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Cutting-Edge Organic Chemistry in Japan
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Cutting-Edge Organic Chemistry in Japan

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (30 April 2017) | Viewed by 37250

Special Issue Editor

Prof. Dr. Shunichi Fukuzumi

E-Mail Website
Editorial Board Member
1. Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2-1 Yamada-oka, Suita, Osaka 565-0871, Japan
2. Faculty of Science and Engineering, Meijo University, Nagoya, Aichi 468-8502, Japan
3. Department of Chemistry and Nano Science, Ewha Womans University, Seoul 03760, Republic of Korea
Interests: artificial photosynthesis; electron transfer chemistry; organic photocatalysis; redox catalysis; dioxygen activation
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The research activities of organic chemists in Japan have been very visible and have gained much recognition all over the world for their originality and high productivity. We are planning to have a Special Issue regarding "Cutting-Edge Organic Chemistry in Japan" in 2017, covering the new discoveries in all aspects of organic chemistry, focusing solely on Japan, in order to highlight the leading role of Japan in this area. The issue is accepting primary research articles and reviews.

Prof. Shunichi Fukuzumi
Guest Editor

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Published Papers (7 papers)

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Research

6990 KiB  
Article
Genealogy of Conjugated Acyclic Polyenes
by Haruo Hosoya
Molecules 2017, 22(6), 896; https://doi.org/10.3390/molecules22060896 - 29 May 2017
Cited by 4 | Viewed by 5067
Abstract
Based on the total π-electron energies Eπs of Hückel Molecular Orbital (HMO) method for all the possible isomers of conjugated acyclic polyenes (C2nH2n+2) up to n = 7, the structure–stability relation of the possible [...] Read more.
Based on the total π-electron energies Eπs of Hückel Molecular Orbital (HMO) method for all the possible isomers of conjugated acyclic polyenes (C2nH2n+2) up to n = 7, the structure–stability relation of the possible isomers was analyzed. It was shown that the mean length of conjugation L can roughly predict the ordering of stability among isomers, while the Z-index, or Hosoya-index, can almost perfectly reproduce their stability. Further, the genealogy of the conjugated acyclic polyene family was obtained by drawing systematic diagrams connecting these isomers of different n, and governed by several simple rules. Namely, the stability change of a given isomer in the genealogy connecting n and n + 1 polyenes can be classified into three different modes of vinyl addition (elongation, inner and outer branching) and horn growing, i.e., substitution of –HC=CH– moiety with –HC(=CH2)–C(=CH2)H–. By using the Z-index, we can extend this type of discussion to polyene radicals and even to “cross-conjugated” cyclic polyenes containing only one odd-membered cycle, such as radialene and fulvene. Full article
(This article belongs to the Special Issue Cutting-Edge Organic Chemistry in Japan)
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1027 KiB  
Article
Photoreactions of Endohedral Metallofullerene with Siliranes: Electronic Properties of Carbosilylated Lu3N@Ih-C80
by Masahiro Kako, Kazuya Minami, Taiki Kuroiwa, Shinpei Fukazawa, Yuki Arikawa, Michio Yamada, Yutaka Maeda, Qiao-Zhi Li, Shigeru Nagase and Takeshi Akasaka
Molecules 2017, 22(5), 850; https://doi.org/10.3390/molecules22050850 - 20 May 2017
Cited by 3 | Viewed by 4235
Abstract
Photochemical carbosilylation of Lu3N@Ih-C80 was performed using siliranes (silacyclopropanes) to afford the corresponding [5,6]- and [6,6]-adducts. Electrochemical studies indicated that the redox potentials of the carbosilylated derivatives were shifted cathodically in comparison with those of the [5,6]-pyrrolidino [...] Read more.
Photochemical carbosilylation of Lu3N@Ih-C80 was performed using siliranes (silacyclopropanes) to afford the corresponding [5,6]- and [6,6]-adducts. Electrochemical studies indicated that the redox potentials of the carbosilylated derivatives were shifted cathodically in comparison with those of the [5,6]-pyrrolidino adducts. The electronic effect of the silirane addends on Lu3N@Ih-C80 was verified on the basis of density functional theory calculations. Full article
(This article belongs to the Special Issue Cutting-Edge Organic Chemistry in Japan)
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Figure 1

2562 KiB  
Article
Loss of the Phenolic Hydroxyl Group and Aromaticity from the Side Chain of Anti-Proliferative 10-Methyl-aplog-1, a Simplified Analog of Aplysiatoxin, Enhances Its Tumor-Promoting and Proinflammatory Activities
by Yusuke Hanaki, Masayuki Kikumori, Harukuni Tokuda, Mutsumi Okamura, Shingo Dan, Naoko Adachi, Naoaki Saito, Ryo C. Yanagita and Kazuhiro Irie
Molecules 2017, 22(4), 631; https://doi.org/10.3390/molecules22040631 - 13 Apr 2017
Cited by 6 | Viewed by 5447
Abstract
Aplysiatoxin (ATX) is a protein kinase C (PKC) activator with potent tumor-promoting activity. In contrast, 10-methyl-aplog-1 (1), a simplified analog of ATX, was anti-proliferative towards several cancer cell lines without significant tumor-promoting and proinflammatory activities. To determine the effects of the [...] Read more.
Aplysiatoxin (ATX) is a protein kinase C (PKC) activator with potent tumor-promoting activity. In contrast, 10-methyl-aplog-1 (1), a simplified analog of ATX, was anti-proliferative towards several cancer cell lines without significant tumor-promoting and proinflammatory activities. To determine the effects of the phenolic group on the biological activities of 1, we synthesized new derivatives (2, 3) that lack the phenolic hydroxyl group and/or the aromatic ring. Compound 2, like 1, showed potent anti-proliferative activity against several cancer cell lines, but little with respect to tumor-promoting and proinflammatory activities. In contrast, 3 exhibited weaker growth inhibitory activity, and promoted inflammation and tumorigenesis. The binding affinity of 3 for PKCδ, which is involved in growth inhibition and apoptosis, was several times lower than those of 1 and 2, possibly due to the absence of the hydrogen bond and CH/π interaction between its side chain and either Met-239 or Pro-241 in the PKCδ-C1B domain. These results suggest that both the aromatic ring and phenolic hydroxyl group can suppress the proinflammatory and tumor-promoting activities of 1 and, therefore, at least the aromatic ring in the side chain of 1 is indispensable for developing anti-cancer leads with potent anti-proliferative activity and limited side effects. In accordance with the binding affinity, the concentration of 3 necessary to induce PKCδ-GFP translocation to the plasma membrane and perinuclear regions in HEK293 cells was higher than that of 1 and 2. However, the translocation profiles for PKCδ-GFP due to induction by 1–3 were similar. Full article
(This article belongs to the Special Issue Cutting-Edge Organic Chemistry in Japan)
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2505 KiB  
Article
[2 + 2] Photodimerization of Naphthylvinylpyridines through Cation-π Interactions in Acidic Solution
by Shinji Yamada and Yuka Nojiri
Molecules 2017, 22(3), 491; https://doi.org/10.3390/molecules22030491 - 20 Mar 2017
Cited by 12 | Viewed by 4839
Abstract
Irradiation of (E)-4-(2-(2-naphthyl)vinyl)pyridine (1a) and (E)-4-(2-(1-naphthyl)vinyl)pyridine (1b) with a 250 W high-pressure mercury lamp in acidic solution afforded synHT dimers in high stereoselectivities. Similar results were obtained by visible light irradiation. On the other [...] Read more.
Irradiation of (E)-4-(2-(2-naphthyl)vinyl)pyridine (1a) and (E)-4-(2-(1-naphthyl)vinyl)pyridine (1b) with a 250 W high-pressure mercury lamp in acidic solution afforded synHT dimers in high stereoselectivities. Similar results were obtained by visible light irradiation. On the other hand, when the reactions were carried out under neutral conditions, the stereoselectivities were very low, and the yields were decreased by visible light irradiation. Comparison of the UV-vis spectra between the acidic and the neutral conditions elucidated that the red shift was observed in acidic solutions. These results show that HCl plays essential roles not only in the preorientation of substrates through cation-π interactions, but also in the changes in the absorption properties of substrates that enable visible light reactions. Full article
(This article belongs to the Special Issue Cutting-Edge Organic Chemistry in Japan)
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1174 KiB  
Communication
A Direct Method for β-Selective Glycosylation with an N-Acetylglucosamine Donor Armed by a 4-O-TBDMS Protecting Group
by Hidenori Tanaka, Yu Hamaya and Hiyoshizo Kotsuki
Molecules 2017, 22(3), 429; https://doi.org/10.3390/molecules22030429 - 8 Mar 2017
Cited by 3 | Viewed by 5559
Abstract
A new direct method for β-selective glycosylation with an N-acetylglucosamine (GlcNAc) donor was developed. This substrate, which can be readily prepared from commercially available GlcNAc in two steps, contains a 4-O-tert-butyldimethylsilyl (TBDMS) protecting group as a key component. [...] Read more.
A new direct method for β-selective glycosylation with an N-acetylglucosamine (GlcNAc) donor was developed. This substrate, which can be readily prepared from commercially available GlcNAc in two steps, contains a 4-O-tert-butyldimethylsilyl (TBDMS) protecting group as a key component. We found that this functionality could have a favorable effect on the reactivity of the GlcNAc donor. Glycosylation with the armed donor using primary alcohols in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf) in 1,2-dichloroethane smoothly gave the desired coupling products in good yields with complete β-selectivity, while sterically hindered acceptors were less efficient. Full article
(This article belongs to the Special Issue Cutting-Edge Organic Chemistry in Japan)
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2125 KiB  
Communication
Modeling of the Bioactivation of an Organic Nitrate by a Thiol to Form a Thionitrate Intermediate
by Tsukasa Sano, Keiichi Shimada, Yohei Aoki, Takayuki Kawashima, Shohei Sase and Kei Goto
Molecules 2017, 22(1), 19; https://doi.org/10.3390/molecules22010019 - 25 Dec 2016
Cited by 4 | Viewed by 5178
Abstract
Thionitrates (R–SNO2) have been proposed as key intermediates in the biotransformation of organic nitrates that have been used for the clinical treatment of angina pectoris for over 100 years. It has been proposed and widely accepted that a thiol would react [...] Read more.
Thionitrates (R–SNO2) have been proposed as key intermediates in the biotransformation of organic nitrates that have been used for the clinical treatment of angina pectoris for over 100 years. It has been proposed and widely accepted that a thiol would react with an organic nitrate to afford a thionitrate intermediate. However, there has been no example of an experimental demonstration of this elementary chemical process in organic systems. Herein, we report that aryl- and primary-alkyl-substituted thionitrates were successfully synthesized by the reaction of the corresponding lithium thiolates with organic nitrates by taking advantage of cavity-shaped substituents. The structure of a primary-alkyl-substituted thionitrate was unambiguously established by X-ray crystallographic analysis. Full article
(This article belongs to the Special Issue Cutting-Edge Organic Chemistry in Japan)
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Figure 1

2595 KiB  
Article
Diphenylcarbene Protected by Four ortho-Iodine Groups: An Unusually Persistent Triplet Carbene
by Katsuyuki Hirai, Kana Bessho, Kosaku Tsujita and Toshikazu Kitagawa
Molecules 2016, 21(11), 1545; https://doi.org/10.3390/molecules21111545 - 15 Nov 2016
Cited by 6 | Viewed by 6016
Abstract
Diphenyldiazomethane with four iodine groups at the ortho positions and two tert-butyl groups at the para positions, i.e., bis(4-tert-butyl-2,6-diiodophenyl)diazomethane (1a-N2), was synthesized as a sterically hindered triplet carbene precursor. Irradiation of 1a-N2 in solution [...] Read more.
Diphenyldiazomethane with four iodine groups at the ortho positions and two tert-butyl groups at the para positions, i.e., bis(4-tert-butyl-2,6-diiodophenyl)diazomethane (1a-N2), was synthesized as a sterically hindered triplet carbene precursor. Irradiation of 1a-N2 in solution effectively generated the corresponding triplet diphenylcarbene 31a, which was characterized by UV-vis spectroscopy at low temperature, along with laser flash photolysis techniques at room temperature. The UV-vis spectrum of 31a was obtained by irradiating 1a-N2 in a 2-methyltetrahydrofuran matrix at 77 K. The ESR spectrum showed no triplet carbene signals, while a radical species was observed at the anticipated temperature of the decomposition of triplet carbene 31a. Transient absorption bands ascribable to 31a were observed by laser flash photolysis of 1a-N2 in a degassed benzene solution and decayed very slowly with a second-order rate constant (2k/εl) of 5.5 × 10−3·s−1. Steady-state irradiation of 1a-N2 in degassed benzene afforded 9,10-diarylphenanthrene derivative 2a in a 31% yield. Triplet carbene 31a was also trapped by either oxygen (kO2 = 6.5 × 105 M−1·s−1) or 1,4-cyclohexadiene (kCHD = 1.5 M−1·s−1) to afford the corresponding ketone 1a-O or the diarylmethane 1a-H2. The carbene was shown to be much less reactive than the triplet diphenylcarbene that is protected by two ortho-iodo and two ortho-bromo groups, 31b. Full article
(This article belongs to the Special Issue Cutting-Edge Organic Chemistry in Japan)
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