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Chan-Evans-Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem

The Chan-Evans-Lam reaction is a valuable C-N bond forming process. However, aryl boronic acid pinacol (BPin) ester reagents can be difficult coupling partners that often deliver low yields, in particular in reactions with aryl amines. Herein, we report effective reaction conditions for the Chan-Evans-Lam amination of aryl BPin with alkyl and aryl amines. A mixed MeCN/EtOH solvent system was found to enable effective C-N bond formation using aryl amines while EtOH is not required for the coupling of alkyl amines.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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BENZODIAZEPINE DERIVATIVES

The invention relates to novel benzodiazepine derivatives with antiproliferative activity and more specifically to novel benzodiazepine compounds of formulae (I), (II) and (III). The invention also provides conjugates of the benzodiazepine compounds linked to a cell-binding agent. The invention further provides compositions and methods useful for inhibiting abnormal cell growth or treating a proliferative disorder in a mammal using the compounds or conjugates of the invention.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Design, synthesis and evaluation of novel, potent DNA alkylating agents and their antibody-drug conjugates (ADCs)

Antibody-drug conjugates (ADCs) incorporating potent indolinobenzodiazepine (IGN) DNA alkylators as the cytotoxic payload are currently undergoing clinical evaluation. The optimized design of these payloads consists of an unsymmetrical dimer possessing both an imine and an amine effectively eliminating DNA crosslinking and demonstrating improved tolerability in mice. Here we present an alternate approach to generating DNA alkylating ADCs by linking the IGN monomer with a biaryl system which has a high DNA binding affinity to potentially enhance tolerability. These BIA ADCs were found to be highly cytotoxic in vitro and demonstrated potent antitumor activity in vivo.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Selective palladium-catalyzed aminocarbonylation of olefins with aromatic amines and nitroarenes

Various olefins can be smoothly transformed in the presence of a Pd-based catalyst system and (hetero)aromatic amines or nitroarenes to synthetically interesting amides in good yields and often with high regioselectivity (see scheme). Combining this atom-efficient procedure with established functionalizations of the resulting products allows the efficient preparation of quinolines. Copyright

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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AZIRIDINE SPINOSYN DERIVATIVES AND METHODS OF MAKING

Compositions including derivatives of spinosyns of the following formulae and methods for the production of derivatives of spinosyns are provided. The spinosyn derivatives described herein include those functionalized on the C-5,6 double bond to provide an aziridine ring system. The method produces spinosyn derivatives that exhibit activity towards insects, arachnids, and nematodes and are useful in the agricultural and animal health markets.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Synthesis of a thiophene-fused isoindigo derivative: A potential building block for organic semiconductors

Thiophene-fused isoindigo (TII) was synthesized from thieno[2,3-f]indol- 6(7H)-one in a one-pot reaction, in which the alkylation, oxidation and condensation were finished in one step. It exhibits better intramolecular charge transfer properties and higher reductive potential compared with isoindigo(II), as evidenced by its optical and electrochemical properties, which shows that it might be used as a building block for n-type or ambipolar OFET materials.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Synthesis and molecular modeling of new 1-aryl-3-[4-arylpiperazin-1-yl]-1-propane derivatives with high affinity at the serotonin transporter and at 5-HT1A receptors

It has been proposed that 5-HT1A receptor antagonists augment the antidepressant efficacy of selective serotonin (5-HT) reuptake inhibitors. In a search toward new and efficient antidepressants, 1-(aryl)-3-[4-arylpiperazin-1-yl]-1-propane molecular hybrids were designed, synthesized, and evaluated for 5-HT reuptake inhibition and 5-HT1A receptor affinity. The design was based in coupling structural moieties related to inhibition of serotonin reuptake, such as benzo[b]-thiophene derivatives to arylpiperazines, typical 5-HT1A receptor ligands. In binding studies, several compounds showed affinity at the 5-HT transporter and at 5-HT1A receptors. Molecular modeling studies predicted the pharmacophore elements required for high affinity binding and the features that enable to discriminate between agonist, partial agonist, or antagonist action at 5-HT1A receptors and 5-HT transporter inhibition. Solvent interactions in desolvation prior to the binding step along with enthalpy and enthropy compensations might be responsible to explain agonist, partial agonist, and antagonist character. Hydrogen-bonding capability seems to be important to break hydrogen interhelical hydrogen bonds or alternatively to form other bonds upon ligand binding. Partial agonists and antagonists are unable to do this as the full agonist, which interacts closely by long-range forces or directly. The compounds showing the higher affinity at both the 5-HT transporter (Ki < 50 nM) and the 5-HT1A receptors (Ki < 20 nM) were further explored for their ability to stimulate [35S]GTPgammaS binding or to antagonize 8-hydroxy-2-di-n-propylamino-tetralin (8-OH-DPAT)-stimulated [35]GTPgammaS binding to rat hippocampal membranes, an index of agonist/antagonist action at 5-HT1A receptors, respectively. Compound 8g exhibited agonist activity (EC50 = 30 nM) in this assay, whereas compounds 7g and 8h,i behaved as weak partial agonists and 7h-j and 8j,1 antagonized the R(+)-8-OH-DPAT-stimulated GTPgammaS binding. Functional characterization was performed by measuring the antagonism to 8-OH-DPAT-induced hypothermia in mice. If you are interested in 20532-28-9, you can contact me at any time and look forward to more communication. name: 5-Aminobenzothiophene

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Catalyst-Free Transamidation of Aromatic Amines with Formamide Derivatives and Tertiary Amides with Aliphatic Amines

A simple catalyst- and promoter-free protocol has been developed for the transamidation of weakly nucleophilic aromatic amines with formamide derivatives and low-reactivity tertiary amides with aliphatic amines. This strategy is advantageous because no catalyst or promoters are needed, no additives are required, separation and purification is easy, and the reaction is scalable. Significantly, this strategy was further applied to synthesize several pharmaceutical molecules on a gram scale, and excellent yields were achieved.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Ligandless copper-catalyzed coupling of heteroaryl bromides with gaseous ammonia

A range of different N- and S-containing heterocyclic bromides can be efficiently coupled with gaseous ammonia in the presence of copper(II) acetylacetonate [Cu(acac)2] as catalyst and in the absence of additional ligands. Unstable aminothiophenes and aminobenzothiophenes can be further reacted in situ to afford functionalized derivatives. Copyright

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Reference£º
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Novel, achiral aminoheterocycles as selective monoamine reuptake inhibitors

A variety of novel aminoheterocycle scaffolds as selective monoamine reuptake inhibitors have been prepared and one of these scaffolds is achiral. The main elements responsible for hERG channel, CYP2D6 and CYP3A4 inhibition were identified.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem