Enantioselective fluorescent sensing of chiral carboxylic acid by engaging boronic acid and BINOL

Reports on structural diversification of steroids by means of multicomponent reactions (MCRs) have significantly increased over the last decade. This review covers the most relevant strategies dealing with the use of steroidal substrates in MCRs, including the synthesis of steroidal heterocycles and macrocycles as well as the conjugation of steroids to amino acids, peptides and carbohydrates. We demonstrate that steroids are available with almost all types of MCR reactive functionalities, e.g., carbonyl, carboxylic acid, alkyne, amine, isocyanide, boronic acid, etc., and that steroids are suitable starting materials for relevant MCRs such as those based on imine and isocyanide. The focus is mainly posed on proving the amenability of MCRs for the diversity-oriented derivatization of naturally occurring steroids and the construction of complex steroid-based platforms for drug discovery, chemical biology and supramolecular chemistry applications.

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A Novel Synthetic Route of Fused Tricyclic Framework Quinoline Derivatives from Readily Available Aliphatic Amino Carboxylic Acid Substrates

Oriental Journal Of Chemistry ◽

10.13005/ojc/350215 ◽

2019 ◽

Vol 35 (2) ◽

pp. 611-617 ◽

Cited By ~ 1

Author(s):

Shireen Mohammed

Keyword(s):

Carboxylic Acid ◽

Boronic Acid ◽

Suzuki Reaction ◽

Main Reaction ◽

Quinoline Derivatives ◽

Synthetic Route ◽

Amino Carboxylic Acid ◽

High Yields ◽

Reaction Processes ◽

Acid Substrate

A novel and an efficient strategy of fused tricyclic quinoline heterocycle compounds from aliphatic amino carboxylic acid substrates is disclosed. The protocol here is proceed over main reaction processes including: cyclization, protection, amidine formation, further cyclization and finally coupling with boronic acid substrate through Suzuki reaction. These reactions afforded the corresponding products in high yields. Furthermore, all synthesized compounds were identiﬁed by spectral data.

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Highly efficient fluorescent sensing for α-hydroxy acids with C3-symmetric boronic acid-based receptors

Tetrahedron Letters ◽

10.1016/j.tetlet.2008.05.139 ◽

2008 ◽

Vol 49 (33) ◽

pp. 4918-4921 ◽

Cited By ~ 14

Author(s):

Wen-Zhi Xu ◽

Zhi-Tang Huang ◽

Qi-Yu Zheng

Keyword(s):

Boronic Acid ◽

Hydroxy Acids ◽

Fluorescent Sensing ◽

Highly Efficient

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Fluorescent sensing of uronic acids based on a cooperative action of boronic acid and metal chelate

Chemical Communications ◽

10.1039/a703471g ◽

1997 ◽

pp. 1731-1732 ◽

Cited By ~ 34

Author(s):

Masayuki Takeuchi ◽

Masashi Yamamoto ◽

Seiji Shinkai

Keyword(s):

Boronic Acid ◽

Metal Chelate ◽

Uronic Acids ◽

Cooperative Action ◽

Fluorescent Sensing

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Synthesis of Hollow Conductive Polypyrrole Balls by the Functionalized Polystyrene as Template

Journal of Nanomaterials ◽

10.1155/2010/168025 ◽

2010 ◽

Vol 2010 ◽

pp. 1-6 ◽

Cited By ~ 5

Author(s):

Choo Hwan Chang ◽

Pyung Soo Son ◽

Jeong-Ah Yoon ◽

Seong-Ho Choi

Keyword(s):

Carboxylic Acid ◽

Boronic Acid ◽

Sulfonic Acid ◽

In Situ Polymerization ◽

The Other ◽

Core Shell ◽

Latex Particles ◽

Spherical Morphology ◽

In Situ Copolymerization

We report the preparation of hollow spherical polypyrrole balls (HSPBs) by two different approaches. In the first approach, core-shell conductive balls, CSCBs, were prepared with poly(styrene) as core and polypyrrole (PPy) as shell by in situ polymerization of pyrrole in the presence of polystyrene (PS) latex particles. In the other approach, CSCBs were obtained by in situ copolymerization of pyrrole in the presence of PS(F) with hydrophilic groups like anhydride, boronic acid, carboxylic acid, or sulfonic acid, and then HSPBs were obtained by the removal of PS or PS(F) core from CSCBs. TEM images reveal the spherical morphology for HSPBs prepared from PS(F). The conductivity of CSCBs and HSPBs was in the range of 0.20–0.90 S/cm2.

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2-(4-Boronophenyl)quinoline-4-carboxylic acid derivatives: Design and synthesis, aggregation-induced emission characteristics, and binding activity studies for D-ribose with long-wavelength emission

Journal of Chemical Research ◽

10.1177/1747519819893642 ◽

2019 ◽

Vol 44 (3-4) ◽

pp. 152-160

Author(s):

Guiqian Fang ◽

Hao Wang ◽

Zhancun Bian ◽

Guimin Zhang ◽

Min Guo ◽

...

Keyword(s):

Carboxylic Acid ◽

Boronic Acid ◽

Clinical Laboratory ◽

Fluorescence Emission ◽

Fluorescent Sensors ◽

Intensity Change ◽

Buffer Solution ◽

Aggregation Induced Emission ◽

Long Wavelength ◽

Phenyl Boronic Acid

Long-wavelength fluorescent sensors with large Stokes shifts show useful applications in chemical biology and clinical laboratory diagnosis. We have recently reported [4-(4-{[3-(4-boronobenzamido)propyl]carbamoyl}quinolin-2-yl)phenyl]boronic acid that can selectively recognize d-ribose in a buffer solution of pH 7.4. However, the short emission wavelength (395 nm) and aggregation-caused quenching effect are not conducive to applications as a sensor. Novel diboronic acid compounds are synthesized using 2-(4-boronophenyl)quinoline-4-carboxylic acid as the building block and p-phenylenediamine as the linker. These compounds show aggregation-induced emission and fluorescence emission at about 500 nm. In addition, after binding to most carbohydrates, the aggregated state of the boronic acid–containing compounds is dissociated, resulting in fluorescence quenching. Using [4-(4-{[4-(3-borono-5-methoxybenzamido)phenyl]carbamoyl}quinoline-2-yl)phenyl]boronic acid as an example, addition of 55 mM of d-ribose resulted in the strongest quenching of 83% for all the tested carbohydrates, indicating selectively recognizing d-ribose. The reciprocal of the fluorescence intensity change showed a good linear relationship with the reciprocal of d-ribose concentration ( R2 ⩾ 0.99), indicating sensor binding to d-ribose in a ratio of 1:1 to form an inclusion complex. The fluorescence emission is red-shifted compared to 2-(4-boronophenyl)quinoline-4-carboxylic acid and its common derivatives, which provides a new method for the development of long-wavelength fluorescent sensors.

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