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Five-Membered Nitrogen Heterocyclic Compounds

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Five-Membered Nitrogen Heterocyclic Compounds Journal of Chemistry Five-Membered Nitrogen Heterocyclic Compounds Guest Editors: Ahmad Sazali Hamzah, Zurina Shaameri, and Suleyman Goksu Five-Membered Nitrogen Heterocyclic Compounds Journal of Chemistry Five-Membered Nitrogen Heterocyclic Compounds Guest Editors: Ahmad Sazali Hamzah, Zurina Shaameri, and Suleyman Goksu Copyright © 2013 Hindawi Publishing Corporation. All rights reserved. This is a special issue published in “Journal of Chemistry.” All articles are open access articles distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is prop- erly cited. Contents Five-Membered Nitrogen Heterocyclic Compounds, Ahmad Sazali Hamzah, Zurina Shaameri, and Suleyman Goksu Volume 2013, Article ID 250381, 2 pages Synthesis, Characterization, and Biological Activity of Novel Schiff and Mannich Bases of 4-Amino-3-(N-phthalimidomethyl)-1,2,4-triazole-5-thione, Uzma Yunus, Moazzam H. Bhatti, Naima Rahman, Nosheen Mussarat, Shazia Asghar, and Bilal Masood Volume 2013, Article ID 638520, 8 pages Imidazole and Triazole Coordination Chemistry for Antifouling Coatings, Markus Andersson Trojer, Alireza Movahedi, Hans Blanck, and Magnus Nyde´ Volume 2013, Article ID 946739, 23 pages Synthesis of Pyrroloquinones via a CAN Mediated Oxidative Free Radical Reaction of 1,3-Dicarbonyl Compounds with Aminoquinones, Thao Nguyen, Dwayaja Nadkarni, Shilpa Dutta, Su Xu, Sanghun Kim, Srinivasan Murugesan, and Sadanandan Velu Volume 2013, Article ID 262580, 12 pages Clauson Kaas Pyrrole Synthesis Catalyzed by Acidic Ionic Liquid under Microwave Irradiation, Feray Aydogan and Cigdem Yolacan Volume 2013, Article ID 976724, 6 pages Convenient Synthesis of 1,4-Dideoxy-1,4-imino-D-ribitol from D-Ribose,MakotoOba,ShoiKawaji, Hironobu Kushima, Takanori Sano, and Kozaburo Nishiyama Volume 2013, Article ID 519415, 5 pages Hindawi Publishing Corporation Journal of Chemistry Volume 2013, Article ID 250381, 2 pages http://dx.doi.org/10.1155/2013/250381 Editorial Five-Membered Nitrogen Heterocyclic Compounds Ahmad Sazali Hamzah,1 Zurina Shaameri,1 and Suleyman Goksu2 1 Institute of Science, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia 2 Chemistry Department, University of Attartuk, 25400 Erzurum, Turkey Correspondence should be addressed to Ahmad Sazali Hamzah; [email protected] Received 21 November 2013; Accepted 21 November 2013 Copyright © 2013 Ahmad Sazali Hamzah et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Five-membered nitrogen heterocycles with a pyrrolidine drugs, agrochemicals, and food additives is rising, because moiety or pyrrolidine derivatives are often found in many pure enantiomers are often more target specific and have bioactive molecules. Pyrrolidine, which is also known as fewer side effects than racemic mixtures. Furthermore, the tetrahydropyrrole, is a cyclic secondary amine with a five- global market for chiral drugs alone currently stands at USD membered heterocycle containing carbon atoms and nitro- 100 billion and steadily grows at the rate of 9% per annum. gen. Pyrrolidine can be prepared from 1,4-diaminobutanes by During the synthesis of a complex product consisting theactionofacids.Furthermore,itcanactasastrongbase, of several steps, it is essential for practical and economical anditisoftenusedinhomogeneousnonaqueousreactions. reasons to introduce the proper stereochemistry in an early Major fractions of organic compounds isolated from stage of the synthesis. This can be achieved by utilizing nature are comprised of nitrogen heterocycles. Such five- chiral building blocks that are enantiomerically pure and membered nitrogen heterocycles with a pyrrolidine ring sys- have functionalities that allow them to be transformed in the tem include nicotine, tryptamine, and vinblastine and possess desired products. Nevertheless, stereocontrolled synthetic considerable biochemical, pharmaceutical, and agricultural strategies will also have to be employed to acquire the poten- importance. These natural compounds may have hydrox- tial products. yproline, 2-pyrrolidone, streptopyrrolidine, or diphenylpro- Diverse synthetic knowledge and chemical possibili- linol rings as part of their well-defined conformations. ties or transformations would be inevitably explored when Apart from having significant structural features in many conducting research in such area. During such synthetic naturally occurring bioactive natural products, these ring processes, novel pharmacological agents beneficial in curing systems can act as versatile intermediates towards the syn- human diseases as well as new scientific findings may well thesis of more complex medicinally important compounds be generated. such as aniracetam, doxapram, cotinine, clausenamide, lacta- Research accounts in the field of organic chemistry and cystin, detoxine, and codonopsinine. These compounds have synthesis of five-membered nitrogen heterocyclic com- received much attention lately due to their diverse medicinal pounds (both aromatic and nonaromatic), as well as nat- properties such as antibacterial, antibiotics, antitumor, and ural products with such heterocyclic systems, submitted cytotoxic effects. and accepted in this publication complement the required Constructing highly functionalized heterocyclic com- standards and features of the journal. pounds would seem to be essential and significant prior to The articles generally contain definitive and compre- furnishing many of these biologically active natural con- hensive reports of significant findings obtained via original stituents. Preparing enantiopure polysubstituted pyrrolidine work in heterocyclic chemistry. Some display novel synthetic derivatives can even be a more challenging task. A number of methodology towards active heterocyclic materials which stereoselective methods for the synthesis of polysubstituted include efficient route, reproducible methodology, stereospe- pyrrolidines have been reported in the last decade. This is cific materials, high product yields, and enantiomeric excess. due to the fact that the demand for enantiomerically pure Someworkshadalsoreportedonfindingsfrombiological 2 Journal of Chemistry studies. Scientifically and fundamentally sound manuscripts with sufficient scientific data and evidence are highly consid- ered. Ahmad Sazali Hamzah Zurina Shaameri Suleyman Goksu Hindawi Publishing Corporation Journal of Chemistry Volume 2013, Article ID 638520, 8 pages http://dx.doi.org/10.1155/2013/638520 Research Article Synthesis, Characterization, and Biological Activity of Novel Schiff and Mannich Bases of 4-Amino-3-(N-phthalimidomethyl)-1,2,4-triazole-5-thione Uzma Yunus, Moazzam H. Bhatti, Naima Rahman, Nosheen Mussarat, Shazia Asghar, and Bilal Masood Department of Chemistry, Allama Iqbal Open University, Islamabad 44000, Pakistan Correspondence should be addressed to Uzma Yunus; uzma [email protected] Received 23 May 2013; Revised 1 August 2013; Accepted 29 August 2013 Academic Editor: Suleyman Goksu Copyright © 2013 Uzma Yunus et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The present work describes the syntheses and antimicrobial activity studies of a series of novel Schiff bases (4a–4i)and their Mannich bases (5a–5h) starting from 4-amino-3-(N-phthalimido-methyl)-1,2,4-triazole-5-thione (3). All the synthesized 1 13 compounds were characterized by IR, H-NMR, C-NMR,andMS.AllthesynthesizedcompoundswerescreenedforfourGram- negative strains, one Gram-positive strain of bacteria, and one diploid fungal strain. In general the antimicrobial activity increased remarkably on the introduction of azomethine functionality in parent triazole (3). The antimicrobial activity further improved when morpholine group was added to them except for Enterobacter cloacae, where loss of activity was observed. The results are promising and show that the fine tuning of the structures (5a, 5b, 5e, 5f, and 5h) can lead to some new antimicrobial compounds. 1. Introduction The literature reveals that the presence of morpholine or piperazine ring on a heterocyclic system contributes to Manyoftheantibioticspresentlyinusearebecominginef- enhanced pharmacological activities in many cases [22–24]. fective due to the emergence of resistant microbial strains. This could be attributed to the increased solubility of the It proves that the microbes are more intelligent than what is compounds in aqueous solvents because of the formation being anticipated by human beings, as they quickly develop of aminium salt [25]. These wide applications of 1,2,4- mechanisms to intercept the antibiotic, thus making them triazole Schiff and Mannich bases motivated us to synthesize ineffective. This situation demands the development of new new derivatives of 4-amino-3-(N-phthalimidomethyl)-1,2,4- antimicrobial agents which can deprive the microbes of their triazole-5-thione and to test their potential as antibacterial pathogenicity by novel multisite mechanisms of action [1– and antifungal agents. 4]. The 1,2,4-triazole nucleus is the main structural unit of many medicines currently in market. Ribavirin (1), letrozole (2), fluconazole3 ( ), itraconazole (4), and anastrozole (5)
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