Month: February 2023

Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials? was written by Terzic, Natasa;Konstantinovic, Jelena;Tot, Miklos;Burojevic, Jovana;Djurkovic-Djakovic, Olgica;Srbljanovic, Jelena;Stajner, Tijana;Verbic, Tatjana;Zlatovic, Mario;Machado, Marta;Albuquerque, Ines S.;Prudencio, Miguel;Sciotti, Richard J.;Pecic, Stevan;D’Alessandro, Sarah;Taramelli, Donatella;Solaja, Bogdan A.. And the article was included in Journal of Medicinal Chemistry in 2016.Quality Control of Methyl 5-bromobenzo[b]thiophene-2-carboxylate This article mentions the following:

The syntheses and antiplasmodial activities of various substituted aminoquinolines coupled to an adamantane carrier are described. The compounds exhibited pronounced in vitro and in vivo activity against Plasmodium berghei in the Thompson test. Tethering a fluorine atom to the aminoquinoline C(3) position afforded fluoroaminoquinolines that act as intrahepatocytic parasite inhibitors, with compound 25 having an IC₅₀ = 0.31 μM and reducing the liver load in mice by up to 92% at 80 mg/kg dose. Screening our peroxides as inhibitors of liver stage infection revealed that the tetraoxane pharmacophore itself is also an excellent liver stage P. berghei inhibitor (78: IC₅₀ = 0.33 μM). Up to 91% reduction of the parasite liver load in mice was achieved at 100 mg/kg. Examination of tetraoxane 78 against the transgenic 3D7 strain expressing luciferase under a gametocyte-specific promoter revealed its activity against stage IV-V Plasmodium falciparum gametocytes (IC₅₀ = 1.16 ± 0.37 μM). To the best of our knowledge, compounds 25 and 78 are the first examples of either an 4-aminoquinoline or a tetraoxane liver stage inhibitors. In the experiment, the researchers used many compounds, for example, Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0Quality Control of Methyl 5-bromobenzo[b]thiophene-2-carboxylate).

Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0) belongs to benzothiophene derivatives. Benzothiophene is a fused ring compound of thiophene ring and benzene ring, which is an important class of heterocycles with advantageous structures. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.Quality Control of Methyl 5-bromobenzo[b]thiophene-2-carboxylate

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Ullmann-Type Intramolecular C-O Reaction Toward Thieno[3,2-b]furan Derivatives with up to Six Fused Rings was written by Chen, Daoliang;Yuan, Dafei;Zhang, Cheng;Wu, Hao;Zhang, Jianyun;Li, Baolin;Zhu, Xiaozhang. And the article was included in Journal of Organic Chemistry in 2017.Safety of 2,3-Dibromobenzo[b]thiophene This article mentions the following:

In the presence of CuI and 1,10-phenanthroline, (fused) bromothienyl phenols such as I underwent intramol. Ullman coupling mediated by either K₂CO₃ or NaHCO₃ in DMF to yield (fused) thienofurans such as II and III in 47-97% yields. The (fused) bromothienyl phenol reactants were prepared by regioselective Suzuki coupling of hydroxyphenylboronic acids with dibromothiophenes. The structures of II, III, and two dibenzothienofurans were determined by X-ray crystallog. The HOMO and LUMO energies were calculated for selected compounds, including III; the oxidation and reduction potentials of III were determined An organic field-effect transistor was prepared using III which exhibited p-type behavior. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Safety of 2,3-Dibromobenzo[b]thiophene).

2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) belongs to benzothiophene derivatives. Functionalized benzothiophenes are important constructs found in molecules with wide ranging biological activity and in organic materials. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.Safety of 2,3-Dibromobenzo[b]thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

New approach to the synthesis of 2-substituted benzothiophenes and their hetero analogs was written by Brown, Kenneth J.;Meth-Cohn, Otto. And the article was included in Tetrahedron Letters in 1974.HPLC of Formula: 55219-11-9 This article mentions the following:

Ozonolysis of thiophene gave 34% (o-OCHC6H4)2S2 (I) which with RCH2CO2H (R = CO2H, CN, Ph, 2-thienyl, 3-thienyl, BzNH, AcNH) gave 2-R-substituted benzothiophenes (II). Similarly, I with MeNO2 gave 2-nitrothiophene. I was also prepared by LiAlH4 reduction of (o-HO2CC6H4)2S2 followed by MnO2 oxidation Similarly the pyrazole III gave the thienopyrazole IV. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9HPLC of Formula: 55219-11-9).

Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9) belongs to benzothiophene derivatives. Benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.HPLC of Formula: 55219-11-9

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis and characterization of unsymmetrical diarylethene based on phenylpentane was written by Zhang, Xiaodong;Wei, Shasha;Pu, Shouzhi. And the article was included in Applied Mechanics and Materials in 2015.Quality Control of 3-Bromo-2-methylbenzo[b]thiophene This article mentions the following:

An unsym. photochromic diarylethene, 1-[2-methyl-3-benzothiophene]-2-[2-methyl-5-(4-pentylphenyl)-3-thienyl]perfluorocyclopentene, has been synthesized, and its properties including photochromism and fluorescence have been investigated. The results showed that this compound undergo reversible cyclization and cycloreversion reactions upon alternating irradiation with UV and visible light in solution In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9Quality Control of 3-Bromo-2-methylbenzo[b]thiophene).

3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.Quality Control of 3-Bromo-2-methylbenzo[b]thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis of novel 2-aminoimidazo[4,5-b]pyridines, including the thieno analogue of the cooked-food mutagen IFP was written by Bjoerk, Malin;Grivas, Spiros. And the article was included in Journal of Heterocyclic Chemistry in 2006.Formula: C8H4Br2S This article mentions the following:

Eight new compounds, including three new ring systems obtained via the Friedlaender condensation of ortho-aminothiophenecarbaldehydes with creatinine, are reported. The condensation afforded I, which is the thieno analog of the cooked-food mutagen IFP (2-amino-1,6-dimethylfuro[2,3-e]imidazo[4,5-b]pyridine), and the benzothieno[2,3-e]- and benzothieno[3,2-e]imidazo[4,5-b]pyridines. Attempts to condense II with isocreatinine were unsuccessful. Desulfurization of III gave the known cooked-food carcinogen PhIP. The 2-nitro and 2-hydroxy derivatives of III are reported. The related 2-amino-1-methyl-imidazo[4,5-b]benzothiophene was synthesized by a different route. Fully assigned ¹H and ¹³C NMR data of all new compounds are reported. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Formula: C8H4Br2S).

2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The core structure is a part of various pharmaceutical substances and natural products. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Formula: C8H4Br2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

A photochromic liquid crystal system was written by Frigoli, Michel;Mehl, Georg H.. And the article was included in ChemPhysChem in 2003.Recommanded Product: 90560-10-4 This article mentions the following:

A photochromic liquid crystal system based on a photochromic core, 1,2-bis(2-methylbenzo[b]thiophen-3-yl)hexafluorocyclopentene system connected to two cyanobiphenyl groups via spacers of ten methylene groups was synthesized. The successful synthesis of the system indicates that the concept of sep. individual functionalities of a photochromic core and mesogens, linked by flexible spacers in a modular approach, allows the design of materials where the mesomorphic phase structure and range, and, addnl., the absorption characteristics, can be modulated in a controlled manner by irradiation In the experiment, the researchers used many compounds, for example, 6-Methoxybenzo[b]thiophene (cas: 90560-10-4Recommanded Product: 90560-10-4).

6-Methoxybenzo[b]thiophene (cas: 90560-10-4) belongs to benzothiophene derivatives. Benzothiophenes are valuable heterocycles that are widely used in medicines, agrochemicals, and materials science. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Recommanded Product: 90560-10-4

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Late-stage Pd-catalyzed Cyanations of Aryl/Heteroaryl Halides in Aqueous Micellar Media was written by Thakore, Ruchita R.;Takale, Balaram S.;Singhania, Vani;Gallou, Fabrice;Lipshutz, Bruce H.. And the article was included in ChemCatChem in 2021.Category: benzothiophene This article mentions the following:

New technol. was described that enables late stage ppm Pd-catalyzed cyanations of highly complex mols., as well as a wide variety of aryl and heteroaryl halides possessing sensitive functional groups. These reactions are efficient in water containing nanomicelles, formed from a com. available and inexpensive surfactant. The implications for advancing drug synthesis and discovery are apparent. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9Category: benzothiophene).

Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9) belongs to benzothiophene derivatives. Benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. It is also used in the manufacturing of dyes such as thioindigo.Category: benzothiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Ring opening/closure reactions of novel diheteroarylethenes derivatives. Solvent effects was written by Vazquez, Alvaro J.;Nudelman, Norma Sbarbati. And the article was included in Journal of Physical Organic Chemistry in 2012.COA of Formula: C9H8OS This article mentions the following:

Three novel diarylethenes, 3,3′-(3,3,4,4,5,5-hexafluoro-1-cyclopentene-1,2-diyl)bis[2-methyl-benzo[b]thiophene] (I), 3-[3,3,4,4,5,5-hexafluoro-2-(2-methylbenzo[b]thien-3-yl)-1-cyclopenten-1-yl]-6-methoxy-2-methyl-benzo[b]thiophene (II), and 3-[3,3,4,4,5,5-hexafluoro-2-(2-methylbenzo[b]thien-3-yl)-1-cyclopenten-1-yl]-6-methoxy-2-methyl-7-nitro-benzo[b]thiophene (III), were synthesized and their photochem. optical properties studied in four solvents (n-hexane, toluene, acetonitrile and methanol). It was determined that these compounds dramatically increase the light absorption in the visible region upon exposure to UV light, showing two absorption maxima at 420 nm and 520 nm, resp. The observed change is completely reverted upon exposure to visible light. The three compounds demonstrate negligible fatigue, excellent stability in the four solvents, and absence of photodegradation and thermal back reactions. This paper also describes a complete study of solvent effects on the kinetics of the ring opening and cycloreversion. While, the UV spectra are little sensitive both to the substitution pattern and to the solvent influence, the kinetics of ring opening/cycloreversion reactions exhibit a more interesting behavior that differs from other diarylethenes reported in the literature. The cyclization kinetics shows a complex order, well fitted by an exponential equation, while the cycloreversion presents first-order kinetics. The whole complex reaction scheme can be explained by the unusual presence of two conformers of the open form, a parallel and an antiparallel conformation. Though other alternative mechanism could explain the kinetics, addnl. evidence is consistent with the conformational equilibrium proposed: i.e. the solvent influence on the kinetics of the nitro-substituted substrate, and the double signals for the Me protons and for the methoxy protons (when present) observed in the NMR spectra. These observations are relevant in relation to the application of these novel diarylethenes as potential optical materials. Copyright © 2012 John Wiley & Sons, Ltd. In the experiment, the researchers used many compounds, for example, 6-Methoxybenzo[b]thiophene (cas: 90560-10-4COA of Formula: C9H8OS).

6-Methoxybenzo[b]thiophene (cas: 90560-10-4) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.COA of Formula: C9H8OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Nucleophilic Activation of Hydrosilanes via a Strain-Imposing Strategy Leading to Functional Sila-aromatics was written by Ikeuchi, Toshiya;Hirano, Keiichi;Uchiyama, Masanobu. And the article was included in Journal of the American Chemical Society in 2021.Related Products of 6287-82-7 This article mentions the following:

Carefully designed cyclic hydrosilanes enable trans-selective hydrosilylation of unactivated alkynes without transition metal catalysts via silicate formation. Employment of sterically demanding bidentate ligands of Si increases steric congestion upon silicate formation, and this strain-imposing strategy facilitates hydride transfer. This hydrosilylation provides efficient access to diverse benzosiloles, silaphenalenes, and related silacycles. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Related Products of 6287-82-7).

2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. The different substitution patterns in these heterocycles offer new opportunities for drug discovery and other applications in materials science.Related Products of 6287-82-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

New derivatives of thianaphthene was written by Ried, Walter;Bender, Heinz. And the article was included in Chemische Berichte in 1955.COA of Formula: C8H4Br2S This article mentions the following:

2-Formylthianaphthene (I) (4.87 g.) and 5.37 g. hippuric acid heated 45 min. with 2.46 g. anhydrous NaOAc and 30 g. Ac₂O and poured into H₂O gave 95% 2-phenyl-4-(2-thianaphthenylmethylene)-2-oxazolin-5-one (II), C₁₈H₁₁NO₂S, m. 206° (from C₆H₆) which gave 74% α-amino-2-thianaphthenepropionic acid, C₁₁H₁₁NO₂S, m. 258° (decomposition) (from aqueous EtOH)[R_f 0.79 (PhOH:H₂O-4:1)], with P and HI. II and 2% alc. aqueous NaOH refluxed 20 min. gave 73% α-benzamido-2-thianaphtheneacrylic acid (III), C₁₈H₁₃NO₃S, m. 245° (decomposition) (from MeOH), reduced (Pt, MeOH) to α-benzamido-2-thianaphthenepropionic acid, C₁₈H₁₅NO₃S, m. 178.5-9° (from MeOH). III heated 1 hr. with Na₂CO₃ and wet H saturated Raney Ni gave Ph(CH₂)₃CH(NHBz)CO₂H, C₁₈H₁₉NO₃, m. 187.5° (from MeOH). I and malonic acid heated 4 hrs. with pyridine, the excess aldehyde steam distilled and the residue acidified gave 75% 2-thianaphtheneacrylic acid (IV), C₁₁H₁₈O₂S, m. 231° (from H₂O). IV reduced to the propionic acid, C₁₁H₈O₂S, m. 138.5° (from MeOH). Similarly malonic acid and 3-formylthianaphthene gave 3-thianaphtheneacrylic acid, m. 225° (from MeOH). I and Br 10 hrs. at room temperature gave 80% 3-bromo-2-formylthianaphthene, C₉H₅BrOS, m. 118-18.5° (from AcOH), which yielded 59% 3-bromo-2-thianaphthenecarboxylic acid (V) when gently heated with 20 g. KMnO₄ in 100 ml. H₂O and 300 ml. Me₂CO and allowed to stand 20 hrs.; V was also obtained in 15% yield by brominating the Na salt of 2-thianaphthenecarboxylic acid 8 days in daylight, or in 79% yield from dibromothianaphthene (VI), BuLi, and CO₂. VI was prepared in 85% yield from Br and thianaphthene (12 hrs.). I with Ac₂O and ZnCl₂ in 24 hrs. gave 2-(diacetoxymethyl)thianaphthene, C₁₃H₁₂O₄S, m. 94° (from petr. ether). In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7COA of Formula: C8H4Br2S).

2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The electrophilic substitution of benzothiophene systems is much less regioselective than that of indoles. It has been used as a raw material for the synthesis of biologically active structures and is found in pharmaceuticals such as leukotriene synthesis inhibitors and antifungals, as well as in many natural products.COA of Formula: C8H4Br2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem