328233-08-5

Basic information

• Product Name: trans-3'-Oxo-spiro[cyclohexane-1,1'(3'H)-isobenzofuran]-4-carboxylic acid
• Synonyms: TRANS-3''-OXO-SPIRO[CYCLOHEXANE-1,1''(3''H)-ISOBENZOFURAN]-4-CARBOXYLIC ACID
• CAS NO: 328233-08-5
• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.261
• Mol File: 328233-08-5.mol

Chemical Properties

• Boiling Point: 504.765 °C at 760 mmHg
• Flash Point: 198.188 °C
• Appearance: /
• Density: 1.35
• CAS DataBase Reference: trans-3'-Oxo-spiro[cyclohexane-1,1'(3'H)-isobenzofuran]-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: trans-3'-Oxo-spiro[cyclohexane-1,1'(3'H)-isobenzofuran]-4-carboxylic acid(328233-08-5)
• EPA Substance Registry System: trans-3'-Oxo-spiro[cyclohexane-1,1'(3'H)-isobenzofuran]-4-carboxylic acid(328233-08-5)

Safety Data

• Hazardous Substances Data: 328233-08-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Trans-3'-Oxo-spiro[cyclohexane-1,1'(3'H)-isobenzofuran]-4-carboxylic acid is used as a potential pharmaceutical agent for [application reason]. Its unique structure and functional groups may offer novel therapeutic opportunities, such as targeting specific biological pathways or interacting with certain receptors. Further research is needed to evaluate its efficacy, safety, and potential side effects in treating various diseases.
Used in Organic Synthesis:
In the field of organic synthesis, trans-3'-Oxo-spiro[cyclohexane-1,1'(3'H)-isobenzofuran]-4-carboxylic acid can be used as a building block or intermediate for the synthesis of more complex molecules. Its unique structure and functional groups may facilitate the development of new synthetic routes or the creation of novel compounds with desired properties.
Used in Material Science:
Trans-3'-Oxo-spiro[cyclohexane-1,1'(3'H)-isobenzofuran]-4-carboxylic acid may also find applications in material science, where its unique structure and functional groups could contribute to the development of new materials with specific properties. For example, it could be used in the design of polymers, coatings, or other materials with tailored characteristics for various applications.

Upstream product

• 20759-14-2 ruthenium(III) chloride hydrate 
• 328233-07-4 4-hydroxymethylspiro[cyclohexane-1,1'(3'H)-isobenzofuran]-3'-one 
• 1075736-35-4 trans-3-oxo-3H-spiro[2-benzofuran-1,1'-cyclohexane]-4'-carbonitrile 

Downstream Products

• 1078728-32-1 C₂₂H₂₂N₆O₃ 
• 1078728-27-4 C₂₀H₁₈Cl₂N₂O₃ 
• 1078728-23-0 C₂₆H₂₃FN₂O₃ 
• 640271-64-3 C₂₆H₂₁FN₂O₂ 
• 1078728-29-6 C₂₆H₂₃ClN₂O₃ 
• 1078728-07-0 C₂₆H₂₁ClN₂O₂ 
• 1078728-30-9 C₂₂H₂₁ClN₂O₅ 
• 1078728-31-0 C₂₂H₂₁ClN₂O₅ 
• 1078728-25-2 C₂₅H₂₃N₃O₃ 
• 1078728-26-3 C₂₅H₂₃N₃O₃ 
• 640271-47-2 C₂₂H₂₂N₂O₅ 
• 1078728-24-1 C₂₇H₂₄N₂O₄ 
• 1078728-03-6 C₂₇H₂₂N₂O₃ 

Relevant articles and documents

Discovery of trans-N-[1-(2-fluorophenyl)-3-pyrazolyl]-3-oxospiro[6-azaisobenzofuran-1(3H),1′-cyclohexane]-4′-carboxamide, a potent and orally active neuropeptide Y Y5 receptor antagonist

A series of trans-3-oxospiro[(aza)isobenzofuran-1(3H),1′-cyclohexane]-4′-carboxamide derivatives were synthesized to identify potent NPY Y5 receptor antagonists. Of the compounds, 21j showed high Y5 binding affinity, metabolic stability and brain and cerebrospinal fluid (CSF) penetration, and low susceptibility to P-glycoprotein transporters. Oral administration of 21j significantly inhibited the Y5 agonist-induced food intake in rats with a minimum effective dose of 1 mg/kg. This compound was selected for proof-of-concept studies in human clinical trials.

Identification of positron emission tomography ligands for NPY Y5 receptors in the brain

A series of trans-3-oxospiro[(aza)isobenzofuran-1(3H),1′-cyclohexane]-4′-carboxamide derivatives were synthesized and profiled for NPY Y5 binding affinity, brain and CSF penetrability in rats, and susceptibility to human and mouse P-glycoprotein transporters in order to develop a PET ligand. Compound 12b exhibited an acceptable profile for a PET ligand, and [11C]12b was successfully utilized in clinical settings as a Y5 PET ligand.

Syntheses and structure-activity relationships of novel, potent, and selective trans-2-[3-oxospiro[isobenzofuran-1(3H),1′-cyclohexan]-4′-yl]benzimidazole NPY Y5 receptor antagonists

Syntheses and structure-activity relationships of a novel class of 2-[3-oxospiro[isobenzofuran-1(3H),1′-cyclohexan]-4′-yl]benzimidazole NPY Y5 receptor antagonists are described. Optimization of the lead compound 2a by incorporating substituents into the 5-position or into both the 5- and 6-positions of the benzimidazole core part led to the identification of 5-(5-methyl-1,2,4-oxadiazol-2-yl)benzimidazole (2r: IC50 = 3.3 nM) and 5-(2-methyltetrazol-5-yl)benzimidazole (2u: IC50 = 5.9 nM), both of which are potent, selective, and orally bioavailable Y5 receptor antagonists. Crown Copyright

Synthesis and evaluation of a spiro-isobenzofuranone class of histamine H3 receptor inverse agonists

Spiro-isobenzofuranones 1a and 1b were discovered as potent, selective, and brain-penetrable non-imidazole H3 receptor inverse agonists. Our corporate sample collection was screened to identify 2a as a lead. Recognizing the right-hand portion of 2a as an essential pharmacophore, an extensive screen of the left-hand piperidine portion was carried out to yield the potent spiro-derivatives 2t-x. Spiro-isobenzofuranone 2x, the most potent among the derivatives, was converted to the corresponding amide 1a, which possessed dramatically improved H3 activity (IC50 = 0.72 nM; more than 20-fold improvement over 2x). Further elaboration led to the identification of 1b, a 5-methoxy derivative with an IC50 of 0.54 nM. Our studies demonstrated that derivatives 1a and 1b to be potent, selective, and brain-penetrable H3 inverse agonists.

Novel spiro compounds

Compounds of the general formula (I): wherein Ar1 represents optionally substituted aryl or heteroaryl; n represents 0 or 1; T, U, V, and W each independently represent nitrogen atom or optionally substituted methine group, where at least two of them represent the said methine group; X represents methine or hydroxy substituted methine; Y represents an optionally substituted imino or oxygen atom are described and claimed. These novel spiro compounds are useful as neuropeptide Y receptor antagonists and as agents for the treatment of various kinds of cardiovascular disorders, central nervous system disorders, metabolic diseases and the like.