Day: July 9, 2021

Chemical Properties and Facts of C10H7BrO2S

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We report the synthesis and biological evaluation of 5-substituted indazoles as kinase inhibitors. The compounds were synthesized in a parallel synthesis fashion from readily available starting materials employing heterocycle forming and multicomponent reactions and were evaluated against a panel of kinase assays. Potent inhibitors were identified for Gsk3beta, Rock2, and Egfr.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Figure presented The ester-directed regioselective borylation of arenes catalyzed by a silica-supported monophosphine-Ir complex displayed a significantly broad substrate scope toward heteroaromatic compounds, including thiophene, pyrrole, furan, benzothiophene, benzofuran, indole, and carbazole derivatives. The regioselectivity is complementary to the selectivities observed in the heteroarene C-H borylation with the dtbpy-Ir catalyst system.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Application of 4923-87-9, Research speed reading in 2021. The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative theoretical assessments of solvent structures. In a article, 4923-87-9, molcular formula is C8H5BrS, introducing its new discovery.

A series of novel 1-substituted-2-aryl imidazoles (SAI) were designed and synthesized based on our previously reported ABI (2-Aryl-4-Benzoyl Imidazole) analogs and on the structure of combretastatin A-4 (CA-4). These compounds showed potent antiproliferative activities against six human cancer cell lines with IC50 values in nano molar range. Among them, compound 3X exhibited the best anticancer activity with an average IC50 value of ?100 nM. The compound maintains the mechanism of action by inhibiting tubulin polymerization, thus causing cell arrest at G2/M phase and apoptosis. In vivo efficacy studies indicated that 3X was highly effective in suppressing tumor growth in a MDA-MB-468 xenograft model of nude mouse with a TGI (Tumor Growth Suppression) of 77% at 60 mg/kg without causing significant toxicity. In addition, 3X displayed significantly better water solubility (36.70 mug/mL) than CA-4 (2.83 mug/mL). Molecular modeling study indicated that 3X binds well to the colchicine binding site in tubulin. Our results suggest that the novel SAI analogs deserve further investigation as potential anticancer agents.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Application of 19301-35-0, Research speed reading in 2021. The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative theoretical assessments of solvent structures. In a article, 19301-35-0, molcular formula is C8H6OS, introducing its new discovery.

Synthesis and biological evaluation of a new series of potential HIV-1 protease inhibitors incorporating different heterocycles are described. The variation of heteroatom in such molecules has displayed totally different biological activities and a benzothiophene containing inhibitor has shown high potency against wild type HIV-1 protease with IC50 = 60 nM, thanks to the lower desolvation penalty to be payed by such hydrophobic moiety.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Application of 19301-35-0, New research progress on 19301-35-0 in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. In a article, 19301-35-0, molcular formula is C8H6OS, introducing its new discovery.

Some members of the thieno<3,2-e><1>benzothiophene, <1>benzothieno<3,2-b>pyrrole, thieno<2,3-g>-1,2-benzisoxazole and thieno<2,3-g>indazole ring systems have been synthesized from 6,7-dihydrobenzothiophen-4(5H)-one derivatives.The unsaturated ethers of 4- and 5-hydroxybenzothiophenes undergo Claisen rearrangement followed by ring closure to give thieno<2,3-h><1>benzopyran and thieno<3,2-e><1>benzopyran ring systems.Syntheses of new thienobenzofurans from 4-hydroxybenzothiophene-5-carbaldehyde, its 2-methyl derivative and 5-hydroxybenzothiophene-4-carbaldehyde are also described.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Electric Literature of 360575-29-7, New research progress on 360575-29-7 in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. In a article, 360575-29-7, molcular formula is C10H7BrO2S, introducing its new discovery.

A comprehensive study was performed for the first time to compare two structurally related substance classes, namely indazole-5-carboxamides (11?16) and (indazole-5-yl)methanimines (17?22). Both chemical entities are potent, selective and reversible MAO-B inhibitors and, therefore, may serve as promising lead structures for the development of drug candidates against Parkinson’s disease (PD) and other neurological disorders. Compounds 15 (Ki = 170 pM, SI = 25907) and 17 (Ki = 270 pM, SI = 16340) were the most potent and selective MAO-B inhibitors in both series. To investigate the multi-target inhibitory activity, all compounds were further screened for their potency against human AChE and BuChE enzymes. Compound 15 was found to be the most potent and selective AChE inhibitor in all series (hAChE IC50 = 78.3 ± 1.7 muM). Moreover, compounds 11 and 17 showed no risk of drug-induced hepatotoxicity and a wider safety window, as determined in preliminary cytotoxicity screening. Molecular modeling studies into the human MAO-B enzyme-binding site supported by a HYDE analysis suggested that the imine linker similarly contributes to the total binding energy in methanimines 17?22 as the amide spacer in their carboxamide analogs 11?16. Amplified photophysical evaluation of compounds 17 and 20, including single X-ray analysis, photochemical experiments, and quantum-chemical calculations, provided insights into their more favourable isomeric forms and structural features, which contribute to their biologically active form and promising drug-like properties.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Application of 6287-82-7, Chemical Research Letters, May 2021. This type of reactivity has quickly become one of the cornerstones of modern catalysis . In a article, 6287-82-7, molcular formula is C8H4Br2S, introducing its new discovery.

Various tetrayne systems were converted under dual gold-catalyzed conditions. For symmetric tetraalkynyl-substituted thiophenes, bearing two alkyl-substituted alkynes and two terminal alkyne units, bidirectional cyclizations led to the efficient formation of dibenzothiophene systems. In all cases, selective CH activation of the C?H bond of the alkyl substituent was observed leading to cyclopentane moieties annelated to the newly formed aromatic cores. If two thiophene moieties were tethered over the attached non-terminal alkynes, depending on the length of the connecting alkyl tether, either bidirectional processes or tandem processes can be addressed leading to interesting molecular structures, such as spiro compounds or isolated benzothiophenes connected by a C?C bond. Other electron-rich heterocycles also reacted. While the reactions even worked for some mixed systems, other cases only delivered the products of a mono-cyclization.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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84449-65-0, Research speed reading in 2021. The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative theoretical assessments of solvent structures. In a article, 84449-65-0, molcular formula is C16H14O6S3, introducing its new discovery.

In an effort to prepare nonsteroidal antiestrogens demonstrating greater antagonism and less intrinsic estrogenicity than those currently available, a series of 3-aroyl-2-arylbenzothiophene derivatives was synthesized.These compounds were prepared by Friedel-Crafts aroylation of appropriate O-protected 2-arylbenzothiophene nuclei with basic side-chain-bearing benzoyl chlorides followed by removal of the protective groups to provide the desired compounds containing both hydroxyl and basic side-chain functionality.A particularly useful method for the cleavage of aryl methoxy ethers without removal of (dialkylamino)ethoxy side chain functionality elsewhere in the molecule was found to be AlCl3/EtSH.The benzothiophene derivatives were tested for their ability to inhibit the growth-stimulating action of estradiol on the immature rat uterus.Seemingly minor changes in the side-chain amine moiety were found to have profound effects on the ability of the compounds to antagonize estradiol.Analogues having basic side chains containing cyclic (pyrrolidine, piperidine, and hexamethyleneamine) moieties were found to have less intrinsic estrogenicity and to antagonize estradiol action more completely than their noncyclic counterparts.The most effective antiestrogen in the series, compound 44, <6-hydroxy-2-(4-hydroxyphenyl)benzothien-3-yl><4-<2-(1-piperidinyl)ethoxy>phenyl>methanone, elicited a modest uterotropic activity that did not increase with increasing dose.In antagonism of estradiol, 44 exhibited a degree of inhibition surpassing that of tamoxifen at any dose tested.The new benzothiophene antiestrogen was also shown to have high affinity for rat uterine cycloplasmic estrogen receptor and to be an inhibitor of the growth of DMBA-induced rat mammary tumors.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Enzyme inhibitors cause a decrease in the reaction rate of an enzyme-catalyzed reaction by binding to a specific portion of an enzyme and thus slowing or preventing a reaction from occurring. Application In Synthesis of 2-Bromobenzo[b]thiophene, C8H5BrS. A document type is Article, introducing its new discovery., Application In Synthesis of 2-Bromobenzo[b]thiophene

A palladium-catalyzed asymmetric carbon-carbon cleavage for the preparation of functionalized axially chiral molecules was reported. Increasing ring distortion not only enhanced the reactivity but also improved the chemoselectivity for different carbon-carbon bonds. This protocol enabled the quick synthesis of ketone-containing axially chiral biaryls in high yields and enantioselectivities.Development of new synthetic strategies for enantioselective carbon-carbon and carbon-heteroatom bond formation is one of the pillars of modern organic chemistry. Whereas significant advances have been achieved in center chirality construction, catalytically asymmetric construction of axial chirality is still under development. Moreover, axially chiral molecules constructed through carbon-carbon and carbon-heteroatom bond cleavage are extremely limited. Here, we report an asymmetric synthesis of biaryl atropisomers via palladium-catalyzed chemoselective carbon-carbon cleavage of 9-aryl-9H-fluoren-9-ols. The reaction demonstrated broad substrate scope and produced the atropisomers in high yields and enantioselectivity. The ring-opening reactivity was considerably accelerated by the torsional strain created by the steric repulsion between two ortho-substituents of the biaryl skeleton in the substrates. The high enantiocontrol hinges on the evolvement of a new TADDOL-based phosphoramidite as ligand. These findings set up a new platform for the development of novel synthetic methods via asymmetric carbon-carbon cleavage.Rapid generation of chirality to increase the complexity of molecules is pivotal for organic synthesis, material chemistry, and drug discovery. By taking advantage of ring strain, we developed a palladium-catalyzed asymmetric carbon-carbon bond cleavage reaction for facile access to a series of axially chiral biaryls in an atom-economical fashion. High functional group tolerance, yields, and enantioselectivities were achieved. The method set up a new platform toward axially chiral biaryl units found in many biologically active natural products, drugs, and catalysts. The present work also showcased a promising strategy for the activation of other non-activated molecules via increasing the ring strain by molecular distortion.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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The present disclosure provides gamma-diketones or analogs thereof, that activate Wnt/beta-catenin signaling and thus treat or prevent diseases related to signal transduction, such as osteoporosis and osteoarthropathy; osteogenesis imperfecta, bone defects, bone fractures, periodontal disease, otosclerosis, wound healing, craniofacial defects, oncolytic bone disease, traumatic brain injuries or spine injuries, brain atrophy/neurological disorders related to the differentiation and development of the central nervous system, including Parkinson’s disease, strokes, ischemic cerebral disease, epilepsy, Alzheimer’s disease, depression, bipolar disorder, schizophrenia; otic disorders like cochlear hair cell loss; eye diseases such as age related macular degeneration, diabetic macular edema or retinitis pigmentosa and diseases related to differentiation and growth of stem cell, such as hair loss, hematopoiesis related diseases and tissue regeneration related diseases.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem