Month: October 2022

Li, Yitao; Yao, Wenqiang; Lin, Jian; Li, Falin; Wu, Yang; Xu, Junxing published an article in 2019, the title of the article was Design, Synthesis and Biological Activity of Novel Triazole Sulfonamide Derivatives Containing a Benzylamine Moiety.Synthetic Route of 16296-68-7 And the article contains the following content:

The 1,2,4-triazole-1,3-disulfonamide derivatives I [Ar = 2-thienyl, 2-pyrrolyl, 3-pyridyl, etc.] were synthesized via coupling of amines with triazole sulfonamide groups and evaluated for their fungicidal activity against cucumber downy mildew (CDM). Most of these derivatives exhibited better fungicidal activities than that of the com. cyanosole using bioassays. In particular, compounds I [Ar = 4-bromo-2-thiazolyl, 5-chloro-2-thienyl] showed the best fungicidal activity against CDM (EC50 = 6.91 and 10.62 mg/L). Comparative experiments demonstrated that the fungicidal activity of I [Ar = 4-bromo-2-thiazolyl, 5-chloro-2-thienyl] was better than the com. pesticides amisulbrom and cyanosole. The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Synthetic Route of 16296-68-7

The Article related to triazole disulfonamide benzylamine preparation fungicidal, Heterocyclic Compounds (More Than One Hetero Atom): Other 5-Membered Rings, Two Or More Hetero Atoms and other aspects.Synthetic Route of 16296-68-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

On March 21, 1997, Taylor, Edward C.; Dowling, James E. published an article.Safety of 3-Bromo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylic acid The title of the article was Replacement of the 1′,4′-Phenylene Region in 5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid (DDATHF) by 4,5,6,7-Tetrahydrobenzo[c]thiophene and 4,5,6,7-Tetrahydroisobenzofuran Nuclei. And the article contained the following:

Two new analogs of DDATHF, in which the 1′,4′-phenylene unit is replaced by 4,5,6,7-tetrahydrobenzo[c]thiophene and 4,5,6,7-tetrahydroisobenzofuran nuclei, have been prepared and evaluated for in vitro cytotoxicity, glycinamide ribonucleotide formyltransferase (GARFT) inhibition, and folyl polyglutamate synthetase (FPGS) affinity as potential antitumor agents. The experimental process involved the reaction of 3-Bromo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylic acid(cas: 188240-63-3).Safety of 3-Bromo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylic acid

The Article related to dideazatetrahydrofolate derivative preparation antitumor, glycinamide ribonucleotide formyltransferase inhibition dideazatetrahydrofolate derivative, folyl polyglutamate synthetase affinity dideazatetrahydrofolate derivative and other aspects.Safety of 3-Bromo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylic acid

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

On January 28, 2021, Cuthbertson, Alan; Boehnke, Niels published a patent.Formula: C9H5ClOS The title of the patent was Targeted radiopharmaceuticals for the diagnosis and treatment of prostate cancer. And the patent contained the following:

The invention is related to the preparation of compounds I [n = 1-3; R1-4 = OH or Q; Q = a tissue-targeting moiety selected from the group consisting of poly- and oligopeptides, proteins, DNA and RNA fragments, aptamers polyclonal or monoclonal antibodies, and a mixture of proteins or fragments or constructs of protein] their stereoisomers, hydrates, solvates and salts, and targeted radiopharmaceuticals, pharmaceutical compositions and combinations comprising them and their use for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of soft tissue diseases, as a sole agent or in combination with other active ingredients. The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Formula: C9H5ClOS

The Article related to peptide chelator conjugate preparation antitumor prostate cancer, preparation peptide chelator thorium 227 her2 fap psma conjugate, prostate specific membrane antigen carboxy hopo thorium 227 conjugate, targeted radiopharmaceutical prostate cancer and other aspects.Formula: C9H5ClOS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

On May 8, 2019, Kurz, Guido; Camacho Gomez, Juan published a patent.Application In Synthesis of 5-Chlorobenzo[b]thiophene-3-carbaldehyde The title of the patent was Preparation of novel dihydropyridine derivatives as androgen receptor and glucocorticoid receptor modulators. And the patent contained the following:

The present invention relates to novel dihydropyridine derivatives I [R1 = CN, CHO, COR5, CO2R5 (wherein R5 = (un)substituted alkyl, cycloalkyl); R2 = CN, COR8, CO2R8, SOnR8, C(O)NR8R9 (n = 1-2; R8 and R9 = (independently) H, (un)substituted alkyl, cycloalkyl, etc.; or R8 and R9 together with the nitrogen atom to which they are attached form (un)substituted 5-6 membered heterocycle which optionally comprises 1 heteroatom selected from O and N); R3 = H, NH2, CN, etc.; R4 = H, CN, (un)substituted alkyl, etc.; or R1 and R3 or R2 and R4 form together (CR10R11)n (n = 3-4 wherein 1, 2 or 3 of CR10R11 moieties may be independently replaced by a group selected from O, S, C(O) and (un)substituted NH; R10, R11 = (independently) H, (un)substituted Ph or 5-6 membered heteroaryl, etc.); X1-X5 = (independently) CB1, N and CH (B1 = halo, CN, (un)substituted 5-6 membered heteroaryl, etc.)] and pharmaceutically acceptable salts thereof, as modulators of nuclear receptors selected from androgen receptor and glucocorticoid receptor, to processes for their preparation, to pharmaceutical compositions comprising said compounds and to the use of said for manufacturing a medicament for the treatment of pathol. conditions or diseases that can improve by modulation of androgen receptor and/or glucocorticoid receptor, selected from cancer, metastasizing cancers, benign prostate hyperplasia, polycystic ovary syndrome (PCOS), hair loss, hirsutism, acne, hypogonadism, muscle wasting diseases, cachexia, Cushing’s syndrome, anti-psychotic drug induced weight gain, obesity, post-traumatic stress disorder and alcoholism. Over two-hundred-seventy compounds I were prepared For example, heating a mixture of 3-(benzo[b]thiophen-3-ylmethylene)pentane-2,4-dione, Me 3-oxobutanoate and 30% aqueous ammonium in iso-PrOH at reflux temperature for 12 h afforded 25% II (both enantiomers were separated). Exemplified compounds I were evaluated for their androgen receptor and glucocorticoid receptor modulatory activities (data given for representative compounds I). The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Application In Synthesis of 5-Chlorobenzo[b]thiophene-3-carbaldehyde

The Article related to pyridine dihydropyridine preparation nuclear androgen glucocorticoid receptor modulator antitumor, benign prostate hyperplasia polycystic ovary syndrome treatment dihydropyridine preparation, hair loss hirsutism acne hypogonadism treatment dihydropyridine pyridine preparation and other aspects.Application In Synthesis of 5-Chlorobenzo[b]thiophene-3-carbaldehyde

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

On May 9, 2019, Kurz, Guido; Camacho Gomez, Juan published a patent.Synthetic Route of 16296-68-7 The title of the patent was Preparation of novel dihydropyridine derivatives as androgen receptor and glucocorticoid receptor modulators. And the patent contained the following:

The present invention relates to novel dihydropyridine derivatives I [R1 = CN, C(O)NH2, COR5, CO2R5 (wherein R5 = (un)substituted alkyl, cycloalkyl); R2 = CN, COR8, CO2R8, SOnR8, C(O)NR8R9 (n = 1-2; R8 and R9 = (independently) H, (un)substituted alkyl, H, etc.; or R8 and R9 together with the nitrogen atom to which they are attached form (un)substituted 5-6 membered heterocycle which optionally comprises 1 heteroatom selected from O and N); R3 = H, NH2, CN, etc.; R4 = H, CN, (un)substituted alkyl, etc.; X1-X5 = (independently) CB1, N and CH (B1 = halo, CN, (un)substituted 5-6 membered heteroaryl, etc.)] and pharmaceutically acceptable salts thereof, as modulators of nuclear receptors selected from androgen receptor and glucocorticoid receptor, to processes for their preparation, to pharmaceutical compositions comprising said compounds and to the use of said for manufacturing a medicament for the treatment of pathol. conditions or diseases that can improve by modulation of androgen receptor and/or glucocorticoid receptor, selected from cancer, metastasizing cancers, benign prostate hyperplasia, polycystic ovary syndrome (PCOS), hair loss, hirsutism, acne, hypogonadism, muscle wasting diseases, cachexia, Cushing’s syndrome, anti-psychotic drug induced weight gain, obesity, post-traumatic stress disorder and alcoholism. Over three-hundred compounds I were prepared For example, heating a mixture of 3-(benzo[b]thiophen-3-ylmethylene)pentane-2,4-dione, Me 3-oxobutanoate and 30% aqueous ammonium in iso-PrOH at reflux temperature for 12 h afforded 25% II (both enantiomers were separated). Exemplified compounds I were evaluated for their androgen receptor and glucocorticoid receptor modulatory activities (data given for representative compounds I). The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Synthetic Route of 16296-68-7

The Article related to pyridine dihydropyridine preparation nuclear androgen glucocorticoid receptor modulator antitumor, benign prostate hyperplasia polycystic ovary syndrome treatment dihydropyridine preparation, hair loss hirsutism acne hypogonadism treatment dihydropyridine pyridine preparation and other aspects.Synthetic Route of 16296-68-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《Palladium-Catalyzed Dual Ligand-Enabled Alkylation of Silyl Enol Ether and Enamide under Irradiation: Scope, Mechanism, and Theoretical Elucidation of Hybrid Alkyl Pd(I)-Radical Species》 was written by Zhao, Bin; Shang, Rui; Wang, Guang-Zu; Wang, Shaohong; Chen, Hui; Fu, Yao. Computed Properties of C6H6OS And the article was included in ACS Catalysis in 2020. The article conveys some information:

We report herein that a palladium catalyst in combination with a dual phosphine ligand system catalyzes alkylation of silyl enol ether and enamide with a broad scope of tertiary, secondary, and primary alkyl bromides under mild irradiation conditions by blue light-emitting diodes. The reactions effectively deliver α-alkylated ketones and α-alkylated N-acyl ketimines, and it is difficult to prepare the latter by other methods in a stereoselective manner. The α-alkylated N-acyl ketimine products can be further subjected to chiral phosphoric acid-catalyzed asym. reduction with Hantzsch ester to deliver chiral N-acyl-protected α-arylated aliphatic amines in high enantioselectivity up to 99% ee, thus providing a method for facile synthesis of chiral α-arylated aliphatic amines, which are of importance in medicinal chem. research. The N-acetyl ketimine product also reacted smoothly with various types of Grignard reagents to afford sterically bulky N-acetyl α-tertiary amines in high yields. Theor. studies in combination with exptl. investigation provide understanding of the reaction mechanism with respect to the dual ligand effect and the irradiation effect in the catalytic cycle. The reaction is suggested to proceed via a hybrid alkyl Pd(I)-radical species generated by inner-sphere electron transfer of phosphine-coordinated Pd(0) species with alkyl bromide. This intriguing hybrid alkyl Pd(I)-radical species is elucidated by theor. calculation to be a triplet species coordinated by three phosphine atoms with a distorted tetrahedral geometry, and spin prohibition rather than metal-to-ligand charge transfer contributes to the kinetic stability of the hybrid alkyl Pd(I)-radical species to impede alkyl recombination to generate Pd(II) alkyl intermediate. The experimental part of the paper was very detailed, including the reaction process of 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

Xu, Jun; Huang, Lin; He, Lei; Ni, Zhigang; Shen, Jiabin; Li, Xiaoling; Chen, Kaixian; Li, Wanmei; Zhang, Pengfei published their research in Green Chemistry in 2021. The article was titled 《A combination of heterogeneous catalysis and photocatalysis for the olefination of quinoxalin-2(1H)-ones with ketones in water: a green and efficient route to (Z)-enaminones》.Recommanded Product: 88-15-3 The article contains the following contents:

Herein, a novel aqueous reaction for the olefination of quinoxalin-2(1H)-ones I (R1 = H, 5-Me, 6-OMe, 6,7-Cl2, etc.; R2 = H, Me, cyclohexylmethyl, allyl, Ph, 2,6-F2C6H3CH2, etc.) with ketones R3C(O)CH2R4 [R3 = Me, cyclopropyl, Ph, 3-thienyl, etc., R4 = H; R3R4 = (CH2)3, CH(cyclopentyl)CH2CH2] through a combinational strategy is described. This reaction features very mild conditions using a simple and cheap catalyst for the synthesis of (Z)-enaminones II in moderate-to-good yields. Such a methodol. successfully combines the heterogeneous Mannich reaction with photocatalysis, and provides a green and practical approach for the synthesis of potentially bioactive (Z)-enaminones with a 3,4-dihydroquinoxalin-2(1H)-one skeleton. The experimental part of the paper was very detailed, including the reaction process of 1-Thiophen-2-yl-ethanone(cas: 88-15-3Recommanded Product: 88-15-3)

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. Recommanded Product: 88-15-3

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Product Details of 13250-82-3On October 26, 2012 ,《Controlling band gap and hole mobility of photovoltaic donor polymers with terpolymer system》 was published in Polymer. The article was written by Lim, Younhee; Ihn, Soo-Ghang; Bulliard, Xavier; Yun, Sungyoung; Chung, Yeonji; Kim, Yungi; Chang, Hyuk; Choi, Yeong Suk. The article contains the following contents:

Energy level, band gap, and hole mobility of photovoltaic donor polymers are crucial factors in achieving high power conversion efficiency. Controlling these characteristics, however, requires complicated synthesis routes. This work reports an effective way to control these properties simultaneously by introducing a simple terpolymer system. Simulation of energy level (band gap), synthesis of donor polymers, and calculation of solubility were systematically coordinated to explain the advantages of the terpolymer system. Anthradithiophene was introduced to elucidate the effect of the extended conjugation length on band gap and hole mobility of donor polymers. Benzodithiophene and thienothiophene which have shown good properties in bulk heterojunction organic solar cells were used as comonomers. Based on the result of the energy level calculation, terpolymers with various mole ratios of the monomers were synthesized; as the ratio of anthradithiophene to benzodithiophene increased, band gap of the terpolymers decreased while hole mobility increased. In addition, we explained the morphol. of the terpolymer:fullerene bulk heterojunction films using solubility parameters of materials. With this method, we investigated the relationship between the properties of donor polymers and device performances systematically. The terpolymer system can be widely utilized for tuning the material properties in a systematic way which is quite similar to the band gap engineering in the inorganic semiconductors. The results came from multiple reactions, including the reaction of 2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3Product Details 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.Product Details of 13250-82-3

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

In 2019,Synthesis included an article by Dar’in, Dmitry; Kantin, Grigory; Krasavin, Mikhail. COA of Formula: C6H6OS. The article was titled 《Practical Application of the Aqueous ‘Sulfonyl-Azide-Free’ (SAFE) Diazo Transfer Protocol to Less α-C-H Acidic Ketones and Esters》. The information in the text is summarized as follows:

The earlier described ‘sulfonyl-azide-free (SAFE) protocol for diazo transfer to CH-acidic 1,3-dicarbonyl compounds (and their similarly activated congeners) has been extended to the less reactive monocarbonyl substrates, which previously required a sep. activation step. Formylation in situ, followed by the addition of an optimized amount of the ‘SAFE cocktail’ (obtained by mixing sodium azide, potassium carbonate, and m-carboxybenzenesulfonyl chloride in water) led to the formation of the desired diazo compounds, which were isolated by extraction in moderate to excellent yields, and, in most cases, with no need for addnl. purification1-Thiophen-2-yl-ethanone(cas: 88-15-3COA of Formula: C6H6OS) was used in this study.

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

In 2019,Food Chemistry included an article by Zhao, Jian; Wang, Tianze; Xie, Jianchun; Xiao, Qunfei; Cheng, Jie; Chen, Feng; Wang, Shi; Sun, Baoguo. Category: benzothiophene. The article was titled 《Formation mechanism of aroma compounds in a glutathione-glucose reaction with fat or oxidized fat》. The information in the text is summarized as follows:

Glutathione and glucose with or without chicken fat/oxidized chicken fat were thermally reacted for generation of stewed meat-like aroma, where 42 sulfur-containing odorants were identified by gas chromatog.-mass spectrometry (GC-MS) and gas chromatog.-olfactometry (GC-O). The observed effects or interactions on meat flavor formation due to the fats were similar to previous reports of cysteine-reducing sugar reactions. Carbohydrate module labeling approach demonstrated ten alkyl chain compounds were indeed resulted from the lipid degradation-Maillard reaction interactions, whereas the fats had little effect on formation pathways of compounds only derived from the Maillard reaction. Formation pathways of 26 potent aroma compounds were proposed, particularly, involving two benzene derivatives and seven complex thiophenes. Notably, it was found for the first time just 2-ethylthiophene could result from both an intact skeleton of glucose and the lipid degradation product of 2,4-hexadienal, and the carbohydrate modules methylglyoxal and hydroxyacetone could arise from the glutamic acid of GSH. In the experimental materials used by the author, we found 1-Thiophen-2-yl-ethanone(cas: 88-15-3Category: benzothiophene)

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. Category: benzothiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem