877065-30-0

Usage

Uses

Used in Pharmaceutical Research and Development:
(E)-Methyl 3-(4-chloro-3-nitrophenyl)acrylate is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique chemical reactivity allows for the creation of complex organic molecules, contributing to the development of new pharmaceuticals with improved efficacy and safety profiles.
Used in Organic Synthesis:
(E)-Methyl 3-(4-chloro-3-nitrophenyl)acrylate is used as a key building block in organic synthesis, enabling the production of a wide range of complex organic molecules. Its versatile chemical reactivity facilitates the synthesis of various compounds, including agrochemicals and other specialty chemicals.
Used in Chemical Research:
(E)-Methyl 3-(4-chloro-3-nitrophenyl)acrylate is employed as a valuable tool in chemical research, allowing scientists to explore new reaction pathways and develop innovative synthetic methods. Its unique properties and reactivity make it an essential component in the study of organic chemistry and the development of novel chemical processes.

Upstream product

• 20797-48-2 (E)-4-chloro-3-nitrocinnamic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 67-56-1 methanol 

Downstream Products

• 383669-60-1 methyl 3-(3-amino-4-chlorophenyl)propanoate 
• 51794-05-9 (E)-methyl 3-(4-amino-3-nitrophenyl)acrylate 
• 929018-83-7 (E)-3-[4-(2-aminoethylamino)-3-nitrophenyl]acrylic acid methyl ester 
• 929019-02-3 C₁₉H₂₅N₃O₆ 
• 929018-81-5 (E)-3-[4-(2-(tert-butoxycarbonylamino)ethylamino)-3-nitrophenyl]acrylic acid methyl ester 
• 929018-70-2 (E)-3-[4-(2-dimethylaminoethylamino)-3-nitrophenyl]acrylic acid methyl ester 
• 849059-79-6 3-[4-(3-dimethylamino-2,2-dimethyl-propylamino)-3-nitro-phenyl]-acrylic acid 
• 929019-12-5 C₁₂H₁₄N₂O₅ 
• 1145979-26-5 C₁₃H₁₄N₂O₆ 
• 929018-74-6 (E)-3-[4-(2-ethylaminoethylamino)-3-nitrophenyl]acrylic acid methyl ester 

Relevant academic research and scientific papers

Minor structural modifications to Pracinostat produce big changes in its biological responses

A series of compounds similar to Pracinostat that contained benzimidazole ring and N-hydroxyacrylamide attached at 5- or 6-position were designed, synthesized, and evaluated as HDAC inhibitors. It was interesting to find that the corresponding derivative 1 with N-hydroxyacrylamide attached at 5-position was a potent HDAC inhibitor while the others at 6-position were not. This is the first time to demonstrate the position difference plays important role in the HDAC inhibitory activities of the cinnamic hydroxamates.

Controlling Plasma Stability of Hydroxamic Acids: A MedChem Toolbox

Hydroxamic acids are outstanding zinc chelating groups that can be used to design potent and selective metalloenzyme inhibitors in various therapeutic areas. Some hydroxamic acids display a high plasma clearance resulting in poor in vivo activity, though they may be very potent compounds in vitro. We designed a 57-member library of hydroxamic acids to explore the structure-plasma stability relationships in these series and to identify which enzyme(s) and which pharmacophores are critical for plasma stability. Arylesterases and carboxylesterases were identified as the main metabolic enzymes for hydroxamic acids. Finally, we suggest structural features to be introduced or removed to improve stability. This work thus provides the first medicinal chemistry toolbox (experimental procedures and structural guidance) to assess and control the plasma stability of hydroxamic acids and realize their full potential as in vivo pharmacological probes and therapeutic agents. This study is particularly relevant to preclinical development as it allows obtaining compounds equally stable in human and rodent models.

NEW CYCLOHEXYL AND QUINUCLIDINYL CARBAMATE DERIVATIVES HAVING BETA2 ADRENERGIC AGONIST AND M3 MUSCARINIC ANTAGONIST ACTIVITY

The present invention relates to novel compounds having β2 adrenergic agonist and M3 muscarinic antagonist dual activity, to pharmaceutical compositions containing them, to the process for their preparation and to their use in respiratory therapies.

Discovery of (2 E)-3-{2-butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5- yl}-N-hydroxyacrylamide (SB939), an orally active histone deacetylase inhibitor with a superior preclinical profile

A series of 3-(1,2-disubstituted-1H-benzimidazol-5-yl)-N-hydroxyacrylamides (1) were designed and synthesized as HDAC inhibitors. Extensive SARs have been established for in vitro potency (HDAC1 enzyme and COLO 205 cellular IC 50), liver microsomal stability (t1/2), cytochrome P450 inhibitory (3A4 IC50), and clogP, among others. These parameters were fine-tuned by carefully adjusting the substituents at positions 1 and 2 of the benzimidazole ring. After comprehensive in vitro and in vivo profiling of the selected compounds, SB939 (3) was identified as a preclinical development candidate. 3 is a potent pan-HDAC inhibitor with excellent druglike properties, is highly efficacious in in vivo tumor models (HCT-116, PC-3, A2780, MV4-11, Ramos), and has high and dose-proportional oral exposures and very good ADME, safety, and pharmaceutical properties. When orally dosed to tumor-bearing mice, 3 is enriched in tumor tissue which may contribute to its potent antitumor activity and prolonged duration of action. 3 is currently being tested in phase I and phase II clinical trials.

N-Hydroxy-1,2-disubstituted-1H-benzimidazol-5-yl acrylamides as novel histone deacetylase inhibitors: Design, synthesis, SAR studies, and in vivo antitumor activity

A series of N-hydroxy-1,2-disubstituted-1H-benzimidazol-5-yl acrylamides were designed and synthesized as novel HDAC inhibitors. General SAR has been established for the substituents at positions 1 and 2, as well as the importance of the ethylene group an

COMBINATION OF BENZIMIDAZOLE ANTI-CANCER AGENT AND A SECOND ANTI-CANCER AGENT

The present invention relates to a pharmaceutical composition for the treatment of cancer as well as methods of treatment of cancer that are based on the finding that certain benzimidazole based anti-cancer agents can be used in combination with a second

HETEROCYCLIC COMPOUNDS

The present invention relates to compounds which are inhibitors of histone deacetylase. More particularly, the present invention relates to heterocyclic compounds and methods for their preparation. These compounds may be useful as medicaments for the trea

INDOLE DERIVATIVES AS ANTIVIRAL AGENTS

The present invention relates to indole compounds of the formula (I): wherein R1, R2, R3, R4, A, E and X are as defined herein, and pharmaceutically acceptable salts thereof, useful in the prevention and treatment of hepatitis C infections.

Benzoxazepinones and their use as squalene synthase inhibitors

There is disclosed a compound represented by the formula [I]: wherein R1 is optionally substituted 1-carboxyethyl group, optionally substituted alkyl-sulfonyl group, optionally substituted (carboxy-cycloalkyl)-alkyl group, -X1-X2-Ar-X3-X4-COOH (wherein X1 and X4 are a bond or alkylene group, X2 and X3 are a bond, -O-, -S-, Ar is divalent aromatic group etc.), R2 is alkyl group optionally substituted with alkanoyloxy group and/or hydroxy group, R3 is alkyl group, and W is halogen atom, etc., or a salt thereof. The compound has the cholesterol lowering activity and the triglyceride lowering activity and is useful for preventing and/or treating hyperlipidemia.