166887-84-9

Usage

Uses

Used in Organic Synthesis:
2-(bromomethyl)-5-nitrothiophene is used as a building block for the synthesis of complex organic molecules, leveraging its reactivity to facilitate the formation of new chemical bonds and structures.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-(bromomethyl)-5-nitrothiophene is employed as a precursor in the development of pharmaceutical compounds. Its unique structure and reactivity contribute to the design and synthesis of novel therapeutic agents.
Used in Research and Development:
2-(bromomethyl)-5-nitrothiophene is utilized in research and development settings to explore its chemical properties and potential applications. This includes studying its reactivity, stability, and interactions with other molecules, which can lead to the discovery of new uses and applications in various industries.

Upstream product

• 42297-94-9 5-nitro-2-methylthiophene 
• 20898-85-5 (5-nitrothiophen-2-yl)methanol 
• 4521-33-9 5-nitro-2-thiophenecarboxaldehyde 
• 558-13-4 carbon tetrabromide 

Downstream Products

• 166887-85-0 Ethyl-N-diphenylmethylene-3-(5-nitro-2-thienyl)-DL-alaninate 
• 82118-18-1 (5-nitrofuran-2-yl)methyl carbamimidothioate hydrobromide 

Relevant academic research and scientific papers

Development and pre-clinical testing of a novel hypoxia-activated KDAC inhibitor

Tumor hypoxia is associated with therapy resistance and poor patient prognosis. Hypoxia-activated prodrugs, designed to selectively target hypoxic cells while sparing normal tissue, represent a promising treatment strategy. We report the pre-clinical efficacy of 1-methyl-2-nitroimidazole panobinostat (NI-Pano, CH-03), a novel bioreductive version of the clinically used lysine deacetylase inhibitor, panobinostat. NI-Pano was stable in normoxic (21% O2) conditions and underwent NADPH-CYP-mediated enzymatic bioreduction to release panobinostat in hypoxia (2). Treatment of cells grown in both 2D and 3D with NI-Pano increased acetylation of histone H3 at lysine 9, induced apoptosis, and decreased clonogenic survival. Importantly, NI-Pano exhibited growth delay effects as a single agent in tumor xenografts. Pharmacokinetic analysis confirmed the presence of sub-micromolar concentrations of panobinostat in hypoxic mouse xenografts, but not in circulating plasma or kidneys. Together, our pre-clinical results provide a strong mechanistic rationale for the clinical development of NI-Pano for selective targeting of hypoxic tumors.

7-((5-Nitrothiophen-2-yl)methoxy)-3H-phenoxazin-3-one as a spectroscopic off-on probe for highly sensitive and selective detection of nitroreductase

A new spectroscopic off-on probe, 7-((5-nitrothiophen-2-yl)methoxy)-3H- phenoxazin-3-one, is developed and applied to real-time detection of nitroreductase produced by Escherichia coli.

2-((3,5-Dinitrobenzyl)thio)quinazolinones: Potent Antimycobacterial Agents Activated by Deazaflavin (F420)-Dependent Nitroreductase (Ddn)

Swapping the substituents in positions 2 and 4 of the previously synthesized but yet undisclosed 5-cyano-4-(methylthio)-2-arylpyrimidin-6-ones 4, ring closure, and further optimization led to the identification of the potent antitubercular 2-thio-substituted quinazolinone 26. Structure-activity relationship (SAR) studies indicated a crucial role for both meta-nitro substituents for antitubercular activity, while the introduction of polar substituents on the quinazolinone core allowed reduction of bovine serum albumin (BSA) binding (63c, 63d). While most of the tested quinazolinones exhibited no cytotoxicity against MRC-5, the most potent compound 26 was found to be mutagenic via the Ames test. This analogue exhibited moderate inhibitory potency against Mycobacterium tuberculosis thymidylate kinase, the target of the 3-cyanopyridones that lies at the basis of the current analogues, indicating that the whole-cell antimycobacterial activity of the present S-substituted thioquinazolinones is likely due to modulation of alternative or additional targets. Diminished antimycobacterial activity was observed against mutants affected in cofactor F420 biosynthesis (fbiC), cofactor reduction (fgd), or deazaflavin-dependent nitroreductase activity (rv3547), indicating that reductive activation of the 3,5-dinitrobenzyl analogues is key to antimycobacterial activity.

Expanding the donor-acceptor toolbox with a minimal 5-(thiophen-2-yl)-1,3-thiazole core: Transition metal-free synthesis and molecular design for HOMO-LUMO energy modulations

Synthesis of a minimal 5-(thiophen-2-yl)-1,3-thiazole core through a transition metal-free, versatile [4+1] route is reported. DFT calculations on a prototype library of D-A-D-A tetrads established the exquisite HOMO-LUMO energy modulation by varying peri

Aminoacid derivatives as no synthase inhibitors

Compounds of formula (I) and salts, esters and amides thereof, wherein R1 is a C1-6 straight or branched chain alkyl group, a C3-6 cycloalkyl group, a thiol group optionally substituted by a C1-6 alkyl group, or an amino group optionally substituted by one or two alkyl or alkenyl groups; R2 is H, C1-7 straight or branched chain alkyl, C3-6 cycloalkyl, C2-7 alkenyl or benzyl; A is a 5 or 6 membered aromatic carbocyclic or heterocyclic ring which may optionally be substituted by one or more suitable substituents such as C1-6 alkyl, C1-6 alkoxy, hydroxy, halo, nitro, cyano, trifluoro C1-6 alkyl, amino, C1-6 alkylamino or di C1-6 alkylamino; r is 0, 1 or 2; their use in medicine and in particular for conditions requiring inhibition of the NO Synthase enzyme, pharmaceutical formulations and processes for the preparation thereof are disclosed. STR1

Phosphonic acid compounds, their production and use

The present invention relates to a compound of the general formula (I): STR1 wherein ring A is a benzene ring that may be substituted; Y is a divalent group as a constituent member of ring B forming a 5- to 8-membered ring; Q1 is a group of the formula --X--P(O)(OR1)(OR2) wherein X is a bond or a divalent group; R1 and R2, identical or different, are hydrogen or a lower alkyl, or may be combined together to form a ring; Q2 is hydrogen, a hydrocarbon group that may be substituted or a heterocyclic group that may be substituted; and the group of the formula --CON(Q1)(Q2) is connected to the a- or b-position carbon atom, or a salt thereof, which is useful as prophylactic and therapeutic agents of various metabolic bone diseases such as osteoporosis.