Tag: M.W=150-200

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

Hirose, Masaaki published the artcileDesign and synthesis of novel DFG-out RAF/vascular endothelial growth factor receptor 2 (VEGFR2) inhibitors: 3. Evaluation of 5-amino-linked thiazolo[5,4-d]pyrimidine and thiazolo[5,4-b]pyridine derivatives, Quality Control of 31784-71-1, the publication is Bioorganic & Medicinal Chemistry (2012), 20(18), 5600-5615, database is CAplus and MEDLINE.

Our aim was to discover RAF/vascular endothelial growth factor receptor 2 (VEGFR2) inhibitors that possess strong activity and sufficient oral absorption, and thus, we selected a 5-amino-linked thiazolo[5,4-d]pyrimidine derivative as the lead compound because of its potential kinase inhibitory activities and its desired solubility The novel tertiary 1-cyano-1-methylethoxy substituent was designed to occupy the hydrophobic region of ‘back pocket’ of BRAF on the basis of the X-ray co-crystal structure data of BRAF. In addition, we found that N-methylation of the amine linker could control the twisted mol. conformation leading to improved solubility These approaches produced N-Me thiazolo[5,4-b]pyridine-5-amine derivative 5 (I). To maximize the in vivo efficacy, we attempted salt formation of 5. Our result indicated that the besylate monohydrate salt form (5c) showed significant improvement of both solubility and oral absorption. Owing to the improved physicochem. properties, compound 5c demonstrated regressive antitumor efficacy in a HT-29 xenograft model.

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

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

Rao, Ashwin U. published the artcileSynthesis and structure-activity relationships of 2-(1,4′-bipiperidin-1′-yl)thiazolopyridines as H₃ receptor antagonists, SDS of cas: 31784-71-1, the publication is Bioorganic & Medicinal Chemistry Letters (2009), 19(21), 6176-6180, database is CAplus and MEDLINE.

A series of 2-(1,4′-bipiperidin-1′-yl)thiazolopyridines I (X = N, Y = CH; X = CH, Y = N; R = H, H₂N, CN, Cl, MeCONH, 4-NCC₆H₄, 2-fluoro-3-pyridyl, 5-pyrimidyl, etc.) was synthesized and evaluated as a new lead of non-imidazole histamine H₃ receptor antagonists. Introduction of diversity at the 6-position of the pyridine ring was designed to enhance in vitro potency and decrease hERG activity. The structure-activity relationships for these new thiazolopyridine antagonists are discussed.

Bioorganic & Medicinal Chemistry Letters 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, SDS of cas: 31784-71-1.

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

Belaidi, Salah published the artcileElectronic structure and physico-chemical property relationship for thiazole derivatives, Synthetic Route of 31784-71-1, the publication is Asian Journal of Chemistry (2013), 25(16), 9241-9245, database is CAplus.

Electronic structure, effect of the substitution and structure physico-chem. property relationship for thiazole derivatives, has been studied by ab initio and DFT method. In the present work, the calculated values, i.e., net charges, bond lengths, dipole moments, electron-affinities, heats of formation and QSPR properties, are reported and discussed in terms of the reactivity of thiazole derivatives

Asian Journal of 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, Synthetic Route of 31784-71-1.

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

Chenard, B. L. published the artcileBenzopentathiepins: synthesis via thermolysis of benzothiadiazoles with sulfur, Application of Benzo[d][1,2,3]thiadiazol-5-amine, the publication is Journal of Organic Chemistry (1984), 49(7), 1221-4, database is CAplus.

A general synthesis of benzopentathiepins I (R = H, 6-Cl, 6-CF₃, 5-MeO, 5-Me₂N, 4-Br, 4-CF₃) has been developed by the thermolysis of benzothiadiazoles II with S. Diazabicyclooctane enhances the yield of benzopentathiepin by approx. 2-fold. The scope and limitations of the method are also discussed.

Journal of Organic Chemistry published new progress about 1753-29-3. 1753-29-3 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Amine, name is Benzo[d][1,2,3]thiadiazol-5-amine, and the molecular formula is C6H5N3S, Application of Benzo[d][1,2,3]thiadiazol-5-amine.

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