17403-47-3

Usage

Uses

Used in Pharmaceutical Industry:
5-Nitro-2,3-dihydro-1-benzofuran is utilized as a synthetic intermediate for the development of various drugs. Its unique chemical structure allows it to be a key component in the creation of medicinal compounds, contributing to the advancement of pharmaceutical formulations.
Used in Agricultural Chemical Production:
In the agricultural sector, 5-Nitro-2,3-dihydro-1-benzofuran serves as a precursor in the manufacturing process of certain agricultural chemicals. Its role is pivotal in the synthesis of products that aid in crop protection and enhancement of agricultural yields.
Safety Precautions:
Given its toxic nature, 5-Nitro-2,3-dihydro-1-benzofuran requires careful handling to prevent skin and eye irritation. It is also harmful if ingested or inhaled, necessitating proper storage in well-ventilated areas and the use of suitable protective equipment during its manipulation.

Upstream product

• 496-16-2 2.3-dihydrobenzofuran 
• 7169-34-8 3-oxo-2,3-dihydrobenzo[b]furan 

Downstream Products

• 42933-43-7 2,3-dihydro-1-benzofuran-5-amine 
• 911300-51-1 6-nitro-2,3-dihydro-1-benzofuran 
• 245762-35-0 5-fluoro-2,3-dihydrobenzofuran 
• 57786-34-2 6-amino-2,3-dihydrobenzofuran 
• 1228880-71-4 5,6-diamino-2,3-dihydrobenzofuran 
• 84594-78-5 6-nitro-2,3-dihydro-1-benzofuran-5-ylamine 

Relevant academic research and scientific papers

Discovery of dual-acting opioid ligand and TRPV1 antagonists as novel therapeutic agents for pain

In order to discover a novel type of analgesic, we investigated dual activity ligands with TRPV1 antagonism and mu-opioid receptor affinity with the goal of eliciting synergistic analgesia while avoiding the side effects associated with single targeting.

Discovery and structure-activity relationship of novel 2,3- dihydrobenzofuran-7-carboxamide and 2,3-dihydrobenzofuran-3(2 h)-one-7-carboxamide derivatives as poly(ADP-ribose)polymerase-1 Inhibitors

Novel substituted 2,3-dihydrobenzofuran-7-carboxamide (DHBF-7-carboxamide) and 2,3-dihydrobenzofuran-3(2H)-one-7-carboxamide (DHBF-3-one-7-carboxamide) derivatives were synthesized and evaluated as inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1). A structure-based design strategy resulted in lead compound 3 (DHBF-7-carboxamide; IC50 = 9.45 μM). To facilitate synthetically feasible derivatives, an alternative core was designed, DHBF-3-one-7-carboxamide (36, IC50 = 16.2 μM). The electrophilic 2-position of this scaffold was accessible for extended modifications. Substituted benzylidene derivatives at the 2-position were found to be the most potent, with 3′,4′-dihydroxybenzylidene 58 (IC50 = 0.531 μM) showing a 30-fold improvement in potency. Various heterocycles attached at the 4′-hydroxyl/4′-amino of the benzylidene moiety resulted in significant improvement in inhibition of PARP-1 activity (e.g., compounds 66-68, 70, 72, and 73; IC50 values from 0.718 to 0.079 μM). Compound 66 showed selective cytotoxicity in BRCA2-deficient DT40 cells. Crystal structures of three inhibitors (compounds (-)-13c, 59, and 65) bound to a multidomain PARP-1 structure were obtained, providing insights into further development of these inhibitors.

Structure-activity relationship of human glutaminyl cyclase inhibitors having an N-(5-methyl-1H-imidazol-1-yl)propyl thiourea template

In an effort to design inhibitors of human glutaminyl cyclase (QC), we have synthesized a library of N-aryl N-(5-methyl-1H-imidazol-1-yl)propyl thioureas and investigated the contribution of the aryl region of these compounds to their structure-activity relationships as cyclase inhibitors. Our design was guided by the proposed binding mode of the preferred substrate for the cyclase. In this series, compound 52 was identified as the most potent QC inhibitor with an IC50 value of 58 nM, which was two-fold more potent than the previously reported lead 2. Compound 52 is a most promising candidate for future evaluation to monitor its ability to reduce the formation of pGlu-Aβ and Aβ plaques in cells and transgenic animals.

BENZIMIDAZOLE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS AND USES THEREOF

The present invention relates to benzimidazole derivatives and their pharmaceutical compositions and uses, specifically to benzimidazole derivatives of Formula (I), or their stereoisomer, pharmaceutically acceptable salt or solvates thereof, in which R1, R2, R3, R4, R5 and n have the definitions in the description; the present invention further relates to a pharmaceutical composition containing the compounds, methods for preparing the compounds, and use of the compounds for manufacturing of a medicament for prophylaxis and/or treatment of peptic ulcer, ulcer hemorrhage and diseases associated with gastric acid.

Design, structure-activity relationship, and highly efficient asymmetric synthesis of 3-phenyl-4-benzylaminopiperidine derivatives as novel neurokinin-1 receptor antagonists

We synthesized a series of novel 3-phenyl-4-benzylaminopiperidine derivatives that were identified as potent tachykinin NK1 receptor antagonists by structural modification of the 3-benzhydrylpiperidone derivative through high-throughput screening. N-{2-[(3R,4S)-4-({2-Methoxy-5-[5-(trifluoromethyl)- 1Htetrazol-1-yl]benzyl}amino)-3-phenyl-1-piperidinyl]-2-oxoethyl}acetamide ((+)-39) was found to be one of the most potent tachykinin NK1 receptor antagonists with high metabolic stability. Highly efficient asymmetric synthesis of (+)-39 was achieved via dynamic kinetic resolution.

Nonsteroidal dissociated glucocorticoid agonists containing azaindoles as steroid A-ring mimetics

Syntheses and structure-activity relationships (SAR) of nonsteroidal glucocorticoid receptor (GR) agonists are described. These compounds contain azaindole moieties as A-ring mimetics and display various degrees of in vitro dissociation between gene trans

GLUCOCORTICOID MIMETICS, METHODS OF MAKING THEM, PHARMACEUTICAL COMPOSITIONS, AND USES THEREOF

Compounds of Formula (IA) and Formula (IB) wherein R1, R2, R3, R4, R5, and R6 are as defined herein for Formula (IA) or Formula (IB), or a tautomer, prodrug, solvate,or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocorticoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.