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We synthesized a series of compounds based on the potent tubulin-polymerization inhibitor 5-hydroxy-2-(2,6-diisopropylphenyl)-1H- isoindole-1,3-dione [5HPP-33 (3)], which is structurally derived from thalidomide (1), and investigated their inhibitory effects on tubulin polymerization. Direct interaction between 5HPP-33 (3) and alpha,beta- tubulin heterodimer protein was demonstrated by means of a surface plasmon resonance study.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H3704O – PubChem

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The reaction of perfluorinated benzocyclobutene and tetraline with SiO 2-SbF5 led to the formation in a high yield of their mono- and further dicarbonyl derivatives. The monocarbonyl derivatives on heating with SbF5 underwent disproportionation into the corresponding perfluorobenzocycloalkenes and diketones. Both mono- and diketones in the SbF5 medium are liable to suffer skeleton rearrangements yielding five- and six-membered oxygen-containing heterocycles and/or products of the opening of the alicyclic fragment of the substrate, and from the perfluorobenzocyclobutenone compounds were also obtained with a number of carbon atoms greater than that of the initial ketone.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H3785O – PubChem

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A novel class of strongly fluorescent rhodamine dyes were designed and synthesized by extending the pi conjugation of chromophore with limited flexibility. These dyes were shown to have longer absorption in the range of 581 to 631 nm with quantum yields between 0.64 and 0.89.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H3734O – PubChem

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Process for the preparation of tetrafluorophthalic acid and/or tetrafluorophthalic anhydride

The present invention relates to a process for the preparation of tetrafluorophthalic acid and/or tetrafluorophthalic anhydride by reacting a compound of the formula STR1 in which X is a radical STR2 which is optionally mono- or polysubstituted on the aromatic nucleus by fluorine and/or chlorine and/or alkyl groups having 1 to 4 carbon atoms, or is a radical STR3 in which R1, R2 and R3 are as defined, with water, and subsequently removing the water still present by azeotropic distillation or extracting the tetrafluorophthalic acid and/or its anhydride with a water-insoluble solvent or solvent mixture.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H3693O – PubChem

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Synthesis and structures of gold perfluorophthalimido complexes

Compounds of the new tetrafluorophthalimido anion, [C6F 4(CO)2N]-, are readily accessible by treatment of tetrafluorophthalimide with either LiNPri2 or mixtures of NEt3 and Me3ECl (E = Si or Sn), to give C 6F4(CO)2N-X (X = Li 3, SiMe34, and SnMe35). The reaction of the trimethylsilyl derivative 4 with AgF leads cleanly to the ion pair complex [Ag(NCMe)2][Ag(N(CO) 2C6F4)2] (6¡¤2MeCN), which contains a linear [Ag{N(CO)2C6F4} 2]- anion and a tetracoordinate Ag+ cation. Compound 6 reacts with iodine to give the N-iodo compound C6F 4(CO)2NI 7, which crystallises as an acetonitrile adduct. Treatment of 6 with LAuCl affords LAu{N(CO)2C6F 4} (L = Ph3P 8a, Cy3P 8b, or THT 9), whereas the reaction with AuCl in acetonitrile affords the heterobinuclear compound [Ag(MeCN)2][Au{N(CO)2C6F4} 2]¡¤MeCN (10¡¤3MeCN). The tetrafluorophthalimido ligand is not readily displaced by donor ligands; however, the addition of B(C 6F5)3(Et2O) to a diethyl ether solution of 8a leads to the salt [Au(PPh3)2][N{COB(C 6F5)3}2C6F4)] 11. The analogous reaction of (THT)Au{N(CO)2C6F 4} with B(C6F5)3 in toluene in the presence of excess norbornene (nb) gives [Au(nb)3][N{COB(C 6F5)3}2C6F4)] 12. Compounds 11 and 12 contain a new non-coordinating phthalimido-bridged diborate anion with O-bonded boron atoms. The crystal structures of compounds 2-11 are reported.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H3761O – PubChem

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Organocatalytic enantioselective Mannich-type reaction of phosphorus ylides: Synthesis of chiral N-Boc-beta-amino-alpha-methylene carboxylic esters

The first asymmetric Mannich-type reaction of stabilized phosphorus ylides and N-Boc aldimines was described promoted by a readily available and recyclable chiral bisthiourea organocatalyst. Subsequent reaction with formalin smoothly provides N-Boc-beta-amino-alpha-methylene carboxylic esters in a highly enantiomerically enriched form (up to 96% ee). Copyright

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H3781O – PubChem

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Parallel synthesis and biological activity of a new class of high affinity and selective delta-opioid ligand

A considerable number of research papers describing the synthesis and testing of the delta opioid receptor (DOR) ligands, SNC-80 and TAN-67, and analogues of these two compounds, have been published in recent years. However, there have been few reports of the discovery of completely new structural classes of selective DOR ligand. By optimising a hit compound identified by high throughput screening, a new series of tetrahydroisoquinoline sulphonamide-based delta opioid ligands was discovered. The main challenge in this series was to simultaneously improve both affinity and physicochemical properties, notably aqueous solubility. The most active ligand had an affinity (IC50) of 6 nM for the cloned human DOR, representing a 15-fold improvement relative to the original hit 1 (IC50 98 nM). Compounds from this new series show good selectivity for the DOR over mu and kappa opioid receptors. However the most active and selective compounds had poor aqueous solubility. Improved aqueous solubility was obtained by replacing the phthalimide group in 1 by basic groups, allowing the synthesis of salt forms. A series of compounds with improved affinity and solubility relative to 1 was identified and these compounds showed activity in an in vivo model of antinociception, the formalin paw test. In the case of compound 19, this analgesic activity was shown to be mediated primarily via a DOR mechanism. The most active compound in vivo, 46, showed superior potency in this test compared to the reference DOR ligand, TAN-67 and similar potency to morphine (68% and 58% inhibition in Phases 1 and 2, respectively, at a dose of 10 mmol/kg i.v.).

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H3705O – PubChem

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The Polycomb Repressor Complex 1 Drives Double-Negative Prostate Cancer Metastasis by Coordinating Stemness and Immune Suppression

The mechanisms that enable immune evasion at metastatic sites are poorly understood. We show that the Polycomb Repressor Complex 1 (PRC1) drives colonization of the bones and visceral organs in double-negative prostate cancer (DNPC). In vivo genetic screening identifies CCL2 as the top prometastatic gene induced by PRC1. CCL2 governs self-renewal and induces the recruitment of M2-like tumor-associated macrophages and regulatory T cells, thus coordinating metastasis initiation with immune suppression and neoangiogenesis. A catalytic inhibitor of PRC1 cooperates with immune checkpoint therapy to reverse these processes and suppress metastasis in genetically engineered mouse transplantation models of DNPC. These results reveal that PRC1 coordinates stemness with immune evasion and neoangiogenesis and point to the potential clinical utility of targeting PRC1 in DNPC. Su et al. show that PRC1 drives metastasis of androgen receptor and neuroendocrine double-negative prostate cancers by regulating CCL2 expression. CCL2 governs self-renewal and recruitment of TAM and Treg. PRC1 inhibition combined with immune checkpoint blockade reverses these processes and suppresses metastasis.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H3767O – PubChem

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Efficient Synthesis of Immunomodulatory Drug Analogues Enables Exploration of Structure?Degradation Relationships

The immunomodulatory drugs (IMiDs) thalidomide, pomalidomide, and lenalidomide have been approved for the treatment of multiple myeloma for many years. Recently, their use as E3 ligase recruiting elements for small-molecule-induced protein degradation has led to a resurgence in interest in IMiD synthesis and functionalization. Traditional IMiD synthesis follows a stepwise route with multiple purification steps. Herein we describe a novel one-pot synthesis without purification that provides rapid access to a multitude of IMiD analogues. Binding studies with the IMiD target protein cereblon (CRBN) reveals a narrow structure?activity relationship with only a few compounds showing sub-micromolar binding affinity in the range of pomalidomide and lenalidomide. However, anti-proliferative activity as well as Aiolos degradation could be identified for two IMiD analogues. This study provides useful insight into the structure?degradation relationships for molecules of this type as well as a rapid and robust method for IMiD synthesis.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H3710O – PubChem

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Synthesis of fluorinated fluoresceins

Several novel fluorinated fluoresceins (Oregon Green dyes) were prepared by the reaction of fluororesorcinols with phthalic anhydride and its derivatives. A novel regiospecific synthesis of fluororesorcinols was key to the successful synthesis of these new fluorophores. (Polyfluoro)- nitrobenzenes were reacted with 2 equiv of sodium methoxide followed by reduction, hydrodediazoniation, and demethylation, giving the first straightforward synthesis of 2-fluororesorcinol, 4-fluororesorcinol, 2,4- difluororesorcinol, and 2,4,5-trifluororesorcinol. These fluorinated fluoresceins have higher photostability and ionize at a lower pH (pK(a) = 3.3-6.1) than fluorescein (pK(a) = 6.5). Some of the fluorinated fluoresceins have very high quantum yields (0.85-0.97), which, in combination with their lower pK(a)s and high photostability, makes them superior fluorescent dyes for use as reporter molecules in biological systems.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H3768O – PubChem