90322-48-8

Usage

Uses

Used in Pharmaceutical Industry:
(5-nitro-1-benzofuran-2-yl)methanol is used as a building block for the synthesis of various pharmaceuticals due to its reactivity and versatility. Its unique chemical structure allows for the preparation of a wide range of organic compounds with potential therapeutic applications.
Used in Agrochemical Industry:
(5-nitro-1-benzofuran-2-yl)methanol is used as a key intermediate in the synthesis of agrochemicals, contributing to the development of effective pesticides and other agricultural chemicals. Its potential biological activities, such as antimicrobial and antifungal properties, make it a valuable component in creating solutions for crop protection and disease management.
Used in Organic Chemistry Research:
(5-nitro-1-benzofuran-2-yl)methanol is utilized as a valuable intermediate in the synthesis of diverse functionalized molecules, making it an important compound for research in organic chemistry. Its unique structure and reactivity allow chemists to explore new reactions and develop innovative synthetic pathways for the creation of novel organic compounds with various applications.

InChI:InChI=1/C9H7NO4/c11-5-8-4-6-3-7(10(12)13)1-2-9(6)14-8/h1-4,11H,5H2

Upstream product

• 89487-91-2 2-iodo-4-nitrophenol 
• 107-19-7 propargyl alcohol 
• 10242-12-3 5-nitrobenzofuran-2-carboxylic acid 
• 541-41-3 chloroformic acid ethyl ester 
• 69604-00-8 ethyl 5-nitrobenzo[d]furan-2-carboxylate 
• 23145-18-8 5-nitro-benzofuran-2-carbaldehyde 

Downstream Products

• 118679-18-8 2-bromomethyl-5-nitro-benzofuran 
• 23145-18-8 5-nitro-benzofuran-2-carbaldehyde 

Relevant academic research and scientific papers

A Novel Model System for Understanding Anticancer Activity of Hypoxia-Activated Prodrugs

Reports on the comprehensive factors for design considerations of hypoxia-activated prodrugs (HAPs) are rare. We introduced a new model system composed of a series of highly water-soluble HAPs, providing a platform to comprehensively understand the interaction between HAPs and hypoxic biosystems. Specifically, four kinds of new HAPs were designed and synthesized, containing the same biologically active moiety but masked by different bioreductive groups. Our results demonstrated that the activity of the prodrugs was strongly dependent on not only the molecular structure but also the hypoxic tumor microenvironment. We found the presence of a direct linear relationship between cytotoxicity of the HAPs and the reduction potential of whole molecule/oxygen concentration/reductase expression. Moreover, limited blood vasculature in hypoxic regions was also a critical barrier for effective activation of the HAPs. This study offers a comprehensive insight into understanding the design factors required for HAPs.

Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids

The palladium-catalyzed synthesis of indole/benzofurancontaining diarylmethanes starting from indolylmethyl or benzofuranylmethyl acetates with boronic acids has been investigated. The success of the reaction is influenced by the choice of precatalyst: with indolylmethyl acetates the reaction works well with [Pd(η3-C3H5)Cl]2/XPhos while with benzofuranylmethyl acetates Pd2(dba)3/XPhos is more efficient. The good to high yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2- and 3-substituted indoles and 2-benzo[b]furans. The methodology can be advantageously extended to the preparation of a key precursor of Zafirlukast.

Palladium-catalyzed Tsuji-Trost-type reaction of benzofuran-2-ylmethyl acetates with nucleophiles

The palladium-catalyzed benzylic-like nucleophilic substitution of benzofuran-2-ylmethyl acetate with N, S, O and C soft nucleophiles has been investigated. The success of the reaction is dramatically influenced by the choice of catalytic system: with nitrogen based nucleophiles the reaction works well with Pd2(dba)3/dppf, while with sulfur, oxygen and carbo-nucleophiles [Pd(η3-C3H5)Cl]2/XPhos is more efficient. The regiochemical outcome shows that the nucleophilic substitution occurs only on the benzylic position of the η3-(benzofuryl)methyl complex. The high to excellent yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2-substituted benzo[b]furans. This journal is

Pyridinium-modified prodrug small molecule containing different nitroaromatic heterocycles

The invention relates to a pyridinium-modified prodrug small molecule containing different nitroaromatic heterocycles. The structural formula is a formula (I), a formula (II) or a formula (III)(pleasesee the see the specification for the formula). A series of novel small molecule hypoxia activated prodrug is synthesized through design, through the screening of synthesized prodrugs, different aromatic heterocyclic modified hypoxia activated prodrugs have different sensitivity to oxygen, and furan-ring-modified prodrug molecule exhibits the best hypoxic toxicity at 3LL, PC-3, HepG2 and B16 at the cellular level. By constructing a mouse lung cancer 3LL cell model and studying anti-tumor activity of the model, it is found that the furan-ring-modified prodrug molecule Q1 can be more effectively inhibit tumor cell proliferation.

Derivatives of Pyrido[2,3-d]pyrimidine, the Preparation Thereof, and the Therapeutic Application of the Same

The invention relates to derivatives of pyrido[2,3-d]pyrimidine, to the preparation thereof, and to the therapeutic application of the same.

TRIAZOLE DERIVATIVES USEFUL AS AXL INHIBITORS

Triazole derivatives and pharmaceutical compositions containing the derivatives are disclosed as being useful in inhibiting the activity of the receptor protein tyrosine kinase Axl. Methods of using the derivatives in treating diseases or conditions associated with Axl catalytic activity are also disclosed.

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.

Pd/C mediated synthesis of 2-substituted benzo[b]furans/nitrobenzo[b] furans in water

An efficient synthesis of 2-alkyl/aryl substituted benzo[b]furans/nitrobenzo[b]furans in water has been accomplished via Pd/C catalyzed reaction of o-iodophenols with terminal alkynes in the presence of PPh3, CuI and prolinol. This method can t

Aminoalkyl-substituted aromatic bicyclic compounds, methods for their preparation and their use as pharmaceuticals

The present invention relates to aminoalkyl-substituted aromatic bicyclic compounds of formula I, which are valuable pharmaceutically active compounds that are suitable, for example, for the treatment of obesity, type II diabetes, arteriosclerosis, high blood pressure, paresthesia, depression, anxiety, anxiety neuroses, schizophrenia, disorders associated with the circadian rhythm, and drug abuse, as well as normalizing lipid metabolism.