HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
Published online by The Japan Institute of Heterocyclic Chemistry
Special Issue
Lutz F. Tietze's Special Issues, Vol. 93, No. 1, 2016
Published online: 28th March, 2016
■ Synthesis of Phenanthroline and Indole Based Hybrid Cyclophane Derivatives via Ring-Closing Metathesis
Sambasivarao Kotha,* Mukesh E. Shirbhate, Ajay Kumar Chinnam, and Gaddamedi Sreevani
*Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India
Abstract
Here, we report new phenanthroline-based cyclophane derivatives via Fischer indolization and ring-closing metathesis (RCM) as key steps. Addition of Grignard reagent to 1,10-phenanthroline-2,9-dicarbaldehyde 2 and subsequent autoxidation gave the bis-alkene dione derivative 3. Further, Fischer indolization of 3 followed by RCM under mild reaction conditions gave indole and phenanthroline containing hybrid cyclophanes such as 6a and 6b.
Published online: 19th October, 2015
■ Synthesis of a Cage-Shaped Nickel(II) Complex of bis(4-Cyclohexylamino-3-pyridyl)disulfide with μ2-Cl Bridging
Kouzou Matsumoto,* Naoki Kitayama, Yasukazu Hirao, Hiroyuki Kurata, and Takashi Kubo*
*Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-8531, Japan
Abstract
A cage-shaped nickel complex with μ2-Cl bridging [Ni2(μ-Cl)(bis(4-cyclohexylamino-3-pyridyl)disulfide)4Cl2]Cl is isolated and characterized by X-ray crystallographic analysis.
Published online: 7th October, 2015
■ Dilithiation of a 2,1-Benzothiazine
Nathan L. Calkins, Carissa S. Hampton, and Michael Harmata*
*Department of Chemistry, University of Missouri-Columbia, Missouri 65211, U.S.A.
Abstract
Treatment of benzothiazine 24 with excess amounts of n-BuLi followed by trapping with selected electrophiles afforded products that suggested the formation of dilithio species. Interestingly, however, the scope of the electrophilic trapping was rather limited, electrophilic sources of halogens and disulfides functioning nearly uniquely and competent electrophilic trapping agents in the process.
Published online: 1st October, 2015
■ A Synthesis of Hexahydro-H-oxazolo[3,4-a]pyrazin-3-ones from Fused Aziridines
Fang Fang, Iwona Maciagiewicz, and Stephen C. Bergmeier*
*Department of Chemistry and Biochemistry, Ohio University, Athens, OH 45701-2979, U.S.A.
Abstract
The piperazine ring is a common structural component of a large variety of biologically active small molecules. While a number of methods to prepare simple piperazine rings are known, the methods available for the synthesis of fused-ring piperazines are lacking. We report here a method for the synthesis of novel fused-ring piperazines through reaction with fused-ring aziridines followed by a ring closure to form the fused-ring piperazine system. The dependence of the reaction on the stereochemistry of the system has also been studied.
Published online: 12th January, 2016
■ Antiproliferative Activity of Hybrid Compounds between 6-Methoxy-3-(4-methoxyphenyl)-1H-indole and 4-Phenylpiperidine against HCT-116 and HL-60 Cells
Noriyuki Hatae,* Takashi Nishiyama, Shoko Tamura, Ryohei Yamamoto, Ayaka Matsui, Hiroki Shinchi, Satoshi Hibino, Chiaki Okada, Teruki Yoshimura, Tominari Choshi, and Eiko Toyota*
*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan
Abstract
Indole derivatives have been potential anticancer drugs. Methyl 6-methoxy-3-(4-methoxyphenyl)-1H-indole-2-carboxylate, in particular, was reported as a potent antiproliferative agent against MCF-7, NCI-H460, and A375-C5 tumor cells. In this study, the 3-arylindole-2-carboxylate exhibited weak activity against HCT-116 colon tumor and HL-60 promyelocytic leukemia cells. To develop the potent antiproliferative indole derivatives against HCT-116 and HL-60 cells, we synthesized 6-methoxy-3-(4-methoxyphenyl)-1H-indoles with various 2-substituents and assessed their activity. The 4-phenylpiperidine derivatives attenuated the tumor cells viability. Furthermore, their calculated structure resembled that of the antiproliferative loperamide derivatives.
Published online: 17th November, 2015
■ Comparing the Extraction of Am(III), Cm(III) and Eu(III) by CyMe4-BTPhen-Functionalized Silica and Zirconia-Coated Magnetic Nanoparticles
James Westwood, Ashfaq Afsar, Laurence M. Harwood,* Michael J. Hudson, Jan John, and Petr Distler
*School of Chemistry, University of Reading, Whiteknights, Reading, Berkshire, RG6 6AD, U.K.
Abstract
Herein, we report the synthesis of CyMe4-BTPhen-functionalized zirconia-coated (ZrO2) maghemite (γ-Fe2O3) magnetic nanoparticles (MNPs) and their ability to extract Am(III) from Eu(III) and Am(III) from Cm(III) in a range of HNO3 concentrations (0.001 – 4 M). Their extraction behavior is compared to our previously tested model based on silica-coated (SiO2) MNPs. Extraction of Am(III) and Eu(III) is reported, but little or no selectivity can be seen between Am(III) and Cm(III) at concentrations of 4 M HNO3.