Tag: M.W=150-200

Sun, Qing published the artcileFacile preparation of dihydro-1,4-benzothiazine derivatives via oxidative ring-expansion of 2-aminobenzothiazoles with olefins, COA of Formula: C7H5ClN2S, the publication is Chemical Communications (Cambridge, United Kingdom) (2022), 58(13), 2216-2219, database is CAplus and MEDLINE.

A concise and efficient approach to prepare dihydro-1,4-benzothiazine derivatives I (R¹ = H, 7-Br, 5,7-difluoro, 5-OMe, etc.; R² = Ph, naphthalen-2-yl, ethyloxidanyl, etc.; R³ = H, Me, Ph), Et 9-cyano-3,3a,9,9a-tetrahydro-2H-benzo[b]furo[2,3-e][1,4]thiazine-6-carboxylate and Et 10-cyano-4b,10,10a,11-tetrahydrobenzo[b]indeno[2,1-e][1,4]thiazine-7-carboxylate is described via oxidative ring-expansion of 2-aminobenzothiazoles II with olefins R²CH=CHR³ under metal-free conditions. This protocol is applicable for a wide range of readily accessible 2-aminobenzothiazoles II and olefins with moderate-to-good yields. The [4+2] heteroannulation between the intermediacy of oxidative ring-opening of 2-aminobenzothiazoles II and olefins is suggested to rationalize the formation of the product.

Chemical Communications (Cambridge, United Kingdom) 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 C8H7ClO3, COA of Formula: C7H5ClN2S.

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

McCarren, Patrick published the artcileAvoidance of the Ames test liability for aryl-amines via computation, Quality Control of 31784-71-1, the publication is Bioorganic & Medicinal Chemistry (2011), 19(10), 3173-3182, database is CAplus and MEDLINE.

Aryl-amines are commonly used synthons in modern drug discovery, however a minority of these chem. templates have the potential to cause toxicity through mutagenicity. The toxicity mostly arises through a series of metabolic steps leading to a reactive electrophilic nitrenium cation intermediate that reacts with DNA nucleotides causing mutation. Highly detailed in silico calculations of the energetics of chem. reactions involved in the metabolic formation of nitrenium cations have been performed. This allowed a critical assessment of the accuracy and reliability of using a theor. formation energy of the DNA-reactive nitrenium intermediate to correlate with the Ames test response. This study contains the largest data set reported to date, and presents the in silico calculations vs. the in vitro Ames response data in the form of beanplots commonly used in statistical anal. A comparison of this quantum mech. approach to QSAR and knowledge-based methods is also reported, as well as the calculated formation energies of nitrenium ions for thousands of com. available aryl-amines generated as a watch-list for medicinal chemists in their synthetic optimization strategies.

Bioorganic & Medicinal Chemistry published new progress about 31784-71-1. 31784-71-1 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorothiazolo[5,4-b]pyridin-2-amine, and the molecular formula is C6H4ClN3S, Quality Control of 31784-71-1.

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

Schmidt, Monika published the artcileBenzothiazolyl ureas are low micromolar and uncompetitive inhibitors of 17β-HSD10 with implications to Alzheimer’s disease treatment, Quality Control of 95-24-9, the publication is International Journal of Molecular Sciences (2020), 21(6), 2059, database is CAplus and MEDLINE.

Human 17β-hydroxysteroid dehydrogenase type 10 is a multifunctional protein involved in many enzymic and structural processes within mitochondria. This enzyme was suggested to be involved in several neurol. diseases, e.g., mental retardation, Parkinson’s disease, or Alzheimer’s disease, in which it was shown to interact with the amyloid-beta peptide. We prepared approx. 60 new compounds based on a benzothiazolyl scaffold and evaluated their inhibitory ability and mechanism of action. The most potent inhibitors contained 3-chloro and 4-hydroxy substitution on the Ph ring moiety, a small substituent at position 6 on the benzothiazole moiety, and the two moieties were connected via a urea linker (4at, 4bb, and 4bg). These compounds exhibited IC₅₀ values of 1-2μ and showed an uncompetitive mechanism of action with respect to the substrate, acetoacetyl-CoA. These uncompetitive benzothiazolyl inhibitors of 17β-hydroxysteroid dehydrogenase type 10 are promising compounds for potential drugs for neurodegenerative diseases that warrant further research and development.

International Journal of Molecular Sciences 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 C7H5ClN2S, Quality Control of 95-24-9.

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

Sharma, Neetesh Kumar published the artcileSynthesis and biological evaluation of 1-(6-chlorobenzo[d]thiazol-2-yl)-2-(disubstituted methylene)hydrazine derivatives, Name: 6-Chlorobenzothiazol-2-ylamine, the publication is Journal of Drug Delivery and Therapeutics (2019), 9(4-ASuppl.2), 561-572, database is CAplus.

Synthesis of a series of various 1-(6-chlorobenzo[d]thiazol-2-yl)-2-(disubstituted methylene)hydrazine derivatives (E/Z)-I [R¹ = Ph, Me; R² = Ph, Me, Et; R¹R² = -(CH₂)₅-], (E)-2-(6-chlorobenzo[d]thiazol-2-yl)-1-(7,7-dimethylbicyclo [2.2.1] heptan-2-ylidene) hydrazine and intermediates 6-chloro-2-amine-1,3-benzothiazole and 2-hydrazino-6-chloro-1,3-benzothiazole have been done. After spectral anal., antibacterial activity has been screened against S. aureus and E. coli.

Journal of Drug Delivery and Therapeutics 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 C8H10S, Name: 6-Chlorobenzothiazol-2-ylamine.

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

Jana, Asim published the artcileI₂/DMSO mediated multicomponent reaction for the synthesis of 2-arylbenzo[d]imidazo[2,1-b]thiazole derivatives, HPLC of Formula: 95-24-9, the publication is Organic & Biomolecular Chemistry (2019), 17(21), 5316-5330, database is CAplus and MEDLINE.

Synthesis of a series of 2-arylbenzo[d]imidazo[2,1-b]thiazoles tethered with barbituric acid moiety was reported from the three component reaction of 2-aminobenzothiazoles, barbituric acids and terminal aryl acetylenes or aryl Me ketones in the presence of I₂ in DMSO medium. Both conventional and microwave heating conditions was used for this multicomponent reaction. The salient features of this methodol. are: (i) formation of one C-C and two C-N bonds in one-pot under metal-free oxidation followed by cyclization (ii) selective formation of the fused imidazole ring, (iii) wide substrate scope (iv) easy purification of the products (v) products having more than one pharmaceutically important motifs and (vi) gram scale synthesis possible.

Organic & Biomolecular 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 C7H5ClN2S, HPLC of Formula: 95-24-9.

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

P, Keerthana published the artcileAn Efficient Inclusion Complex Based Fluorescent Sensor for Mercury (II) and its Application in Live-Cell Imaging, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is Journal of Fluorescence (2022), 32(3), 1109-1124, database is CAplus and MEDLINE.

The formation of an inclusion complex between hydroxypropyl-β-cyclodextrin (H-CD) and 4-acetylphenyl-4-(((6-chlorobenzo[d]thiazol-2-yl)-imino)-methyl)-benzoate (L) was investigated by FT-IR, 1H-NMR, X-ray diffraction (XRD), FT-Raman, scanning electron microscope (SEM) techniques in the solid-state, absorption and emission spectroscopy in the liquid state and the virtual state as mol. docking technique. The binding properties of the inclusion complex (H-CD: L) with cations in deionized water was observed via absorbance and photoluminescence (PL) emission spectroscopy. The fluorescence probe (H-CD: L) inclusion complex (IC) was examined for several heavy metal cations, and identified that the PL emission wavelength of the complex displayed a continuous rise in the fluorescence intensity for Hg2+. A linearity range of 1 x 10-8 – 11 x 10-8 M and limit of detection value of 2.71 x 10-10 M was found to be achieved for the detection of Hg2+. This outcome proves that the inclusion complex H-CD: L would be a promising material for the development a solid-state fluorescence probe for detecting Hg2+. It also shows application in real sample anal. and cell imaging.

Journal of Fluorescence 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 C7H5ClN2S, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine.

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

Al-Hamdani, Uhood J. published the artcileChloro-benzothiazole Schiff base ester liquid crystals: synthesis and mesomorphic investigation, Safety of 6-Chlorobenzothiazol-2-ylamine, the publication is Liquid Crystals, database is CAplus.

Nine new rod-like chlorobenzothiazole based liquid crystals – containing Schiff base and ester linking groups bearing different terminal substituents I [R = H, Cl; R¹ = (4-methoxyphenyl), nonyl, (4-octylsulfanylphenyl), etc.] and II [R² = acetyl, ethoxycarbonyl, [(3,4,5-trimethoxyphenyl)methyleneamino], etc.] were described. Although a few similar chloro substituted benzothiazole compounds were known, none was studied for their liquid crystal properties. All these compounds I and II possess liquid crystal behavior except compds I [R = Cl; R¹ = (3,4,5-trimethoxyphenyl)] and II [R² = [(3,4,5-trimethoxyphenyl)methyleneamino]]. The effect of the nature of the terminal groups on thermal stability and optical properties of the mesomorphic compounds I and II was evaluated. With the exception of compound I [R = H; R¹ = (4-octylsulfanylphenyl)] , all the other compounds possess polarity resulting from the polar chloride atom substituted at position-6 of the benzene ring of the benzothiazole moiety which provides a polar group at the one terminal end of the mols. The presence of the fused-ring system (benzothiazole) adds a mol. width that contributes to increase the mol. breadth, causing a thickening effect which disrupts the liquid crystalline packing. New compounds I and II were prepared via reaction of phenolic Schiff bases with the corresponding carboxylic acids or the carboxyl Schiff bases with the corresponding phenols. The synthesized compounds I and II were characterized using ¹H- and ¹³C-NMR and FT-IR spectroscopy, mass spectrometry and elemental anal. Polarised optical microscope and thermal properties were measured to study the thermal and mesophase behaviors.

Liquid Crystals 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 C7H5ClN2S, Safety of 6-Chlorobenzothiazol-2-ylamine.

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

Jethava, Divya J. published the artcileDesign, synthesis, biological evaluation and computational study of novel triazolo[4,3-a]pyrazine analogues, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is Journal of Molecular Structure (2019), 168-192, database is CAplus.

In search of suitable potent drug candidate, the design, synthesis, characterization, biol. activities and computation study of novel triazolo[4,3-a]pyrazine analogs was reported. The newly synthesized compounds were evaluated for their in vitro biol. activities such as anti-malarial, anti-tuberculosis, anti-bacterial and anti-fungal activities against plasmodium falciparum, H₃₇Rv, various bacterial and fungal strains, resp. The mol. docking study was carried out with enzyme aspartic proteinase zymogen proplasmepsin II from plasmodium falciparum to analyze their binding orientation in the active site of the aspartic proteinase enzyme. The best docking complex was subjected to mol. dynamics simulation to illustrate the stability of these complexes and the most prominent interactions during the simulated trajectory. ADMET properties of all the synthesized compounds to predict the pharmacokinetic properties for the selection of the active and bioavailability of compounds has been calculated

Journal of Molecular Structure 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 C7H5ClN2S, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine.

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

Barilli, Alessio published the artcileFrom High-Throughput Screening to Target Validation: Benzo[d]isothiazoles as Potent and Selective Agonists of Human Transient Receptor Potential Cation Channel Subfamily M Member 5 Possessing In Vivo Gastrointestinal Prokinetic Activity in Rodents, Category: thiazole, the publication is Journal of Medicinal Chemistry (2021), 64(9), 5931-5955, database is CAplus and MEDLINE.

Transient receptor potential cation channel subfamily M member 5 (TRPM5) is a nonselective monovalent cation channel activated by intracellular Ca²⁺ increase. Within the gastrointestinal system, TRPM5 is expressed in the stoma, small intestine, and colon. In the search for a selective agonist of TRPM5 possessing in vivo gastrointestinal prokinetic activity, a high-throughput screening was performed and compound 1 was identified as a promising hit. Hit validation and hit to lead activities led to the discovery of a series of benzo[d]isothiazole derivatives Among these, compounds 61 and 64 showed nanomolar activity and excellent selectivity (>100-fold) vs. related cation channels. The in vivo drug metabolism and pharmacokinetic profile of compound 64 was found to be ideal for a compound acting locally at the intestinal level, with minimal absorption into systemic circulation. Compound 64 was tested in vivo in a mouse motility assay at 100 mg/kg, and demonstrated increased prokinetic activity.

Journal of Medicinal Chemistry published new progress about 101012-16-2. 101012-16-2 belongs to thiazole, auxiliary class Thiazole,Chloride,Carboxylic acid, name is 5-Chlorothiazole-2-carboxylic acid, and the molecular formula is C4H2ClNO2S, Category: thiazole.

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

Barilli, Alessio published the artcileFrom High-Throughput Screening to Target Validation: Benzo[d]isothiazoles as Potent and Selective Agonists of Human Transient Receptor Potential Cation Channel Subfamily M Member 5 Possessing In Vivo Gastrointestinal Prokinetic Activity in Rodents, COA of Formula: C4H3Cl2NS, the publication is Journal of Medicinal Chemistry (2021), 64(9), 5931-5955, database is CAplus and MEDLINE.

Transient receptor potential cation channel subfamily M member 5 (TRPM5) is a nonselective monovalent cation channel activated by intracellular Ca²⁺ increase. Within the gastrointestinal system, TRPM5 is expressed in the stoma, small intestine, and colon. In the search for a selective agonist of TRPM5 possessing in vivo gastrointestinal prokinetic activity, a high-throughput screening was performed and compound 1 was identified as a promising hit. Hit validation and hit to lead activities led to the discovery of a series of benzo[d]isothiazole derivatives Among these, compounds 61 and 64 showed nanomolar activity and excellent selectivity (>100-fold) vs. related cation channels. The in vivo drug metabolism and pharmacokinetic profile of compound 64 was found to be ideal for a compound acting locally at the intestinal level, with minimal absorption into systemic circulation. Compound 64 was tested in vivo in a mouse motility assay at 100 mg/kg, and demonstrated increased prokinetic activity.

Journal of Medicinal Chemistry published new progress about 50398-77-1. 50398-77-1 belongs to thiazole, auxiliary class Thiazoles, name is 5-Chloro-2-(chloromethyl)-1,3-thiazole, and the molecular formula is C4H3Cl2NS, COA of Formula: C4H3Cl2NS.

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