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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Most Cited Articles
The most cited articles are updated on a monthly basis and available as Last 3 Years. Citation data is obtained through CrossRef's Cited-Linking service.
Note: The Top 20 Citations are published across all volumes.
Published online: 1 January, 1970
■ Recent Progress in the Chemistry of Polyacylated Anthocyanins as Flower Color Pigments
Toshio Honda* and Norio Saito
*Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan
Abstract
It is recognized that the bluing effect and stabilization of flower colors will remarkably depend on the number of aromatic acids presented in the polyacylated anthocyanins. Although polyacyl functions would be considered to contribute strongly in the bluing of the flower color at the early stage of the investigation of polyacylated anthocyanin chemistry, the stabilization of flower color is considered to be another important objective by the presence of these aromatic acids at the present time. Since aromatic acids in the polyacylated anthocyanins are obviously linked with the sugar residues through the ester bonds, the polyacylated anthocyanins are classified into seven types by the substitution pattern of acyl functions, and the effect of the stacking structures of polyacyl anthocyanins on the stabilization of the flower color depending on the substitution pattern of acyl groups will be discussed. The physicochemical properties (NMR, UV-VIS spectra) in relation to the stability of the anthocyanins will also be discussed.
Published online: 1 January, 1970
■ Recent Developments of Free-Radical Substitutions of Heteroaromatic Bases
Francesco Minisci,* Elena Vismara, and Francesca Fontana
*Dipartimento di Chimica, Politecnico di Milano, Piazza Leonardo da Vinci 32, 20133 Milano, Italy
Abstract
The most recent mechanistic and synthetic aspects of the substitution of protonated heteroaromatic bases by nucleophilic carbon-centered radicals are reviewed. From mechanistic point of view the following aspects are discussed; i ) Structurereactivity relationship; i i ) Rearomatization of the radical adducts; iii) Solvent and isotope effects; iv) Overlap area with ionic reactions. The synthetic developments concern the following topics: i) Selectivity with carbonyl radicals; ii) Alkyl iodides as sources of alkyl radicals; iii) Alkylation by carboxylic acids; iv) Vinylation by olefins; v) Oxyalkylation by ethers; vi) Catalytic processes; vii) Substitution with strongly nucleophilic radicals.
Published online: 1 January, 1970
■ Cyclic Carboxylic Imide Structures as Structure Elements of High Stability. Novel Developments in Perylene Dye Chemistry
Heinz Langhals
*Institut für Organische Chemie, Universität München, Karlstrasse 23, D-80333 München, Germany
Abstract
Cyclic carboxylic imides are structure elements in aromatic heterocycles with high persistency. Their attachment to perylene leads to the perylene dyes; the synthesis and unique properties of the dyes are reported and discussed. An extension of the principle to other aromatics is made.
Published online: 1 January, 1970
■ Synthesis and Biological Evaluation of Water Soluble Taxoids Bearing Sugar Moieties
Tadakatsu Mandai,* Hiroshi Okumoto, Tetsuta Oshitari, Katsuyoshi Nakanishi, Katsuhiko Mikuni, Ko-ji Hara, Ko-zo Hara, Wakao Iwatani, Tetsuya Amano, Kosho Nakamura, and Yoshinori Tsuchiya
*Department of Chemical Technology, Kurashiki University of Science & the Arts, 2640 Nishinoura, Tsurajima-cho, Kurashiki 712-8505, Japan
Abstract
Synthesis and biological evaluation of a variety of water soluble taxoids with sugar moieties are described.
Published online: 15 June, 2007
■ From Haloquinolines and Halopyridines to Quinoline- and Pyridinesulfonyl Chlorides and Sulfonamides
Andrzej Maslankiewicz,* Krzysztof Marciniec, Maciej Pawlowski, and Pawel Zajdel
*Department of Organic Chemistry, The Medical University of Silesia
Jagiellonska 4, 41-200 Sosnowiec, Poland
Abstract
The action of sodium methanethiolate (in boiling DMF) towards haloazines (i.e. chloro- or bromo-pyridines and quinolines) (1) (with halogen substituent in non-aza-activated position) causes sequentially halogen ipso-substitution to methylthioazines (2) and then S-demethylation to azinethiolates (3A), which were: i) subjected to S-methylation, ii) oxidized to diazinyl disulfides (4) and iii) oxidatively chlorinated to azinesulfonyl chlorides (5). α- and β-pyridine- and quinolinesulfonyl chlorides (5a, 5c, 5d and 5f) were prepared by oxidative chlorination of respective disulfides (4) performed in conc. hydrochloric acid and characterized by 1H and 13C NMR spectra. All azinesulfonyl chlorides (5) were effectively converted to corresponding azinesulfonamides (6).
Published online: 1 February, 2005
■ Two New Alkaloids from Dendrobium chrysanthum
Li Yang, Chaofeng Zhang, Hong Yang, Mian Zhang, Zhengtao Wang,* and Luoshan Xu
*Department of Pharmacognosy, China Pharmaceutical University, Naning 210038, China
Abstract
Two new alkaloids, trans- and cis-dendrochrysanines (1 and 2) were isolated from the stems of Dendrobium chrysanthum Wall. and their structures were identified as (2S)-N-trans-cinnamoyl-2-oxopropyrrolidine (1) and (2S)-N-cis-cinnamoyl-2-oxopropyrrolidine (2), respectively, on the basis of spectroscopic methods.
Published online: 1 January, 1970
■ LI-F Antibiotics, a Family of Antifungal Cyclic Depsipeptides Produced by Bacillus polymyxa L-1129
Jun Kuroda, Toshio Fukai, Masataka Konishi, Jun Uno, Keiji Kurusu, and Taro Nomura*
*Faculty of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan
Abstract
Twelve antifungal depsipeptide antibiotics named as LI-F03a, LI-F03b, LI-F04a, LI-F04b, LI-F05a, LI-F05b, LI-F06a, LI-F06b, LI-F07a, LI-F07b, LI-F08a and LI-F08b have been isolated from the fermentation broth of Bacillus polymyxa L-1129 by use of extensive preparative HPLC. Not only their intrinsic antifungal and anti-Gram positive bacterial activity, they also showed unique synergistic antifungal effect in combination with the azole group antifungal agents. The structural studies disclosed that they are cyclic depsipeptides composed of six amino acids (three of them, L-threonine, D-allo-threonine and D-alanine being in common among all components and other three amino acids variable) on which is substituted by a 15-guanidino-3-hydroxypentadecanoic acid.
Published online: 4 February, 2013
■ Synthetic and Theoretical Approach towards Spirothiazolidinone Systems
Johnson George, Saurabh Singh, Rahul Joshi, Pushpa Pardasani, and Ramchand T. Pardasani*
*Department of Chemistry, Central University of Rajasthan, Bandarsindri, Distt. Ajmer-305802, India
Abstract
A convenient synthesis of spirothiazolidinones by nucleophilic cyclocondensation of intermediate imine with mercaptoacetic acid is described. Computational studies have been performed to substantiate the proposed mechanism as well as to ascertain transition state of the system.
Published online: 28 October, 2008
■ New [11C]Phosgene Based Synthesis of [11C]Pyrimidines for Positron Emission Tomography
Koh-ichi Seki,* Ken-ichi Nishijima, Kimihito Sanoki, Yuji Kuge, Masayuki Takahashi, Hiromichi Akizawa, Nagara Tamaki, Leonard I. Wiebe, and Kazue Ohkura*
*Central Institute of Radio Isotope Science, Hokkaido University, Kita 15 Nishi 7, Kita-ku, Sapporo, Hokkaido 060-0815, Japan
Abstract
Thymine, 5-FU, and uracil were successfully synthesized through a procedure involving a cyclocondensation of triphosgene with newly developed α-substituted β-aminoacrylamides intermediates (1a, X = Me; 1b, X = F; 1c, X = H). The radioligands [2-11C]thymine and [2-11C]5-fluorouracil were synthesized in high radiochemical yields in 16-17 minutes from the end of bombardment by applying the cyclocondensation method with [11C]COCl2.
Published online: 8 July, 2010
■ Synthesis and Anti-HIV Activity of New 3’-O-Phosphonomethyl Nucleosides
Michal Cesnek and Piet Herdewijn*
*K.U. Leuven, Rega Institute for Medical Research, Minderbroedersstraat 10, B-3000 Leuven, Belgium
Abstract
The synthesis of 4’(S)-ethynyl-2’-deoxythreosyl and β-D-galactofuranose nucleosides starting from D-galactose is described. The nucleobase is introduced using Vorbruggen glycosylation. The 4’(S)-ethynyl derivatives are obtained by selective oxidation of vicinal diol to the aldehyde and subsequent Bestmann modification of Seyferth-Gilbert homologation. All compounds were evaluated for activity against HIV (MT4 cells), RSV (Hep2 cells) and HCV (HCV replicon cells), however, none of these compounds demonstrate biological activity.
Published online: 20 December, 2018
■ Multigram-Scale and Column Chromatography-Free Synthesis of L-Azetidine-2-carboxylic Acid for the Synthesis of Nicotianamine and Its Derivatives
Tomohiro Takaishi, Kyosuke Wakisaka, Christopher J Vavricka, Hiromasa Kiyota, and Minoru Izumi*
*Graduate School of Environmental and Life Science, Okayama University, 1-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan
Abstract
Multigram-scale synthesis of L-azetidine-2-carboxylic acid from L-aspartic acid was achieved in 13 conventional synthetic steps, without the need for purification by silica-gel column chromatography and expensive reagents. Nicotianamine and its fluorescence-labeled derivatives could be obtained from this synthetic strategy.
Published online: 30 May, 2013
■ ent-3,4-seco-Labdane Diterpenoids from Callicarpa nudiflora Leaves with Anti-inflammatory Activity
Lei Zhang, Jian Huang, Mingsheng Liu,* Cui Zhang, Guoyu Li, Ke Zhang, Lin Dong, and Jinhui Wang*
*School of Traditional Chinese Materia Medicine, Shenyang Pharmaceutical University, No.103, Wenhua Road, Shenyang, China
Abstract
Two new ent-3,4-seco-labdane diterpenoids, ent-3,4-seco-16-hydroxy-12,15-epoxy-4(18),8(17),12,14-labdatetraen-3-oic acid (1) and ent-3,4-seco-12R,15-epoxy-4(18),8(17),13-labdatrien-3-oic acid (2), were isolated from the leaves of Callicarpa nudiflora. Their structures were elucidated by extensive spectroscopic analysis and the biosynthetic pathways leading to these compounds were proposed. The two compounds both exerted potent inhibitory activity against the production of nitric oxide (NO) in RAW264.7 stimulated by lipopolysaccharide (LPS).
Published online: 13 December, 2013
■ Solvent-Free Synthesis of New Chiral 3-Phenylamino-3,5-dihydro-4H-imidazol-4-one Derivatives from α-Amino Acid Phenylhydrazides
Yakdhane Kacem and Béchir Ben Hassine*
*Department of Chemistry, Faculty of Sciences, Laboratoire de Synthèse Organique Asymétrique et Catalyse Homogène, Avenue of the Environment, 5019 Monastir, Tunisia
Abstract
Enantiopure 2,5-disubstituted 3-phenylamino-3,5-dihydro-4H-imidazol-4-one derivatives were obtained in good to excellent yields by condensation of chiral α-amino acid phenylhydrazides and triethyl orthoesters in the presence of dry acetic acid as catalyst. All reactions are performed under solvent-free and mild conditions.
Published online: 1 January, 1970
■ Kinetic Resolution of 2-Furylcarbinols Using the Sharpless Oxidation and Its Application to the Synthesis of (5R,6S)-6-Acetoxy-5-hexadecanolide
Tetsuji Kametani,* Masayoshi Tsubuki, Yoko Tatsuzaki, and Toshio Honda
*Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan
Abstract
Kinetic resolution of 2-furylcarbinols employing 10 mol % of Ti(0iPr)4 in the presence of molecular sieves 3A under the Sharpless oxidation condition generally affords corresponding optically actlve 2-furylcarbinols in a range of 80-98% ee. Application of the optically active 1f to the synthesis of (5R,6S)-6-acetoxy-5-hexadecanolide (8), the major component of the oviposition attractant pheromone of the mosquito Culex pipens fatigans, has also been achieved.
Published online: 28 April, 2021
■ Recent Achievements in the Synthesis of Heterocyclic Compounds by Phthalhydrazide-Based Multicomponent Reactions
Ghodsi Mohammadi Ziarani,* Negar Jamasbi, and Fatemeh Mohajer
*Department of Chemistry, Faculty of Physic and Chemistry, Alzahra University, Tehran, Iran. P. O. Box 1993893973
Abstract
Phthalhydrazide is one of the useful starting material toward the synthesis of heterocyclic compounds, and considered as a valuable structural unit in organic synthesis due to its significant pharmacological and biological activities. There are many multicomponent reactions using phthalhydrazide under different conditions. This review article aims to give an overview of recent applications of phthalhydrazide in the multicomponent reactions during the period of 2006 to 2021.
Published online: 21 May, 2013
■ Whitmanoside A, a New α-Pyrone Glycoside from the Leech Whitmania pigra
Tao Li, Guo-Cai Wang,* Xiao-Jun Huang, and Wen-Cai Ye*
*College of Pharmacy, Jinan University, 601 West Huangpu Avenue, Guangzhou, 510632, China
Abstract
A new α-pyrone glycoside, whitmanoside A (1), along with eight known compounds, including two furanones (2, 3) and six proline-derived cyclic dipeptides (4-9), were isolated from the dried material of the leech Whitmania pigra. The structures of these compounds were established on the basis of their spectroscopic data and acid hydrolysis. This is the first report on the isolation of these compounds from a leech.
Published online: 1 January, 1970
■ The Crystal and Molecular Structure of 2,3,5,6-Tetraphenyl-1,4-dithiin
Ian W. Jones and Patrick E. Hoggard*
*Department of Chemistry, Santa Clara University, 500 El Camino Real, Santa Clara, California 95053-270, U.S.A.
Abstract
The phenyl rings in 2,3,5,6-tetraphenyl-1,4-dithiin have neither of the two most obvious configurations: all perpendicular to the dithiin ring (paddlewheel), or parallel to the dithiin double bonds (butterfly). Instead, there are two phenyls in each orientation.
Published online: 9 August, 2017
■ Three New Lactone-Type Diterpenoid Alkaloids from Aconitum rotundifolium Kar. & Kir.
Firas Obaid Arhema Frejat, Wenliang Xu, Lianhai Shan, and Xianli Zhou*
*School of Life Science and Engineering, Southwest Jiaotong University, NO.111, North Second Ring Road Chengdu 610031, Sichuan, China
Abstract
Three new lactone-type C19-diterpenoid alkaloids, rotundifosines A – C (1 - 3) along with two known diterpenoid alkaloids, heterophyllidine (4) and chellespontine (5) were isolated from the whole plant of Aconitum rotundifolium Kar. & Kir. Their structures were established on the basis of extensive spectroscopic analysis, including 1D and 2D NMR experiments. Compounds 1–3 were evaluated for cytotoxicity against MCF-7, MDA-MB-231, 786-0 and HepG2 human cancer cell lines.
Published online: 21 November, 2008
■ Facile Syntheses of Three Ahp-Type Building Blocks with Complementary Reactivity
Wen Chen, Xiao Zheng, Yuan-Ping Ruan, and Pei-Qiang Huang*
*Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China
Abstract
Two protected 3-amino-6-hydroxy-2-piperidone derivatives (Ahp, 12 and 6), as well as a thioether analogue (7) were synthesized starting from L-glutamic acid in four, five, and six steps respectively. The Ahp derivatives 12 and 6 are not only the structural feature found in many naturally occurring bioactive depsipeptides, but also precursors of the N-acyliminium such as D; while the (S)-thioether 7 was shown to be an effective synthetic equivalent of the novel 2-piperidone N-α-carbanion E via the lithium-naphthalenide (LN)-mediated reductive lithiation, capable of reacting with carbonyl compounds without an acidic α–position to give the α-hydroxyalkylation products.
Published online: 9 September, 2008
■ Synthetic Studies of Mangostin Derivatives with an Inhibitory Activity on PDGF-Induced Human Aortic Smooth Cells Proliferation
Yuko Nishihama, Takahisa Ogamino, Wen Lei Shi, Byung-Yoon Cha, Takayuki Yonezawa, Toshiaki Teruya, Kazuo Nagai, Kiyotake Suenaga, Je-Tae Woo, and Shigeru Nishiyama*
*Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku Yokohama 223-8522, Japan
Abstract
The mangostin derivatives 3-10, were synthesized by halogenation, electrochemical oxidation, and mCPBA oxidation of α- and γ-mangostins (1, 2). Among them, the hydroxyl 9 and the benzopyran 10 derivatives produced by mCPBA, showed remarkable antiproliferative activities against human aortic smooth muscle cells (HASMC) induced by platelet-derived growth factor (PDGF).
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