61921-33-3

Basic information

• Product Name: TRANS-4-NITROCINNAMOYL CHLORIDE
• Synonyms: TRANS-4-NITROCINNAMOYL CHLORIDE;(2E)-3-(4-nitrophenyl)acryloyl chloride;2-propenoyl chloride, 3-(4-nitrophenyl)-, (2E)-;(E)-3-(4-nitrophenyl)acryloyl chloride;trans-4-Nitrocinnamoyl chloride 97%;3-(4-nitrophenyl)acryloyl chloride
• CAS NO: 61921-33-3
• Molecular Formula: C₉H₆ClNO₃
• Molecular Weight: 211.6
• Product Categories: Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 61921-33-3.mol

Chemical Properties

• Melting Point: 150-153 °C(lit.)
• Boiling Point: 319.6°C at 760 mmHg
• Flash Point: 147.1°C
• Appearance: /
• Density: 1.403g/cm³
• Vapor Pressure: 0.000336mmHg at 25°C
• Refractive Index: 1.628
• CAS DataBase Reference: TRANS-4-NITROCINNAMOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-4-NITROCINNAMOYL CHLORIDE(61921-33-3)
• EPA Substance Registry System: TRANS-4-NITROCINNAMOYL CHLORIDE(61921-33-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 61921-33-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Analysis:
TRANS-4-NITROCINNAMOYL CHLORIDE is used as a derivatization reagent for the analysis of perhexiline and its monohydroxy metabolite in plasma by HPLC. This application is crucial for monitoring the levels of these compounds in patients undergoing treatment with perhexiline, ensuring optimal therapeutic outcomes and minimizing potential side effects.
Used in Enzyme Kinetics Studies:
In the field of biochemistry, TRANS-4-NITROCINNAMOYL CHLORIDE is employed as a derivatization reagent to investigate the in vitro enzyme kinetics and CYP isoform selectivity of perhexiline monohydroxylation using human liver microsomes. This application aids in understanding the metabolic pathways and enzyme interactions involved in the biotransformation of perhexiline, which can be vital for drug development and optimization of treatment regimens.

InChI:InChI=1/C9H6ClNO3/c10-9(12)6-3-7-1-4-8(5-2-7)11(13)14/h1-6H/b6-3+

Upstream product

• 619-89-6 p-nitrocinnamic acid 
• 882-06-4 4-nitro-trans-cinnamic acid 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 51983-83-6 4-nitro-trans-cinnamic acid-(2-diethylamino-ethyl ester) 
• 13546-92-4 phenyl p-nitrocinnamate 
• 57259-92-4 1-[3-(4-nitro-phenyl)-acryloyl]-4-(4-oxo-5-phenyl-4,5-dihydro-oxazol-2-yl)-piperazine 
• 72129-95-4 3,3'-bis-(4-nitro-phenyl)-1,1'-benzo[1,2-d;4,5-d']bisoxazole-2,6-diyl-bis-propenone 
• 1734-79-8 3-(4-nitrophenyl)-2-propenal 
• 35271-56-8 3-(4-nitrophenyl)propyl-2-en-1-ol 
• 66061-52-7 1-naphtho[1,2-d]oxazol-2-yl-3-(4-nitro-phenyl)-propenone 
• 76098-35-6 (E)-N-[1-Chloro-1-pyrrolidin-1-yl-meth-(E)-ylidene]-3-(4-nitro-phenyl)-acrylamide 
• 76098-37-8 (E)-N-[1-Chloro-1-piperidin-1-yl-meth-(E)-ylidene]-3-(4-nitro-phenyl)-acrylamide 
• 76098-36-7 (E)-N-[1-Chloro-1-morpholin-4-yl-meth-(E)-ylidene]-3-(4-nitro-phenyl)-acrylamide 
• 105625-82-9 3-[(E)-3-(4-Nitro-phenyl)-acryloyl]-2-phenyl-5-[1-phenyl-meth-(E)-ylidene]-3,5-dihydro-imidazol-4-one 
• 102197-31-9 4-(p-nitrocinnamoyl)-4-azatricyclo<4.3.1.1^3,8>undecane 
• 75614-46-9 (Z)-N-[1-Mercapto-1-methylsulfanyl-meth-(E)-ylidene]-3-(4-nitro-phenyl)-acrylamide 
• 135529-09-8 (S)-2-hydroxypropyl 4-nitrocinnamate 

Relevant articles and documents

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.

Piperlongumine analogs promote A549 cell apoptosis through enhancing ROS generation

Chemotherapeutic agents, which contain the Michael acceptor, are potent anticancer molecules by promoting intracellular reactive oxygen species (ROS) generation. In this study, we synthesized a panel of PL (piperlongumine) analogs with chlorine attaching at C2 and an electronwithdrawing/electron-donating group attaching to the aromatic ring. The results displayed that the strong electrophilicity group at the C2–C3 double bond of PL analogs plays an important role in the cytotoxicity whereas the electric effect of substituents, which attached to the aromatic ring, partly contributed to the anticancer activity. Moreover, the protein containing sulfydryl or seleno, such as TrxR, could be irreversibly inhibited by the C2–C3 double bond of PL analogs, and boost intracellular ROS generation. Then, the ROS accumulation could disrupt the redox balance, induce lipid peroxidation, lead to the loss of MMP (Mitochondrial Membrane Potential), and ultimately result in cell cycle arrest and A549 cell line death. In conclusion, PL analogs could induce in vitro cancer apoptosis through the inhibition of TrxR and ROS accumulation.

Radiosensitization of human pancreatic cancer by piperlongumine analogues

Radiotherapy is commonly used to treat advanced pancreatic cancers and can improve survival by 2 months in combination with gemcitabine. However, prognosis and survival improvement remain unsatisfactory, and effective therapies are urgently needed. Piperlongumine has been demonstrated to have therapeutic potentials against various cancers. In this study, we synthesized a series of piperlongumine derivatives and provided evidence that piperlongumine derivatives could be used as effective radiosensitizers in pancreatic cancer. Two compounds enhanced the radiosensitivity of Panc-1 and SW1990 cells. In a pancreatic bi-flank xenograft tumor model, they significantly inhibited tumor growth. Piperlongumine derivatives could induce reactive oxygen species (ROS) expression and regulate the Keap1-Nrf2 protective pathway with enhancement of radiation-induced DNA damage, G2/M-phase cell cycle arrest, and apoptosis. Collectively, our data offer a proof of concept for the use of piperlongumine derivatives as a novel class of radiosensitizers for the treatment of pancreatic cancer.

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.

Practical access to fluorescent 2,3-naphthalimide derivatives: Via didehydro-Diels-Alder reaction

A practical and efficient approach for the synthesis of fluorescent 2,3-naphthalimide derivatives has been developed from readily available starting materials via an intramolecular didehydro-Diels-Alder reaction, which proceeded well under room temperature, exhibiting a wide substrate scope and good functional group tolerance. The practicability of this methodology has been verified by one-step synthesis of the environmentally sensitive fluorophore 6-DMN on a gram scale with a shorter time, fewer steps and less waste disposal, and without the utilization of toxic transition metals. The present experimental and computational studies support the crucial role of the propiolimide moiety in the transformation.

Selected class of enamides bearing nitro functionality as dual-acting with highly selective monoamine oxidase-b and bace1 inhibitors

A small series of nitro group-bearing enamides was designed, synthesized (NEA1–NEA5), and evaluated for their inhibitory profiles of monoamine oxidases (MAOs) and β-site amyloid precursor protein cleaving enzyme 1 (β-secretase, BACE1). Compounds NEA3 and NEA1 exhibited a more potent MAO-B inhibition (IC50 value = 0.0092 and 0.016 μM, respectively) than the standards (IC50 value = 0.11 and 0.14 μM, respectively, for lazabemide and pargyline). Moreover, NEA3 and NEA1 showed greater selectivity index (SI) values toward MAO-B over MAO-A (SI of >1652.2 and >2500.0, respectively). The inhibition and kinetics studies suggested that NEA3 and NEA1 are reversible and competitive inhibitors with Ki values of 0.013 ± 0.005 and 0.0049 ± 0.0002 μM, respectively, for MAO-B. In addition, both NEA3 and NEA1 showed efficient BACE1 inhibitions with IC50 values of 8.02 ± 0.13 and 8.21 ± 0.03 μM better than the standard quercetin value (13.40 ± 0.04 μM). The parallel artificial membrane permeability assay (PAMPA) method demonstrated that all the synthesized derivatives can cross the blood–brain barrier (BBB) successfully. Docking analyses were performed by employing an induced-fit docking approach in the GLIDE module of Schrodinger, and the results were in agreement with their in vitro inhibitory activities. The present study resulted in the discovery of potent dual inhibitors toward MAO-B and BACE1, and these lead compounds can be fruitfully explored for the generation of newer, clinically active agents for the treatment of neurodegenerative disorders.

Thiourea derivatives, and preparation method and application thereof

The invention relates to thiourea derivatives represented by formula I, pharmaceutically acceptable salts thereof and a pharmaceutical composition thereof, and an application of the thiourea derivatives in the preparation of an influenza virus neuraminida

Baicalein or derivative thereof, preparation method and application of baicalein or derivative of baicalein

The invention discloses baicalein or a derivative thereof. The structure is shown in the specification, wherein R1 is hydrogen, alkyl, substituted or unsubstituted aryl; R2 is hydrogen, halogen, alkyl, alkoxy, substituted or unsubstituted amino, and subst

Novel paeonol derivatives: Design, synthesis and anti-inflammatory activity in vitro and in vivo

Paeonol has been proved to have potential anti-inflammatory activity, but its clinical application is not extensive due to the poor anti-inflammatory activity (14.74% inhibitory activity at 20 μM). In order to discover novel lead compound with high anti-inflammatory activity, series of paeonol derivatives were designed and synthesized, their anti-inflammatory activities were screened in vitro and in vivo. Structure-activity relationships (SARs) have been fully concluded, and finally (E)-N-(4-(2-acetyl-5-methoxyphenoxy)phenyl)-3-(3,4,5-trimet-hoxyphenyl)acrylamide (compound 11a) was found to be the best active compound with low toxicity, which showed 96.32% inhibitory activity at 20 μM and IC50 value of 6.96 μM against LPS-induced over expression of nitric oxide (NO) in RAW 264.7 macrophages. Preliminary mechanism studies indicated that it could inhibit the expression of TLR4, resulting in inhibiting of NF-κB and MAPK pathways. Further studies have shown that compound 11a has obvious therapeutic effect against the adjuvant-induced rat arthritis model.

Mild, Metal-Free and Protection-Free Transamidation of N-Acyl-2-piperidones to Amino Acids, Amino Alcohols and Aliphatic Amines and Esterification of N-Acyl-2-piperidones

Amides are indispensable building blocks of biological systems, pharmaceuticals, and materials. We report a highly selective method for the synthesis of amides via transamidation process. Transamidation of N-acyl-2-piperidones with a broad range of amines is demonstrated under exceedingly mild and metal-free reaction condition that relies on the amide bond twist to weaken the amidic resonance. Transamidation proceeds under the neat condition at room temperature, in short reaction times (30–90 min) with good yields. Considerable variation is tolerated with both amine and imide substrates. Of note, amines bearing carboxylic acids (glycine and serine) and hydroxyl groups (dopamine, tyramine, etc.) are well tolerated which are otherwise problematic under the metal-catalyzed protocol. Our current method is applicable for transamidation of both alkyl and aryl-N-acyl-2-piperidones. The practical value of the method is highlighted by the synthesis of four natural product amide alkaloids in high yields under mild reaction conditions. In the absence of nucleophilic amines, N-acyl-2-piperidones undergoes esterification with EtOH at elevated temperature. Single crystal X-ray analysis of an N-acyl-2-piperidone shows amide bond twist, τ = –20.39° and pyramidalization, χN = –11.73°. This weakens the amidic conjugation and might be the factor controlling the reactivity and selectivity of these imides. We envision that the N-acyl-2-piperidone scaffold would be useful in the synthesis of pharmaceuticals and materials.