4965-26-8

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
5-Nitrobenzothiophene is used as a key intermediate in the synthesis of pharmaceuticals and agrochemicals due to its potential for biological activity. It contributes to the development of new drugs and pesticides by serving as a building block in organic synthesis.
Used in Organic Synthesis:
5-Nitrobenzothiophene is used as a building block in organic synthesis, allowing chemists to create a variety of complex organic compounds. Its unique structure and reactivity make it a valuable component in the synthesis of various organic molecules.
Used as a Precursor to Other Chemical Compounds:
5-Nitrobenzothiophene serves as a precursor to other chemical compounds, enabling the production of a range of substances with diverse applications. Its versatility in chemical reactions makes it an essential starting material in the synthesis of various target compounds.
However, it is important to note that 5-Nitrobenzothiophene is known to be toxic and can be harmful if swallowed or inhaled. It may also cause skin and eye irritation upon contact, necessitating proper handling and safety precautions during its use in various applications.

InChI:InChI=1/C8H5NO2S/c10-9(11)7-1-2-8-6(5-7)3-4-12-8/h1-5H

Upstream product

• 20699-86-9 methyl 5-nitrobenzo[b]thiophene-2-carboxylate 
• 20532-38-1 5-iodobenzo[b]thiophene 
• 81146-79-4 1-[(2,2-diethoxyethyl)sulfanyl]-4-nitrobenzene 
• 2365-48-2 Methyl thioglycolate 
• 6361-21-3 2-chloro-5-nitrobenzaldehyde 
• 25785-09-5 ethyl 5-nitro-2-benzo[b]thiophenecarboxylate 
• 869624-56-6 (1E,3Z)-3-(4-methanesulfonyl-2-nitrobuta-1,3-dien-1-yl)thiophene 
• 81146-80-7 (4-nitro-phenylsulfanyl)-acetaldehyde dimethylacetal 
• 6345-55-7 5-nitrobenzo[b]thiophene-2-carboxylic acid 

Downstream Products

• 1935534-79-4 3-bromo-2-chlorobenzo[b]thiophen-5-amine 
• 16957-97-4 3-bromobenzothiophene S,S-dioxide 
• 127973-90-4 N-{3-[4-(2-Chloro-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-benzo[b]thiophen-5-yl}-2-cyclopentyl-acetamide 
• 127973-89-1 2-Cyclopentyl-N-{3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-benzo[b]thiophen-5-yl}-acetamide 
• 107786-74-3 N-[4-[5-(cyclopentyloxycarbonyl)aminobenzo[b]thien-3-ylmethyl]-3-methoxybenzoyl]benzenesulphonamide 
• 107786-72-1 methyl 4-<<5-<<(cyclopentyloxy)carbonyl>amino>benzothien-3-yl>methyl>-3-methoxybenzoate 
• 127973-87-9 methyl 4-<<5-(2-cyclopentylacetamido)benzothien-3-yl>methyl>-3-methoxybenzate 
• 107786-73-2 4-<<5-<<(cyclopentyloxy)carbonyl>amino>benzothien-3-yl>methyl>-3-methoxybenzoic acid 
• 127973-88-0 4-<<5-(2-cyclopentylacetamido)benzothien-3-yl>methyl>-3-methoxybenzoic acid 
• 107754-49-4 methyl 4-<(5-aminobenzothien-3-yl)methyl>-3-methoxybenzoate 
• 19301-35-0 benzo[b]thiophen-5-ol 
• 433303-94-7 1-(5-benzo[b]thiophenyl)piperazine 
• 20532-28-9 5-aminobenzo[b]thiophene 
• 107754-50-7 methyl 3-methoxy-4-<(5-nitrobenzothien-3-yl)methyl>benzoate 

Relevant academic research and scientific papers

Ring closure strategy leads to potent RIPK3 inhibitors

Necroptosis is a form of regulated necrotic cell death that is independent of caspases. Receptor-interacting protein kinase 3 (RIPK3) has been identified as a key regulator for necroptosis, and has been proposed as a potential therapeutic target for the treatment of diseases associated with necroptosis. In this report, we describe the design, synthesis, and evaluation of a series of novel RIPK3 inhibitors. The lead compound 38 exhibited potent activity (EC50 = 0.42 μM) in blocking TNFα, Smac mimetic and z-VAD (TSZ) induced cell death in HT-29 cells. Mechanistic studies showed that compound 38 bound to RIPK3 with high affinity (Kd = 7.1 nM), and inhibited RIPK3 kinase activity in a ADP-Glo functional assay. In addition, compound 38 displayed good selectivity over another necroptosis regulator RIPK1 (Kd = 6000 nM). Furthermore, compound 38 demonstrated excellent in vitro safety profiles with minimal inhibition of CYP isozymes and hERG potassium channel. Lastly, compound 38 efficiently blocked hypothermia and death in mice in the TNFα-induced systemic inflammatory response syndrome model.

HETEROARYL COMPOUNDS AS INHIBITORS OF PROGRAMMED NECROSIS PATHWAY, COMPOSITION AND METHOD USING THE SAME

The present disclosure provides heteroaryl compounds of Formula (I), processes for their preparation, pharmaceutical compositions containing them, and their use in the treatment of diseases and disorders, arising from or related to the programmed necrosis pathway.

Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer

A photoinduced iron-catalyzed ipso-nitration of aryl halides with KNO2 has been developed, in which aryl iodides, bromides, and some of aryl chlorides are feasible. The mechanism investigations show that the in situ formed iron complex by FeSO4, KNO2, and 1,10-phenanthroline acts as the light-harvesting photocatalyst with a longer lifetime of the excited state, and the reaction undergoes a photoinduced single-electron transfer (SET) process. This work represents an example for the photoinduced iron-catalyzed Ullmann-type couplings.

Discovery of Potent, Selective, and Structurally Novel Dot1L Inhibitors by a Fragment Linking Approach

Misdirected catalytic activity of histone methyltransferase Dot1L is believed to be causative for a subset of highly aggressive acute leukemias. Targeting the catalytic domain of Dot1L represents a potential therapeutic approach for these leukemias. In the context of a comprehensive Dot1L hit finding strategy, a knowledge-based virtual screen of the Dot1L SAM binding pocket led to the discovery of 2, a non-nucleoside fragment mimicking key interactions of SAM bound to Dot1L. Fragment linking of 2 and 3, an induced back pocket binder identified in earlier studies, followed by careful ligand optimization led to the identification of 7, a highly potent, selective and structurally novel Dot1L inhibitor.

Bicyclic heterocyclic anthranilic diamides as ryanodine receptor modulators with insecticidal activity

The diamide insecticides act on the ryanodine receptor (RyR). The synthesis of various bicyclic anthranilic derivatives is reported. Their activity against the insect ryanodine receptor (RyR) and their insecticidal activity in the greenhouse is presented,

Discovery of Novel Dot1L Inhibitors through a Structure-Based Fragmentation Approach

Oncogenic MLL fusion proteins aberrantly recruit Dot1L, a histone methyltransferase, to ectopic loci, leading to local hypermethylation of H3K79 and misexpression of HoxA genes driving MLL-rearranged leukemias. Inhibition of the methyltransferase activity of Dot1L in this setting is predicted to reverse aberrant H3K79 methylation, leading to repression of leukemogenic genes and tumor growth inhibition. In the context of our Dot1L drug discovery program, high-throughput screening led to the identification of 2, a weak Dot1L inhibitor with an unprecedented, induced pocket binding mode. A medicinal chemistry campaign, strongly guided by structure-based consideration and ligand-based morphing, enabled the discovery of 12 and 13, potent, selective, and structurally completely novel Dot1L inhibitors.

5-Substituted Benzothiophenes: Synthesis, Mechanism, and Kinetic Studies

The kinetics of the reaction of 4-methoxythiophenoxyacetaldehyde diethyl acetal, 4-nitrothiophenoxyacetaldehyde diethyl acetal, and 3-methoxythiophenoxyacetaldehyde diethyl acetal in polyphosphoric acid has been explained. The kinetic behavior has been ex

AMINOPYRIMIDINE COMPOUNDS AND METHODS OF USE

The invention relates to aminopyrimidine compounds useful for treating diseases mediated by polo-like kinase 1 (Plk1). The invention also relates to the therapeutic use of such aminopyrimidine compounds and compositions thereof in treating disease states associated with abnormal cell growth and unwanted cell proliferation.

From β-nitrothiophenes to ring-fused nitrobenzenes: An overall ring-enlargement process via a facile, aromatization-driven, thermal 6π electrocyclization

In prosecution of previous work on the thermal cyclization of 1-aryl-4-methanesulfonyl-2-nitro-3-phenylsulfonyl-1,3-butadienes (7), the 3-unsubstituted derivatives 8, deriving from the initial ring opening of 3-nitrothiophene (2), have been likewise found herein to undergo cyclization, followed by aromatization, in analogous mild experimental conditions, leading to the ring-fused homo- or heteroaromatic nitro derivatives 10. The concerted electrocyclic nature of the process is strongly supported by the outcome of tests based on the variation of the polarity of the solvent or of the electron density on the aryl of 8. Thus, the successful application of the process to the non-phenylsulfonyl-activated 8 significantly widens the scope of a synthetically valuable overall ring-opening/ring-closing procedure from nitrothiophenes. Support to the recently renewed interest in thermal 6π electrocyclizations as a tool for the construction of the benzene ring is furthermore provided.

Synthesis and cytotoxic activity of lipophilic sulphonamide derivatives of the benzo[b]thiophene 1,1-dioxide

In the search of new compounds with antineoplastic activity, we have analysed the effect of several structural modifications on the nucleus 6-benzo[b]thiophenesulphonamide 1,1-dioxide on its cytotoxic activity on tumour cells. Lipophilic substituents on t