Category: benzothiophene

Reference of 4-Fluorobenzo[b]thiophene-2-carboxylic acidOn March 14, 2013, Katane, Masumi; Osaka, Naoko; Matsuda, Satsuki; Maeda, Kazuhiro; Kawata, Tomonori; Saitoh, Yasuaki; Sekine, Masae; Furuchi, Takemitsu; Doi, Issei; Hirono, Shuichi; Homma, Hiroshi published an article in Journal of Medicinal Chemistry. The article was 《Identification of Novel d-Amino Acid Oxidase Inhibitors by in Silico Screening and Their Functional Characterization in Vitro》. The article mentions the following:

D-Amino acid oxidase (DAO) is a degradative enzyme that is stereospecific for d-amino acids, including d-serine and d-alanine, which are potential coagonists of the N-methyl-d-aspartate (NMDA) receptor. Dysfunction of NMDA receptor-mediated neurotransmission has been implicated in the onset of various mental disorders such as schizophrenia. Hence, a DAO inhibitor that augments the brain levels of d-serine and/or d-alanine and thereby activates NMDA receptor function is expected to be an antipsychotic drug, for instance, in the treatment of schizophrenia. In the search for potent DAO inhibitor(s), a large number of compounds were screened in silico, and several compounds were estimated as candidates. These compounds were then characterized and evaluated as novel DAO inhibitors in vitro. The results reported in this study indicate that some of these compounds are possible lead compounds for the development of a clin. useful DAO inhibitor and have the potential to serve as active site probes to elucidate the structure-function relationships of DAO. The results came from multiple reactions, including the reaction of 4-Fluorobenzo[b]thiophene-2-carboxylic acid(cas: 310466-37-6Reference of 4-Fluorobenzo[b]thiophene-2-carboxylic acid)

4-Fluorobenzo[b]thiophene-2-carboxylic acid(cas: 310466-37-6) belongs to benzothiophene.Benzothiophene is a fused ring compound of thiophene ring and benzene ring, which is an important class of heterocycles with advantageous structures. It has been used as a raw material for the synthesis of biologically active structures and is found in pharmaceuticals such as selective estrogen receptor modulators, leukotriene synthesis inhibitors and antifungals, as well as in many natural products. Reference of 4-Fluorobenzo[b]thiophene-2-carboxylic acid

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Kaloglu, Murat; Kaloglu, Nazan; Ozdemir, Namik; Ozdemir, Ismail published an article in 2021. The article was titled 《The first use of [PdBr2(imidazolidin-2-ylidene)(pyridine)] catalysts in the direct C-H bond arylation of C2-substituted furan and thiophene》, and you may find the article in Research on Chemical Intermediates.Recommanded Product: 1-Thiophen-2-yl-ethanone The information in the text is summarized as follows:

In this study, four new 1,3-disubstituted imidazolinium salts as NHC ligand precursors I [R = 4-i-Pr, 4-Cl, 3,5-di-Me, 2,3,5,6-tetra-Me], and their four new PEPPSI-type palladium complexes II were synthesized. The structures of all new compounds were fully characterized by different spectroscopic and anal. techniques. The more detailed structural characterization of one of the palladium complexes was determined by single-crystal X-ray diffraction study. The catalytic activities of all palladium complexes were evaluated in the direct C-H bond arylation of 2-acetylfuran and 2-acetylthiophene with (hetero) aryl bromides and readily available and inexpensive aryl chlorides in presence of 1 mol% catalyst loading at 120°C. Under the given conditions, (hetero)aryl halides were successfully applied as the arylating reagents to achieve the C5-arylated furans/thiophenes III [R1 = Ph, 2-thienyl, 2-MeC6H4, etc.; Y = O, S] in acceptable to high yields. The experimental process involved the reaction of 1-Thiophen-2-yl-ethanone(cas: 88-15-3Recommanded Product: 1-Thiophen-2-yl-ethanone)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Reflecting their high stabilities, thiophenes arise from many reactions involving sulfur sources and hydrocarbons, especially unsaturated ones. Thiophenes are classically prepared by the reaction of 1,4-diketones, diesters, or dicarboxylates with sulfidizing reagents such as P4S10 such as in the Paal-Knorr thiophene synthesis. Recommanded Product: 1-Thiophen-2-yl-ethanone

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

The author of 《Palladium-Catalyzed C-H Arylation of Aliphatic and Aromatic Ketones using Dipeptide Transient Directing Groups》 were Cheng, Yaohang; Zheng, Jie; Tian, Chao; He, Yuhang; Zhang, Cong; Tan, Qi; An, Guanghui; Li, Guangming. And the article was published in Asian Journal of Organic Chemistry in 2019. Computed Properties of C6H6OS The author mentioned the following in the article:

Transition metal-catalyzed C-H bond functionalization is one of the most efficient tactics for diversification of ketones, e.g., 1-tetralone. Palladium-catalyzed C-H arylation of aliphatic and aromatic ketones has been achieved by utilizing an inexpensive dipeptide as a transient directing group. The tridentate coordination used in this reaction enhances the reactivity of the substrates and allows reduction of the loading of the directing group compounds to 20%. This approach allows rapid arylation of complex natural products, medicinal-chem.-related scaffolds, and even remote C(sp2)-H bonds. In the experiment, the researchers used 1-Thiophen-2-yl-ethanone(cas: 88-15-3Computed Properties of C6H6OS)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Reflecting their high stabilities, thiophenes arise from many reactions involving sulfur sources and hydrocarbons, especially unsaturated ones. Thiophenes are classically prepared by the reaction of 1,4-diketones, diesters, or dicarboxylates with sulfidizing reagents such as P4S10 such as in the Paal-Knorr thiophene synthesis. Computed Properties of C6H6OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Prugh, John D.; Hartman, George D.; Mallorga, Pierre J.; McKeever, Brian M.; Michelson, Stuart R.; Murcko, Mark A.; Schwam, Harvey; Smith, Robert L.; Sondey, John M. published an article in Journal of Medicinal Chemistry. The title of the article was 《New isomeric classes of topically active ocular hypotensive carbonic anhydrase inhibitors: 5-substituted thieno[2,3-b]thiophene-2-sulfonamides and 5-substituted thieno[3,2-b]thiophene-2-sulfonamides》.Application In Synthesis of 2-(Thiophen-3-yl)-1,3-dioxolane The author mentioned the following in the article:

A series of 5-substituted thieno[2,3-b]thiophene-2-sulfonamides I (R = substituted aminomethyl, oxazinylmethyl, thiazinylmethyl, substituted carbamoyl) and thieno[3,2-b]thiophene-2-sulfonamides II (R1 = Me2CHCH2, Me, MeOCH2CH2, R2 = H, MeOCH2CH2) was prepared and evaluated for topical ocular hypotensive activity in glaucoma models. The 5-substituents were varied to maximize both inhibitory potency against carbonic anhydrase and water solubility At the same time, these substituents were varied in order to obtain compounds with the appropriate pKa to minimize pigment binding in the iris. All of these variables were optimized best in compound I.HCl (R = NR3R4, R3 = MeOCH2CH2OCH2CH2, R4 = MeOCH2CH2).2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3Application In Synthesis of 2-(Thiophen-3-yl)-1,3-dioxolane) was used in this study.

2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3) is one of dioxolane. 1,3-Dioxolane derivatives are recognized as important motifs for the construction of numerous pharmacologically active molecules as antiviral, antifungal, anti-HIV, and adrenoreceptor antagonists.Application In Synthesis of 2-(Thiophen-3-yl)-1,3-dioxolane

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Plevova, Kristina; Kisszekelyi, Peter; Vargova, Denisa; Andrejcak, Samuel; Toth, Viktor; Fertal, Lukas; Rakovsky, Erik; Filo, Juraj; Sebesta, Radovan published their research in Chemistry – A European Journal in 2021. The article was titled 《Diastereoselective Double C-H Functionalization of Chiral Ferrocenes with Heteroaromatics》.COA of Formula: C6H6OS The article contains the following contents:

Diastereoselective double C-H heteroarylation of chiral ferrocenes provides valuable compounds with multiple functionalities using mild reaction conditions and simple reagents. Pd-Complexes with chiral mono-protected amino acids afforded corresponding heteroarylated ferrocenyl amines in good yields and high diastereomeric purities. In this way, a variety of indole, thiophene, pyrrole, or furan substituents were introduced to the ferrocene moiety. Furthermore, a range of relevant functional groups, for example ketone, ester, chloro, nitro, or silyl, are tolerated by this method. An alternative combination of amino acid and ferrocenyl amine configurations was leveraged to provide the complementary diastereomeric products. The products of C-H heteroarylation can be transformed into corresponding phosphines. Absolute configurations of CH-activation products were confirmed by the combination of X-ray crystallog. anal. and CD spectroscopy. 19F NMR kinetic study and DFT calculations provided insights into the reaction mechanism and reasons governing stereoinduction. The experimental part of the paper was very detailed, including the reaction process of 1-Thiophen-2-yl-ethanone(cas: 88-15-3COA of Formula: C6H6OS)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Specialized thiophenes can be synthesized similarly using Lawesson’s reagent as the sulfidizing agent, or via the Gewald reaction, which involves the condensation of two esters in the presence of elemental sulfur. Another method is the Volhard–Erdmann cyclization. COA of Formula: C6H6OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《One-Pot Transfer Hydrogenation Reductive Amination of Aldehydes and Ketones by Iridium Complexes “”on Water””》 was written by Ouyang, Lu; Xia, Yanping; Liao, Jianhua; Luo, Renshi. Safety of 1-Thiophen-2-yl-ethanone And the article was included in European Journal of Organic Chemistry in 2020. The article conveys some information:

An efficient and practical one-pot transfer hydrogenation reductive amination of aldehydes and ketones with amines has been developed by using iridium complexes as catalysts and formic acid as hydrogen source in aqueous solution, providing an environmentally friendly methodol. for the construction of a wide range of functionalized amine compounds in excellent yields (≈ 80%-95%). This effective methodol. can be scaled up to gram scale with 0.1 mol-% catalyst loading and also be employed in the synthesis of medical substances such as Meclizine. In the experiment, the researchers used 1-Thiophen-2-yl-ethanone(cas: 88-15-3Safety of 1-Thiophen-2-yl-ethanone)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Reflecting their high stabilities, thiophenes arise from many reactions involving sulfur sources and hydrocarbons, especially unsaturated ones. Thiophenes are classically prepared by the reaction of 1,4-diketones, diesters, or dicarboxylates with sulfidizing reagents such as P4S10 such as in the Paal-Knorr thiophene synthesis. Safety of 1-Thiophen-2-yl-ethanone

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《Assessment of headspace solid-phase microextraction (HS-SPME) for control of asymmetric bioreduction of ketones by Alternaria alternata》 was published in Biocatalysis and Biotransformation in 2020. These research results belong to Ogorek, Rafal; Jarosz, Bogdan. Synthetic Route of C6H6OS The article mentions the following:

The aim of this study was to assess the effectiveness of headspace solid-phase microextraction (HS-SPME) compared to liquid-liquid extractions using with methylene chloride (CH2Cl2) for control of fungal biotransformation of ketones of varying volatility. The proposed method was successfully applied. The best way to extract all the components of the mixture (alcs., aldehydes) in quantities similar to the extraction of methylene chloride was the use of fibers coated with a combination of nonpolar material. SPME fiber assembly polydimethylsiloxane/divinylbenzene (PDMS/DVB) was most suitable for the extraction of the products mixture obtained after biotransformation of acetylcyclohexane and acetophenone. On the other hand, the best results were obtained for 2-acetylthiophene, α,α,α-trifluoroacetophenone and their derivatives using divinylbenzene/carboxen/polydimethylsiloxane (DVB/CAR/PDMS) fiber. In addition, our study showed that Alternaria alternata is a good biocatalyst for bioreduction of ketones to alcs. according to Prelogs rule. In the experiment, the researchers used many compounds, for example, 1-Thiophen-2-yl-ethanone(cas: 88-15-3Synthetic Route of C6H6OS)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Specialized thiophenes can be synthesized similarly using Lawesson’s reagent as the sulfidizing agent, or via the Gewald reaction, which involves the condensation of two esters in the presence of elemental sulfur. Another method is the Volhard–Erdmann cyclization. Synthetic Route of C6H6OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《Functionalization of SBA-15 mesoporous materials with 2-acetylthiophene for adsorption of Cr(III) ions》 was published in Microporous and Mesoporous Materials in 2020. These research results belong to Wu, Hongmei; Xiao, Yu; Guo, Yu; Miao, Shiju; Chen, Qiangqiang; Chen, Zan. Electric Literature of C6H6OS The article mentions the following:

SBA-15 mesoporous materials functionalized with 2-acetylthiophene-derived Schiff’s base denoted as A-SBA-15, were synthesized for removal of Cr(III) ions from aqueous solution The adsorbent materials were characterized by XRD, SEM, TEM, N2 adsorption-desorption, TGA, EDXS, FTIR, 13C CP-MASNMR and XPS. Tests were then performed to study the adsorption of Cr(III) ions onto A-SBA-15 in batch systems. The maximum adsorption capacity of A-SBA-15 (114.2 mg/g) for Cr(III) ions was much higher than that of the pure SBA-15 (15.6 mg/g). The kinetics anal. revealed that the adsorption process was well described by pseudo-second-order kinetic model. The Langmuir isotherm model was better fitted with the adsorption data for Cr(III) compared to the Freundlich isotherm model. Also, the Cr(III) adsorption onto A-SBA-15 is spontaneous, endothermic, and mainly chem. adsorption as shown by the study of various thermodn. parameters, such as, ΔG°, ΔH°, and ΔS°. The characterization of A-SBA-15 materials before and after adsorption of Cr(III) ions showed that the chem. combination of the organic groups on A-SBA-15 and Cr(III) ions through coordination bond. The as-prepared A-SBA-15 materials could be reused in 5 successive recycles without significantly decreasing its adsorption capacity. Also, 4 batches of A-SBA-15 prepared at different synthesis times have the similar adsorption capacity. Besides, the adsorbent showed good selective separation of Cr(III) ion in the presence of Cu(II), Zn(II) and Ni(II) ions. The good reproductivity, reusability and selectivity suggest that A-SBA-15 material can be used as a promising adsorbent for efficient removal of heavy metals from aqueous solution The experimental part of the paper was very detailed, including the reaction process of 1-Thiophen-2-yl-ethanone(cas: 88-15-3Electric Literature of C6H6OS)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Specialized thiophenes can be synthesized similarly using Lawesson’s reagent as the sulfidizing agent, or via the Gewald reaction, which involves the condensation of two esters in the presence of elemental sulfur. Another method is the Volhard–Erdmann cyclization. Electric Literature of C6H6OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Hibino, Satoshi; Kano, Shinzo; Mochizuki, Naoki; Sugino, Eiichi published their research in Journal of Organic Chemistry on December 14 ,1984. The article was titled 《A new route to the pyridine nucleus fused to some heterocycles》.Related Products of 13250-82-3 The article contains the following contents:

Thermal cyclization of the appropriate 1-aza-1,3,5-hexatriene systems (oximes) gave the thieno[3,2-c]pyridines I (R = H, Me, Ph) and the 5H-pyrido[4,3-b]indoles II (R, R1, R2 = CO2Me, H, Me; CO2Me, Me, Ph; H, Me, Ph). In the experiment, the researchers used 2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3Related Products of 13250-82-3)

2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3) is one of dioxolane. 1,3-Dioxolane derivatives are recognized as important motifs for the construction of numerous pharmacologically active molecules as antiviral, antifungal, anti-HIV, and adrenoreceptor antagonists.Related Products of 13250-82-3

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Application In Synthesis of 2-(Thiophen-3-yl)-1,3-dioxolaneOn May 31, 2000, Chen, H.-H.; Gross, S.; Liao, J.; McLaughlin, M.; Dean, T.; Sly, W. S.; May, J. A. published an article in Bioorganic & Medicinal Chemistry. The article was 《2H-Thieno[3,2-e]- and [2,3-e]-1,2-thiazine-6-sulfonamide 1,1-dioxides as ocular hypotensive agents: synthesis, carbonic anhydrase inhibition and evaluation in the rabbit》. The article mentions the following:

Novel non-chiral 2H-thieno[3,2-e]- and [2,3-e]-1,2-thiazine-6-sulfonamide 1,1-dioxides were synthesized for evaluation as potential candidates for the treatment of glaucoma. All of the compounds prepared were potent high affinity inhibitors of human carbonic anhydrase II, Ki<0.5 nM. Addnl., inhibition of recombinant human carbonic anhydrase IV was determined for selected compounds; these were shown to be moderate to potent inhibitors of this isoenzyme with IC50 values ranging from 4.25 to 73.6 nM. Of the compounds evaluated for their ability to lower intraocular pressure in naturally hypertensive Dutch-belted rabbits, several showed significant efficacy (>20% decrease) in this model following topical ocular administration. The experimental process involved the reaction of 2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3Application In Synthesis of 2-(Thiophen-3-yl)-1,3-dioxolane)

2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3) is one of dioxolane. 1,3-Dioxolane derivatives are recognized as important motifs for the construction of numerous pharmacologically active molecules as antiviral, antifungal, anti-HIV, and adrenoreceptor antagonists.Application In Synthesis of 2-(Thiophen-3-yl)-1,3-dioxolane

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem