28166-41-8

Usage

Uses

1. Used in Pharmaceutical Industry:
α-Cyano-4-hydroxyciannamic acid is used as an inhibitor of mitochondrial pyruvate transport, playing a crucial role in the regulation of cellular metabolism and energy production.
2. Used in Drug Delivery Systems:
α-Cyano-4-hydroxyciannamic acid is used as a matrix for encapsulation into NaY zeolite, enhancing the delivery and bioavailability of various drugs, including paclitaxel derivatives. It aids in investigating the activity of these derivatives using well-established in vitro angiogenesis assays.
3. Used in Mass Spectroscopic Analysis:
α-Cyano-4-hydroxyciannamic acid is employed as a matrix for peptides and nucleotides in mass spectroscopic analysis, facilitating the study of their structures and interactions.
4. Used in Angiogenesis Research:
α-Cyano-4-hydroxyciannamic acid is used as a matrix to investigate the activity of paclitaxel derivatives in several well-established in vitro angiogenesis assays, contributing to the understanding of their potential applications in cancer treatment and other related fields.

Biochem/physiol Actions

α-Cyano-4-hydroxycinnamic acid acts as a specific inhibitor of monocarboxylic acid transport, including lactate and pyruvate transport. It is also reported to block β-cell apical anion exchange (IC50 of 2.4 mM).

InChI:InChI=1/C10H7NO3/c11-6-8(10(13)14)5-7-1-3-9(12)4-2-7/h1-5,12H,(H,13,14)/p-1/b8-5+

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 64-19-7 acetic acid 
• 372-09-8 cyanoacetic acid 
• 6935-44-0 ethyl (E)-2-cyano-3-(4-hydroxyphenyl)-2-propenoate 

Relevant academic research and scientific papers

Enhanced antioxidation capacity endowed to a mixed type aldose reductase inhibitor leads to a promising anti-diabetic complications agent

A series of 5f-based new compounds has been designed and synthesized. In vitro screening demonstrated that the binding affinity and selectivity on aldose reductase (AR) were positively correlated with its antioxidation capacity. Compound 6d was verified t

Development of Novel Mitochondrial Pyruvate Carrier Inhibitors to Treat Hair Loss

Herein, we report the synthesis and evaluation of novel analogues of UK-5099 both in vitro and in vivo for the development of mitochondrial pyruvate carrier (MPC) inhibitors to treat hair loss. A comprehensive understanding of the structure-activity relationship was obtained by varying four positions of the hit compound, namely, the alkyl group on the N1 position, substituents on the indole core, various aromatic and heteroaromatic core structures, and various Michael acceptors. The major discovery was that the inhibitors with a 3,5-bis(trifluoromethyl)benzyl group at the N1 position were shown to have much better activity than JXL001 (UK-5099) to increase cellular lactate production. Additionally, analogue JXL069, possessing a 7-azaindole heterocycle, was also shown to have significant MPC inhibition activity, which further increases the chemical space for drug design. Finally, more than 10 analogues were tested on shaved mice by topical treatment and promoted obvious hair growth on mice.

COMPOSITIONS AND METHODS FOR MODULATING HAIR GROWTH

The present disclosure relates to compounds that are capable of inhibiting the mitochondrial pyruvate carrier and promoting hair growth. The disclosure further relates to methods of promoting hair growth or treating conditions or disorders affecting hair growth, such as baldness or alopecia.

Design, synthesis and biological evaluation of pyrido[2,3-d] pyrimidine derivatives as potential anticancer agents

Background: CDK2 shows a fundamental role as a controller of cell growing, which makes it as one of the goals of anticancer inhibitors. Methods: The current study participated in design (docking and binding energy), which used to select the promising prop

Development of the First Two-Pore Domain Potassium Channel TWIK-Related K+ Channel 1-Selective Agonist Possessing in Vivo Antinociceptive Activity

The TWIK-related K+ channel, TREK-1, has recently emerged as an attractive therapeutic target for the development of a novel class of analgesic drugs, suggesting that activation of TREK-1 could result in pain inhibition. Here, we report the synthesis of a series of substituted acrylic acids (1-54) based on our previous work with caffeate esters. The analogues were evaluated for their ability to modulate TREK-1 channel by electrophysiology and for their in vivo antinociceptive activity (acetic acid-induced writhing and hot plate assays), leading to the identification of a series of novel molecules able to activate TREK-1 and displaying potent antinociceptive activity in vivo. Furyl analogue 36 is the most promising of the series.

4-phenyl-α-cyanocinnamic acid amide: Screening for a negative ion matrix for MALDI-MS imaging of multiple lipid classes

Matrix-assisted laser desorption/ionization imaging mass spectrometry (MALDI-IMS) has become a method of choice in lipid analysis, as it provides localization information for defined lipids that is not readily accessible with nonmass spectrometric methods. Most current MALDI matrices have been found empirically. Nevertheless, preferential matrix properties for many analyte classes are poorly understood and may differ between lipid classes. We used rational matrix design and semiautomated screening for the discovery of new matrices suitable for MALDI-IMS of lipids. Utilizing Smartbeam- and nitrogen lasers for MALDI, we systematically compared doubly substituted α-cyanocinnamic acid derivatives (R1-CCA-R2) with respect to their ability to serve as negative ion matrix for various brain lipids. We identified 4-phenyl-α-cyanocinnamic acid amide (Ph-CCA-NH 2) as a novel negative ion matrix that enables analysis and imaging of various lipid classes by MALDI-MS. We demonstrate that Ph-CCA-NH2 displays superior sensitivity and reproducibility compared to matrices commonly employed for lipids. A relatively small number of background peaks and good matrix suppression effect could make Ph-CCA-NH2 a widely applicable tool for lipid analysis.

Compelling evidence for lucky survivor and gas phase protonation: The unified MALDI analyte protonation mechanism

This work experimentally verifies and proves the two long since postulated matrix-assisted laser desorption/ionization (MALDI) analyte protonation pathways known as the Lucky Survivor and the gas phase protonation model. Experimental differentiation betwe

Insulin Derivatives Conjugated with Structurally Well Defined Branched Polymers

Insulin conjugated with structurally well defined, bifurcated and trifurcated polymers can be use by pulmonary delivery for systemic absorption through the lungs to reduce or eliminate the need for administering other insulins by injection.

CO2 absorbing cost-effective ionic liquid for synthesis of commercially important alpha cyanoacrylic acids: A safe process for activation of cyanoacetic acid

Cost-effective and carbon dioxide absorbing ionic liquid, tri-(2-hydroxyethyl) ammonium acetate, was shown to perform multiple roles in Knoevenagel condensation. It acted as an environmentally benign solvent, as an activating catalyst for the less reactive cyanoacetic acid and also as a risk reduction medium for the unevenly generated large amount of CO2 gas for large scale reactions. The reaction was scaled up for multi-gram synthesis of commercially important alpha cyanoacrylic acids.

Knoevenagel condensation in heterogeneous phase catalyzed by IR radiation and Tonsil Actisil FF

Infrared radiation promoted the synthesis of benzylidenemalononitriles, benzylidenecyanoacetamides and benzylidenecyanoacetic acids by condensation of aromatic aldehydes with the corresponding active methylene compound in the presence of Tonsil Actisil FF, without solvent. Mass of catalyst, solvent, and reaction time were assessed in order to improve the efficiency of this process.