118409-66-8

Usage

Also known as

4-fluoro-α-cyanocinnamic acid

Type

Synthetic organic compound
Derivative of cinnamic acid
Versatile reactivity
Precursor for various functionalized compounds

Specific content

Commonly used in the synthesis of pharmaceuticals and agrochemicals
Used as a building block in the production of dyes, fragrances, and other fine chemicals
Fluorinated phenyl group provides unique properties
Potential applications in materials science
Possible use in the development of novel polymers or advanced materials with specific optical or electronic properties

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 372-09-8 cyanoacetic acid 
• 456-22-4 4-Fluorobenzoic acid 
• 5676-81-3 4-fluorobenzalaniline 
• 50737-52-5 ethyl 2-cyano-3-(4-fluorophenyl)acrylate 
• 98-86-2 acetophenone 
• 7677-24-9 trimethylsilyl cyanide 
• 706-06-9 3-(4-flurophenyl)prop-2-ynoic acid 
• 18861-57-9 ethyl (E)-2-cyano-3-(4-fluorophenyl)-2-propenoate 

Downstream Products

• 1573123-95-1 isobutyl 2-(tert-butylcarbamoyl)-3-(4-fluorophenyl)acrylate 

Relevant academic research and scientific papers

Discovery of novel dihydroartemisinin-cinnamic hybrids inducing lung cancer cells apoptosis via inhibition of Akt/Bad signal pathway

A series of dihydroartemisinin-cinnamic acid hybrids were designed, synthesized and evaluated. Most of the tested compounds showed enhanced anti-proliferative activities than artemisinin and dihydroartemisinin, among which 16 g had the superior potency with IC50 values ranging from 5.07 μM to 7.88 μM against four tested cancer cell lines. The cell cycle arrest revealed that 16 g induced A549 cell cycle arrest at G0/G1 phase via regulation of G1-related protein expression (Cdk4). Further mechanism studies reveal that 16 g induced A549 cells apoptosis via inhibiting Akt/Bad pathway. Moreover, 16 g depolarized the mitochondria membrane potentials and induced ROS generation in A549. Additionally, 16 g blocked migration of A549 cells in a concentration-dependent manner. What's more, 16 g is barely nontoxic to zebrafish embryos. Overall, the cell cycle arrest, inhibition of Akt/Bad signal pathway, ROS generation and migration blocked might explain the potent anti-proliferative activities of these compounds.

trans-Selective hydrocyanation of ynoates, ynones and ynoic acids catalyzed by nucleophilic phosphines

trans-Selective hydrocyanation of ynoates and ynones in the presence of TMSCN and an alcohol additive are catalyzed by nucleophilic phosphines. The trisubstituted E-olefin products of anti-addition of hydrogen cyanide to the alkyne are produced with high regio- and stereoselectivity. The alcohol additive reacts with TMSCN to produce hydrogen cyanide in situ. Ynoic acids undergo the phosphine catalyzed hydrocyanation in the presence of TMSCN under aprotic conditions only. In these reactions, TMSCN reacts with the acid to generate hydrogen cyanide and the silyl ester which, unlike the acid, undergoes phosphine catalyzed hydrocyanation and gives the stereo-defined E-2-cyano-acrylic acids after work up.

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.

Discovery of Novel Celastrol Derivatives as Hsp90-Cdc37 Interaction Disruptors with Antitumor Activity

To develop novel and efficient heat shock protein 90-cell division cycle 37 (Hsp90-Cdc37) interaction disruptors, several lipophilic fragments were introduced into celastrol (CEL) to synthesize 48 new CEL derivatives. Among all the target compounds, 41 wa

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.

Monocarboxylate transporter 1 inhibitors as potential anticancer agents

Potent monocarboxylate transporter 1 inhibitors (MCT1) have been developed based on α-cyano-4-hydroxycinnamic acid template. Structure-activity relationship studies demonstrate that the introduction of p-N, N-dialkyl/diaryl, and o-methoxy groups into cyanocinnamic acid has maximal MCT1 inhibitory activity. Systemic toxicity studies in healthy ICR mice with few potent MCT1 inhibitors indicate normal body weight gains in treated animals. In vivo tumor growth inhibition studies in colorectal adenocarcinoma (WiDr cell line) in nude mice xenograft models establish that compound 27 exhibits single agent activity in inhibiting the tumor growth.

CINNAMIC ACID AMIDE DERIVATIVE

The present invention provides a cinnamic acid amide derivative having an excellent analgesic action. The cinnamic acid amide derivative of the present invention is a compound showing excellent analgesic actions to not only a nociceptive pain model animal but also a neuropathic pain model animal, which is very useful as an agent for treating various pain diseases showing acute or chronic pains or neuropathic pains.

Base catalyzed formation and ring cleavage of 2- acyl-4- alkoxycarbonyl- 4-cyano substituted cyclohexanoles

THE REACTION of 1,3-diaryl-2-propen-1-ones (1a,b) with ethyl cyanoacetate in absolute ethanol in the presence of a catalytic amount of KOH at 50-55 °C afforded 3-aroyl-1-cyano-4-hydroxy-2,4, 6-triarylcyclohexanecarboxylates (2a,b). Base-catalyzed ring cleavage of 2a,b in refluxing ethanolic KOH solution afforded the corresponding 3-aryl- 2-cyano-2-propenoic acid 4 along with 1a,b. The structure of 2 was established through different spectroscopic techniques and confirmed via dehydration using thionyl chloride in refluxing pyridine afforded 3. However, reaction of 1a with ethyl cyanoacetate in refluxing ethanol in the presence of secondary amine (piperidine or morpholine) as a basic catalyst gave the open-chain Michael adduct 6. Treatment of the latter with ethanolic KOH solution yielded 1,5-pentanedione derivative 7. The relative configurations of 3b and 6 were determined through single crystal X-ray diffraction analysis.

Reaction of active methylene compounds with 4-fluorobenzalanilines and antifungal potential of the products

Condensation of active methylene compounds (1-6) with 4-fluorobenzalaniline resulted in the formation of addition-elimination products 1a-6a respectively. The products were identified on the basis of elemental analysis, m.m.p. determination and spectral studies and were screened in vitro for their antifungal potential against four phytopathogenic fungi.