: 22nd June, 2016

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)5
Synthesis of (±)-Cephalanthrin A Using Baeyer-Villiger Oxidation

Tomoki Itoh, Takumi Abe, Tominari Choshi, Takashi Nishiyama, and Minoru Ishikura*

*School of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan


Indoloquinazoline alkaloid (±)-cephalanthrin A was synthesized through the Baeyer-Villiger oxidation of the phenyl ketone derived from aldol reaction of tryptanthrin and acetophenone.

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71 data found. 1 - 30 listed Next Last