Synthesis of 2-amino- and 2-arylazoazulenes via nucleophilic aromatic substitution of 2-chloroazulenes with amines and arylhydrazines

The SNAr reaction of 2-chloroazulene derivative 1 with ethoxycarbonyl groups at the 1,3-positions of the azulene ring with several amines afforded the corresponding 2-aminoazulenes 3-9 in excellent yields. 2-Chloroazulene (2) without the electron-withdrawing groups reacted with highly nucleophilic cyclic amines (i.e., morpholine, piperidine and pyrrolidine) under the high-temperature conditions in a sealed tube to produce the corresponding 2-aminoazulenes 10-12 in good yields. 2-Aminoazulenes 10-14 without the electron-withdrawing groups were also obtained in good yields by the treatment of compounds 3-7 with 100% H3PO4, but in the cases of the reaction of 8 and 9 with a secondary amine function, the decomposition of the products resulted. The synthesis of 2-arylazoazulenes 15-18 was also established via the SNAr reaction of 1 with arylhydrazines. The optical and electrochemical properties of the 2-arylazoazulene derivatives were examined by UV/Vis spectroscopy, theoretical calculations and voltammetric experiments.ArticleORGANIC & BIOMOLECULAR CHEMISTRY. 94(10):3917-3923 (2017)journal articl

Genome Features and Secondary Metabolites Biosynthetic Potential of the Class Ktedonobacteria

The prevalence of antibiotic resistance and the decrease in novel antibiotic discovery in recent years necessitates the identification of potentially novel microbial resources to produce natural products. Ktedonobacteria, a class of deeply branched bacterial lineage in the ancient phylum Chloroflexi, are ubiquitous in terrestrial environments and characterized by their large genome size and complex life cycle. These characteristics indicate Ktedonobacteria as a potential active producer of bioactive compounds. In this study, we observed the existence of a putative “megaplasmid,” multiple copies of ribosomal RNA operons, and high ratio of hypothetical proteins with unknown functions in the class Ktedonobacteria. Furthermore, a total of 104 antiSMASH-predicted putative biosynthetic gene clusters (BGCs) for secondary metabolites with high novelty and diversity were identified in nine Ktedonobacteria genomes. Our investigation of domain composition and organization of the non-ribosomal peptide synthetase and polyketide synthase BGCs further supports the concept that class Ktedonobacteria may produce compounds structurally different from known natural products. Furthermore, screening of bioactive compounds from representative Ktedonobacteria strains resulted in the identification of broad antimicrobial activities against both Gram-positive and Gram-negative tested bacterial strains. Based on these findings, we propose the ancient, ubiquitous, and spore-forming Ktedonobacteria as a versatile and promising microbial resource for natural product discovery

Dust from Comet 209P/LINEAR during its 2014 Return: Parent Body of a New Meteor Shower, the May Camelopardalids

We report a new observation of the Jupiter-family comet 209P/LINEAR during its 2014 return. The comet is recognized as a dust source of a new meteor shower, the May Camelopardalids. 209P/LINEAR was apparently inactive at a heliocentric distance rh = 1.6 au and showed weak activity at rh < 1.4 au. We found an active region of <0.001% of the entire nuclear surface during the comet's dormant phase. An edge-on image suggests that particles up to 1 cm in size (with an uncertainty of factor 3-5) were ejected following a differential power-law size distribution with index q=-3.25+-0.10. We derived a mass loss rate of 2-10 kg/s during the active phase and a total mass of ~5x10^7 kg during the 2014 return. The ejection terminal velocity of millimeter- to centimeter-sized particles was 1-4 m/s, which is comparable to the escape velocity from the nucleus (1.4 m/s). These results imply that such large meteoric particles marginally escaped from the highly dormant comet nucleus via the gas drag force only within a few months of the perihelion passage.Comment: 18 pages, 4 figures, accepted on 2014 December 11 for publication in the Astrophysical Journal Letter

Diel patterns of zooplankton community structure in nearshore waters of different substrates off Tinggi and Sibu Islands, Malaysia, with special reference to copepods

The relationship between zooplankton community structure and selected environmental conditions was investigated by simultaneous two-day consecutive sampling in the waters overlying coral and sand sites off Sibu Island and a seagrass site off Tinggi Island, Johor, Malaysia. A total of 129 taxa were identified, 60 non-copepod taxa and 69 copepod species in all samples. Uni- and multi-variate analyses reveal distinct coral, sand, seagrass copepod assemblages with indicator copepod species and attributes of their size fractions. Small fraction (100–335 μm) samples contained greatest number of individuals, few rare species and were densest at onshore depths, and the opposite for large fraction (>335 μm) samples but were densest at nighttime and most species rich in the coral site at night. Higher species diversity at offshore stations is due likely to ecotonal effects of overlapping oceanic and nearshore communities. This study demonstrates the usefulness of uni- and multi-variate analyses in identifying patterns in zooplankton community structure in representative shallow tropical habitats, and the need for accurate zooplankton taxonomy, nighttime and daytime and onshore and offshore sampling, and size fractionation of samples

Synthesis of Azulene-Substituted Tetraarylpyrroles by Reaction of 1-Azulenyl Ketones with Benzoin and Ammonium Acetate

Tetraarylpyrroles with a 1-azulenyl substituent were prepared by the reaction of 1-azulenyl ketones, which have various aryl-substituents at their alpha-position, with benzoin in the presence of ammonium acetate as a nitrogen source of the pyrrole ring. Optical property of the tetraarylpyrroles obtained by the reaction was clarified by UV/Vis spectroscopy and/or time-dependent density functional theory (TD-DFT) calculations.ArticleHETEROCYCLES. 94(10):1870-1883 (2017)journal articl

A case of mid‐ureteral stricture with ipsilateral atrophic kidney in a young adult

Introduction Most congenital ureteral strictures occur at the ureteropelvic or ureterovesical junction in children. Mid‐ureteral stricture is very rare and can cause congenital hydronephrosis. Only a few studies have reported on coexisting mid‐ureteral stricture with ipsilateral atrophic kidney in young adults. Case presentation A 16‐year‐old girl presented with repeated urinary tract infection. Computed tomography revealed a right atrophic kidney and hydroureter. Retrograde pyelography showed a mid‐ureteral stricture. Laparoscopic nephroureterectomy was performed, and histological examination revealed mid‐ureteral stricture with hyperplasia of the fibrous connective tissue and an atrophic kidney. Conclusion Mid‐ureteral stricture in a young adult is extremely rare. Appropriate imaging studies including retrograde pyelography are necessary for accurate diagnosis of mid‐ureteral stricture