39856-08-1

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dimethoxycinnamoyl chloride is used as an intermediate in the synthesis of various pharmaceuticals for its reactivity as an acylating agent, enabling the preparation of esters and amides that are essential in the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical industry, 3,4-Dimethoxycinnamoyl chloride serves as a key intermediate in the production of agrochemicals, contributing to the development of effective and innovative solutions for crop protection and pest management.
Used in Fine Chemicals Production:
3,4-Dimethoxycinnamoyl chloride is used as a building block in the synthesis of fine chemicals, which are high-purity, specialty chemicals used in various applications, including fragrances, flavors, and dyes.
Used in Material Science:
3,4-Dimethoxycinnamoyl chloride has applications in material science, specifically in the production of polymers and resins. Its reactivity and versatility make it a valuable component in the development of advanced materials with unique properties and applications.
Used in Synthesis of Biologically Active Compounds:
3,4-Dimethoxycinnamoyl chloride is used as a building block in the synthesis of natural and synthetic compounds with potential biological activities, contributing to the discovery and development of new therapeutic agents and bioactive molecules.

InChI:InChI=1/C11H11ClO3/c1-14-9-5-3-8(4-6-11(12)13)7-10(9)15-2/h3-7H,1-2H3/b6-4+

Upstream product

• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 5396-64-5 methyl (E)-3-(3,4-dimethoxyphenyl)acrylate 
• 121-33-5 vanillin 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 331-39-5 caffeic acid 
• 2316-26-9 3,4-dimethoxycinnamic acid 

Downstream Products

• 75-77-4 chloro-trimethyl-silane 
• 81787-68-0 5-(3',4'-dimethoxyphenyl)-1-(4'-methoxyphenyl)-pent-1-yn-4-enone 
• 25356-83-6 3,4-dimethoxycinnamohydroxamic acid 
• 1148129-11-6 ethyl 1-[3-(3,4-dimethoxyphenyl)acrylamido]-4-oxo-4H-quinolizine-3-carboxylate 
• 127978-77-2 N-[3-(3,4-dimethoxyphenyl)acryloyl]pyrrolidin-2-one 
• 1186073-31-3 (E)-3-(3,4-dimethoxyphenyl)-N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)acrylamide 
• 162102-39-8 C₁₉H₁₈O₅ 
• 1001129-71-0 (7S)-(+)-3-(3,4-dimethoxyphenyl)acrylic acid 8,8-dimethyl-2-oxo-6,7-dihydro-2H,8H-pyrano[3,2-g]chromen-7-yl ester 
• 1415215-71-2 C₂₉H₃₆O₉ 
• 1415215-74-5 C₃₁H₃₁IO₉ 
• 88909-07-3 (E)-3-(3,4-dimethoxyphenyl)acrylic anhydride 

Relevant academic research and scientific papers

Quorum sensing and nf-κb inhibition of synthetic coumaperine derivatives from piper nigrum

Bacterial communication, termed Quorum Sensing (QS), is a promising target for virulence attenuation and the treatment of bacterial infections. Infections cause inflammation, a process regulated by a number of cellular factors, including the transcription Nuclear Factor kappa B (NF-κB); this factor is found to be upregulated in many inflammatory diseases, including those induced by bacterial infection. In this study, we tested 32 synthetic derivatives of coumaperine (CP), a known natural compound found in pepper (Piper nigrum), for Quorum Sensing Inhibition (QSI) and NF-κB inhibitory activities. Of the compounds tested, seven were found to have high QSI activity, three inhibited bacterial growth and five inhibited NF-κB. In addition, some of the CP compounds were active in more than one test. For example, compounds CP-286, CP-215 and CP-158 were not cytotoxic, inhibited NF-κB activation and QS but did not show antibacterial activity. CP-154 inhibited QS, decreased NF-κB activation and inhibited bacterial growth. Our results indicate that these synthetic molecules may provide a basis for further development of novel therapeutic agents against bacterial infections.

Cinnamyl-containing rupestonic acid methyl ester derivative as well as preparation method and application of rupestonic acid methyl ester derivative

The invention relates to a cinnamyl-containing rupestonic acid methyl ester derivative as well as a preparation method and application thereof, the derivative is prepared by the following steps: reacting rupestonic acid with dimethyl sulfate to obtain rupestonic acid methyl ester, and then obtaining 2-hydroxyl rupestonic acid methyl ester under the oxidation of camphor sulfonyl acridine. and then reacting with cinnamyl chloride under the catalysis of DMAP to obtain 20 rupestonic acid methyl ester derivatives containing cinnamyl groups. The method has the advantages of mild reaction conditions and simple experimental steps. The obtained 1d-20d rupestonic acid methyl ester derivatives containing the cinnamyl groups are subjected to a preliminary in-vitro anti-influenza A H3N2 virus activity test. Experimental results show that the compounds show good activity in 7d, 15d and 18d, and can be used as drugs for resisting influenza A H3N2 virus.

Aziridine-2-carboxylic acid derivatives and its open-ring isomers as a novel PDIA1 inhibitors

[Figure not available: see fulltext.] Acyl derivatives of aziridine-2-carboxylic acid have been synthesized and tested as PDIA1 inhibitors. Calculations of charge value and distribution in aziridine ring system and some alkylating agents were performed. For the first time was found that acyl derivatives of aziridine-2-carboxylic acid are weak to moderately active PDIA1 inhibitors.

In quest of small-molecules as potent non-competitive inhibitors against influenza

A series of scaffolds namely aurones, 3-indolinones, 4-quinolones and cinnamic acid-piperazine hybrids, was designed, synthesized and investigated in vitro against influenza A/H1N1pdm09 virus. Designed molecules adopted different binding mode i.e., in 430-cavity of neuraminidase, unlike sialic acid and oseltamivir in molecular docking studies. All molecules reduced the viral titer and exhibited non-cytotoxicity along with cryo-protective property towards MDCK cells. Molecules (Z)-2-(3′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2f), (Z)-2-(4′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2g) and 2-(2′-Methoxy-phenyl)-1H-quinolin-4-one (3a) were the most interesting molecules identified in this research, endowed with robust potencies showing low-nanomolar EC50 values of 4.0 nM, 6.7 nM and 4.9 nM, respectively, compared to reference competitive and non-competitive inhibitors: oseltamivir (EC50 = 12.7 nM) and quercetin (EC50 = 0.56 μM), respectively. Besides, 2f, 2g and 3a exhibited good neuraminidase inhibitory activity in sub-micromolar range (IC50 = 0.52 μM, 3.5 μM, 1.3 μM respectively). Moreover, these molecules were determined as non-competitive inhibitors similar to reference non-competitive inhibitor quercetin unlike reference competitive inhibitor oseltamivir in kinetics studies.

Double asymmetric intramolecular aza-Michael reaction: a convenient strategy for the synthesis of quinolizidine alkaloids

A new methodology to access the quinolizidine skeleton in an asymmetric fashion was devised. It involves two consecutive intramolecular aza-Michael reactions of sulfinyl amines bearing a bis-enone moiety, in turn generated by a monodirectional cross metat

Design, synthesis and biological evaluation of novel carboline-cinnamic acid hybrids as multifunctional agents for treatment of Alzheimer's disease

Alzheimer's disease (AD) is a complex neurodegenerative disease with multiple pathological features. Multifunctional compounds able to simultaneously interact with several pathological components have been considered as a solution to treat the complex pathologies of neurodegenerative diseases. β-carboline and cinnamic acid have been extensively studied for their widespread biological effects in treatment of AD, further application is limited due to its poor solubility and high toxicity. Herein, a series of carboline-cinnamic acid hybrids was designed and synthesized to obtain new multifunctional molecules with low toxicity and good physicochemical properties. In particular, e3 and e12 exhibited significant inhibition of Aβ aggregation (inhibitory rate at 25 μM: 65% and 72% respectively), moderate BuChE inhibition, excellent neuroprotective effects and low neurotoxicity. Furthermore, in the AD mice model, e3 and e12 could restore learning and memory function to a comparable level to that of the control and did not exhibit any acute toxicity in vivo at a relatively high dose of 600 mg/kg. Thus, these new compounds can be further studied as multifunctional molecules for AD.

Separation and identification of an impurity from the istradefylline intermediate

Istradefylline is a selective adenosine antagonist for the A2a receptor, and it is used to treat the Parkinson's disease and improve dyskinesia in the early stage of the Parkinson's disease. An impurity in the istradefylline intermediate A1 (6-amino-1,3-diethyl-2,4-(1H,3H)-pyrimidinedione) was identified by high performance liquid chromatography (HPLC); it was separated by preparative HPLC and further characterized by UV, IR, MS, NMR, 2D NMR and single-crystal XRD analyses. The impurity was identified as (E)-N-ethyl-2-cyano-3-ethylamino-2-butenamide, which originated from the synthetic process of the intermediate A1. The structure of this impurity might affect the efficiency and safety of istradefylline; therefore, the research and control of this impurity are necessary for ensuring the quality of istradefylline.

New coumarin/sulfocoumarin linked phenylacrylamides as selective transmembrane carbonic anhydrase inhibitors: Synthesis and in-vitro biological evaluation

Two novel series of phenylacrylamide linked coumarins and sulfocoumarins (6a-p, 8a-i, and 14a-g) were synthesized and evaluated against four physiologically relevant human carbonic anhydrases (hCAs, EC 4.2.1.1), isoforms hCA I, hCA II, hCA IX and hCA XII for their inhibitory action. All new compounds when screened for carbonic anhydrase inhibitory activity have shown selective inhibition towards the tumor associated isoforms hCA IX and XII over CA I and II, with inhibition constants in the submicromolar to low nanomolar range. Compound 6b and 14g exhibited significant inhibition with low nanomolar potency against hCA IX, whereas 6k was effective against hCA XII. Compounds 6b, 14g and 6k may be considered as lead molecules for future development of cancer therapeutics based on a novel mechanism of action.

Natural product derivatization with β-lactones, β-lactams and epoxides toward ‘infinite’ binders

β-Lactones, β-lactams and epoxides are privileged structural motifs found in both therapeutics and natural products. Herein we report several strategies for annulation of these motifs onto natural products that are not known to covalently modify their cellular targets. These strategies can facilitate identification of previously unidentified cellular targets or identify novel cellular targets of these natural products. The reported strategies include telescoped synthesis of β-lactones from allylic alcohols, nucleophile-catalyzed Michael aldol-β-lactonizations, and [2 + 2] β-lactam annulations with complex, commercially available alkene-containing natural products as substrates. A novel method for the tagging of phenolic natural products with epoxides is also reported.

Synthesis of Dicarbonyl Curcumin Analogues Containing the Tropane Scaffold

A general synthetic route to the unknown 1,3-dicarbonyl tropane derived curcumin analogues was developed. The method was based on the aldol condensation reaction (40–90 % yield, two steps without product isolation) and acylation of the resulting 2-benzylidenetropinones with substituted cinnamoyl cyanides (yields 41–91 %). Overall 18 new tropane derivatives featuring the characteristic curcuminoid hepta-1,6-dien-3,5-dione structure were synthesized and characterized. The range of the substituted aromatic rings in the prepared analogues included Ph, m-MeO-C6H4, 3,4-di-MeO-C6H3, 3,4,5-tri-MeO-C6H2, p-Br-C6H4, p-F-C6H4, p-CF3-C6H4, p-NO2-C6H4, 2-NO2-4,5-di-CH3O-C6H2, 2-NO2-4,5-O-CH2-O-C6H2, 3-MeO-4-[CH(CH3)-OEt]-C6H3, 3-MeO-4-OH-C6H3, p-MeO-C6H4, 4,5-O-CH2-O-C6H3, 3-MeO-4-MeOCOO. Two orthogonal protective groups for hydroxyl (acetal or carbonate), removable in acidic or basic conditions, were used for synthesizing curcuminoids with free phenolic groups (3-MeO-4-OH-C6H3).