Unmasking Dipole Character of Acyl Ketene Dithioacetals via a Cascade Reaction with Arynes: Synthesis of Benzo[<i>b</i>]thiophenes

An unusual strategy toward novel substituted benzo­[<i>b</i>]­thiophenes has been developed. The generation of arynes in the presence of acyl ketene dithioacetals resulted in a cascade reaction involving [3 + 2] cycloaddition, and a dealkylative arylation of a thioether moiety to afford 2,3-disubstuted benzo­[<i>b</i>]­thiophenes. This route represents an expeditious approach to benzothiophenes that employs acyl ketene dithioacetals as dipoles

Synthesis of 2‑Aryl/Heteroaryloxazolines from Nitriles under Metal- and Catalyst-Free Conditions and Evaluation of Their Antioxidant Activities

The synthesis of structurally diverse 2-aryl/heteroaryloxazolines from nitriles and aminoalcohols has been achieved under metal- and catalyst-free conditions in good to excellent yields. An array of functional groups are well-tolerated, thus, allowing the introduction of many important biologically active motifs such as azoles, ring-fused azoles, saturated heterocyclics, and amines in 2-aryloxazoline scaffolds. An evaluation of the antioxidant properties using the DPPH (diphenyl picryl hydrazyl) assay method shows the pyrrole-functionalized 2-aryloxazoline to be the best antioxidant among all the synthesized 2-aryl/heteroaryloxazolines

The heatmap shows 74 HGCs absent from reference strains Mtb ATCC H37Ra and Mtb ATCC H37Rv but present in most of the clinical isolates.

<p>Predicted annotation of each of the cluster family is also represented. The genes validated using PCR are also shown adjacent to the annotations.</p

Core and accessory genome size evolution.

<p>(A) Each point indicates the number of HGCs conserved in a genome. The red line indicates an exponential decay function based on the median values of core HGCs when each time a new genome is added to the analysis. (B) Accessory genome of MTBC. The MTBC has an open pangenome model.</p

Genome Assembly Statistics of the eight Indian strains sequenced and assembled as part of the present study.

<p>Genome Assembly Statistics of the eight Indian strains sequenced and assembled as part of the present study.</p

(A) PCR validation of the 10 candidate genes (subset of 74 clusters identified) in 8 Indian clinical isolates (OSDD strains) and reference strains ATCC H37Ra and ATCC H37Rv.

<p>Arrow heads indicate the variably sized products in ATCC H37Ra and ATCC H37Rv genomes. Gene 4 and Gene 8 shares partial homology with laboratory strains and showed the presence of a differently sized product in ATCC H37Rv and ATCC H37Ra. (B) The alignment of Gene 4 against reference genomes showed an insertion of 175bp sequence in Gene 4 of OSDD strains with respect to reference strains. (C) The alignment of Gene 8 against reference genomes showed a deletion of 1,352bp sequence in Gene 8 of OSDD strains.</p

Molecular function GO annotations of the soft-core component.

<p>GO annotation for Biological process and Cellular component is provided in <a href="http://www.plosone.org/article/info:doi/10.1371/journal.pone.0122979#pone.0122979.s005" target="_blank">S5</a> and <a href="http://www.plosone.org/article/info:doi/10.1371/journal.pone.0122979#pone.0122979.s006" target="_blank">S6</a> Figs.</p

Overlap of accessory orthologous clusters shared within each strain pair.

<p>The diagonal represent the number of clusters present in any given strain and divides the data into exactly similar halves. Color key indicates the distribution of clusters. The sharing is irrespective of the cluster being present in any other strain. The minimum number of shared clusters is 109 clusters between Mcan CIPT 140070008 and Mbovis BCG Phipps and maximum (521) is between Mbovis BCG Sweden and Mbovis BCG Prague9.</p

Summary of sequence annotation statistics from BLAST2GO.

<p>Representative sequences from all the 8,099 HGCs were subjected to annotation out of which 47.77% (3,869) sequences were annotated with GO slim terms, 26.63% (2,157) sequences were without any BLAST hits, 23.43% (1,898) sequences had only blast results but didn’t had annotation and 1.65% (134) sequences retrieved mapping results but were without GO slim terms. A small fraction of 0.5% (41) sequences failed to fetch BLAST results.</p

Core-gene Tree.

<p>The un-rooted MTBC tree was created from alignment of 971 orthologous core-genes from 96 strains. A tree with Bootstrapped values is presented in <a href="http://www.plosone.org/article/info:doi/10.1371/journal.pone.0122979#pone.0122979.s003" target="_blank">S3 Fig</a> (details in text).</p