Category: 95-24-9

Ding, Hongyan published the artcileSKA3 promotes the proliferation, migration and invasion of endometrial carcinoma cells, Application of 6-Chlorobenzothiazol-2-ylamine, the publication is Chengdu Yixueyuan Xuebao (2021), 16(3), 293-298, database is CAplus.

Objective To investigate the effects of spindle and kinetochore associated complex subunit 3 (SKA3) on the proliferation, migration and invasion of endometrial carcinoma cells. Methods Real-time quant. polymerasechain reaction (RT-qPCR) and Western blotting were used to detect the levels of SKA3 mRNA and protein expression in endometrial epithelial cells HEECs and endometrial carcinoma cells KLE, JEC and Ishikawa cells. And the Ishikawa cells with the highest expression level were selected for subsequent research. Ishikawa cells were divided into three groups. In the control group, Ishikawa cells were cultured normally. In the si-SKA3 group, 50 nmol/L siRNA-SKA3 was transfected into Ishikawa cells according to liposome 2000 instructions. In the NC group, 50 nmol/L siRNA-NC was transfected into Ishikawa cells according to liposome 2000 instructions. Cell proliferation was detected by cell counting kit-8 (CCK8) and clonal formation assay. Cell invasion and migration were detected by Transwell and scratch assay. And protein expression of CyclinD1, MMP-2, AKT, and p-AKT were detected by Western blotting. Results Compared with the HEECs of endometrial epithelial cells, the expression levels of SKA3 mRNA and protein in each endometrial carcinoma cell line were significantly increased (P<0.05). After interference with SKA3 expression, the proliferation and invasion ability of Ishikawa cells were decreased, the width of scratches were enlarged, and the protein expression of CyclinD1 and MMP-2 were significantly decreased (P<0.05). Compared with the control group and the NC group, the expression of AKT protein in si-SKA3 group was not significantly changed (P>0.05), while the expression of p-AKT protein decreased (P<0.05). Conclusion Interference with SKA3 can inhibit the proliferation, migration and invasion of Ishikawa cells of endometrial carcinoma, of which the mechanism may be related to the inhibition of SKA3 on PI3K/AKT signaling pathway.

Chengdu Yixueyuan Xuebao 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

Khan, Takallum published the artcileSilica-Supported P₂O₅ as an Efficient Heterogeneous Catalyst for the One Pot Synthesis of 3-Amino-imidazo[2,1-b](1,3)benzothiazole under Green Conditions, HPLC of Formula: 95-24-9, the publication is Journal of Heterocyclic Chemistry (2019), 56(1), 11-17, database is CAplus.

The new approach involving the solid supported catalyst for the formation of C-N bond followed by cyclization has been reported. In this work we have reported a facile, efficient, and environment-friendly protocol for the synthesis of some new 3-amino-imidazo[2,1-b](1,3)benzothiazole derivatives by one-pot condensation of 2-aminobenzothiazole, indole-3-carbaldehyde, and aryl isocyanide in the presence of silica-supported P2O5 as a heterogeneous solid acid catalyst. The reaction was performed using conventional method under green conditions. The present approach offers the advantages of simple methodol., inexpensive acid catalyst, short reaction time, easy work up with excellent yield, simple purification and use of green solvent. All the newly synthesized compounds were characterized in details using phys. and chem. techniques such as m.p., 1H NMR, 13C NMR, and FTIR spectroscopy.

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, HPLC of Formula: 95-24-9.

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

Wu, Feng published the artcileSynthesis and evaluation of novel 2,4-diaminopyrimidines bearing a sulfoxide moiety as anaplastic lymphoma kinase (ALK) inhibition agents, Product Details of C7H5ClN2S, the publication is Bioorganic & Medicinal Chemistry Letters (2021), 128253, database is CAplus and MEDLINE.

Herein, 16 new 2,4-diaminopyrimidines I (R¹ = H, F, Cl; R² = EtS, EtSO, i-PrSO; R³ = Me₂NCH₂CH₂NMe, 4-methylpiperazin-1-yl, 4-methyl-1,4-diazepan-1-yl, 4-dimethylaminopiperidin-1-yl, etc.; R⁴ = H, H₂N, EtCONH) bearing a sulfide or sulfoxide moiety were synthesized and evaluated for anaplastic lymphoma kinase (ALK) inhibitory activity. The optimal compound I [R¹ = F; R² = EtSO; R³ = 4-methylpiperazin-1-yl; R⁴ = EtCONH; (II)] exhibited excellent antiproliferative activity against non-small cell lung cancer NCI-H2228 cells, which was better than that of Brigatinib and similar to Ceritinib. Mechanism study revealed that the compound II decreased the mitochondrial membrane potential and arrested NCI-H2228 cells in the G0/G1 phase, finally resulting in cellular apoptosis. It is interesting that the compound II could effectively inhibit the migration of NCI-H2228 cells and may be a promising leading compound for chemotherapy of metastatic cancer.

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 C11H8N2O2, Product Details of C7H5ClN2S.

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

Giovannucci, Tatiana A. published the artcileInhibition of the ubiquitin-proteasome system by an NQO1-activatable compound, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is Cell Death & Disease (2021), 12(10), 914, database is CAplus and MEDLINE.

Malignant cells display an increased sensitivity towards drugs that reduce the function of the ubiquitin-proteasome system (UPS), which is the primary proteolytic system for destruction of aberrant proteins. Here, we report on the discovery of the bioactivatable compound CBK77, which causes an irreversible collapse of the UPS, accompanied by a general accumulation of ubiquitylated proteins and caspase-dependent cell death. CBK77 caused accumulation of ubiquitin-dependent, but not ubiquitin-independent, reporter substrates of the UPS, suggesting a selective effect on ubiquitin-dependent proteolysis. In a genome-wide CRISPR interference screen, we identified the redox enzyme NAD(P)H:quinone oxidoreductase 1 (NQO1) as a critical mediator of CBK77 activity, and further demonstrated its role as the compound bioactivator. Through affinity-based proteomics, we found that CBK77 covalently interacts with ubiquitin. In vitro experiments showed that CBK77-treated ubiquitin conjugates were less susceptible to disassembly by deubiquitylating enzymes. In vivo efficacy of CBK77 was validated by reduced growth of NQO1-proficient human adenocarcinoma cells in nude mice treated with CBK77. This first-in-class NQO1-activatable UPS inhibitor suggests that it may be possible to exploit the intracellular environment in malignant cells for leveraging the impact of compounds that impair the UPS.

Cell Death & Disease 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

Pan, Zi-Tong published the artcileRegulable cross-coupling of alcohols and benzothiazoles via a noble-metal-free photocatalyst under visible light, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is Chemical Communications (Cambridge, United Kingdom) (2022), 58(63), 8810-8813, database is CAplus and MEDLINE.

Two series of alkyl-derived benzothiazoles I [R = Et, iPr, cyclohexyl, etc.; R¹ = H, 4-Cl, 7-Br, etc.] and acetyl-derived benzothiazoles II [R² = Me, Et, n-Bu, etc.; R³ = H, 4-Cl, 6-Br, etc.] were synthesized via noble-metal-free photocatalyzed regulable cross-coupling reaction of benzothiazoles and alcs. with the highest isolated yields of up to 99% and 90% resp.

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 C7H5ClN2S, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine.

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

Capaldo, Luca published the artcilePhotoelectrochemical cross-dehydrogenative coupling of benzothiazoles with strong aliphatic C-H bonds, HPLC of Formula: 95-24-9, the publication is Chemical Communications (Cambridge, United Kingdom) (2021), 57(36), 4424-4427, database is CAplus and MEDLINE.

A photoelectrochem. strategy for the cross-dehydrogenative coupling of unactivated aliphatic H donors (e.g. alkanes) with benzothiazoles is reported. The authors used Bu₄N decatungstate as the photocatalyst to activate strong C(sp³)-H bonds in the chosen substrates, while electrochem. scavenged the extra electrons.

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 C7H5ClN2S, HPLC of Formula: 95-24-9.

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

Mallikarjun, G. published the artcileSynthesis and antimicrobial evaluation of benzothiazole linked isoxazole Schiff bases, Category: thiazole, the publication is Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (2021), 60B(11), 1463-1470, database is CAplus.

A new series of benzothiazole linked isoxazole Schiff base derivatives have been prepared I [R = R¹ = H, OMe, RR¹ = -OCH₂O-, R² = H, OMe; R³ = 5-Cl, 4-OMe, 6-CF₃, etc.] characterized by suitable spectroscopic methods via ¹H and ¹³C NMR, ESI-MS and IR spectra. These compounds have been further screened for their antimicrobial activity against a panel of microorganisms. Among them, compounds [R = R¹ = OMe, R² = H, R³ = 6-Me (II); R = H, R¹ = OMe, R² = H, R³ = 6-OMe (III); R = R¹ = R² = OMe, R³ = 6-F (IV)] demonstrate promising antimicrobial activity against all the tested strains with MIC values ranging between 3.9 – 62.5μg/mL. Further, compounds II, III and IV exhibit promising antifungal activity with MIC values ranging between 7.8 – 32.5μg/mL. Further studies are underway for determining the antifungal mol. mechanisms of these potential compounds

Indian Journal of Chemistry, Section B: Organic Chemistry Including 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

Tikhonova, Tatyana A. published the artcileDevelopment of 1,3-thiazole analogues of imidazopyridines as potent positive allosteric modulators of GABA_A receptors, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is Bioorganic Chemistry (2020), 103334, database is CAplus and MEDLINE.

Structure-activity relationship studies were conducted in the search for 1,3-thiazole isosteric analogs of imidazopyridine drugs (Zolpidem, Alpidem). Three series of novel γ-aminobutyric acid receptor (GABA_AR) ligands belonging to imidazo[2,1-b]thiazoles I [R¹ = OMe, NMe₂, OEt; R² = p-chlorophenyl], [R¹ = OMe, R² = p-nitrophenyl] and [R¹ = OEt, R² = o,p-dichlorophenyl], imidazo[2,1-b][1,3,4]thiadiazoles II [R³ = OEt, NMe₂, NPr₂; R⁴ = p-chlorophenyl; R⁵ = Et, iso-Pr, MOM] and benzo[d]imidazo[2,1-b]thiazoles III [R⁶ = NH₂, OEt, NMe₂, NEt₂, NPr₂; R⁷ = Ph, p-fluorophenyl o,p-dimethoxyphenyl, etc.; R⁸ = H, Cl, OMe] were synthesized and characterized as active agents against GABA_AR benzodiazepine-binding site. In each of these series, potent compounds were discovered using a radioligand competition binding assay. The functional properties of highest-affinity compounds III [R⁶ = NH₂, R⁷ = p-chlorophenyl, R⁸ = H] and [R⁶ = NMe₂, R⁷ = o-chlorophenyl, R⁸ = H] as GABA_AR pos. allosteric modulators (PAMs) were determined by electrophysiol. measurements. In-vivo studies on zebrafish demonstrated their potential for the further development of anxiolytics. Using the OECD “Fish, Acute Toxicity Test” active compounds were found safe and non-toxic. Structural bases for activity of benzo[d]imidazo[2,1-b]thiazoles were proposed using mol. docking studies. The isosteric replacement of the pyridine nuclei by 1,3-thiazole, 1,3,4-thiadiazole, or 1,3-benzothiazole in the ring-fused imidazole class of GABA_AR PAMs was showed to be promising for the development of novel hypnotics, anxiolytics, anticonvulsants and sedatives drug-candidates.

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 C6H4BF4KO, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine.

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

Reddy, Velma Ganga published the artcilePyrazolo-benzothiazole hybrids: synthesis, anticancer properties and evaluation of antiangiogenic activity using in vitro VEGFR-2 kinase and in vivo transgenic zebrafish model, Formula: C7H5ClN2S, the publication is European Journal of Medicinal Chemistry (2019), 111609pp., database is CAplus and MEDLINE.

A series of new pyrazolo-benzothiazole hybrids I [R¹ = H, MeO, F, Cl; R² = H, Me, MeO, F, Cl] was synthesized and screened for their anticancer activity against several cancer cell lines [colon (HT-29), prostate (PC-3), lung (A549), glioblastoma (U87MG)] and normal human embryonic kidney cell line (Hek-293T). Compounds I [R¹ = H, R² = F, Cl; R¹ = F, R² = F, Cl; R¹ = Cl, R² = F, Cl; R¹ = MeO, R² = F, Cl] displayed significant anticancer activity against all tested cancer cell lines and compound I [R¹ = F, R² = Cl] showed most potent activity among the series with IC₅₀ values in the range 3.17-6.77 μM, even better than reference drug axitinib (4.88-21.7 μM). Compound I [R¹ = F, R² = Cl] also showed the strongest growth inhibition in 3D multicellular spheroids of PC-3 and U87MG cells. The mechanism of cellular toxicity in PC-3 cells was found to be cell cycle arrest and apoptosis induction through depolarisation of mitochondrial membrane potential, increased ROS production and subsequent DNA damage. Further, compound I [R¹ = F, R² = Cl] displayed significant in vitro (VEGFR-2 inhibition) and in vivo [transgenic zebrafish Tg(flila:EGFP) model] antiangiogenic properties. Overall, these results provided strong evidence that compound I [R¹ = F, R² = Cl] could be considered for a lead candidate in anticancer and antiangiogenic drug discovery.

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, Formula: C7H5ClN2S.

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

Jakopec, Silvio published the artcileFerrocene conjugates linked by 1,2,3-triazole and their Zn(II) and Cu(II) complexes: Synthesis, characterization and biological activity, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is Applied Organometallic Chemistry (2022), 36(4), e6575, database is CAplus.

Ferrocene derivatives with mono- Py₂NCH₂Trz-1-R (8a–c; Py = 2-pyridyl, Trz = 1,2,3-triazol-5-yl; R = Fc, FcCH₂, FcCHMe) and bis-1,2,3-triazolyl fc(CH₂-1-TrzCH₂NPy₂)₂(9, fc = 1,1′-ferrocenediyl) and ArN(CH₂Trz-1-R)₂ (10a–13c; R = Fc, FcCH₂, FcCHMe; Ar = Ph, 2-benzothiazolyl, 6-chloro-2-benzothiazolyl, 6-nitro-2-benzothiazolyl) chelating groups were synthesized by regioselective copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes with ferrocene azides. Metal complexes of the ligands were prepared with Cu(II) and Zn(II) salts. Crystal structures of ligands 9 and 11a were determined, as well as the structures of complexes [Cu(8a)₂](CF₃SO₃)₂ (8a-Cu) and [Cu(8c)₂(MeOH)₂](BF₄)₂ (8c-Cu). In addition to NMR and UV-Vis spectroscopy, the metal complexes were characterized by cyclic voltammetry. The cytotoxic effect of ferrocene conjugates and their Zn(II) and Cu(II) complexes was explored, and cell cycle anal. was performed. The complex [Cu(8c)₂](CF₃SO₃)₂ showed the most prominent and selective cytotoxicity on cervical carcinoma (HeLa), ovarian cancer (MES-OV), non-small cell lung cancer (A549) and breast carcinoma (MDA-MB-231) cells. This complex increased cell population in the S and G₂/M phase of the cell cycle, which was accompanied by an increase of the cells present in the sub-G₀/G₁ fraction.

Applied Organometallic 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, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine.

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