

HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
Published online by The Japan Institute of Heterocyclic Chemistry
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Regular & Special Issues
Published online: 13th May, 2020
Short Paper | Special issue | Prepress■ Conjugate Addition Reaction of Indole to Protected 2-Amino-1-Nitroethenes Mediated by Silica Gel
Kenichi Murai,* Shuji Miyazaki, and Hiromichi Fujioka*
*Graduate School of Pharmaceutical Science, Osaka University, 1-6 Yamadaoka, Suita, Osaka 560-0871, Japan
Abstract
We have developed a silica-gel-mediated route for the conjugate addition of indole to protected 2-amino-1-nitroethenes for the synthesis of 1-indolyl-1,2-ethanediamines. This is the first demonstration of indole as the nucleophile for addition to protected 2-amino-1-nitroethenes.
Published online: 12th May, 2020
Paper | Special issue | Prepress■ Concise Preparation and Biological Evaluations of 9-cis-Retinoic Acid Analogues Having an Aromatic Ring
Takashi Okitsu,* Kinya Iwatsuka, Kimie Nakagawa, Toshio Okano, and Akimori Wada*
*Faculty of Pharmaceutical Science, Kobe Pharmaceutical University, 4-19-1, Motoyamakita, Higashinada, Kobe 658-8558, Japan
Abstract
A series of 9-cis-retinoic acid analogues having an aromatic ring were prepared in only two steps, and were evaluated for transcriptional activities with retinoic acid response element (RARE) and retinoid X response element (RXRE). Among them, compound 6c, bearing a 2-naphthyl substituent, exhibited the highest transcriptional activity with RXR selectivity.
Published online: 8th May, 2020
Communication | Special issue | Prepress■ Synthesis of Lactone-Fused Cyclopropanes by Ring Contractive α-Ketol Rearrangement of Ketal-Fused Cyclobutanones
Kiyosei Takasu,* Koichi Shigenaga, Kazuma Shimoda, Hiroshi Takikawa, and Yousuke Yamaoka
*Graduate School of Pharmaceutical Sciences, Kyoto University, 46-29 Yoshida-shimoadachi-machi, Sakyo-ku, Kyoto 606-8501, Japan
Abstract
Ring contraction of cyclic silyl ketal-fused cyclobutanones into lactone-fused cyclopropanes under desilylative conditions is described. The reaction affords 1-hydroxy- and 1-amino-1-cyclopropanecarboxylic acid derivatives from cyclobutanone substrates and their imine congeners, respectively.
Published online: 28th April, 2020
Paper | Special issue | Prepress■ Thermally-Induced Doping of The Regioregular Polythiophene Bearing Alkylene Spacered Benzene Sulfonate Group at The Side Chain
Chihiro Kubota, Daisuke Morita, Keisuke Fujita, Sonoka Yamamoto, Toyoko Suzuki, Kentaro Okano, Masahiro Funahashi, Masaki Horie, and Atsunori Mori*
*Department of Chemical Science and Engineering, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan
Abstract
Regioregular polythiophene bearing a benzenesulfonate group, which involved an alkylene spacer between thiophene and benzene ring, was synthesized. The obtained polythiophene was shown to improve its conductivity by heating the polymer thin film through the transformation of the ester group into the corresponding sulfonic acid.
Published online: 17th April, 2020
Paper | Special issue | Prepress■ Synthesis of Probe Molecules, 6-(Dimethylamino)-2-Phenylisoindolin-1-Ones, for Mechanistic Studies of Firefly Luciferase Inhibition
Medha J. Gunaratna, Bo Hao, Man Zhang, Madoka Nakagomi, Ai Ito, Takeo Iwamoto, and Duy H. Hua*
*Department of Chemistry, Kansas State University, Manhattan, KS 66506, U.S.A.
Abstract
Firefly luciferase is used in high-throughput screening based on the detection of chemiluminescence. It catalyzes an esterification reaction of luciferin with adenosine 5’-triphosphate (ATP) followed by decarbonylation with oxygen and concomitance of light. Previously, we reported that firefly luciferase also possesses acyl-CoA synthetase activity and catalyzes an aromatic carboxylic acid group of F-53, using ATP, Mg2+ and coenzyme A (CoA), to produce F-53 covalently attached to active-site lysine-529 residue of firefly luciferase through the formation of an amide group. The amidation of lysine-529 resulted in a deactivation of luciferase. In order to probe firefly luciferase inhibition’s mechanism, we synthesized two probe molecules 1 and 2, mimicking F-53. Molecule 1 contains an azido-appended side chain in the aromatic ring of F-53, while 2 possesses an azido and a carboxylic acid group appended side chains. Both synthetic schemes are readily amenable to large-scale syntheses. Molecule 1 was made from 2-allylaniline, which was derived from a thermal-induced aromatic-Claisen rearrangement of N-allylaniline. The azido-appended side chain of 2 was installed from a Horner-Wadsworth-Emmons reaction and the carboxylic acid side chain from a Sonogashira reaction.
Published online: 16th April, 2020
Communication | Special issue | Prepress■ Synthetic Studies on Densanins: Stereoselective Construction of A Pyrrolidine Ring Containing a Quaternary Carbon
Kyosuke Ueda and Satoshi Yokoshima*
*Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8601, Japan
Abstract
We disclose our synthetic studies on densanins, which feature the stereoselective cycloaddition of a cycloheptenone and an azomethine ylide to construct a pyrrolidine ring containing a quaternary carbon
Published online: 16th March, 2020
Communication | Special issue | Prepress■ 5-Arylidenetetronate as A Versatile Electrophore for Pi-Extended Electron Acceptors
Yuki Hayashi, Yusuke Ishigaki, Jérémy Merad, Takanori Suzuki,* and Maurice Médebielle*
*Department of Chemistry, Faculty of Science, Hokkaido University, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan
Abstract
Bis[4-methoxy-5-methylenefuran-2(5H)-one]-type electron acceptors with anthracene-9,10-diyl and thiophene-2,5-diyl spacer were prepared by one-pot condensation of methyl tetronate with the corresponding dialdehydes. They undergo reversible electrochemical reduction, thus showing the potential utility of 5-arylidenetetronate as an electrophore for developing novel electron acceptors.