Discovery of Benzofuran-2-carboxylic acid

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This invention provides compounds of formula (I): wherein ring A, X1 , X2 , X3 , R2, R4b, R10, and G have values as described in the specification, useful as inhibitors of HDAC6. The invention also provides pharmaceutical compositions comprising the compounds of the invention, and methods of using the compositions in the treatment of proliferative, inflammatory, infectious, neurological or cardiovascular diseases or disorders

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1630O – PubChem

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The coumarilate (coum?) and 1,10-phenanthroline (phen) mixed ligand complexes of Co(II) (1), Ni(II) (2) Cu(II) (3) and Zn(II) (4) were synthesized and structural characterizations were performed by using elemental analysis, magnetic susceptibility, solid-state UV?Vis, FTIR spectra, thermoanalytical TG-DTG/DTA and single-crystal X-ray diffraction methods. The Co(II) and Ni(II) complexes are salt-type compounds, and they have two moles phen ligands bound as bidentate, two moles aqua ligands in coordination sphere and two moles anionic coum? ligand outside of the coordination unit as the counter-ion of the molecular structure. At the same time, the Co(II) and Ni(II) complexes have five moles of aqua ligands as hydrated water outside of the molecules. It was obtained that Cu(II) and Zn(II) complex structures contain one mole of phen ligand, two moles coordinated (coum?) ligand and a one-mole aqua ligand, and the molecules (Cu(II) and Zn(II)) have fivefold structure and obey square pyramidal geometry. Thermal decomposition of each complex started with dehydration (the first removal is the dehydration of complex Co(II) and Ni(II) as removal of hydrate?aqua molecules), and then, the decomposition of organic parts was observed. The thermal dehydration of the complexes takes place in one (Cu(II) and Zn(II)) or two (Co(II) and Co(II)) steps. The decomposition mechanism, thermal decomposition steps and thermal stability of the investigated complexes provide useful data for the interpretation of their structures. The final decomposition products were found to be metal oxides. Some biological applications (antifungal/antibacterial) were performed using structurally characterized compounds.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1779O – PubChem

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Rational drug design method has been used to generate 4-arylpiperazine carboxamides in an effort to develop safer, more potent and effective monoamine neurotransmitters reuptake inhibitors. Out of twenty-seven synthesized compounds, compound 9 displayed potent monoamine neurotransmitter reuptake inhibitory activity against HEK cells transfected with hSERT or hNET. A Surflex-Dock docking model of 9 was also studied.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1923O – PubChem

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Several analogs of the alpha-tropanyl esters of 2-(4-chlorophenoxy)butyric acid (SM21) and 2-phenylthiobutyric acid (SM32), endowed with potent antinociceptive and cognition enhancing activity, were synthesized, aimed at obtaining more potent and safe drug candidates. Variation of the acyl moiety, as well as the conformational restriction of atropine to give the alpha-tropanyl ester of 2,3-dihydrobenzofurane-3-carboxylic acid (18), practically abolished activity. In the case of 18, the antimuscarinic activity was also severely affected by the conformation restrain. On the contrary, conformational restriction of phenoxybutyric and phenylthiobutyric acid derivatives to give the alpha-tropanyl ester of 2,3-dihydro-benzofurane-2-carboxylic acid and 2,3-dihydro-benzothiophene-2-carboxylic acid, afforded potent analgesic drugs that unfortunately were too toxic to be reliable drug candidates. A series of related esters of benzofurane-3-carboxylic acid and benzothiophene-3-carboxylic acid were also studied and found to be potent but toxic analgesics.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1954O – PubChem

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The invention provides 1-(1-imido)-2-aryl methyl-1,2,3,4-tetrahydroisoquinoline derivatives and a preparation method and application thereof. Stirring is conducted for 10-24 h at a certain temperature in organic solvent methylbenzene with 1,2,3,4-tetrahydroisoquinoline, aldehyde, carboxylic acid and isonitrile as raw materials and molecular sieves as additives. High-purity 1-(1-imido)-2-aryl methyl-1,2,3,4-tetrahydroisoquinoline derivatives are obtained after vacuum concentration, column chromatography and other operation are conducted on reaction mixed liquid. Raw materials are easy to obtain, reaction conditions are mild, and operation is easy; 1-(1-imido)-2-aryl methyl-1,2,3,4-tetrahydroisoquinoline derivatives with various substituent groups are easy to obtain, the requirement of high-flux sieving for tetrahydroisoquinoline derivatives can be well met, and great application and market value is achieved.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1686O – PubChem

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Alzheimer?s disease (AD), the most common cause of dementia, is a neurodegenerative disorder characterized by progressive deterioration of memory and cognition. The evidenced multifactorial nature of AD has been considered the main reason for the absence of cure so far. Therefore, the development of novel hybrids to treat the disease is very much essential. Focusing on this, a novel series of coumarin?benzofuran hybrids have been designed and screened as anti-Alzheimer?s disease agents. The strategy is to obtain an effective mimetic of donepezil, which is acetylcholinesterase inhibitor. Herein, the two main scaffolds namely coumarin and benzofuran are known pharmacophore moieties and we have performed their molecular design, pharmacokinetic descriptor studies for drug-likeliness. Further, in vitro studies such as antioxidant capacity, acetylcholinesterase (AChE) inhibition and amyloid-beta (Abeta) self-aggregation inhibition have also been performed. Most importantly, these studies revealed that the newly synthesized hybrids can be versatile and promising drug-like moieties as efficient anti-AD agents.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1818O – PubChem

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The ortho-olefination of benzoic acids can be achieved effectively through rhodium-catalyzed oxidative coupling with alkenes. The carboxylic group is readily removable to allow ortho-olefination/decarboxylation in one pot. alpha,beta-Unsaturated carboxylic acids such as methacrylic acid also undergo the olefination at the beta-position. Under the rhodium catalysis, the cine-olefination of heteroarene carboxylic acids such as thiophene-2-carboxylic acid proceeds smoothly accompanied by decarboxylation to selectively produce the corresponding vinylheteroarene derivatives.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1906O – PubChem

Discovery of Benzofuran-2-carboxylic acid

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Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1676O – PubChem

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Benzofuran derivatives represented by formula (I) or salts thereof: (wherein R1 represents a phenyl group or a hydrogen atom; k is 0 or 1; each of m, n, o, p, and q is an integer of 0 to 5; and each of R2 and R3 represents a hydrogen atom or a hydroxyl group, or R2 and R3 together represent an oxygen atom, with proviso that k, q, and m, or n, o, and p are not simultaneously 0).The compounds inhibit phosphorylation of STAT 6 and are useful in the treatment or prevention of allergic diseases.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1695O – PubChem

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Occasionally, results from the highly reproducible automated log P(o/w) measurement (ALPM) differ from those determined by shake-flask methods. Several specific examples affording different values are presented. One source of these differences may be curvilinearity in plots of log (t – t0) versus percent methanol, which complicate accurate intercept determinations and, thus, estimates of log P(o/w). Other sources of these differences are presented and discussed, although their cause remains unclear. Equilibrium ALPM log P(o/w) measurements of various phenyl-, methyl-, fluoro-, chloro-, and bromobenzenes, suggest substituent constants are not strictly additive. Moreover, the higher values indicate that calculated values may not be accurate for those compounds having multiple substituents or high log P(o/w) values. ALPM gives better predictability of the in vivo concentration process of 8 or 13 toxicants in fish than the shake-flask method, another HPLC method, or even calculated log P(o/w) values. However, it equally correlates the binding to bovine serum albumin by 34 chemicals as predicted by a combination of shake-flask and calculated log P(o/w) values reported elsewhere.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1801O – PubChem