Day: November 21, 2022

Wu, Yingtao published the artcileSynthesis of Axially Chiral Aldehydes by N-Heterocyclic-Carbene-Catalyzed Desymmetrization Followed by Kinetic Resolution, Name: Benzo[b]thiophen-7-ylboronic acid, the publication is Angewandte Chemie, International Edition (2022), 61(14), e202117340, database is CAplus and MEDLINE.

Herein an NHC-catalyzed atroposelective esterification of biaryl dialdehydes as a general and practical strategy for the construction of axially chiral aldehydes I [Ar = Ph, 1-naphthyl, 9-phenanthryl, etc.; R¹ = Et, CH₂CF₃, cyclopropyl, etc.] was described. Mechanistic studies indicated that coupling proceeds through a novel combination of NHC-catalyzed desymmetrization of the dialdehydes and kinetic resolution This protocol featured excellent enantioselectivity, mild conditions, good functional-group tolerance and applicability to late-stage functionalization and provided a modular platform for the synthesis of axially chiral aldehydes and their derivatives

Angewandte Chemie, International Edition published new progress about 628692-17-1. 628692-17-1 belongs to benzothiophene, auxiliary class Boronic acid and ester,Benzothiophene,Benzothiophene,Boronic Acids,Boronic Acids,Boronic acid and ester, name is Benzo[b]thiophen-7-ylboronic acid, and the molecular formula is C12H14O2, Name: Benzo[b]thiophen-7-ylboronic acid.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

He, Shasha published the artcileCharge-Reversal Polymer Nano-modulators for Photodynamic Immunotherapy of Cancer, Related Products of benzothiophene, the publication is Angewandte Chemie, International Edition (2021), 60(35), 19355-19363, database is CAplus and MEDLINE.

Nanomedicine can regulate the balance between cytotoxic T lymphocytes (CTLs) and suppressive regulatory T lymphocytes (Tregs), which however has been rarely exploited for cancer immunotherapy. We report a charge-reversal polymer nano-modulator (SPDMCN) activated by tumor microenvironment (TME) for photodynamic immunotherapy of cancer. SPDMCN is constructed by conjugating an immunomodulator (demethylcantharidin, DMC) to the side chains of a photodynamic polymer via an acid-liable linker. The neg. charge of SPDMCN ensures its high stability in blood circulation and ideal tumor accumulation; exposure to acidic TME reverses its surface charge to pos., enhancing tumor penetration and locally releasing DMC. Upon near-IR photoirradiation, SPDMCN generates singlet oxygen to ablate tumors and promote maturation of dendritic cells. Released DMC inhibits protein phosphatase 2 (PP2A) activity and decreases Tregs differentiation. Such combinational action induces a sharp increase in CTL/Treg ratio in TME and effectively inhibits both primary and distant tumors in living mice.

Angewandte Chemie, International Edition published new progress about 1426829-76-6. 1426829-76-6 belongs to benzothiophene, auxiliary class Other Aromatic Heterocyclic,Bromide, name is 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene, and the molecular formula is C21H26Br4S2, Related Products of benzothiophene.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Huber, Johannes published the artcileNanoparticles of Low Optical Band Gap Conjugated Polymers, Computed Properties of 1401018-41-4, the publication is Macromolecules (Washington, DC, United States) (2012), 45(19), 7799-7805, database is CAplus.

Sonogashira coupling of 9,9-bis(2-ethylhexyl)-2,7-diethynyl-9H-fluorene (1) with 2,7-dibromo-9,9-bis(2-ethylhexyl)-9H-fluorene (2) and dibromo-substituted electron accepting arylenes 5,7-bis(5-bromothiophen-2-yl)-2,3-dihexylthieno[3,4-b]pyrazine (3), 4,7-bis(5-bromo-4-(2-ethylhexyl)thiophene-2-yl)bis(benzothiadiazole) (4) or 4,9-bis(5-bromo-4-(2-ethylhexyl)thiophen-2-yl)-6,7-dihexylthiadiazolo[3,4-g]quinoxaline (5), resp., in a miniemulsion polymerization process afforded colloidally stable dispersions of poly(arylene ethynylene) nanoparticles with an average size in the range of 50 to 120 nm. For these poly[1-alt-(2-co-X)] (X = 3, 4, or 5), poly(1-alt-3), poly(1-alt-4), and poly(1-alt-5) aqueous nanoparticle dispersions absorption occurs increasingly in the red and NIR regime with increasing incorporation of acceptor monomer, with a strong absorption up to λ_abs = 1 μm for poly(1-alt-4) dispersions. For poly[1-alt-(2-co-3)] nanoparticles fluorescence is also observed at λ_em = ca. 700 nm, which occurs at this long wavelength exclusively even at an incorporation of only 1 mol % of 3 due to energy transfer to the low-energy chromophores. An alternative postpolymn. approach by change of solvent quality yielded dilute aqueous dispersions of self-stabilized nanoparticles from an amphiphilic block copolymer, poly(ethylene glycol)-block-poly(1-alt-6)-block-poly(ethylene glycol) generated from alkyne-terminated poly(1-alt-6) via azide-alkyne coupling (6 = 4,7-bis(5-bromo-4-(2-ethylhexyl)thiophene-2-yl)benzothiadiazole), which fluoresce at λ_em max = 672 nm.

Macromolecules (Washington, DC, United States) published new progress about 1401018-41-4. 1401018-41-4 belongs to benzothiophene, auxiliary class Organic Photo-Voltaic Materials, OPV,BT Acceptors, name is 4,8-Bis(5-bromo-4-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-c:4,5-c’]bis[1,2,5]thiadiazole, and the molecular formula is C30H36Br2N4S4, Computed Properties of 1401018-41-4.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Huber, Johannes published the artcileNanoparticles of Low Optical Band Gap Conjugated Polymers, Quality Control of 1401018-39-0, the publication is Macromolecules (Washington, DC, United States) (2012), 45(19), 7799-7805, database is CAplus.

Sonogashira coupling of 9,9-bis(2-ethylhexyl)-2,7-diethynyl-9H-fluorene (1) with 2,7-dibromo-9,9-bis(2-ethylhexyl)-9H-fluorene (2) and dibromo-substituted electron accepting arylenes 5,7-bis(5-bromothiophen-2-yl)-2,3-dihexylthieno[3,4-b]pyrazine (3), 4,7-bis(5-bromo-4-(2-ethylhexyl)thiophene-2-yl)bis(benzothiadiazole) (4) or 4,9-bis(5-bromo-4-(2-ethylhexyl)thiophen-2-yl)-6,7-dihexylthiadiazolo[3,4-g]quinoxaline (5), resp., in a miniemulsion polymerization process afforded colloidally stable dispersions of poly(arylene ethynylene) nanoparticles with an average size in the range of 50 to 120 nm. For these poly[1-alt-(2-co-X)] (X = 3, 4, or 5), poly(1-alt-3), poly(1-alt-4), and poly(1-alt-5) aqueous nanoparticle dispersions absorption occurs increasingly in the red and NIR regime with increasing incorporation of acceptor monomer, with a strong absorption up to λ_abs = 1 μm for poly(1-alt-4) dispersions. For poly[1-alt-(2-co-3)] nanoparticles fluorescence is also observed at λ_em = ca. 700 nm, which occurs at this long wavelength exclusively even at an incorporation of only 1 mol % of 3 due to energy transfer to the low-energy chromophores. An alternative postpolymn. approach by change of solvent quality yielded dilute aqueous dispersions of self-stabilized nanoparticles from an amphiphilic block copolymer, poly(ethylene glycol)-block-poly(1-alt-6)-block-poly(ethylene glycol) generated from alkyne-terminated poly(1-alt-6) via azide-alkyne coupling (6 = 4,7-bis(5-bromo-4-(2-ethylhexyl)thiophene-2-yl)benzothiadiazole), which fluoresce at λ_em max = 672 nm.

Macromolecules (Washington, DC, United States) published new progress about 1401018-39-0. 1401018-39-0 belongs to benzothiophene, auxiliary class Organic Photo-Voltaic Materials, OPV,BT Acceptors, name is 2Lambda4delta2-Benzo[1,2-c:4,5-c’]bis[1,2,5]thiadiazole, 4,8-bis[4-(2-ethylhexyl)-2-thienyl]-, and the molecular formula is C30H38N4S4, Quality Control of 1401018-39-0.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Zhang, Zhongqiang published the artcilePhosphate ester side-chain modified conjugated polymer for hybrid solar cells, Application of 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene, the publication is Journal of Applied Polymer Science (2017), 134(26), n/a, database is CAplus.

Although nanocrystals have several advantages of tunable bandgap and high carrier mobility, it is still challenging to achieve high-performance polymer: nanocrystals hybrid solar cells (HSC) due to the complicated surface problem. Many efforts have been devoted to replace the long alkyl chain on the surface of nanocrystals to improve the charge transfer and transport. We modified the alkyl chain in poly[2,6-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b’]-dithiophene)-alt-4,7-(2,1,3-benzothiadiazole)] (PCPDTBT) by phosphate ester. Due to its strong affinity to CdSe nanocrystals, the resulting polymers can spontaneously exchange the long chain ligands in 1-step process. With the improved morphol. of polymer: CdSe blended film, a power conversion efficiency (PCE) of 3.12% was achieved for hybrid solar cells. © 2017 Wiley Periodicals, Inc., J. Appl. Polym. Sci. 2017, 134, 45003.

Journal of Applied Polymer Science published new progress about 1426829-76-6. 1426829-76-6 belongs to benzothiophene, auxiliary class Other Aromatic Heterocyclic,Bromide, name is 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene, and the molecular formula is 0, Application of 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Xu, Cheng published the artcileSecond Near-Infrared Light-Activatable Polymeric Nanoantagonist for Photothermal Immunometabolic Cancer Therapy, HPLC of Formula: 1426829-76-6, the publication is Advanced Materials (Weinheim, Germany) (2021), 33(36), 2101410, database is CAplus and MEDLINE.

Immunometabolic modulation offers new opportunities to treat cancers as it is highly associated with cancer progression and immunosuppressive microenvironment. However, traditional regimens using nonselective small-mol. immunomodulators lead to the off-target adverse effects and insufficient therapeutic outcomes. Herein a second near-IR (NIR-II) photothermally activatable semiconducting polymeric nanoantagonist (ASPA) for synergistic photothermal immunometabolic therapy of cancer is reported. ASPA backbone is obtained by conjugating vipadenant, an antagonist to adenosine A2A receptor, onto NIR-II light-absorbing semiconducting polymer via an azo-based thermolabile linker. Under deep-penetrating NIR-II photoirradiation, ASPA induces tumor thermal ablation and subsequently immunogenic cell death, triggers the cleavage of thermolabile linker, and releases the antagonist to block the immunosuppressive adenosinergic pathway. Such a remotely controlled immunometabolic regulation potentiates cytotoxic T cell functions while suppresses regulatory T cell activities, leading to efficient primary tumor inhibition, pulmonary metastasis prevention, and long-term immunol. memory. Thereby, this work provides a generic polymeric approach for precise spatiotemporal regulation of cancer immunometabolism.

Advanced Materials (Weinheim, Germany) published new progress about 1426829-76-6. 1426829-76-6 belongs to benzothiophene, auxiliary class Other Aromatic Heterocyclic,Bromide, name is 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene, and the molecular formula is C5H10Cl3O3P, HPLC of Formula: 1426829-76-6.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Matsuoka, Wataru published the artcileRapid Access to Nanographenes and Fused Heteroaromatics by Palladium-Catalyzed Annulative π-Extension Reaction of Unfunctionalized Aromatics with Diiodobiaryls, Name: 5-(tert-Butyl)benzo[b]thiophene, the publication is Angewandte Chemie, International Edition (2017), 56(40), 12224-12228, database is CAplus and MEDLINE.

Efficient and rapid access to nanographenes and π-extended fused heteroaromatics is important in materials science. Herein, we report a palladium-catalyzed efficient one-step annulative π-extension (APEX) reaction of polycyclic aromatic hydrocarbons (PAHs) and heteroaromatics, producing various π-extended aromatics In the presence of a cationic Pd complex, triflic acid, silver pivalate, and diiodobiaryls, diverse unfunctionalized PAHs and heteroaromatics were directly transformed into larger PAHs, nanographenes, and π-extended fused heteroaromatics in a single step. In the reactions that afford [5]helicene substructures, simultaneous dehydrogenative ring closures occur at the fjord regions to form unprecedented larger nanographenes. This successive APEX reaction is notable as it stiches five aryl-aryl bonds by C-H functionalization in a single operation. Moreover, the unique mol. structures, crystal-packing structures, photophys. properties, and frontier MOs of the thus-formed nanographenes were elucidated.

Angewandte Chemie, International Edition published new progress about 17515-00-3. 17515-00-3 belongs to benzothiophene, auxiliary class 5.6_Aromatics,Benzothiophens, name is 5-(tert-Butyl)benzo[b]thiophene, and the molecular formula is C12H14S, Name: 5-(tert-Butyl)benzo[b]thiophene.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Li, Jingchao published the artcilePhotoactivatable Organic Semiconducting Pro-nanoenzymes, Safety of 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene, the publication is Journal of the American Chemical Society (2019), 141(9), 4073-4079, database is CAplus and MEDLINE.

Therapeutic enzymes hold great promise for cancer therapy; however, in vivo remote control of enzymic activity to improve their therapeutic specificity remains challenging. This study reports the development of an organic semiconducting pro-nanoenzyme (OSPE) with a photoactivatable feature for metastasis-inhibited cancer therapy. Upon near-IR (NIR) light irradiation, this pro-nanoenzyme not only generates cytotoxic singlet oxygen (¹O₂) for photodynamic therapy (PDT), but also triggers a spontaneous cascade reaction to induce the degradation of RNA specifically in tumor microenvironment. More importantly, OSPE-mediated RNA degradation is found to downregulate the expression of metastasis-related proteins, contributing to the inhibition of metastasis after treatment. Such a photoactivated and cancer-specific synergistic therapeutic action of OSPE enables complete inhibition of tumor growth and lung metastasis in mouse xenograft model, which is not possible for the counterpart PDT nanoagent. Thus, our study proposes a phototherapeutic-proenzyme approach toward complete-remission cancer therapy.

Journal of the American Chemical Society published new progress about 1426829-76-6. 1426829-76-6 belongs to benzothiophene, auxiliary class Other Aromatic Heterocyclic,Bromide, name is 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene, and the molecular formula is C21H26Br4S2, Safety of 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Syeda, Madiha Zahra published the artcileA prodrug nanoplatform via esterification of STING agonist and IDO inhibitor for synergistic cancer immunotherapy, Name: 4-(5,6-Dimethoxybenzo[b]thiophen-2-yl)-4-oxobutanoic acid, the publication is Nano Research, database is CAplus.

Cancer immunotherapy has made significant progress in the last few decades, revolutionizing oncol. However, low patient response rates and potential immune-related adverse events continue to be major clin. challenges. Cancer nanomedicine, by virtue of its regulated delivery and modular flexibility, has shown the potential to strengthen antitumor immune responses and sensitize tumors to immunotherapy. In this study, we developed tumor microenvironment (TME) responsive nanomedicine to achieve specific and localized amplification of the immune response in tumor tissue in a safe and effective manner, while simultaneously reducing immune-related side effects. We synthesized the TME responsive prodrug by coupling MSA-2, a stimulator of interferon genes (STING) agonist, and NLG-919, an indoleamine 2,3 dioxygenase (IDO) inhibitor. The prodrug was assembled into nanoparticles to enhance the solubility and bioavailability. By synthesizing a TME responsive prodrug, we aim to explore the therapeutic efficacy of combined regimen (STING agonist and IDO inhibitor) for cancer, and reduce the unwanted side effects of STING agonism on normal tissues. Free prodrug and nanoparticles were characterized by mass spectrometry, dynamic light scattering (DLS), and transmission electron microscopy (TEM). Following that, we investigated the tumor accumulation, anti-tumor activity, and toxicity in vitro and in vivo. Prodrug nanoparticles demonstrated the ability to inhibit the tumor growth and activate antitumor immune response by modulating immune cells populations in tumor microenvironment. The TME responsive nanomedicine provided an effective tool for precise targeting, promoting antitumor immunity, and efficient tumor growth inhibition with safety. Outcomes of this study may have implications for future clin. trials.

Nano Research published new progress about 129425-81-6. 129425-81-6 belongs to benzothiophene, auxiliary class Inhibitor, name is 4-(5,6-Dimethoxybenzo[b]thiophen-2-yl)-4-oxobutanoic acid, and the molecular formula is C5H7NO, Name: 4-(5,6-Dimethoxybenzo[b]thiophen-2-yl)-4-oxobutanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Zhang, Yan published the artcileActivatable Polymeric Nanoprobe for Near-Infrared Fluorescence and Photoacoustic Imaging of T Lymphocytes, Synthetic Route of 1426829-76-6, the publication is Angewandte Chemie, International Edition (2021), 60(11), 5921-5927, database is CAplus and MEDLINE.

Development of real-time non-invasive imaging probes to assess infiltration and activation of cytotoxic T cells (CTLs) is critical to predict the efficacy of cancer immunotherapy, which however remains challenging. Reported here is an activatable semiconducting polymer nanoprobe (SPNP) for near-IR fluorescence (NIRF) and photoacoustic (PA) imaging of a biomarker (granzyme B) associated with activation of CTLs. SPNP comprises a semiconducting polymer (SP) conjugated with a granzyme B cleavable and dye-labeled peptide as the side chain, both of which emit NIRF and PA signals. After systemic administration, SPNP passively targets the tumor and in situ reacts with granzyme B to release the dye-labeled peptide, leading to decreased NIRF and PA signals from the dye but unchanged signals from the polymer. Such ratiometric NIRF and PA signals of SPNP correlate well with the expression level of granzyme B and intratumoral population of CTLs. Thus, this study not only presents the first PA probes for in vivo imaging of immune activation but also provides a mol. design strategy that can be generalized for mol. imaging of other immune-related biomarkers.

Angewandte Chemie, International Edition published new progress about 1426829-76-6. 1426829-76-6 belongs to benzothiophene, auxiliary class Other Aromatic Heterocyclic,Bromide, name is 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene, and the molecular formula is C7H11N, Synthetic Route of 1426829-76-6.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem