Category: 7312-11-0

Benzo[b]thiophene-2-carboxamide derivatives as potent urotensin-II receptor antagonists was written by Lim, Chae Jo;Woo, Seong Eun;Ko, Su Ik;Lee, Byung Ho;Oh, Kwang-Seok;Yi, Kyu Yang. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2016.Application of 7312-11-0 This article mentions the following:

Members of a series of benzo[b]thiophene-2-carboxamide derivatives, possessing an N-(1-(3-bromo-4-(piperidin-4-yloxy)benzyl)piperidin-4-yl) group, were synthesized and evaluated as urotensin-II receptor antagonists. The results show that these substances have potent UT binding affinities. Observations made in a systematic SAR investigation of the effects of a variety of substituents at the 5- and 6-positions in the benzo[b]thiophene-2-carboxamide moiety on UT binding affinities led to identification of the 5-cyano analog I as a highly potent UT antagonist with an IC₅₀ value of 25 nM. Despite having a good metabolic stability, compound I is a potent inhibitor of CYP isoenzyme and displays an unsuitable PK profile. In the experiment, the researchers used many compounds, for example, Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0Application of 7312-11-0).

Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0) 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.Application of 7312-11-0

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Design, synthesis, and biological activity evaluation of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives as broad-spectrum antifungal agents was written by Zhao, Liyu;Sun, Yin;Yin, Wenbo;Tian, Linfeng;Sun, Nannan;Zheng, Yang;Zhang, Chu;Zhao, Shizhen;Su, Xin;Zhao, Dongmei;Cheng, Maosheng. And the article was included in European Journal of Medicinal Chemistry in 2022.Application of 7312-11-0 This article mentions the following:

To discover antifungal compounds with broad-spectrum and stable metabolism, a series of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives were designed and synthesized. Compounds I [R¹ = 6-F, 6-Cl, 6-Br; R² = 4-F] and [R¹ = 6-Cl, 6-Br; R² = 4-Cl] exhibited excellent broad-spectrum antifungal activity against Candida albicans with MIC values in the range of 0.03-0.5μg/mL, and against Cryptococcus neoformans and Aspergillus fumigatus with MIC values in the range of 0.25-2μg/mL. In addition, compounds I [R¹ = 6-Cl; R² = 4-F] and [R¹ = 6-Cl; R² = 4-Cl] showed high metabolic stability in human liver microsomes in vitro, with the half-life of 80.5 min and 69.4 min, resp. Moreover, compounds I [R¹ = 6-Cl; R² = 4-F] and [R¹ = 6-Cl; R² = 4-Cl] showed weak or almost no inhibitory effect on the CYP3A4 and CYP2D6. The pharmacokinetic evaluation in SD rats showed that compoundI [R¹ = 6-Cl; R² = 4-F] had suitable pharmacokinetic properties and was worthy of further study. In the experiment, the researchers used many compounds, for example, Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0Application of 7312-11-0).

Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0) belongs to benzothiophene derivatives. Functionalized benzothiophenes are important constructs found in molecules with wide ranging biological activity and in organic materials. It is found within the chemical structures of pharmaceutical drugs such as zileuton, raloxifene, and sertaconazole, and also BTCP.Application of 7312-11-0

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Discovery of fluorescent coumarin-benzo[b]thiophene 1, 1-dioxide conjugates as mitochondria-targeting antitumor STAT3 inhibitors was written by Cai, Guiping;Yu, Wenying;Song, Dongmei;Zhang, Wenda;Guo, Jianpeng;Zhu, Jiawen;Ren, Yuhao;Kong, Lingyi. And the article was included in European Journal of Medicinal Chemistry in 2019.Computed Properties of C10H7BrO2S This article mentions the following:

STAT3 has been extensively studied as a potential antitumor target. Though studies on regulating STAT3 mainly focus on the inhibition of STAT3 phosphorylation at Tyr705 residue, the phosphorylation at Ser727 residue of STAT3 protein is also closely associated with the mitochondrial import of STAT3 protein. N, N-diethyl-7-aminocoumarin is a fluorescent mitochondria-targeting probe. In this study, a series of STAT3 inhibitors were developed by connecting N, N-diethyl-7-aminocoumarin fluorophore with benzo [b]thiophene 1, 1-dioxide moiety. All designed compounds displayed potent anti-proliferative activity against cancer cells. The representative compound 7a(I) was mainly accumulated in mitochondria visualized by its fluorescence. STAT3 phosphorylation was inhibited by I at both Tyr705 and Ser727 residues. I inhibited STAT3 phosphorylation whereas had no influence on the phosphorylation levels of STAT1, JAK2, Src and Erk1/2, indicating good selectivity of I. Moreover, I down-regulated the expression of STAT3 target genes Bcl-2 and Cyclin D1, increased ROS production and remarkably reduced the mitochondrial membrane potential to induce mitochondrial apoptotic pathway. Furthermore, I in vivo suppressed breast cancer 4T1 implanted tumor growth. Taken together, these results highlighted that I might be a promising mitochondria-targeting STAT3 inhibitor for cancer therapy. In the experiment, the researchers used many compounds, for example, Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0Computed Properties of C10H7BrO2S).

Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The core structure is a part of various pharmaceutical substances and natural products. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP.Computed Properties of C10H7BrO2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Design, synthesis, and biological evaluation of benzo[b]thiophene 1,1-dioxide derivatives as potent STAT3 inhibitors was written by Li, Wen-Zhen;Xi, Hui-Zhi;Wang, Yi-Jie;Ma, Hong-Bo;Cheng, Zhi-Qiang;Yang, Yu;Wu, Meng-Ling;Liu, Ting-Mei;Yang, Wen;Wang, Qin;Liao, Meng-Ya;Xia, Yong;Zhang, Yi-Wen. And the article was included in Chemical Biology & Drug Design in 2021.Formula: C10H7BrO2S This article mentions the following:

As a member of the signal transducer and activator of transcription (STAT) family, STAT3 plays a critical role in several biol. pathways such as cell proliferation, migration, survival, and differentiation. Due to abnormal continuous activation in tumors, inhibition of STAT3 has emerged as an attractive approach for the treatment of various cancer cells. Herein, we report a series of novel STAT3 inhibitors based on benzo[b]thiophene 1,1-dioxide scaffold and evaluated their anticancer potency. Among them, compound I exhibited the best activity against cancer cells. Compound I induced apoptosis and blocked the cell cycle. Meanwhile, I reduced intracellular ROS content and caused the loss of mitochondrial membrane potential. Further research revealed that I significantly blocked STAT3 phosphorylation and STAT3-dependent dual-luciferase reporter gene experiments showed that compound I has a marked inhibition of STAT3-mediated Firefly luciferase activity. Mol. modeling studies revealed compound I occupied the pocket well with the SH2 domain in a favorable conformation. In the experiment, the researchers used many compounds, for example, Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0Formula: C10H7BrO2S).

Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The core structure is a part of various pharmaceutical substances and natural products. The different substitution patterns in these heterocycles offer new opportunities for drug discovery and other applications in materials science.Formula: C10H7BrO2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

CYP17 inhibitors. Annulations of additional rings in methylene imidazole substituted biphenyls: synthesis, biological evaluation and molecular modeling was written by Pinto-Bazurco Mendieta, Mariano A. E.;Negri, Matthias;Hu, Qingzhong;Hille, Ulrike E.;Jagusch, Carsten;Jahn-Hoffmann, Kerstin;Mueller-Vieira, Ursula;Schmidt, Dirk;Lauterbach, Thomas;Hartmann, Rolf W.. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2008.Quality Control of Methyl 5-bromobenzo[b]thiophene-2-carboxylate This article mentions the following:

Twenty-one novel compounds originating from two classes of annulated biphenyls were synthesized as mimetics of the steroidal A- and C-rings and examined for their potency as inhibitors of human CYP17. Selected compounds were tested for inhibition of the hepatic CYP enzyme 3A4. Potent CYP17 inhibitors were found for each class, compound I (17 and 71% at 0.2 and 2 μM, resp.) and II (591 nM). Compound II showed only weak inhibition of CYP3A4 (32 and 64% at 2 and 10 μM, resp.). Both compounds, however, exhibited moderate to strong inhibition of the glucocorticoid-forming enzyme CYP11B1. The most interesting compounds were docked into our protein model. They bound into one of the modes which we have previously published. New interaction regions were identified. 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 relatively a stable molecule. The electrophilic substitution of benzothiophene systems is much less regioselective than that of indoles. It is found within the chemical structures of pharmaceutical drugs such as zileuton, raloxifene, and sertaconazole, and also BTCP.Quality Control of Methyl 5-bromobenzo[b]thiophene-2-carboxylate

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem