53910-10-4

Usage

Uses

Used in Organic Synthesis:
6-IODO-3 H-ISOBENZOFURAN-1-ONE is utilized as a building block for the synthesis of various organic molecules. Its unique isobenzofuranone ring system and halogen substitution at the 6-position contribute to the formation of complex organic structures, facilitating the creation of new compounds with potential applications in various fields.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 6-IODO-3 H-ISOBENZOFURAN-1-ONE serves as a key intermediate in the development of new drugs. Its distinct structure and reactivity allow for the synthesis of bioactive molecules with potential therapeutic properties, contributing to the advancement of medicinal chemistry.
Used as a Reagent in Chemical Reactions:
6-IODO-3 H-ISOBENZOFURAN-1-ONE is employed as a reagent in chemical reactions, particularly in the formation of carbon-carbon and carbon-heteroatom bonds. Its unique reactivity enables the formation of new chemical entities, expanding the scope of chemical synthesis and facilitating the discovery of novel compounds with diverse applications.

InChI:InChI=1/C8H5IO2/c9-6-2-1-5-4-11-8(10)7(5)3-6/h1-3H,4H2

Upstream product

• 57319-65-0 6-aminophthalide 
• 610-93-5 6-nitrophthalide 
• 87-41-2 2-benzofuran-1(3H)-one 

Downstream Products

• 886499-25-8 2-FORMYL-5-IODO-BENZOIC ACID 
• 481075-47-2 6-(trifluoromethyl)isobenzofuran-1(3H)-one 
• 374119-30-9 (S)-6-[1-carboxy-2-(3-methylphenyl)-ethylamino]-phthalide 

Relevant academic research and scientific papers

Discovery of potent indenoisoquinoline topoisomerase i poisons lacking the 3-nitro toxicophore

3-Nitroindenoisoquinoline human topoisomerase IB (Top1) poisons have potent antiproliferative effects on cancer cells. The undesirable nitro toxicophore could hypothetically be replaced by other functional groups that would retain the desired biological activities and minimize potential safety risks. Eleven series of indenoisoquinolines bearing 3-nitro bioisosteres were synthesized. The molecules were evaluated in the Top1-mediated DNA cleavage assay and in the National Cancer Institute's 60 cell line cytotoxicity assay. The data reveal that fluorine and chlorine may substitute for the 3-nitro group with minimal loss of Top1 poisoning activity. The new information gained from these efforts can be used to design novel indenoisoquinolines with improved safety.

A novel series of N-(azetidin-3-yl)-2-(heteroarylamino)acetamide CCR2 antagonists

The inflammatory response associated with the activation of C-C chemokine receptor CCR2 via it's interaction with the monocyte chemoattractant protein-1 (MCP-1, CCL2) has been implicated in many disease states, including rheumatoid arthritis, multiple sclerosis, atherosclerosis, asthma and neuropathic pain. Small molecule antagonists of CCR2 have been efficacious in animal models of inflammatory disease, and have been advanced into clinical development. The necessity to attenuate hERG binding appears to be a common theme for many of the CCR2 antagonist scaffolds appearing in the literature, presumably due the basic hydrophobic motif present in all of these molecules. Following the discovery of a novel cyclohexyl azetidinylamide CCR2 antagonist scaffold, replacement of the amide bond with heterocyclic rings was explored as a strategy for reducing hERG binding and improving pharmacokinetic properties.

Furan ring opening - Isocoumarine ring closure: A recyclization reaction of 2-carboxyaryldifurylmethanes

A general method for the synthesis of isocoumarine derivatives has been developed. Bis(5-R-2-furyl)methylbenzoic acids (R = methyl, ethyl) underwent recyclization and subsequent cyclization into tetracyclic isochromene-1-one derivatives under treatment with hydrogen chloride in methanol. It has been shown that intermediate 4-(5-R-furan-2-yl)-3-(3-oxo-3-R-propyl)-isochromene-1- ones can be obtained selectively by varying a concentration of the hydrogen chloride and reaction times. In the case of R = tert-butyl only corresponding 4-[5-(tert-butyl)-2-furyl]-3-(4,4-dimethyl-3-oxopentyl)-1-isochromenones were isolated regardless of the reaction conditions.

Anti-inflammatory phthalazinones

A compound useful as anti-inflammatory agents in warm-blooded animals of the formula STR1 wherein X is a member of the class of ethylene and ethenyl and is substituted for hydrogen in the sixth or seventh position of the 1(2H)-phthalazinone ring Y is a member of the class of hydrogen and hydroxyl R1 is a member of the class of hydrogen, alkyl, alkoxy, hydroxyl, halogen, nitro, --NR3 R4, --COR5 and --O--A wherein A is a mineral acid residue which with --O-- forms an ester or the alkali metal salt of said ester, R2 is a member of the class of hydrogen, alkyl, phenyl, substituted phenyl, heteroaryl, hydroxyalkylene, polyhydroxyalkylene, aminoalkylene, alkylaminoalkylene, and carboxyalkylene, R3, R4 are independently from the class of hydrogen, alkyl, aminoalkylene or alkylaminoalkylene, R5 is a member of the class of OR3 and STR2 for example hydroxyl, methoxyl, 2-dimethylaminoethoxyl or 2-dimethylaminoethylamino, and wherein by alkyl and alkylene is meant respectively a mono- or divalent saturated aliphatic radical containing up to about eight carbon atoms, wherein the nitrogen of the alkylamino or alkylaminoalkylene may form a heterocycle with the alkyl or alkylene groups, wherein substituted phenyl may be substituted by, for example, alkyl, hydroxyl, alkoxy, halogen, nitro or amino, wherein heteroaryl may be, for example, 2-pyridyl.