Category: 95-24-9

Laghezza, Antonio published the artcileVirtual screening identification and chemical optimization of substituted 2-arylbenzimidazoles as new non-zinc-binding MMP-2 inhibitors, Category: thiazole, the publication is Bioorganic & Medicinal Chemistry (2020), 28(3), 115257, database is CAplus and MEDLINE.

Matrix metalloproteinases (MMPs) are a large family of zinc-dependent endoproteases known to exert multiple regulatory roles in tumor progression and invasiveness. This encouraged over the years the approach of MMP, and particularly MMP-2, targeting for anticancer treatment. Early generations of MMP inhibitors, based on aspecific zinc binding groups (ZBGs) assembled on (pseudo)peptide scaffolds, have been discontinued due to the clin. emergence of toxicity and further drawbacks, giving the way to inhibitors with alternative zinc-chelator moieties or not binding the catalytic zinc ion. In the present paper, we continue the search for new non-zinc binding MMP-2 inhibitors: exploiting previously identified compounds, a virtual screening (VS) campaign was carried out and led to the identification of a new class of ligands. The structure-activity relationship (SAR) of the benzimidazole scaffold was explored by synthesis of several analogs whose inhibition activity was tested with enzyme inhibition assays. By performing the mol. simplification approach, we disclosed different sets of single-digit micromolar inhibitors of MMP-2, with up to a ten-fold increase in inhibitory activity and ameliorated selectivity towards off-target MMP-8, compared to selected lead compound Mol. dynamics calculations conducted on complexes of MMP-2 with docked privileged structures confirmed that analyzed inhibitors avoid targeting the zinc ion and dip inside the S1′ pocket. Present results provide a further enrichment of our insights for the design of novel MMP-2 selective inhibitors.

Bioorganic & 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, Category: thiazole.

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

Tokala, Ramya published the artcileDevelopment of β-carboline-benzothiazole hybrids via carboxamide formation as cytotoxic agents: DNA intercalative topoisomerase IIα inhibition and apoptosis induction, Computed Properties of 95-24-9, the publication is Bioorganic Chemistry (2021), 104481, database is CAplus and MEDLINE.

In quest of promising anticancer agents, the pharmacophores of natural (β-carboline) and synthetic origin (benzothiazole) were adjoined by a carboxamide bridge and three-point diversification was accomplished. The in vitro cytotoxic ability of the compounds was established on adherent and suspension human cancer cell lines and compounds I and II advanced as pre-eminent mols. with IC₅₀ values of 1.46 and 1.81μM resp. in A549 cell line. The cytospecificity was entrenched for potent compounds I and II by evaluating against normal human lung epithelial cells and selectivity index was calculated Furthermore, EtBr displacement, relative viscosity and gel-based topoisomerase II target assays unveiled the intercalative topo-II inhibitory capability and DNA binding studies (absorbance) revealed the dissociation constant (K_d) for compounds I and II as 98 and 103μM resp. Addnl., cell-based flow cytometric assays like Annexin-V/PI dual staining aids in the quantification of apoptosis induced and JC-1 staining disclosed the depolarization of mitochondrial membrane potential by compound I in A549 cells in a dose-dependent manner. Moreover, wound healing assay established the inhibition of in vitro cell migration by compound I on A549 cells. In addition, mol. docking studies proved the binding of compounds I and II in the active site of DNA complexed with topo IIα and stabilized by interactions with DNA base pairs and amino acid residues. Remarkably, the compounds I and II follow Lipinski’s rule of five and are in the recommended range for Jorgensen’s rule of three with a minimal violation and other pharmacokinetic parameters revealing druggability of the synthesized hybrids.

Bioorganic 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 C30H42NOP, Computed Properties of 95-24-9.

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

de Oliveira Lima Filho, Edson published the artcileMechanochemical Thiocyanation of Aryl Compounds via C-H Functionalization, Formula: C7H5ClN2S, the publication is ACS Omega (2020), 5(51), 33329-33339, database is CAplus and MEDLINE.

Aryl thiocyanate compounds are important building blocks for the synthesis of bioactive compounds and intermediates for several functional groups. Reported thiocyanation reactions via C-H functionalization have limited substrate scope and low RME. The ball-milling method reported here uses ammonium persulfate and ammonium thiocyanate as reagents and silica as a grinding auxiliary. It afforded aryl thiocyanates with moderate to excellent yields for a wide variety of aryl compounds (36 examples, 8-96% yield), such as anilines, phenols, anisoles, thioanisole, and indole, thus tolerating substrates with sensitive functional groups. New products such as benzo[d][1,3]oxathiol-2-ones were obtained with C-4 substituted phenols. Thus, to our knowledge, we report, for the first time, aryl thiocyanation reaction by ball-milling at room temperature and solvent-free conditions, with short reaction times and no workup. Anal. of several mass-based green metrics indicates that it is an efficient greener method.

ACS Omega 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

Zaldivar-Diez, Josefa published the artcileBenzothiazole-Based LRRK2 Inhibitors as Wnt Enhancers and Promoters of Oligodendrocytic Fate, Related Products of thiazole, the publication is Journal of Medicinal Chemistry (2020), 63(5), 2638-2655, database is CAplus and MEDLINE.

Leucine rich repeat kinase 2 (LRRK2) is an enigmatic enzyme and a relevant target for Parkinson’s disease (PD). However, despite the significant amount of research done in the past decade, the precise function of LRRK2 remains largely unknown. Moreover, the therapeutic potential of its inhibitors is in its infancy with the first clin. trial having just started. In the present work, the mol. mechanism of LRRK2 in the control of neurogenesis or gliogenesis was investigated. We designed and synthesized novel benzothiazole-based LRRK2 inhibitors and showed that they can modulate the Wnt/β-catenin signaling pathway. Furthermore, compounds I and II were able to promote neural progenitors proliferation and drive their differentiation toward neuronal and oligodendrocytic cell fates. These results suggest potential new avenues for the application of LRRK2 inhibitors in demyelinating diseases in which oligodendrocyte cell-death is one of the pathol. features.

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 C10H16O2, Related Products of thiazole.

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

Yue, Xiaoping published the artcileBiocatalytic dynamic reductive kinetic resolution of aryl α-chloro β-keto esters: divergent, stereocontrolled synthesis of diltiazem, clentiazem, and siratiazem, Formula: C7H5ClN2S, the publication is Chemical Communications (Cambridge, United Kingdom) (2022), 58(64), 9010-9013, database is CAplus and MEDLINE.

The first systematic study of ketoreductase (KRED)-catalyzed dynamic reductive kinetic resolution (DYRKR) on aryl α-chloro β-keto esters was performed and 15 structurally diverse chiral anti-aryl α-chloro β-hydroxy esters were synthesized in 74-98% isolated yields, along with moderate-to-excellent diastereoselectivity (up to >99 : 1 dr) and good-to-excellent enantioselectivity (mostly >99% ee). LfSDR1-catalyzed complete reduction of 100 g L^-1 of substrate 6b at a ten-gram scale was achieved with a continuous fed-batch strategy, afforded anti-(2S,3S)-1b, the key intermediate of diltiazem, in a record-breaking space-time yield of 96 g L^-1 d^-1. An eight-step synthesis of diltiazem, clentiazem and siratiazem was accomplished in 32-45% overall yields, featuring this versatile biocatalytic reduction reaction as well as an efficient, green chlorination reaction in flow.

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 C12H10F2Si, Formula: C7H5ClN2S.

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

Hou, Yue published the artcileA dihedral-angle-controlled mechanochromic luminescent material: Application for pressure sensing, Name: 6-Chlorobenzothiazol-2-ylamine, the publication is Dyes and Pigments (2020), 108505, database is CAplus.

For most of the mechanochromic luminescent (MCL) materials, their mechanisms are based on the phase transition. When they are fabricated into devices or films, the MCL cannot be fully activated due to uncontrollable phase state of the materials. In this study, a new MCL material, (E)-6-chloro-N-(4-(dimethylamino)benzylidene)benzo[d]thiazol-2-amine (CDBTA), functioning based on dihedral-angle change, was reported. The initial state of CDBTA glows green emission (520 nm), while grinding changes its color into yellow-orange (551 nm). The switching between two emission states can be stably switched with high fatigue resistance. The underlying MCL mechanism was verified by crystal analyses on two forms of single crystal, namely Green-form (G-form) and Yellow-form (Y-form), resp. Mols. in G-form crystal adopt the twisted conformation by the rotation of the donor-acceptor (D-A) biplane. The dihedral angle is thus fixed by a variety of intermol. interactions. Under mech. stimuli, these interactions are destructed and the intramol. torsional stress is released. Thus the mols. cannot maintain twisted conformation but form D-A coplane similar to the Y-form. Such dihedral-angle-controlled structural relaxation makes the π-electron highly delocalized to facilitate bathochromic-shift. The MCL stems from the changes of dihedral angle of the D-A biplane rather than that in packing mode or phase state, therefore CDBTA offers the possibility to fully activate the MCL performances when instrumented. Encouraged by this advantage, a CDBTA film sensor for pressure detection was fabricated, which exhibits a gradual red-shift with pressure and low detection limit down to 15.21 MPa.

Dyes and Pigments 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

Shang, Junfeng published the artcileSynthesis and evaluation of novel 1-(((6-substituted benzo[d]thiazol-2-yl)amino)(heteroaryl)methyl)naphthalen-2-ol as pesticidal agents, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is Journal of Enzyme Inhibition and Medicinal Chemistry (2022), 37(1), 641-651, database is CAplus and MEDLINE.

To discover new agrochems. with prominent pesticidal properties, a series of novel β-naphthol derivatives containing benzothiazolylamino and various heteroaryl groups I (R = H, CF₃, Cl; Het = pyrazol-5-yl, imidazol-2-yl, pyrimidin-5-yl, etc.) were efficiently synthesized via Betti reaction. The bioassay results showed that most of the synthesized compounds exhibited favorable insecticidal potentials, particularly towards oriental armyworm (50-100% at 200 mg·L^-1) and diamondback moth (50-95% at 10 mg·L^-1). Some compounds possessed LC₅₀ values of 0.0988-5.8864 mg·L^-1 against diamondback moth. Compounds I (R = H; Het = 2-phenyl-2H-1,2,3-triazol-4-yl), I (R = H; Het = 6-chloroimidazo[1,2-a]pyridin-3-yl), I (R = H; Het = 6-bromoimidazo[1,2-a]pyridin-3-yl) also displayed lethality rates of 30-90% against spider mite at the concentration of 100 mg·L^-1. Overall, some compounds could be considered as new insecticidal/acaricidal leading structures for further investigation. The calcium imaging experiments revealed that compound I (R = H; Het = 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl), I (R = H; Het = 2-phenyl-2H-1,2,3-triazol-4-yl), and 1-((benzo[d]thiazol-2-ylamino)(4-methoxyphenyl)- Methyl)naphthalen-2-ol could activate the release of calcium ions in insect (M. separata) central neurons at a higher concentration (50 mg·L^-1). The SAR anal. provided valuable information for further structural modifications.

Journal of Enzyme Inhibition and 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 C12H14O2, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine.

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

Zhang, Yan published the artcileSynthesis and insecticidal evaluation of novel sulfide-containing amide derivatives as potential ryanodine receptor modulators, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is Chinese Chemical Letters (2022), 33(1), 501-507, database is CAplus.

With the aim of discovering new bioactive pesticides for crop protection, a series of novel sulfide-containing amide derivatives A were efficiently synthesized via a strategy of modifying the “amide” structure of anthranilic diamide insecticides. The single-crystal structures of A2-3 and A4-5 were firstly reported. The bioassay results showed that most of the synthesized compounds display moderate to high insecticidal activities. Particularly, some sulfone-containing compounds, e.g.,A2-3,A3-3 and A6-3, not only possessed favorable lethality rate (50%-100%) against P. xylostella at a concentration of 0.1 mg/L, but also held good activities towards a variety of agricultural pests such as M. separata, C. pipiens pallen, H. armigera and O. nubilalis; the larvicidal activities of A4-1 and A6-1 towards P. xylostella were close to that of chlorantraniliprole at 0.01 mg/L. The calcium imaging experiments revealed that the representative compounds A2-3 and A6-3 are potential ryanodine receptor (RyR) modulators. The structure-activity relationships were discussed in detail. These results provide useful information for further design and development of novel insecticides.

Chinese Chemical 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 C5H5ClIN, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine.

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

Diao, Peng-Cheng published the artcileDiscovery of novel pyrimidine-based benzothiazole derivatives as potent cyclin-dependent kinase 2 inhibitors with anticancer activity, Safety of 6-Chlorobenzothiazol-2-ylamine, the publication is European Journal of Medicinal Chemistry (2019), 196-207, database is CAplus and MEDLINE.

To develop novel CDK2 inhibitors as anticancer agents, a series of novel pyrimidine-based benzothiazole derivatives I (R = 4-(S(O)₂NH₂), 4-(piperidin-1-yl), 3-F, etc.) and II (R¹ = H, F, Cl, Me, MeO; R² = H, Me, F; R³ = Me, NH₂) was designed and synthesized. Initial biol. evaluation demonstrated that some of target compounds displayed potent antitumor activity in vitro against five cancer cell lines. Especially, the analog II (R¹ = F; R² = H; R³ = NH₂) exhibited approx. potency with AZD5438 toward four cells including HeLa, HCT116, PC-3, and MDA-MB-231 with IC₅₀ values of 0.45, 0.70, 0.92, 1.80 μM, resp. More interestingly, the most highly active compound II (R¹ = F; R² = H; R³ = NH₂) in this study also possessed promising CDK2/cyclin A2 inhibitory activities with IC₅₀ values of 15.4 nM, which was almost 3-fold potent than pos. control AZD5438, and mol. docking studies revealed that the analog bound efficiently with the CDK2 binding site. Further studies indicated that compound II (R¹ = F; R² = H; R³ = NH₂) could induce cell cycle arrest and apoptosis in a concentration-dependent manner. These observations suggest that pyrimidine-benzothiazole hybrids represent a new class of CDK2 inhibitors and well worth further investigation aiming to generate potential anticancer agents.

European 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, Safety of 6-Chlorobenzothiazol-2-ylamine.

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

Nagaraju, Burri published the artcileSynthesis and biological evaluation of pyrazole linked benzothiazole-β-naphthol derivatives as topoisomerase I inhibitors with DNA binding ability, Synthetic Route of 95-24-9, the publication is Bioorganic & Medicinal Chemistry (2019), 27(5), 708-720, database is CAplus and MEDLINE.

A series of new pyrazole linked benzothiazole-β-naphthol derivatives were designed and synthesized using a simple, efficient and ecofriendly route under catalyst-free conditions in good to excellent yields. These derivatives were evaluated for their cytotoxicity on selected human cancer cell lines. Among those, the derivatives 4j, 4k and 4l exhibited considerable cytotoxicity with IC₅₀ values ranging between 4.63 and 5.54 μM against human cervical cancer cells (HeLa). Structure activity relationship was elucidated by varying different substituents on benzothiazoles and pyrazoles. Further, flow cytometric anal. revealed that these derivatives induced cell cycle arrest in G2/M phase and spectroscopic studies such as UV-visible, fluorescence and CD studies showed that these derivatives exhibited good DNA binding affinity. Addnl., these derivatives can effectively inhibit the topoisomerase I activity. Viscosity studies and mol. docking studies demonstrated that the derivatives bind with the minor groove of the DNA.

Bioorganic & 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, Synthetic Route of 95-24-9.

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