343975-46-2

Upstream product

• 347-81-9 4-nitro-N-(4-fluorophenyl)benzamide 
• 555-16-8 4-nitrobenzaldehdye 
• 33264-82-3 5-fluoro-2-aminobenzenethiol 
• 122-04-3 4-nitro-benzoyl chloride 
• 371-40-4 4-fluoroaniline 
• 167565-72-2 N-(4-fluorophenyl)-4-nitro-1-benzenecarbothioamide 

Downstream Products

• 1071423-41-0 2-(4'-(methylamino)phenyl)-6-fluorobenzothiazole 
• 1393816-17-5 C₂₁H₁₄F₂N₂OS 
• 1393815-45-6 6-fluoro-2-(4-(5-(4-fluoro-3-methoxyphenyl)-1H-imidazol-1-yl)phenyl)benzo[d]thiazole 
• 485843-26-3 4-(6-fluorobenzo[d]thiazol-2-yl)-4-hydroxycyclohexa-2,5-dienone 
• 1446322-37-7 N-(4-(6-fluorobenzo[d]thiazol-2-yl)phenyl)hydroxylamine 
• 1446322-31-1 C₁₃H₈FN₂S⁽¹⁺⁾ 
• 1446322-25-3 O-acetyl-N-(4-(6-fluorobenzo[d]thiazol-2-yl)phenyl)hydroxylamine 
• 1226795-20-5 6-fluoro-2-(4-acetamido-phenyl)benzothiazole 
• 1226795-23-8 6-fluoro-2-(4'-N-(2''-(2''-methoxyethoxy)ethylamino)phenyl)benzothiazole 
• 1226795-21-6 6-fluoro-2-(4'-N-(2''-(2''-methoxyethoxy)acetamido)phenyl)benzothiazole 
• 1458715-49-5 6-fluoro-2-(4-(2-methyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 
• 1458715-48-4 6-fluoro-2-(4-(2-methyl-5-(4-nitrophenyl)-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 
• 1458715-47-3 6-fluoro-2-(4-(2-(4-methoxyphenyl)-5-methyl-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 
• 1458715-46-2 6-fluoro-2-(4-(2-(4-fluorophenyl)-5-methyl-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 

Relevant academic research and scientific papers

Novel series of benzo[d]thiazolyl substituted-2-quinolone hybrids: Design, synthesis, biological evaluation and in-silico insights

A novel series of 3-(2-(4-(substituted-benzo[d]thiazol-2-yl)phenylamino)acetyl)-4?hydroxy-1-methyl/phenyl quinolin-2(1H)-one (7a-f and 8a-f) were synthesized. Reaction of appropriately substituted-2-(4-amino phenyl)benzo[d]thiazole (4a-f) with 3-(2-bromoacetyl)-4?hydroxy-1-methyl/phenyl quinolin-2(1H)-one (5/6) in the presence of glacial acetic acid resulted in desired compounds. Structures of the synthesized compounds were characterized based on their spectral (IR, 1H NMR, 13C NMR and MS) and elemental analysis. The cytotoxicity screening studies revealed that MCF-7 and WRL68 cancer cells were sensitive to all the tested compounds. Out of twelve novel hybrids, compound 8f displayed the most significant anticancer activity. Docking studies were performed in order to understand the binding mode of the title compounds at the active site of the target enzyme (EGFR tyrosine kinase, 1M17). Compounds 8f and 7f displayed prominent and conserved binding interactions against 1M17. In addition, compounds 7e, 7f, 8e, and 8f exhibited interesting in vitro antibacterial activity, especially against Gram-negative bacteria E. coli. In summary, the novel benzo[d]thiazolyl substituted-2-quinolone hybrid (8f) could be considered as promising hit and could be further exploited for developing potential anticancer/antimicrobial agents.

Synthesis and biological evaluation of cis-restricted triazole/tetrazole mimics of combretastatin-benzothiazole hybrids as tubulin polymerization inhibitors and apoptosis inducers

A series of colchicine site binding tubulin inhibitors were synthesized by the modification of the combretastatin pharmacophore. The ring B was replaced by the pharmacologically relevant benzothiazole scaffolds, and the cis configuration of the olefinic b

Design, synthesis and structure-activity relationship of rhenium 2-arylbenzothiazoles as β-amyloid plaque binding agents

To continue our efforts toward the development of 99mTc PiB analogs, we have synthesized 24 neutral and lipophilic Re (as a surrogate of 99mTc) 2-arylbenzothiazoles, and explored their structure-activity relationship for binding to Aβ1-40 fibrils. These Re complexes were designed and synthesized via the integrated approach, so their 99mTc analogs would have a greater chance of crossing the blood-brain barrier. While the lipophilicities (log PC18 = 1.59-3.53) of these Re 2-arylbenzothiazoles were all within suitable range, their binding affinities (Ki = 30-617 nM) to Aβ1-40 fibrils varied widely depending on the selection and integration of the tetradentate chelator into the 2-phenylbenzothiazole pharmacophore. For potential clinical applications, further refinement to obtain Re 2-arylbenzothiazoles with better binding affinities (99mTc analogs for more widespread application via the use of SPECT scanners.

Synthesis and study of benzothiazole conjugates in the control of cell proliferation by modulating Ras/MEK/ERK-dependent pathway in MCF-7 cells

By applying a methodology, a series of benzothiazole-pyrrole based conjugates (4a-r) were synthesized and evaluated for their antiproliferative activity. Compounds such as 4a, 4c, 4e, 4g-j, 4m, 4n, 4o and 4r exhibited significant cytotoxic effect in the MCF-7 cell line. Cell cycle effects were examined for these conjugates at 2 μM as well as 4 μM concentrations and FACS analysis show an increase of G2/M phase cells with concomitant decrease of G1 phase cells thereby indicating G2/M cell cycle arrest by them. Interestingly 4o and 4r are effective in causing apoptosis in MCF-7 cells. Moreover, 4o showed down regulation of oncogenic expression of Ras and its downstream effector molecules such as MEK1, ERK1/2, p38 MAPK and VEGF. The apoptotic aspect of this conjugate is further evidenced by increased expression of caspase-9 in MCF-7 cells. Hence these small molecules have the potential to control both the cell proliferation as well as the invasion process in the highly malignant breast cancers.

2-PHENYL BENZOTHIAZOLE LINKED IMIDAZOLE COMPOUNDS AS POTENTIAL ANTICANCER AGENTS AND PROCESS FOR THE PREPARATION THEREOF

The present invention provides 2-phenyl benzothiazole linked imidazole compounds of formula A as anti cancer agent against fifty three human cancer cell lines. (General formula A) wherein (II) R=H or OCH3; R1=H, F or OCH3; R2=H or OCH3; R3=H, NH2, F or OCH3; R4=H, NH2 or OCH3; R5=H, NH2, F, CF3 or OCH3; R6=H or OCH3; R7=H or OCH3; R8=H or OCH3.

Aromatic radiofluorination and biological evaluation of 2-aryl-6-[ 18F]fluorobenzothiazoles as a potential positron emission tomography imaging probe for β-amyloid plaques

To develop agents for radionuclide imaging Aβ plaques in vivo, we prepared three fluorine-substituted analogs of arylbenzothiazole class; compound 2 has a high affinity for Aβ (Ki = 5.5 nM) and the specific binding to Aβ in fluorescent staining. In preparation for the synthesis of these arylbenzothiazole analogs in radiolabeled form as an Aβ plaques-specific positron emission tomography (PET) imaging probe, we investigated synthetic route suitable for its labeling with the short-lived PET radionuclide fluorine-18 (t1/2 = 110 min) and diaryliodonium tosylate precursors (12, 13a-e and 14). 2-Aryl-6-[18F]fluorobenzothiazoles ([18F]1-3) were synthesized in efficiently short reaction times (40-60 min) with high radiochemical yields (19-40%), purities (>95%) and specific activities (85-118 GBq/μmol). Tissue distribution studies showed that high radioactivity of [18F]2 accumulated in the brain with rapid clearance in healthy mice. Radioactive metabolites were analyzed in brain samples of mice and corresponded to 81% of parent remained by 30 min after a tail-vein injection. These results suggest that [18F]2 is a promising probe for evaluation of Aβ plaques imaging in brain using PET.

FLUORINATED BENZOTHIAZOLE DERIVATIVES, PREPARATION METHOD THEREOF AND IMAGING AGENT FOR DIAGNOSING ALTZHEIMER'S DISEASE USING THE SAME

The present invention relates to fluorinated benzothiazole derivatives, a preparation method thereof, and an imaging agent for diagnosing Alzheimer's disease using the same, and more particularly to fluorinated benzothiazole derivatives represented by Che

An efficient one-pot synthesis of benzothiazolo-4β-anilino- podophyllotoxin congeners: DNA topoisomerase-II inhibition and anticancer activity

An efficient one-pot iodination methodology for the synthesis of benzothiazolo-4β-anilino-podophyllotoxin (5a-h) and benzothiazolo-4β- anilino-4-O-demethylepipodophyllotoxin (6a-h) congeners has been successfully developed by using zirconium tetrachloride

FLUORINATED BENZOTHIAZOLE DERIVATIVES, PREPARATION METHOD THEREOF AND IMAGING AGENT FOR DIAGNOSING ALTZHEIMER'S DISEASE USING THE SAME

The present invention relates to fluorinated benzothiazole derivatives, a preparation method thereof, and an imaging agent for diagnosing Alzheimer' s disease using the same, and more particularly to fluorinated benzothiazole derivatives represented by Chemical Formula 1, derivatives of Chemical Formula 2 as a starting material for preparation thereof, a preparation method thereof, and an imaging agent for diagnosing Alzheimer's disease using fluorinated benzothiazole derivatives with a strong binding force to beta-amyloid plaque, which is a kind of biomarker for Alzheimer's disease. According to the present invention, fluorine-labeled benzothiazole derivatives, which have been difficult to synthesize by conventional methods, may be obtained by simple processes and the thus-obtained benzothiazole derivatives may be useful in diagnosing the presence and severity of Alzheimer's disease.

Synthesis, DNA-binding ability and anticancer activity of benzothiazole/benzoxazole-pyrrolo[2,1-c][1,4]benzodiazepine conjugates

A series of benzothiazole and benzoxazole linked pyrrolobenzodiazepine conjugates attached through different alkane or alkylamide spacers was prepared. Their anticancer activity, DNA thermal denaturation studies, restriction endonuclease digestion assay and flow cytometric analysis in human melanoma cell line (A375) were investigated. One of the compounds of the series 17d showed significant anticancer activity with promising DNA-binding ability and apoptosis caused G0/G1 phase arrest at sub-micromolar concentrations. To ascertain the binding mode and understand the structural requirement of DNA binding interaction, molecular docking studies using gold program and more rigorous 2 ns molecular dynamic simulations using Molecular Mechanics-Poisson-Boltzman Surface Area (MM-PBSA) approach including the explicit solvent were carried out. Further, the compound 17d was evaluated for in vivo efficacy studies in human colon cancer HT29 xenograft mice.