Category: 95-24-9

Prajapat, Prakash published the artcileSynthesis of biologically potent alkoxyphthalimido plugged N-(2,4-dioxo-1,4-dihydroquinazolin)-3(2H)-yl)-4-oxo-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxamide via Gould Jacobs reaction, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is Heterocyclic Letters (2021), 11(1), 63-72, database is CAplus.

Convenient methods for the synthesis of new alkoxyphthalimidoquinazolinedione and their pyrimidobenzothiazole derivatives I [R¹ = H, Cl, O₂N; R² = H, 2-(1,3-dioxoisoindolin-2-yl)oxyethyl] were reported. A series of benzothiazolopyrimidine-3-carboxamides I were prepared starting from substituted 2-aminobenzothiazoles via solvent free multi-component Gould-Jacobs reaction. Structures of newly synthesized compounds were established based on IR, ¹H-NMR, mass, anal. studies and fluorescence tests. Some of synthesized mols. I were assayed for their antimalarial activity. IC₅₀ values of antimalarial activity of compounds were also determined

Heterocyclic Letters 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

Huddar, Srigouri published the artcileDiscovery of 4-hydroxy-2-oxo-1,2-dihydroquinolines as potential inhibitors of Streptococcus pneumoniae, including drug-resistant strains, SDS of cas: 95-24-9, the publication is Bioorganic & Medicinal Chemistry Letters (2020), 30(9), 127071, database is CAplus and MEDLINE.

New therapies for treating drug-resistant pneumococcal infections are urgently needed. The novel scaffold 6-hydroxy-4-oxo-1,2-dihydro-4H-quinoline was shown to have similar efficacies against all three different serotypes of S. pneumoniae, ATCC 49617 (19F), ATCC BAA-1663 (15B), and ATCC 700904 (19A), in a resazurin-based high-throughput screen using the Korea Chem. Bank library. Further studies to identify a new lead with this scaffold, including tricyclic pyrrolo[3,2,1-ij]quinolone and pyrido[3,2,1-ij]quinolone derivatives, led to the identification of 6d, 7d and 12a. Compound 6d (IC₅₀ = 0.92, 0.75, and 0.77μM), 7d (IC₅₀ = 0.57, 0.66, and 0.38μM) and 12a() (IC₅₀ = 0.27, 1.03, and 0.62μM) showed submicromolar IC₅₀ values against 19F, 15B, and 19A, resp., and thus serve as a starting point for further optimization. While some of compounds in this series exhibited acceptable pharmacokinetic profiles in preliminary in vivo rat experiments, the most active compound 12a showed poor solubility and high plasma protein binding. Our current research efforts are focused on optimizing compounds to improve physicochem. properties as well as potency.

Bioorganic & Medicinal Chemistry Letters 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, SDS of cas: 95-24-9.

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

Dass, Reuben published the artcileAn efficient one-pot synthesis of 2-aminobenzothiazoles from substituted anilines using benzyltrimethylammonium dichloroiodate and ammonium thiocyanate in DMSO:H₂O, Name: 6-Chlorobenzothiazol-2-ylamine, the publication is Tetrahedron Letters (2021), 153388, database is CAplus.

Treatment of anilines with benzyltrimethylammonium dichloroiodate and ammonium thiocyanate in DMSO:H₂O at 70°C gave the 2-aminobenzothiazoles I [R = 6-F, 6-Me, 4-F, etc.] in excellent isolated yields (75-97% and ave. yield for all substrates is 90%). The reaction worked well for 2(4)mono-2,4-di- or 3,4,5-tri-substituted anilines and a wide range of both electron donating groups (MeO, HO, CF₃O, Me) and electron withdrawing groups (NO₂, CN, CO₂Et, CO₂H, Cl, F) were well tolerated. This method provided a useful alternative to other methods that are either less efficient (requiring 3-7 fold equivalent of reagents) or utilize highly toxic and corrosive liquid Br₂ as the oxidizing agent.

Tetrahedron Letters 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, Name: 6-Chlorobenzothiazol-2-ylamine.

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

Geronikaki, A. published the artcileMolecular docking, design, synthesis and biological evaluation of novel 2,3-aryl-thiazolidin-4-ones as potent NNRTIs, COA of Formula: C7H5ClN2S, the publication is SAR and QSAR in Environmental Research (2019), 30(10), 697-714, database is CAplus and MEDLINE.

A series of thiazolidinone derivatives I [R¹ = 6-Cl, 6-cyano, 6-(adamant-1-yl), 6-CF₃, 4-Me-6-(adamant-1-yl), R² = 4-F, 4-NO₂, 2-F-6-Cl, 2,6-Cl₂, 2,6-F₂] and II [R³ = 4-(pyridin-2-yl)thiazol-2-yl, 5-ethyl-4-methylthiazol-2-yl] was designed based on a butterfly mimicking scaffold consisting of a substituted benzothiazolyl moiety connected with a substituted Ph ring via a thiazolidinone moiety. The most promising derivatives were selected using mol. docking anal. and PASS prediction program, synthesized and evaluated for HIV-1 RT inhibition. Five out of fifteen tested compounds exhibited good inhibitory action. It was observed that the presence of Cl or CN substituents at position 6 of the benzothiazole ring in combination with two fluoro atoms at the ortho-positions or a hydrogen acceptor substituent at the 4-position of the Ph ring were favorable for the HIV RT inhibitory activity.

SAR and QSAR in Environmental Research 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, COA of Formula: C7H5ClN2S.

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

Tsemeugne, Joseph published the artcileSynthesis, characteristic fragmentation patterns and antibacterial activity of new azo compounds from the coupling reaction of diazobenzothiazole ions and acetaminophen, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is Heterocyclic Communications (2021), 27(1), 79-89, database is CAplus.

A series of azobenzothiazole dyes were synthesized via diazotization of substituted benzothiazole derivatives followed by azo coupling with acetaminophen. The chem. structures of all synthesized compounds were confirmed using anal. data and spectroscopic techniques, including UV-visible, IR, mass spectra and ¹H- and ¹³C-NMR. The in situ formed diazobenzothiazole ions regiospecifically reacted with acetaminophen derivatives in the Hollemann-guided electrophilic aromatic substitution mechanism. The regio-orientations were established, on the one hand, by a rigorous interpretation of ¹H-NMR spectra and, on the other hand, by the characteristic fragmentation patterns observed on the electrospray mass spectra. In the cases of I and II, multisubstitutions occurred. The antimicrobial activity of synthesized azobenzothiazole dyes, along with all the starting materials, was investigated on Pseudomonas aeruginosa PA01, Staphylococcus aureus 18, Escherichia coli 64R and S. aureus ATCC 25923. The results showed that this skeletal framework exhibited marked potency as antibacterial agents. The most active antibacterial agent against both targeted organisms was 1,2-bis(benzo[d]thiazol-2-yl)diazene trihydrate.

Heterocyclic Communications 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 C8H7NO4, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine.

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

Roeder, Liesa published the artcileFlow hydrodediazoniation of aromatic heterocycles, Formula: C7H5ClN2S, the publication is Molecules (2019), 24(10), 1996pp., database is CAplus and MEDLINE.

Continuous flow processing was applied for the rapid replacement of an aromatic amino group with a hydride. The approach was applied to a range of aromatic heterocycles RNH₂ (R = 1,3-benzoxazol-2-yl, 2-pyridyl, 4-cyano-1-phenyl-1H-1,2,3-triazol-5-yl, etc.) confirming the wide scope and substituent-tolerance of the processes. Flow equipment was utilized and the process optimized to overcome the problematically-unstable intermediates that have restricted yields in previous studies relying on batch procedures. Various common organic solvents were investigated as potential hydride sources. The approach has allowed key structures, such as amino-pyrazoles and aminopyridines to be deaminated in good yield using a purely organic-soluble system.

Molecules 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, Formula: C7H5ClN2S.

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

Acar Cevik, Ulviye published the artcileSynthesis of new benzothiazole derivatives bearing thiadiazole as monoamine oxidase inhibitors, Application of 6-Chlorobenzothiazol-2-ylamine, the publication is Journal of Heterocyclic Chemistry (2020), 57(5), 2225-2233, database is CAplus.

In this study, a novel series of benzothiazole-thiadiazole I (R¹ = Et, methoxyethyl, n-Pr, n-Bu; R² = H, Cl, NO₂) was synthesized. These compounds I were evaluated as inhibitors for types A and B MAO enzymes. Compounds I [(A), R¹ = methoxyethyl, R² = NO₂; R¹ = n-Bu, R² = NO₂, (B)] were the most active derivatives in the series with IC₅₀ values of 0.107 ± 0.003 and 0.128 ± 0.004, resp. Furthermore, compounds (A) and (B) were investigated for their cytotoxicity and found as non-cytotoxic.

Journal of Heterocyclic 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, Application of 6-Chlorobenzothiazol-2-ylamine.

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

Fleau, Charlotte published the artcileChagas Disease Drug Discovery: Multiparametric Lead Optimization against Trypanosoma cruzi in Acylaminobenzothiazole Series, COA of Formula: C7H5ClN2S, the publication is Journal of Medicinal Chemistry (2019), 62(22), 10362-10375, database is CAplus and MEDLINE.

Acylaminobenzothiazole hits were identified as potential inhibitors of T. cruzi replication, a parasite responsible for Chagas Disease. We selected compound 1, N-(6-chlorobenzo[d]thiazol-2-yl)cyclopropanecarboxamide, for lead optimization, aiming to improve in parallel its anti-T. cruzi activity (IC50 = 0.630μM) and its human metabolic stability (human clearance = 9.57mL/min/g). A total of 39 analogs of 1 were synthesized and tested in vitro. We established a multiparametric structure activity relationship, allowing optimization of both anti-parasite activity, physicochem. parameters and ADME properties. We identified compound 50, N-(5-Fluoro-6-(trifluoromethyl)benzothiazol-2-yl)cyclopropanecarboxamide, as an advanced lead with an improved anti-T. cruzi activity in vitro (IC50 = 0.079μM), an enhanced metabolic stability (Human Clearance = 0.413mL/min/g) and opportunity for oral route of administration. After tolerability assessment, compound 50 demonstrated a promising in vivo efficacy.

Journal of Medicinal 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, COA of Formula: C7H5ClN2S.

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

Moodley, Rashmika published the artcileNew Quinoline-Urea-BenzΞothiazole Hybrids as Promising Antitubercular Agents: Synthesis, In Vitro Antitubercular Activity, Cytotoxicity Studies, and In Silico ADME Profiling, Product Details of C7H5ClN2S, the publication is Pharmaceuticals (2022), 15(5), 576, database is CAplus and MEDLINE.

A series of 25 new benzothiazole-urea-quinoline hybrid compounds, I (X = H, Me, F, NO₂, etc.) and II (n = 0, 2, 3, 4, and 6) were synthesized successfully via a three-step synthetic sequence involving an amidation coupling reaction as a critical step. In vitro evaluation of these hybrid compounds for their antitubercular inhibitory activity against the Mycobacterium tuberculosis H37Rv pMSp12::GPF bioreporter strain was undertaken. Of the 25 tested compounds, 17 compounds exhibited promising anti-TB activities of less than 62.5μM (MIC90) and 13 compds showed promising activity with MIC90 values in the range of 1-10μM, while compound I(X = CF₃), being the most active, exhibited sub-micromolar activity (0.968μM) in the CAS assay. In addition, minimal cytotoxicity against the HepG2 cell line (cell viability above 75%) in 11 of the 17 compounds, at their resp. MIC90 concentrations, was observed, with compound I(X = CF₃), exhibiting 100% cell viability. The hybridization of the quinoline, urea, and benzothiazole scaffolds demonstrated a synergistic relationship because the activities of resultant hybrids were vastly improved compared to the individual entities. In silico ADME predictions showed that the majority of these compounds have drug-like properties and are less likely to potentially cause cardiotoxicity (QPlogHERG > -5).

Pharmaceuticals 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, Product Details of C7H5ClN2S.

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

Kallur, H. J. published the artcileSynthesis, characterization and anthelmintic screening of some new benzothiophene derivatives, Application In Synthesis of 95-24-9, the publication is World Journal of Pharmaceutical Research (2020), 9(5), 1838-1849, database is CAplus.

The proposed work was carried out by following Schemes. In the Scheme-I the starting material cinnamic acid was reacted with thionyl chloride, in presence of pyridine in chlorobenzene medium to yield 3- chlorobenzo[b]thiophene-2-carbonylchloride. Where as in the Scheme-II the 2-amino-6-substituted benzothiazoles I (R = Me, COOEt, Cl, OMe, F, nitro) was prepared by the reaction of 4-substituted anilines 4-RC₆H₄NH₂ and potassium thiocyanate in presence of bromine in acetic acid. In the scheme-III, the compound N-(6-substituted-1,3-benzothiazol-2-yl)-3-chloro-1-benzothiophene-2-carboxamides II was prepared by reacting 3-chlorobenzo[b]thiophene-2-carbonylchloride and 2-amino-6-substituted benzothiazoles I in pyridine medium refluxed for 10-15 h. The synthesized compounds II were evaluated for the anthelmintic activity.

World Journal of Pharmaceutical Research 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, Application In Synthesis of 95-24-9.

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