122024-75-3

Usage

Uses

Used in Pharmaceutical Industry:
3-BENZYLOXYCINNAMIC ACID is used as a key intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique structure allows for the creation of molecules with specific biological activities, making it a valuable component in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 3-BENZYLOXYCINNAMIC ACID is utilized as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its chemical properties enable the production of effective compounds for crop protection and management.
Used in Organic Synthesis:
3-BENZYLOXYCINNAMIC ACID is employed as a versatile building block in organic synthesis, allowing for the creation of a wide range of organic compounds. Its reactivity and structural features make it suitable for various synthetic routes, facilitating the production of complex molecules for research and industrial applications.
Used in Material Development:
3-BENZYLOXYCINNAMIC ACID has potential applications in the development of new materials, such as polymers and composites, due to its unique chemical properties. Its incorporation into these materials can lead to enhanced performance characteristics, making it a valuable component in material science research.
Used in Chemical Process Innovation:
As a chemical compound with distinct properties, 3-BENZYLOXYCINNAMIC ACID can be employed in the innovation of chemical processes, improving the efficiency and selectivity of reactions. Its use in process development can lead to the discovery of new synthetic methods and the optimization of existing ones, contributing to advancements in the field of chemistry.

Upstream product

• 141-82-2 malonic acid 
• 1700-37-4 3-Benzyloxybenzaldehyde 
• 14755-02-3 3-hydroxycinnamic acid 
• 3943-95-1 m-coumaric acid methyl ester 
• 100-39-0 benzyl bromide 
• 495399-41-2 methyl 3-(3-benzyloxyphenyl)propenoate 
• 14755-02-3 3-hydroxy-trans-cinnamic acid 
• 1026884-98-9 benzyl (E)-3'-benzyloxycinnamate 
• 208836-69-5 3-(3'-benzyloxyphenyl)-(E)-propenoic acid ethyl ester 

Downstream Products

• 122024-71-9 3-Chloro-5-(phenylmethoxy)-benzo[b]thiophene-2-carbonyl chloride 
• 1418183-67-1 (R)-2-ethylhexyl (E)-3-[3-(benzyloxy)phenyl]acrylate 
• 1418183-68-2 C₁₇H₂₆O₃ 
• 155697-42-0 (E)-3-(3-(benzyloxy)phenyl)prop-2-en-1-ol 
• 175591-23-8 tapentadol 
• 1443156-34-0 (2R,3R)-3-(3-(benzyloxy)phenyl)-2-methylpent-4-enal 
• 1367878-83-8 (2R,3R)-3-(3-(benzyloxy)phenyl)-N,N,2-trimethylpent-4-en-1-amine 
• 1443156-35-1 (2R,3R)-3-(3-(benzyloxy)phenyl)-N,N,2-trimethylpent-4-en-1-amine hydrochloride 
• 1259977-93-9 methyl 5-(benzyloxy)-3-chlorobenzo[b]thiophene-2-carboxylate 
• 1259977-97-3 kb-NB₁₂₃-66 
• 1259978-05-6 Kb-NB₁₆₅-89 
• 1233533-04-4 kb-NB142-70 
• 172832-10-9 3,4-dihydro-9-methoxy[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one 
• 1266714-67-3 C₁₆H₁₃ClO₂ 

Relevant academic research and scientific papers

Synthesis of novel 1-phenyl-benzopyrrolizidin-3-one derivatives and evaluation of their cytoneuroprotective effects against NMDA-induced injury in PC12 cells

A range of novel 1-phenyl-benzopyrrolizidin-3-one derivatives were synthesized and evaluated for neuroprotective effects against N-methyl-?-aspartate (NMDA)-induced injury in PC12 cells. Interestingly, derivatives that 1-phenyl moiety bearing electron-donating group, especially benzyloxy, and the trans-forms exhibited better protective activity against NMDA-induced neurotoxicity. Compound 11 m demonstrated the best neuroprotective potency and shown a dose-dependent prevention. The increased intracellular calcium (Ca2+) influx caused by NMDA in PC12 cells was reversed in the case of compound 11 m pretreatment at 15 μM. These results suggested that the synthesized 1-phenyl-benzopyrrolizidin-3-one derivatives exerted neuroprotective effect on NMDA-induced excitotoxicity in PC12 cells associated with inhibition of Ca2+ overload and can be further optimized for the development of neuroprotective agents.

Synthesis and evaluation of new sesamol-based phenolic acid derivatives with hypolipidemic, antioxidant, and hepatoprotective effects

The objective of this study is to synthesize a series of sesamol-based phenolic acid derivatives, which were designed by combination principle. The hypolipidemic activity of all these compounds was preliminarily screened by acute hyperlipidemic mice model induced by Triton WR 1339, in which compound T6 exhibited more significant reducing plasma TG and TC than fenofibrate. Compound T6 was also found to obviously decrease TG and TC both in the plasma and hepatic tissue of high-fat-diet-induced hyperlipidemic mice. Moreover, T6 showed hepatoprotective effects, which remarkable amelioration in characteristic liver enzymes was examined and the histopathological observation displayed that compound T6 inhibited lipids accumulation in the hepatic. The levels of PPAR-α receptor related to lipids metabolism in hepatic tissue were upregulated after T6 treatment. Other potent effects of T6 such as antioxidant and anti-inflammatory activity were also observed. On the bases of these findings, compound T6 may serve as an effective hypolipidemic and hepatoprotective agent. [Figure not available: see fulltext.]

Structural isomers of cinnamic hydroxamic acids block HCV replication via different mechanisms

A set of ortho-, meta- and para-substituted cinnamic hydroxamic acids (CHAs) was synthesized. In each series of structural isomers, a phenyl substituent was linked to an aromatic ring of the parent cinnamic acid via a linker of one to four atoms in length

Design, synthesis,: In vitro and in vivo evaluation of tacrine-cinnamic acid hybrids as multi-target acetyl- and butyrylcholinesterase inhibitors against Alzheimer's disease

Previously, we have reported tacrine-ferulic acid hybrids as multi-target cholinesterase inhibitors against Alzheimer's disease. However, the detailed structure-activity relationship (SAR), especially regarding the ferulic acid moiety, has yet to be eluci

Compositions for the prevention or treatment of neurodegenerative disease containing alkoxyphenylpropenone derivatives or pharmaceutically acceptable salts thereof as an active ingredient

PURPOSE: An alkoxyphenylpropenone derivative is provided to efficiently use as a pharmaceutical composition for preventing or treating a degenerative brain disease; or pharmaceutical composition for protecting a brain cell by having an excellent protecting effect of the brain cell. CONSTITUTION: An alkoxyphenylpropenone derivative or a pharmaceutically acceptable salt thereof is indicated as below chemical formula 1; and R^1 is hydrogen or O-R^4; R^2 is hydrogen or O-R^5; R^3 is hydroxy, O-R^6 or -NR^7R^8; R^4, R^5 and R^6 are C_1-C_12 straight chain or a side chain alkyl, C_2-C_12 straight chain or a side chain alkenyl, and unsubstituted or C_5-C_6 aryl which is substituted as C_1-C_4 straight chain, or a side chain alkoxy, C_5-C_6 aryl C_1-C_4 alkyl; R^7 is hydrogen, C_1-C_4 straight chain, or a side chain alkyl; R^8 is hydrogen, the C_1-C_4 straight chain or the side chain alkyl, and the C5-C6 aryl which is unsubstituted or hydroxy-substituted, the C1-C4 alkyl or the C5-C6.

Vitamin D3 analogues that contain modified A- and seco-B-rings as hedgehog pathway inhibitors

The hedgehog (Hh) signaling pathway is a developmental signaling pathway that has been implicated as a target for anti-cancer drug development in a variety of human malignancies. Several natural and synthetic vitamin D-based seco-steroids have been identified as potent inhibitors of Hh signaling with chemotherapeutic potential. These include the previously characterized analogue 4, which contains the northern CD-ring/side chain region of vitamin D3 (VD3) linked to an aromatic A-ring mimic through an ester bond. To further explore structure-activity relationships for this class of VD3-based Hh pathway inhibitors, we have designed, synthesized and evaluated several series of compounds that modify the length, composition, and stereochemical orientation of the ester linker. These studies have identified compounds 54 and 55, which contain an amine linker and an aromatic A-ring incorporating a para-phenol, as new lead compounds with enhanced potency against the Hh pathway (IC50 values Combining double low line 0.40 and 0.32 μM, respectively).

Synthesis, cytotoxicity and molecular modelling studies of new phenylcinnamide derivatives as potent inhibitors of cholinesterases

The present study reports the synthesis of cinnamide derivatives and their biological activity as inhibitors of both cholinesterases and anticancer agents. Controlled inhibition of brain acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) may slow neurodegeneration in Alzheimer's diseases (AD). The anticholinesterase activity of phenylcinnamide derivatives was determined against Electric Eel acetylcholinesterase (EeAChE) and horse serum butyrylcholinesterase (hBChE) and some of the compounds appeared as moderately potent inhibitors of EeAChE and hBChE. The compound 3-(2-(Benzyloxy)phenyl)-N- (3,4,5-trimethoxyphenyl)acrylamide (3i) showed maximum activity against EeAChE with an IC50 0.29 ± 0.21 μM whereas 3-(2-chloro-6- nitrophenyl)-N-(3,4,5-trimethoxyphenyl)acrylamide (3k) was proved to be the most potent inhibitor of hBChE having IC50 1.18 ± 1.31 μM. To better understand the enzyme-inhibitor interaction of the most active compounds toward cholinesterases, molecular modelling studies were carried out on high-resolution crystallographic structures. The anticancer effects of synthesized compounds were also evaluated against cancer cell line (lung carcinoma). The compounds may be useful leads for the design of a new class of anticancer drugs for the treatment of cancer and cholinesterase inhibitors for Alzheimer's disease (AD).

STEREOSELECTIVE SYNTHESIS OF TAPENTADOL AND ITS SALTS

A process for the synthesis of a salt of tapentadol.

PROTEIN KINASE D INHIBITORS

Compounds according to Formula (I), are potent inhibitors of protein kinase D (pan-PKD) activity. PKD controls key signaling cascades in cells, affecting cell proliferation, gene transcription, and protein trafficking. Accordingly, pharmaceutically acceptable compositions of the inventive compounds are candidate therapeutics for pathological conditions conditioned by changes in PKD activity.

Synthesis of the structure proposed for natural meliloester

In an attempt to establish the absolute configuration of meliloester, a natural product isolated from Melilotus alba, the literature structure was synthesized in an enantiopure form. Unexpectedly, the 1H and 13C NMR data was completely incompatible with those reported for the natural product. The corresponding m-hydroxy isomer was also excluded as the structure for the natural product.