538-41-0Relevant articles and documents
Novel Synthesis of 2-Amino-1,4-benzoquinone-4-phenylimides from Anilines via Dess-Martin Periodinane Oxidation
Ma, Heng Chang,Jiang, Xuan Zhen
, p. 1679 - 1682 (2007)
A synthetic investigation on oxidation of anilines to 2-amino-1,4-benzoquinone-4-phenylimides via Dess-Martin periodinane (DMP) was carried out. This facile protocol offered the advantage of short reaction times, mild reaction conditions, high yields and compatibility with a wide range of functional groups.
Interactions of 4,4′-diaminoazobenzene derivatives with telomeric G-quadruplex DNA
McCallum, Jeremy E. B.,Coyle, Christopher W.,Elson, Ryan R.,Titterington, Blake A.
, p. 169 - 178 (2018)
The development of small molecules to stabilize the G-quadruplex structure has garnered significant attention for anticancer drug discovery. Herein, we report the synthesis of several 4,4′-diaminoazobenzene derivatives containing different substituent groups and their ability to bind and stabilize telomeric G-quadruplex DNA. Circular dichroism (CD) spectroscopy was performed to characterize the quadruplex topologies, measure stabilization effects, and evaluate their capabilities for conformational photoregulation. 4,4′-Diaminoazobenzene derivatives were found to moderately stabilize quadruplex structures but not affect conformational photoregulation. This work further develops the design and general understanding of the stabilization effects of small molecules with telomeric G-quadruplex DNA.
Conversion of anilines into azobenzenes in acetic acid with perborate and Mo(VI): correlation of reactivities
Karunakaran,Venkataramanan
, p. 375 - 385 (2019/02/14)
Azobenzenes are extensively used to dye textiles and leather and by tuning the substituent in the ring, vivid colours are obtained. Here, we report preparation of a large number of azobenzenes in good yield from commercially available anilines using sodium perborate (SPB) and catalytic amount of Na2MoO4 under mild conditions. Glacial acetic acid is the solvent of choice and the aniline to azobenzene conversion is zero, first and first orders with respect to SPB, Na2MoO4 and aniline, respectively. Based on the kinetic orders, UV–visible spectra and cyclic voltammograms, the conversion mechanism has been suggested. The reaction rates of about 50 anilines at 20–50?°C and their energy and entropy of activation conform to the isokinetic or Exner relationship and compensation effect, respectively. However, the reaction rates, deduced by the so far adopted method, fail to comply with the Hammett correlation. The specific reaction rates of molecular anilines, obtained through a modified calculation, conform to the Hammett relationship. Thus, this work presents a convenient inexpensive non-hazardous method of preparation of a larger number of azobenzenes, and shows the requirement of modification in obtaining the true reaction rates of anilines in acetic acid and the validity of Hammett relationship in the conversion process, indicating operation of a common mechanism.
A Natural Glycyrrhizic Acid-Tailored Light-Responsive Gelator
Fang, Heshu,Zhao, Xia,Lin, Yuan,Yang, Song,Hu, Jun
, p. 1192 - 1198 (2018/04/02)
The construction of stimuli-responsive materials by using naturally occurring molecules as building blocks has received increasing attention owing to their bioavailability, biocompatibility, and biodegradability. Herein, a symmetrical azobenzene-functionalized natural glycyrrhizic acid (trans-GAG) was synthesized and could form stable supramolecular gels in DMSO/H2O and MeOH/H2O. Owing to trans–cis isomerization, this gel exhibited typical light-responsive behavior that led to a reversible gel–sol transition accompanied by a variation in morphology and rheology. Additionally, this trans-GAG gel displayed a distinct injectable self-healing property and outstanding biocompatibility. This work provides a simple yet rational strategy to fabricate stimuli-responsive materials from naturally occurring, eco-friendly molecules.
