16642-93-6

Usage

Uses

Used in Pharmaceutical Industry:
3-Cyanocinnamic acid is used as a key intermediate in the synthesis of various pharmaceutical compounds. It serves as a building block for the development of new drugs with potential therapeutic applications.
Used in Antifungal Applications:
3-Cyanocinnamic acid is used as a starting material for the synthesis of triazoles, which exhibit antifungal activities. These synthesized compounds can be employed in the development of antifungal medications to treat various fungal infections.
Used in Dopamine Receptor Antagonist Applications:
3-Cyanocinnamic acid is used as a precursor in the preparation of aminocyclohexylethyl-substituted methylsulfonyloxy and methylsulfonyl tetrahydrobenzazepines. These compounds act as dopamine receptor antagonists and have potential applications in the treatment of psychiatric disorders, such as schizophrenia and other antipsychotic treatments.

InChI:InChI=1/C10H7NO2/c11-7-9-3-1-2-8(6-9)4-5-10(12)13/h1-6H,(H,12,13)/b5-4+

Upstream product

• 141-82-2 malonic acid 
• 24964-64-5 3-Cyanobenzaldehyde 
• 7732-18-5 water 
• 193151-10-9 3-(3-cyano-phenyl)-acrylic acid methyl ester 
• 6952-59-6 3-cyanobromobenzene 
• 79-10-7 acrylic acid 
• 57180-84-4 3-(3-oxo-propenyl)-benzonitrile 
• 98116-25-7 3-(3-carbamoylphenyl)-acrylic acid 
• 620-22-4 3-Methylbenzonitrile 

Downstream Products

• 138611-02-6 (1R,2S,3R,4S)-3,4-Bis-(3-cyano-phenyl)-cyclobutane-1,2-dicarboxylic acid 
• 42287-97-8 3-(3-cyanophenyl)propanoic acid 
• 193151-10-9 3-(3-cyano-phenyl)-acrylic acid methyl ester 
• 705250-93-7 (1S,2S)-2-(3-Cyano-phenyl)-cyclopropanecarboxylic acid 
• 193151-11-0 3-(3-cyano-phenyl)-propionic acid methyl ester 

Relevant academic research and scientific papers

Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes

β-Substituted acrylamides have low electrophilicity and are yet to be exploited in the enantioselective Rauhut–Currier reaction. By exploiting electron-withdrawing protection of the amide and moderate nucleophilicity N-heterocyclic carbenes, such substrates have been converted to enantioenriched quinolones. The reaction proceeds with complete diastereoselectivity, good yield, and modest enantioselectivity. Derivatizations are reported, as are computational studies, supporting decreased amide bond character with electron-withdrawing protection of the nitrogen.

Iodine-Catalyzed Facile Approach to Sulfones Employing TosMIC as a Sulfonylating Agent

A novel iodine-catalyzed functionalization of a variety of olefins and alkynes and direct decarboxylative functionalization of cinnamic and propiolic acids with TosMIC to provide access to various vinyl, allyl, and β-iodo vinylsulfones is described. This simple, efficient, and environmentally benign approach employing inexpensive molecular iodine as a catalyst demonstrates a versatile protocol for the synthesis of highly valuable sulfones, rendering it attractive to both synthetic and medicinal chemistry.

Monoamine oxidase inhibition by selected anilide derivatives

A series of anilide derivatives were synthesized and evaluated as inhibitors of recombinant human monoamine oxidase (MAO) A and B. The most potent inhibitors among the derivatives that were initially evaluated were (2E)-N-(3-chlorophenyl)-3-phenylprop-2-enamide (2c) and (2E)-N-(3-bromophenyl)- 3-phenylprop-2-enamide (2d) with IC50 values of 0.53 μM and 0.45 μM, respectively. These derivatives exhibited reversible and selective inhibition of MAO-B with binding affinities 37 fold higher for MAO-B than for MAO-A. Analysis of the possible binding interactions of these inhibitors with active site models of human MAO-A and -B led to the design of phenolic and benzonitrile derivatives of 2c and 2d. Among these were (2E)-N-(3-chlorophenyl)- 3-(4-hydroxyphenyl)prop-2-enamide (7c) and (2E)-N-(3-bromophenyl)-3-(4- hydroxyphenyl)prop-2-enamide (7d) which inhibited MAO-B selectively and reversibly with IC50 values of 0.032 μM and 0.026 μM, respectively. These inhibitors were at least 14 fold more potent than 2c and 2d. This study concludes that N,3-diphenylprop-2-enamide is a suitable scaffold for the design of selective MAO-B inhibitors and structural modifications to enhance the binding affinities of the inhibitors for the MAO-B active site include substitution with halogens on the N-phenyl ring and substitution with hydroxyl and nitrile functional groups on the para and meta positions, respectively, of the C3 phenyl ring. Possible binding modes of these structures within the MAO-B active site are proposed with the emphasis on the interactions of the inhibitor halogens and the hydroxyl and nitrile functional groups with active site residues and water molecules.

Cinnamamide compounds as metabotropic glutamate receptor antagonists

The invention relates to compounds of formula I or pharmaceutically acceptable salts or solvates thereof: where R1, R2, R3, A, X, and n are defined in the description. The invention also includes pharmaceutical composition

PYRROLIDINE DERIVATIVE OR SALT THEREOF

[PROBLEMS] To provide a compound which can be used for the treatment of a disease associated with a calcium-sensing receptor (CaSR), particularly hyperparathyroidism. [MEANS FOR SOLVING PROBLEMS] It is found that a novel pyrrolidine derivative having an aminomethyl group substituted by an arylaklyl group or the like or a salt thereof has an excellent CaSR agonistic modulation effect and also has an excellent selectivity in the inhibition of CYP2D6 which may cause a drug-drug interaction. Thus, the novel pyrrolidine derivative is useful as a therapeutic agent for a disease associated with CaSR (e.g., hyperparathyroidism, renal osteodystrophy and hypercalcemia).

Exploring distal regions of the A3 adenosine receptor binding site: Sterically constrained N6-(2-phenylethyl)adenosine derivatives as potent ligands

We synthesized phenyl ring-substituted analogues of N6-(1S,2R)- (2-phenyl-1-cyclopropyl)adenosine, which is highly potent in binding to the human A3AR with a Ki value of 0.63nM. The effects of these structural changes on affinity at human and rat adenosine receptors and on intrinsic efficacy at the hA3AR were measured. A 3-nitrophenyl analogue was resolved chromatographically into pure diastereomers, which displayed 10-fold stereoselectivity in A3AR binding in favor of the 1S,2R isomer. A molecular model defined a hydrophobic region (Phe168) in the putative A3AR binding site around the phenyl moiety. A heteroaromatic group (3-thienyl) could substitute for the phenyl moiety with retention of high affinity of A3AR binding. Other related N6-substituted adenosine derivatives were included for comparison. Although the N 6-(2-phenyl-1-cyclopropyl) derivatives were full A3AR agonists, several other derivatives had greatly reduced efficacy. N 6-Cyclopropyladenosine was an A3AR antagonist, and adding either one or two phenyl rings at the 2-position of the cyclopropyl moiety restored efficacy. N6-(2,2-Diphenylethyl)adenosine was an A 3AR antagonist, and either adding a bond between the two phenyl rings (N6-9-fluorenylmethyl) or shortening the ethyl moiety (N 6-diphenylmethyl) restored efficacy. A QSAR study of the N 6 region provided a model that was complementary to the putative A3AR binding site in a rhodopsin-based homology model. Thus, a new series of high-affinity A3AR agonists and related nucleoside antagonists was explored through both empirical and theoretical approaches.

Scalability of microwave-assisted organic synthesis. From single-mode to multimode parallel batch reactors

The direct scalability of microwave-assisted organic synthesis (MAOS) in a prototype laboratory-scale multimode microwave batch reactor is investigated. Several different organic reactions have been scaled-up typically from 1 mmol to 100 mmol scale. The transformations include multicomponent chemistries (Biginelli dihydropyrimidine and Kindler thioamide synthesis), transition metal-catalyzed carbon - carbon cross-coupling protocols (Heck and Negishi reactions), solid-phase organic synthesis, and Diels - Alder cycloaddition reactions using gaseous reagents in prepressurized reaction vessels. A range of different solvents (high and low microwave absorbing), Pd catalysts (homogeneous and heterogeneous), and varying reaction times and temperatures have been explored in these investigations. In all cases, it was possible to achieve similar isolated product yields on going from a small scale (ca. 5 mL processing volume) to a larger scale (max 500 mL volume) without changing the previously optimized reaction conditions (direct scalability). The prototype, benchtop multimode microwave reactor used in the present study allows parallel processing in either quartz or PTFE-TFM vessels with maximum operating limits of 300°C and 80 bar of pressure. The system features magnetic stirring in all vessels, complete on-line monitoring of temperature, pressure and microwave power, and the ability to maintain inert or reactive gas atmosphere.

AMIDINOPHENYL-PYRROLIDINES, -PYRROLINES, AND -ISOXAZOLIDINES AND DERIVATIVES THEREOF

The present application describes amidinophenyl-pyrrolidines, -pyrrolines, and -isoxazolidines and derivatives thereof of formula (I), or pharmaceutically acceptable salt forms thereof, wherein one of D and D' may be C(=NH)NH2 and the other H and J and J may be O or CH2, which are useful as inhibitors of factor Xa.

Amides of aminoalkyl-substituted azetidines, pyrrolidines, piperidines and azepanes

Novel amides of aminoalkyl-substituted azetidines, pyrrolidines, piperidines and azepanes, use of these compounds as pharmaceutical compositions, pharmaceutical compositions comprising the compounds, and a method of treatment employing these compounds and compositions. The compounds show a high and selective binding affinity to the histamine H3 receptor indicating histamine H3 receptor antagonistic, inverse agonistic or agonistic activity. As a result, the compounds are useful for the treatment of diseases and disorders related to the histamine H3 receptor.

Amidinophenyl-pyrrolidines, -pyrrolines, and -isoxazolidines and derivatives thereof

The present application describes amidinophenyl-pyrrolidines, -pyrrolines, and -isoxazolidines and derivatives thereof of formula I: or pharmaceutically acceptable salt forms thereof, wherein one of D and D' may be C(=NH)NH2 and the other H, and J1 and J2 may be O or CH2, which are useful as inhibitors of factor Xa.