120681-07-4

Upstream product

• 16642-92-5 4-(trifluoromethyl)cinnamic acid 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 2062-26-2 3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid 
• 115093-99-7 (E)-3-(4-trifluoromethylphenyl)-2-propenamide 
• 95123-61-8 (2E)-3-(4-trifluoromethylphenyl)prop-2-enal 
• 79-37-8 oxalyl dichloride 

Downstream Products

• 57260-02-3 1-(4-oxo-5-phenyl-4,5-dihydro-oxazol-2-yl)-4-[3-(4-trifluoromethyl-phenyl)-acryloyl]-piperazine 
• 536760-75-5 3-(4-(trifluoromethyl)phenyl)acrylamide 
• 1227794-62-8 (S)-2-{(6-morpholin-4-yl-pyridin-3-ylmethyl)-[3-(4-trifluoromethyl-phenyl)-acryloyl]-amino}-3-phenyl-propionic acid methyl ester 
• 1448547-85-0 (E)-N,N-diisopropyl-3-(4-(trifluoromethyl)phenyl)acrylamide 
• 1448548-14-8 (Z)-3-iodo-N,N-diisopropyl-3-(4-(trifluoromethyl)phenyl)acrylamide 
• 101466-85-7 ethyl 4-trifluoromethylcinnamate 
• 499219-22-6 t-butyl 4-trifluoromethylcinnamate 
• 1352050-79-3 (E)-1-(piperazin-1-yl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one 
• 1146354-41-7 tert-butyl 4-((E)-3-[4-(trifluoromethyl)phenyl]-2-propenoyl)-1-piperazinecarboxylate 
• 137872-88-9 4-Amino-6-(4'-trifluoromethyl-trans-cinnamoyl)amino-2-methyl-quinoline 
• 88556-19-8 3-Phenyl-2-[(E)-3-(4-trifluoromethyl-phenyl)-acryloylamino]-propionic acid 
• 136186-49-7 (2Z,4E)-2-Cyano-3-hydroxy-5-(4-trifluoromethyl-phenyl)-penta-2,4-dienoic acid (4-trifluoromethyl-phenyl)-amide 
• 126917-03-1 (E)-N-[(1S,2S)-2-(2,4-Difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl]-3-(4-trifluoromethyl-phenyl)-acrylamide 
• 126917-19-9 (E)-1-[(4S,5S)-5-(2,4-Difluoro-phenyl)-4-methyl-5-[1,2,4]triazol-1-ylmethyl-oxazolidin-3-yl]-3-(4-trifluoromethyl-phenyl)-propenone 

Relevant academic research and scientific papers

Photoredox Cyclization of N-Arylacrylamides for Synthesis of Dihydroquinolinones

Metal- and additive-free photoredox cyclization of N-arylacrylamides is herein reported that provides a concise access to the formation of dihydroquinolinones. In this protocol, sustainable visible light was used as the energy source, and the organic light-emitting molecule 4CzIPN served as the efficient photocatalyst. This reaction system features exclusive 6-endo-trig cyclization selectivity with a generally good yield of a range of functionalized dihydroquinolinones and dihydrobenzoquinolinones. Mechanistical studies reveal the feasibility of both 1,3-H shift and intersystem crossing of the diradical intermediate.

(E)-4-methyl-2-(4-(trifluoromethyl) styryl) oxazole compound as well as preparation method and application thereof

The invention belongs to the technical field of medicines, relates to a compound with anti-tumor activity and a specific chemical structure, and in particular relates to an (E)-4-methyl-2-(4-(trifluoromethyl) styryl) oxazole compound as well as a preparation method and an application thereof. The structural general formula of the compound is shown in the specification, wherein an R1 group is substituted by a 2-position, 3-position or 4-position mono-substituted fluorine atom, methyl, chlorine atom, methoxy group, bromine atom or an unsubstituted group; and the R2 group is substituted by a 2-position, 3-position or 4-position mono-substituted methoxy group, a chlorine atom or an unsubstituted group. Pharmacological studies show that the compound has certain inhibitory activity on human non-small cell lung cancer A549 cells, can be used for preparing anti-tumor drugs, and opens up a new way for deep research and development of tumor drugs in the future. The preparation method provided by the invention is simple and feasible, relatively high in yield and easy for large-scale production.

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.

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.

Antifungal Exploration of Quinoline Derivatives against Phytopathogenic Fungi Inspired by Quinine Alkaloids

Enlightened from our previous work of structural simplification of quinine and innovative application of natural products against phytopathogenic fungi, lead structure 2,8-bis(trifluoromethyl)-4-quinolinol (3) was selected to be a candidate and its diversified design, synthesis, and antifungal evaluation were carried out. All of the synthesized compounds Aa1-Db1 were evaluated for their antifungal activity against four agriculturally important fungi, Botrytis cinerea, Fusarium graminearum, Rhizoctonia solani, and Sclerotinia sclerotiorum. Results showed that compounds Ac3, Ac4, Ac7, Ac9, Ac12, Bb1, Bb10, Bb11, Bb13, Cb1. and Cb3 exhibited a good antifungal effect, especially Ac12 had the most potent activity with EC50 values of 0.52 and 0.50 μg/mL against S. sclerotiorum and B. cinerea, respectively, which were more potent than those of the lead compound 3 (1.72 and 1.89 μg/mL) and commercial fungicides azoxystrobin (both >30 μg/mL) and 8-hydroxyquinoline (2.12 and 5.28 μg/mL). Moreover, compound Ac12 displayed excellent in vivo antifungal activity, which was comparable in activity to the commercial fungicide boscalid. The preliminary mechanism revealed that compound Ac12 might cause an abnormal morphology of cell membranes, an increase in membrane permeability, and release of cellular contents. These results indicated that compound Ac12 displayed superior in vitro and in vivo fungicidal activities and could be a potential fungicidal candidate against plant fungal diseases.

Design, Synthesis, Structure-Activity Relationship, Molecular Docking, and Herbicidal Evaluation of 2-Cinnamoyl-3-Hydroxycyclohex-2-en-1-one Derivatives as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

Cinnamic acid, isolated from cinnamon bark, is a natural product with excellent bioactivity, and it effectively binds with cyclohexanedione to form novel 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors. According to the active sub-structure combinat

Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives

This work deals with the design and synthesis of 18 barbituric acid derivatives bearing 1,3-dimethylbarbituric acid and cinnamic acid scaffolds to find potent anticancer agents. The target molecules were obtained through Knoevenagel condensation and acylation reaction. The cytotoxicity was assessed by the MTT assay. Flowcytometry was performed to determine the cell cycle arrest, apoptosis, ROS levels and the loss of MMP. The ratios of GSH/GSSG and the MDA levels were determined by using UV spectrophotometry. The results revealed that introducing substitutions (CF3, OCF3, F) on the meta- of the benzyl ring of barbituric acid derivatives led to a considerable increase in the antiproliferative activities compared with that of corresponding ortho- and para-substituted barbituric acid derivatives. Mechanism investigation implied that the 1c could increase the ROS and MDA level, decrease the ratio of GSH/GSSG and MMP, and lead to cell cycle arrest. Further research is needed for structural optimization to enhance hydrophilicity, thereby improve the biological activity of these compounds.

Meta-substituted piperlongumine derivatives attenuate inflammation in both RAW264.7 macrophages and a mouse model of colitis

Piperlongumine (PL) has been showed to have multiple pharmacological activities. In this study, we reported the synthesis of three series of PL derivatives, and evaluation of their anti-inflammatory effects in both lipopolysaccharide (LPS)-induced Raw264.7 macrophages and a dextran sulfate sodium (DSS)-induced mouse model of colitis. Our results presented that two meta-substituent containing derivatives 1–3 and 1–6, in which γ-butyrolactam replaced α,β-unsaturated δ-valerolactam ring of PL, displayed low cytotoxicity and effective anti-inflammatory activity. Molecular docking also showed that the meta-substituted derivative, compared with the corresponding ortho- or para-substituted derivative, had significant interactions with the amino acid residues of CD14, which was the core receptors recognizing LPS. In vitro and in vivo studies, 1–3 and 1–6 could inhibit the expression of pro-inflammatory cytokines, and the excessive production of reactive nitrogen species and reactive oxygen species. Oral administration of 100 mg/kg/day of 1–3 or 1–6 alleviated the severity of clinical symptoms of colitis in mice, and significantly reduced the colonic tissue damage to protect the colonic tissue from the DSS-induced colitis. These results suggested that meta-substituted derivatives 1–3 and 1–6 were potential anti-inflammatory agents, which may lead to future pharmaceutical development.

DUAL INHIBITORS OF SOLUBLE EPOXIDE HYDROLASE AND 5-LIPOXYGENASE

The invention pertains to a novel structure (I) that provides an activity as a dual inhibitor of the enzymes soluble epoxide hydrolase (sEH) and 5-lipoxygenase (5-LOX). The invention pertains to multiple derivatives of the new class of dual inhibitors, their application in medicine, pharmaceutical compositions comprising them as well as to methods for synthesizing the new compounds.

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.