Month: November 2022

Wu, Chunying published the artcileLipophilic analogs of thioflavin S as novel amyloid-imaging agents, Synthetic Route of 92-36-4, the publication is Current Alzheimer Research (2006), 3(3), 259-266, database is CAplus and MEDLINE.

Lipophilic analogs of thioflavin S were synthesized and radiolabeled with positron or single photon emitting radionuclides. The binding affinity for Aβ was evaluated using isolated amyloid fibrils from human brain tissue. Binding specificity was assessed using fluorescent tissue staining. In vivo brain uptake was evaluated in mice. Following synthesis, neutral analogs of thioflavin S capable of radiolabeling with ¹¹C or ¹²⁵I, were found to bind isolated human Aβ with affinities in the nanomolar range. Fluorescent tissue staining showed selective binding to Aβ deposits in vitro. Biodistribution of selected compounds displayed high brain permeability at early time points. At later points, the compounds were cleared from the normal brain, indicating low non-specific binding in vivo. These studies indicated that novel amyloid imaging probes can be developed based on thioflavin S that readily entered the brain and selectively bound to Aβ deposits and neurofibrilary tangles. Potential applications of these amyloid binding agents include facilitating drug screening in animal models and use as in vivo markers of early and definitive diagnosis of AD.

Current Alzheimer Research published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C8H5F3N4, Synthetic Route of 92-36-4.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Mugherli, Laurent published the artcileIn Situ Assembly and Screening of Enzyme Inhibitors with Surface-Tension Microarrays, Recommanded Product: Methyl 2-(2-aminothiazol-4-yl)acetate, the publication is Angewandte Chemie, International Edition (2009), 48(41), 7639-7644, database is CAplus and MEDLINE.

Hundreds of reactions were conducted in parallel in droplets maintained on a glass slide through differential surface tension in a new approach to submicroliter-scale synthesis. This surface-tension microarray was applied to the in situ assembly of thousands of derivatives of phenylboronic acid and their profiling against the NS3/4A protease of the hepatitis C virus. Several potent inhibitors of the enzyme were identified.

Angewandte Chemie, International Edition published new progress about 64987-16-2. 64987-16-2 belongs to thiazole, auxiliary class Thiazole,Amine,Ester, name is Methyl 2-(2-aminothiazol-4-yl)acetate, and the molecular formula is C6H8N2O2S, Recommanded Product: Methyl 2-(2-aminothiazol-4-yl)acetate.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Toshniwal, Madhu published the artcileAntibacterial activity and greener method of synthesis of heterocyclic compounds incorporating benzothiazole moiety using ionic liquid as solvent, Safety of 6-Chlorobenzothiazol-2-ylamine, the publication is Rasayan Journal of Chemistry (2019), 12(3), 1294-1297, database is CAplus.

A novel series of substituted dimethylimidazo{2,1-b}[1,3]benzothiazoles have been synthesized by reaction of 2-amino-6-substituted benzothiazoles with halo ketone by conventional method as well as microwave conditions using ionic liquids The yield of products obtained by microwave synthesis with ionic liquids is much better than the conventional method. The reported compounds were further screened for their antibacterial activity using ampicillin as standard drug. The compounds showed excellent activity against Pseudomonas Aeruginosa, Klebsiella pneumonia and Staphylococcus aureus.

Rasayan Journal of Chemistry published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C7H9BO3, Safety of 6-Chlorobenzothiazol-2-ylamine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Trofymchuk, Serhii published the artcileScalable Approach to Fluorinated Heterocycles with Sulfur Tetrafluoride (SF₄), Recommanded Product: 1-(2-Chlorothiazol-5-yl)ethanone, the publication is Journal of Organic Chemistry (2021), 86(17), 12181-12198, database is CAplus and MEDLINE.

A general approach to fluorinated (hetero)aromatic derivatives was elaborated. The key reaction was a deoxofluorination of substituted acetophenones with sulfur tetrafluoride (SF₄). In contrast to previous deoxofluorination methods, this transformation was fast, scalable (up to 70 g), and high-yielding. More than 100 novel or previously hardly accessible fluorinated heterocycles, interesting for medicinal chem. and agrochem., were synthesized.

Journal of Organic Chemistry published new progress about 885229-41-4. 885229-41-4 belongs to thiazole, auxiliary class Thiazole,Chloride,Ketone, name is 1-(2-Chlorothiazol-5-yl)ethanone, and the molecular formula is C17H26BNO3, Recommanded Product: 1-(2-Chlorothiazol-5-yl)ethanone.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Kucukbay, F. Zehra published the artcileSynthesis, characterization and carbonic anhydrase inhibitory activity of novel benzothiazole derivatives, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Journal of Enzyme Inhibition and Medicinal Chemistry (2016), 31(6), 1221-1225, database is CAplus and MEDLINE.

N-protected amino acids I [Pg = Cbz, Boc, R = H, Me; Pg =Boc, R = CH₂Ph] were reacted with substituted benzothiazoles to give the corresponding N-protected amino acid-benzothiazole conjugates II [Pg = Cbz, R = H; Pg = Boc, R = H, CH₂Ph], III [Pg = Cbz, R = H, Me; Pg = Boc, R = H, CH₂Ph] and IV [Pg = CBz, R = H, Me; Pg = Boc, R = H, Me, CH₂Ph] (60-89%). Their structures were confirmed by proton NMR (¹H NMR), carbon-13 NMR (¹³C NMR), IR and elemental anal. Their carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activities were determined against two cytosolic human isoforms (hCA I and hCA II), one membrane-associated (hCA IV) and one transmembrane (hCA XII) enzyme by a stopped-flow CO₂ hydrase assay method. The new compounds showed rather weak, micromolar inhibitory activity against most of these enzymes.

Journal of Enzyme Inhibition and Medicinal Chemistry published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Leng, Yan published the artcileA colorimetric immunosensor based on Hemin@MI nanozyme composites, with peroxidase-like activity for point-of-care testing of pathogenic E. coli O157:H7, Name: Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate), the publication is Analytical Sciences (2021), 37(7), 941-947, database is CAplus and MEDLINE.

Recently, nanozymes have become a topic of particular interest due to their high activity level, stability and biocompatibility. In this study, a visual, sensitive and selective point-of-care immunosensor was established to test the pathogen Escherichia coli O157:H7 (E. coli O157:H7). Hemin and magainin I (MI) hybrid nanocomposites (Hemin@MI) with peroxidase-mimicking activities were synthesized via a “one-pot” method, involving the simple mixing of an antimicrobial peptide (MI) against E. coli O157:H7 and hemin in a copper sulfate sodium phosphate saline buffer. Hemin@MI nanocomposites integrating target recognition and signal amplification were developed as signal probes for the point-ofcare colorimetric detection of pathogenic E. coli O157:H7. Hemin@MI nanocomposites exhibit excellent peroxidase activity for the chromogenic reaction of ABTS, which allows for the visual point-of-care testing of E. coli O157:H7 in the range of 102 to 108 CFU/mL, with a limit of detection of 85 CFU/mL. These data suggest this immunosensor provides accessible and portable assessments of pathogenic E. coli O157:H7 in real samples.

Analytical Sciences published new progress about 30931-67-0. 30931-67-0 belongs to thiazole, auxiliary class Salt,Hydrazine,Amine,Benzothiazole, name is Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate), and the molecular formula is C18H24N6O6S4, Name: Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate).

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Capule, Christina C. published the artcileOligovalent Amyloid-Binding Agents Reduce SEVI-Mediated Enhancement of HIV-1 Infection, Related Products of thiazole, the publication is Journal of the American Chemical Society (2012), 134(2), 905-908, database is CAplus and MEDLINE.

This paper evaluates the use of oligovalent amyloid-binding mols. as potential agents that can reduce the enhancement of human immunodeficiency virus-1 (HIV-1) infection in cells by semen-derived enhancer of virus infection (SEVI) fibrils. These naturally occurring amyloid fibrils found in semen have been implicated as mediators that can facilitate the attachment and internalization of HIV-1 virions to immune cells. Mols. that are capable of reducing the role of SEVI in HIV-1 infection may, therefore, represent a novel strategy to reduce the rate of sexual transmission of HIV-1 in humans. Here, we evaluated a set of synthetic, oligovalent derivatives of benzothiazole aniline (BTA, a known amyloid-binding mol.) for their capability to bind cooperatively to aggregated amyloid peptides and to neutralize the effects of SEVI in HIV-1 infection. We demonstrate that these BTA derivatives exhibit a general trend of increased binding to aggregated amyloids as a function of increasing valence number of the oligomer. Importantly, we find that oligomers of BTA show improved capability to reduce SEVI-mediated infection of HIV-1 in cells compared to a BTA monomer, with the pentamer exhibiting a 65-fold improvement in efficacy compared to a previously reported monomeric BTA derivative These results, thus, support the use of amyloid-targeting mols. as potential supplements for microbicides to curb the spread of HIV-1 through sexual contact.

Journal of the American Chemical Society published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, Related Products of thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Sheik, Daniel A. published the artcileInhibition of the Enhancement of Infection of Human Immunodeficiency Virus by Semen-Derived Enhancer of Virus Infection Using Amyloid-Targeting Polymeric Nanoparticles, Application of 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is ACS Nano (2015), 9(2), 1829-1836, database is CAplus and MEDLINE.

The semen-derived enhancer of virus infection (SEVI) is a natural amyloid material that has been shown to substantially increase viral attachment and infectivity of HIV in cells. The authors previously reported that synthetic monomeric and oligomeric amyloid-targeting mols. could form protein-resistive coatings on SEVI and inhibit SEVI- and semen-mediated enhancement of HIV infectivity. While oligomeric amyloid-binding compounds showed substantial improvement in apparent binding to SEVI compared to monomeric compounds, the authors observed only a modest correlation between apparent binding to SEVI and activity for reducing SEVI-mediated HIV infection. Here, the authors synthesized amyloid-binding polyacrylate-based polymers and polymeric nanoparticles of comparable size to HIV virus particles (∼150 nm) to assess the effect of sterics on the inhibition of SEVI-mediated enhancement of HIV infectivity. The authors show that these polymeric materials exhibit excellent capability to reduce SEVI-mediated enhancement of HIV infection, with the nanoparticles exhibiting the greatest activity (IC₅₀ value of ∼4 μg/mL, or 59 nM based on polymer) of any SEVI-neutralizing agent reported to date. The results support that the improved activity of these nanomaterials is likely due to their increased size (diameters = 80-200 nm) compared to amyloid-targeting small mols. and that steric interactions may play as important a role as binding affinity in inhibiting viral infection mediated by SEVI amyloids. In contrast to the previously reported SEVI-neutralizing, amyloid-targeting mols. (which required concentrations at least 100-fold above the K_d to observe activity), the approx. 1:1 ratio of apparent K_d to IC₅₀ for activity of these polymeric materials suggests the majority of polymer mols. that are bound to SEVI contribute to the inhibition of HIV infectivity enhanced by SEVI. Such size-related effects on phys. inhibition of protein-protein interactions may open further opportunities for the use of targeted nanomaterials in disease intervention.

ACS Nano published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C5H6N2O2, Application of 2-(4-Aminophenyl)-6-methylbenzothiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Crawley, Graham C. published the artcileChiral Dioxolane Inhibitors of Leukotriene Biosynthesis: Structure-Activity Relationships and Syntheses Using Asymmetric Dihydroxylation, Recommanded Product: 2-(Methylthio)thiazole, the publication is Journal of Medicinal Chemistry (1995), 38(20), 3951-6, database is CAplus and MEDLINE.

1,3-Dioxolanes have been described as chiral inhibitors of 5-lipoxygenase (5LO). In the present work, this series has been developed further to provide agents which showed comparable or superior potency in vivo to ZD2138, a methoxytetrahydropyran inhibitor of 5LO, which is currently undergoing clin. evaluation. An asym. synthesis was developed of these dioxolanes based on asym. dihydroxylation. (S)-N-Methyl-4′-[[4-(2,2,4-trimethyl-1,3-dioxolan-4-yl)thien-2-yl]thio]acetanilide [(S)-I] inhibited leukotriene B₄ (LTB₄) synthesis in A23187-stimulated human whole blood in vitro with IC₅₀ 0.039 μM, 25-fold more potent than (R)-I. In vivo, (S)-I inhibited LTB₄ synthesis by 70% in zymosan-inflamed air pouch exudate in rat 10 h after an oral dose of 1.5 mg/kg. Structure-activity relationship considerations suggested that the dioxolane and methoxytetrahydropyran series are related, a conclusion which can be supported by mol. modeling.

Journal of Medicinal Chemistry published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, Recommanded Product: 2-(Methylthio)thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Kumar, Nag S. published the artcileSynthesis of a tritium-labeled photo-affinity probe based on an atypical leukotriene biosynthesis inhibitor, Synthetic Route of 5053-24-7, the publication is Journal of Labelled Compounds and Radiopharmaceuticals (2011), 54(1), 43-50, database is CAplus.

A radiolabeled photo-affinity probe containing a diazirine group was designed and synthesized based on an atypical leukotriene (LT) biosynthesis inhibitor to determine whether this type of inhibitor (such as 5) interacts with a novel protein, critical for LT biosynthesis. One of the key transformations was to introduce a tritium label in the thiazole ring. This was eventually achieved by treating the iodinated compound with tritium, Pt/C (sulfided) and triethylamine in anhydrous aprotic solvent, to give the tritiated compound I with a specific activity of 303 GBq/mmol. The affinity probe will be used to identify the proteins and protein complexes with which this type of mols. interacts with in inflammatory cells. Copyright © 2010 John Wiley & Sons, Ltd.

Journal of Labelled Compounds and Radiopharmaceuticals published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, Synthetic Route of 5053-24-7.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica